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Isopropyl alcohol (IUPAC name propan-2-ol), also called dimethyl carbinol or, isopropanol, is a compound with the chemical formula C₃H₈O or C₃H₇OH or CH₃CHOHCH₃ (sometimes represented as i-PrOH). It is a colorless, flammable chemical compound with a strong odor. As an isopropyl group linked to a hydroxyl group, it is the simplest example of a secondary alcohol, where the alcohol carbon atom is attached to two other carbon atoms, sometimes shown as (CH₃)₂CHOH. It is a structural isomer of 1-propanol. It has a wide variety of industrial and household uses, and is a common ingredient in chemicals such as antiseptics, disinfectants and detergents.

1 Properties
2 Reactions
3 Production
- 3.1 Indirect hydration
- 3.2 Direct hydration
- 3.3 Hydrogenation of acetone
4 Uses
- 4.1 Solvent
- 4.2 Intermediate
- 4.3 Medical
  - 4.3.1 Early uses as an anesthetic
- 4.4 Automotive
- 4.5 Laboratory
5 Safety
6 Toxicology
7 History
8 Terminology
9 References
10 External links

Properties

Isopropyl alcohol is miscible in water, ethanol, ether, and chloroform. It will dissolve ethyl cellulose, polyvinyl butyral, many oils, alkaloids, gums and natural resins.^[6] Unlike ethanol or methanol, isopropyl alcohol is not miscible with salt solutions and can be separated from aqueous solutions by adding a salt such as sodium chloride. The process is colloquially called salting out, and causes concentrated isopropyl alcohol to separate into a distinct layer.^[7]

Isopropyl alcohol forms an azeotrope with water, which gives a boiling point of 80.37 °C (176.67 °F) and a composition of 87.7 wt% (91 vol%) isopropyl alcohol. Water-isopropyl alcohol mixtures have depressed melting points.^[7] It has a slightly bitter taste, and is not safe to drink.^[7]^[8]

Isopropyl alcohol becomes increasingly viscous with decreasing temperature and will freeze at −89 °C (−128 °F).

Isopropyl alcohol has a maximum absorbance at 205 nm in an ultraviolet-visible spectrum.^[9]^[10]

Reactions

Isopropyl alcohol can be oxidized to acetone, which is the corresponding ketone. This can be achieved using oxidizing agents such as chromic acid, or by dehydrogenation of isopropyl alcohol over a heated copper catalyst:

(CH₃)₂CHOH → (CH₃)₂CO + H₂

Isopropyl alcohol is often used as both solvent and hydride source in the Meerwein-Ponndorf-Verley reduction and other transfer hydrogenation reactions. Isopropyl alcohol may be converted to 2-bromopropane using phosphorus tribromide, or dehydrated to propene by heating with sulfuric acid.

Like most alcohols, isopropyl alcohol reacts with active metals such as potassium to form alkoxides that can be called isopropoxides. The reaction with aluminium (initiated by a trace of mercury) is used to prepare the catalyst aluminium isopropoxide.^[11]

Production

In 1994, 1.5 million tonnes of isopropyl alcohol was produced in the United States, Europe, and Japan.^[12] This compound is primarily produced by combining water and propene in a hydration reaction. It is also produced by hydrogenating acetone.^[12]^[13]

There are two routes for the hydration process: indirect hydration using the sulfuric acid process, and direct hydration. The former process, which can use low-quality propene, predominates in the USA while the latter process, which requires high-purity propene, is more commonly used in Europe. These processes give predominantly isopropyl alcohol rather than 1-propanol because the addition of water or sulfuric acid to propene follows Markovnikov's rule.

Indirect hydration

The indirect process reacts propene with sulfuric acid to form a mixture of sulfate esters. Subsequent hydrolysis of these esters by steam produces isopropyl alcohol, which is distilled. Diisopropyl ether is a significant by-product of this process; it is recycled back to the process and hydrolyzed to give the desired product.^[12]

Direct hydration

Direct hydration reacts propene and water, either in gas phase or in liquid phase, at high pressures in the presence of solid or supported acidic catalysts. Higher-purity propylene (> 90%) tends to be required for this type of process.^[12]

Both processes require that the isopropyl alcohol be separated from water and other by-products by distillation. Isopropyl alcohol and water form an azeotrope and simple distillation gives a material that is 87.9% by weight isopropyl alcohol and 12.1% by weight water.^[14] Pure (anhydrous) isopropyl alcohol is made by azeotropic distillation of the wet isopropyl alcohol using either diisopropyl ether or cyclohexane as azeotroping agents.^[12]

Hydrogenation of acetone

Crude acetone is hydrogenated in the liquid phase over Raney nickel or a mixture of copper and chromium oxide to give isopropyl alcohol. This process is useful when coupled with excess acetone production, such as the cumene process.^[12]

Uses

One of the small scale uses of isopropanol is in cloud chambers. Isopropanol has ideal physical and chemical properties to form a supersaturated layer of vapor which can be condensed by particles of radiation

In 1990, 45 thousand metric tons of isopropyl alcohol were used in the United States. The vast majority of isopropyl alcohol was used as a solvent for coatings or for industrial processes. In that year, 5.4 thousand metric tons were consumed for household use and in personal care products. Isopropyl alcohol in particular is popular for pharmaceutical applications,^[12] it is presumed due to the low toxicity of any residues. Some isopropyl alcohol is used as a chemical intermediate. Isopropyl alcohol may be converted to acetone, but the cumene process is more significant. It is also used as a gasoline additive.^[12]

Solvent

Isopropyl alcohol dissolves a wide range of non-polar compounds. It also evaporates quickly, leaves nearly zero oil traces, compared to ethanol, and is relatively non-toxic, compared to alternative solvents. Thus, it is used widely as a solvent and as a cleaning fluid, especially for dissolving oils. Together with ethanol, n-butanol, and methanol, it belongs to the group of alcohol solvents, about 6.4 million tonnes of which were utilized worldwide in 2011.^[15]

Examples of this application include cleaning electronic devices such as contact pins (like those on ROM cartridges), magnetic tape and disk heads (such as those in audio and video tape recorders and floppy disk drives), the lenses of lasers in optical disc drives (e.g., CD, DVD) and removing thermal paste from heatsinks and IC packages (such as CPUs^[16]).

Intermediate

Isopropyl alcohol is esterified to give isopropyl acetate, another solvent. It reacts with carbon disulfide and sodium hydroxide to give sodium isopropylxanthate, an herbicide^[17] and an ore flotation reagent.^[18] Isopropyl alcohol reacts with titanium tetrachloride and aluminium metal to give titanium and aluminium isopropoxides, respectively, the former a catalyst, and the latter a chemical reagent.^[12] This compound may serve as a chemical reagent in itself, by acting as a dihydrogen donor in transfer hydrogenation.

Medical

Rubbing alcohol, hand sanitizer, and disinfecting pads typically contain a 60–70% solution of isopropyl alcohol in water. Water is required to open up membrane pores of bacteria, which acts as a gateway inside for isopropyl. A 75% v/v solution in water may be used as a hand sanitizer.^[19] Isopropyl alcohol is used as a water-drying aid for the prevention of otitis externa, better known as swimmer’s ear.^[20]

Early uses as an anesthetic

Although isopropyl alcohol can be technically used for anesthesia, its many negative drawbacks prohibit this use. Isopropyl alcohol can also be used similarly to ether as a solvent^[21] or as an anesthetic by inhaling the fumes or orally. Early uses included using the solvent as general anesthetic for small mammals^[22] and rodents by scientists and some veterinarians. However, it was soon discontinued, as many complications arose, including respiratory irritation, internal bleeding, and visual and hearing problems. In rare cases, respiratory failure leading to death in animals was observed.

Automotive

Isopropyl alcohol is a major ingredient in "gas dryer" fuel additives. In significant quantities water is a problem in fuel tanks as it separates from the gasoline and can freeze in the supply lines at cold temperatures. Alcohol does not remove water from gasoline; rather, the alcohol solubilizes water in gasoline. Once soluble, water does not pose the same risk as insoluble water, as it will no longer accumulate in the supply lines and freeze, but will be consumed along with the fuel itself. Isopropyl alcohol is often sold in aerosol cans as a windshield or door lock de-icer. Isopropyl alcohol is also used to remove brake fluid traces from hydraulic braking systems, so that the brake fluid (usually DOT 3, DOT 4, or mineral oil) does not contaminate the brake pads, which would result in poor braking.

Laboratory

As a biological specimen preservative, isopropyl alcohol provides a comparatively non-toxic alternative to formaldehyde and other synthetic preservatives. Isopropyl alcohol solutions of 70–99% are used to preserve specimens.

Isopropyl alcohol is often used in DNA extraction. It is added to a DNA solution in order to precipitate the DNA which then forms a pellet after centrifugation. This is possible because DNA is insoluble in isopropyl alcohol.

Safety

Isopropyl alcohol vapor is denser than air and is flammable, with a flammability range of between 2 and 12.7% in air. It should be kept away from heat and open flame.^[23] Isopropyl alcohol has been reported to form peroxides, which may explode upon concentration.^[24] Isopropyl alcohol is a skin irritant.^[23]

Toxicology

Isopropyl alcohol and its metabolite, acetone, act as central nervous system (CNS) depressants,^[25] and around 15 g of isopropyl alcohol can have a toxic effect on a 70 kg human if left untreated.^[26] Poisoning can occur from ingestion, inhalation, or skin absorption. Symptoms of isopropyl alcohol poisoning include flushing, headache, dizziness, CNS depression, nausea, vomiting, anesthesia, hypothermia, hypotension, shock, respiratory depression, and coma.^[25] Overdoses may cause a fruity odor on the breath as a result of its metabolism to acetone.^[27] Isopropyl alcohol does not cause an anion gap acidosis but it produces an osmolal gap between the calculated and measured osmolalities of serum, as do the other alcohols.^[25]

Isopropyl alcohol is oxidized to form acetone by alcohol dehydrogenase in the liver,^[25] and has a biological half-life in humans between 2.5 and 8.0 hours.^[25]. Unlike methanol or ethylene glycol poisoning, the metabolites of isopropyl alcohol are less toxic, and treatment is largely supportive. Furthermore, there is no indication for the use of fomepizole, an alcohol dehydrogenase inhibitor, unless co-ingestion with methanol or ethylene glycol is suspected.^[28]

Isopropyl alcohol is denatured for certain uses, in which case the NFPA 704 rating is changed to 2,3,1.

History

In 1920, Standard Oil first produced isopropyl alcohol by hydrating propene. Its major use at the time was not rubbing alcohol but for oxidation to acetone, whose first major use was in World War One for the preparation of the smokeless propellant, cordite.^[29]

Terminology

The compound has been conventionally called "isopropanol" in laboratories. However, the orthodox name, as proposed forth by scientists, should be "isopropyl alcohol", as there does not exist an "isopropane" to which the suffix "-ol" can be added.

References

^ "Alcohols Rule C-201.1". Nomenclature of Organic Chemistry (The IUPAC 'Blue Book'), Sections A, B, C, D, E, F, and H. Oxford: Pergamon Press. 1979.
^ Reeve, W.; Erikson, C.M.; Aluotto, P.F. (1979). "A new method for the determination of the relative acidities of alcohols in alcoholic solutions. The nucleophilicities and competitive reactivities of alkoxides and phenoxides". Can. J. Chem. 57 (20): 2747–2754. doi:10.1139/v79-444.
^ ^a ^b Yaws, C.L. (1999). Chemical Properties Handbook. McGraw-Hill. ISBN 0-07-073401-1.
^ ^a ^b ^c "NIOSH Pocket Guide to Chemical Hazards #0359". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b ^c "Isopropyl alcohol". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
^ Doolittle, Arthur K. (1954). The Technology of Solvents and Plasticizers. New York: John Wiley & Sons, Inc. p. 628.
^ ^a ^b ^c The Merck Index (10th ed.). Rahway, NJ: Merck & Co. 1983. p. 749.
^ Logsden, John E.; Loke, Richard A (1999). "Propyl Alcohols". In Jacqueline I., Kroschwitz. Kirk-Othmer Concise Encylclopedia of Chemical Technology, (4th ed.). New York: John Wiley & Sons, Inc. pp. 1654–1656. ISBN 978-0471419617.
^ "Isopropyl Alcohol, UltimAR, Suitable for Liquid Chromatography, Extract/Conc, UV-Spectrophotometry". VWR International. Retrieved 25 August 2014.
^ "UV Cutoff" (PDF). University of Toronto. Retrieved 25 August 2014.
^ Young, W.; Hartung, W.; Crossley, F. (1936). "Reduction of Aldehydes with Aluminum Isopropoxide". J. Am. Chem. Soc. 58: 100–2. doi:10.1021/ja01292a033.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Papa, A. J. (2005), "Propanols", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a22_173
^ Logsdon, John E.; Loke, Richard A. (December 4, 2000). "Isopropyl Alcohol". Kirk‑Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. doi:10.1002/0471238961.0919151612150719.a01.
^ CRC Handbook of Chemistry and Physics, 44th ed. pp 2143–2184
^ Market Study Solvents, Ceresana, published Apr 2012
^ Arctic Silver thermal compound. arcticsilver.com
^ "proxan-sodium". alanwood.net.
^ "Sodium Isopropyl Xanthate, SIPX, Xanthate". 3DChem.com. Retrieved 2012-06-17.
^ "Guide to Local Production: WHO-recommended Handrub Formulations" (PDF). World Health Organization. August 2009.
^ Otitis Externa (Swimmers Ear). Medial College of Wisconsin
^ Burlage, Henry M.; Welch, H; Price, CW (2006). "Pharmaceutical applications of isopropyl alcohol II. Solubilities of local anesthetics". Journal of the American Pharmaceutical Association. 36 (1): 17–9. PMID 20285822. doi:10.1002/jps.3030360105.
^ Society for Experimental Biology and Medicine (1922). Proceedings of the Society for Experimental Biology and Medicine, Volume 19. p. 85.
^ ^a ^b "Isopropanol". Sigma-Aldrich. 19 January 2012. Retrieved 6 July 2012.
^ Kolar, Wes (July 11, 2000). "Lab Safety Review: Danger! – Peroxides Present".
^ ^a ^b ^c ^d ^e Slaughter RJ, Mason RW, Beasley DM, Vale JA, Schep LJ (2014). "Isopropanol poisoning". Clinical Toxicology. 52 (5): 470–8. PMID 24815348. doi:10.3109/15563650.2014.914527.
^ Calculated from TDLO listed at Oxford University MSDS, assuming weight of 70 kg
^ Kalapos, MP (2003). "On the mammalian acetone metabolism: from chemistry to clinical implications". Biochimica et Biophysica Acta. 1621 (2): 122–39. PMID 12726989. doi:10.1016/S0304-4165(03)00051-5.
^ "Isopropyl alcohol poisoning". www.uptodate.com. Retrieved 2017-10-10.
^ Wittcoff, M.M. Green ; H.A. (2003). Organic chemistry principles and industrial practice (1. ed., 1. reprint. ed.). Weinheim: Wiley-VCH. p. 4. ISBN 3-527-30289-1.

External links

CDC – NIOSH Pocket Guide to Chemical Hazards - Isopropyl alcohol
Environmental Health Criteria 103: 2-Propanol

UpToDate Contents

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2. 不安定ヘモグロビン変異体 unstable hemoglobin variants
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Rapid separation and characterisation of triacylglycerols in ostrich oil by ultra performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry.

Zhou Y, Xue Y, Chen GC, Zhang AJ, Chen ZF, Liao X, Ding LS.SourceChengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China.
Food chemistry.Food Chem.2013 Dec 1;141(3):2098-102. doi: 10.1016/j.foodchem.2013.05.079. Epub 2013 May 23.
The triacylglycerol (TAG) composition of ostrich oil (Struthio camelus) was determined by non-aqueous reversed-phase ultra-performance liquid chromatography-mass spectrometry. Using a column with 150mm in length, the TAGs were separated efficiently with acetonitrile/2-propanol gradient at flow rate
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Effects of binary organic solvents and heating on lipid removal and the reduction of beany odour in Bambara groundnut (Vigna subterranean) flour.

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Food chemistry.Food Chem.2013 Nov 15;141(2):1390-7. doi: 10.1016/j.foodchem.2013.04.047. Epub 2013 Apr 24.
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Materials science & engineering. C, Materials for biological applications.Mater Sci Eng C Mater Biol Appl.2013 Oct;33(7):4444-52. doi: 10.1016/j.msec.2013.06.042. Epub 2013 Jul 5.
The morphology of fibers synthesized through electrospinning has been found to mimic extracellular matrix. Coaxially electrospun fibers of gelatin (sheath) coated poly (3-hydroxybutyric acid) (PHB) (core) was developed using 2,2,2 trifluoroethanol(TFE) and 1,1,1,3,3,3 hexafluoro-2-propanol(HFIP) as
PMID 23910364

Japanese Journal

2P-207 藍藻イソプロパノール耐性株の光合成特性(生物化学工学,一般講演)

日本生物工学会大会講演要旨集 67, 226, 2015-09-25
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Related Pictures

★リンクテーブル★

リンク元	「イソプロパノール」「rubbing alcohol」「isopropyl alcohol」「2-propanol」

「イソプロパノール」

Isopropyl alcohol
Names
	Preferred IUPAC name Propan-2-ol
	Other names 2-Propanol; Isopropanol (incorrect ); Rubbing alcohol; sec-Propyl alcohol; s-Propanol; iPrOH; Dimethyl carbinol; IPA
Identifiers
CAS Number	67-63-0 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	635639
ChEBI	CHEBI:17824 ;
ChemSpider	3644 ;
ECHA InfoCard	100.000.601
Gmelin Reference	1464
KEGG	D00137 ;
PubChem CID	3776;
RTECS number	NT8050000
UNII	ND2M416302 ;
UN number	1219
	InChI InChI=1S/C3H8O/c1-3(2)4/h3-4H,1-2H3 Key: KFZMGEQAYNKOFK-UHFFFAOYSA-N ;
	SMILES CC(O)C ;
Properties
Chemical formula	C3H8O
Molar mass	60.10 g·mol−1
Appearance	Colorless liquid
Density	0.786 g/cm3 (20 °C)
Melting point	−89 °C (−128 °F; 184 K)
Boiling point	82.6 °C (180.7 °F; 355.8 K)
Solubility in water	miscible in water
Solubility	miscible in benzene, chloroform, ethanol, ether, glycerin; soluble in acetone
Acidity (pKa)	16.5
Magnetic susceptibility (χ)	-45.794·10−6 cm3/mol
Refractive index (nD)	1.3776
Viscosity	2.86 cP at 15 °C; 1.96 cP at 25 °C; 1.77 cP at 30 °C
Dipole moment	1.66 D (gas)
Pharmacology
ATC code	D08AX05 (WHO)
Hazards
Main hazards	Flammable
Safety data sheet	See: data page; External MSDS
GHS pictograms
GHS signal word	Danger
GHS hazard statements	H225, H319, H336
GHS precautionary statements	P210, P261, P305+351+338
NFPA 704	3 1 0
Flash point	Open cup: 11.7 °C (53.1 °F; 284.8 K); Closed cup: 13 °C (55 °F)
Autoignition; temperature	399 °C (750 °F; 672 K)
Explosive limits	2–12.7%
Threshold limit value	980 mg/m3 (TWA), 1225 mg/m3 (STEL)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	12800 mg/kg (dermal, rabbit)[citation needed]; 3600 mg/kg (oral, mouse); 5045 mg/kg (oral, rat); 6410 mg/kg (oral, rabbit)
LC50 (median concentration)	53000 mg/m3 (inhalation, mouse)[citation needed]; 12,000 ppm (rat, 8 hr)
LCLo (lowest published)	16,000 ppm (rat, 4 hr); 12,800 ppm (mouse, 3 hr)
	US health exposure limits (NIOSH):
PEL (Permissible)	TWA 400 ppm (980 mg/m3)
REL (Recommended)	TWA 400 ppm (980 mg/m3) ST 500 ppm (1225 mg/m3)
IDLH (Immediate danger)	2000 ppm
Related compounds
Related alcohols	1-Propanol, ethanol, 2-butanol
Supplementary data page
Structure and; properties	Refractive index (n),; Dielectric constant (εr), etc.
Thermodynamic; data	Phase behaviour; solid–liquid–gas
Spectral data	UV, IR, NMR, MS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

英: isopropanol
ラ: isopropanolum
同: イソプロピルアルコール isopropyl alcohol
商: イソプロ、イソプロピルアルコール、イソプロ消アル、イソプロ液、グリジールスカルプ、スチックゼノール、ゼスタック、ネオプロパノール、ネオ純生消アル、ネオ消アル、フェルビナクパップ、プレポダインフィールド、マルプロ消毒用液、モービリン、ヤクハンヨウチン、ラミテクト、消エタサラコール、エタプロコール、エタライトB液、エタライト液、ネオアルコール

「rubbing alcohol」

　　[★]

消毒用アルコール、消毒用エタノール

関: 2-propanol、isopropanol、isopropyl alcohol

「isopropyl alcohol」

　　[★]

イソプロピルアルコール

関: 2-propanol、isopropanol、rubbing alcohol

「2-propanol」

　　[★]

2-プロパノール

関: isopropanol、isopropyl alcohol、rubbing alcohol

[BlueBook79-1] "Alcohols Rule C-201.1". Nomenclature of Organic Chemistry (The IUPAC 'Blue Book'), Sections A, B, C, D, E, F, and H. Oxford: Pergamon Press. 1979.

[2] Reeve, W.; Erikson, C.M.; Aluotto, P.F. (1979). "A new method for the determination of the relative acidities of alcohols in alcoholic solutions. The nucleophilicities and competitive reactivities of alkoxides and phenoxides". Can. J. Chem. 57 (20): 2747–2754. doi:10.1139/v79-444.

[yaws-3] Yaws, C.L. (1999). Chemical Properties Handbook. McGraw-Hill. ISBN 0-07-073401-1.

[PGCH-4] "NIOSH Pocket Guide to Chemical Hazards #0359". National Institute for Occupational Safety and Health (NIOSH).

[IDLH-5] "Isopropyl alcohol". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).

[Doolittle-6] Doolittle, Arthur K. (1954). The Technology of Solvents and Plasticizers. New York: John Wiley & Sons, Inc. p. 628.

[Merck-7] The Merck Index (10th ed.). Rahway, NJ: Merck & Co. 1983. p. 749.

[8] Logsden, John E.; Loke, Richard A (1999). "Propyl Alcohols". In Jacqueline I., Kroschwitz. Kirk-Othmer Concise Encylclopedia of Chemical Technology, (4th ed.). New York: John Wiley & Sons, Inc. pp. 1654–1656. ISBN 978-0471419617.

[Macron-9] "Isopropyl Alcohol, UltimAR, Suitable for Liquid Chromatography, Extract/Conc, UV-Spectrophotometry". VWR International. Retrieved 25 August 2014.

[UToronto-10] "UV Cutoff" (PDF). University of Toronto. Retrieved 25 August 2014.

[11] Young, W.; Hartung, W.; Crossley, F. (1936). "Reduction of Aldehydes with Aluminum Isopropoxide". J. Am. Chem. Soc. 58: 100–2. doi:10.1021/ja01292a033.

[Ullmann-12] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Papa, A. J. (2005), "Propanols", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a22_173

[13] Logsdon, John E.; Loke, Richard A. (December 4, 2000). "Isopropyl Alcohol". Kirk‑Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. doi:10.1002/0471238961.0919151612150719.a01.

[14] CRC Handbook of Chemistry and Physics, 44th ed. pp 2143–2184

[15] Market Study Solvents, Ceresana, published Apr 2012

[16] Arctic Silver thermal compound. arcticsilver.com

[17] "proxan-sodium". alanwood.net.

[18] "Sodium Isopropyl Xanthate, SIPX, Xanthate". 3DChem.com. Retrieved 2012-06-17.

[19] "Guide to Local Production: WHO-recommended Handrub Formulations" (PDF). World Health Organization. August 2009.

[20] Otitis Externa (Swimmers Ear). Medial College of Wisconsin

[21] Burlage, Henry M.; Welch, H; Price, CW (2006). "Pharmaceutical applications of isopropyl alcohol II. Solubilities of local anesthetics". Journal of the American Pharmaceutical Association. 36 (1): 17–9. PMID 20285822. doi:10.1002/jps.3030360105.

[22] Society for Experimental Biology and Medicine (1922). Proceedings of the Society for Experimental Biology and Medicine, Volume 19. p. 85.

[Sigma-23] "Isopropanol". Sigma-Aldrich. 19 January 2012. Retrieved 6 July 2012.

[24] Kolar, Wes (July 11, 2000). "Lab Safety Review: Danger! – Peroxides Present".

[pmid24815348-25] Slaughter RJ, Mason RW, Beasley DM, Vale JA, Schep LJ (2014). "Isopropanol poisoning". Clinical Toxicology. 52 (5): 470–8. PMID 24815348. doi:10.3109/15563650.2014.914527.

[26] Calculated from TDLO listed at Oxford University MSDS, assuming weight of 70 kg

[27] Kalapos, MP (2003). "On the mammalian acetone metabolism: from chemistry to clinical implications". Biochimica et Biophysica Acta. 1621 (2): 122–39. PMID 12726989. doi:10.1016/S0304-4165(03)00051-5.

[28] "Isopropyl alcohol poisoning". www.uptodate.com. Retrieved 2017-10-10.

[29] Wittcoff, M.M. Green ; H.A. (2003). Organic chemistry principles and industrial practice (1. ed., 1. reprint. ed.). Weinheim: Wiley-VCH. p. 4. ISBN 3-527-30289-1.

v t e Alcohols
Straight-chain primary alcohols (1°)	Methanol (C 1) Ethanol (C 2) 1-Propanol (C 3) n-Butanol (C 4) 1-Pentanol (C 5) 1-Hexanol (C 6) 1-Heptanol (C 7) 1-Octanol (C 8) 1-Nonanol (C 9) 1-Decanol (C 10) Undecanol (C 11) Dodecanol (C 12) Tridecan-1-ol (C 13) 1-Tetradecanol (C 14) Pentadecan-1-ol (C 15) Cetyl alcohol (C 16) Heptadecan-1-ol (C 17) Stearyl alcohol (C 18) Nonadecan-1-ol (C 19) Arachidyl alcohol (C 20) Heneicosan-1-ol (C 21) Docosanol (C 22) Tricosan-1-ol (C 23) 1-Tetracosanol (C 24) Pentacosan-1-ol (C 25) 1-Hexacosanol (C 26) 1-Heptacosanol (C 27) 1-Octacosanol (C 28) 1-Nonacosanol (C 29) Triacontanol (C 30)
Other primary alcohols	Isobutanol (C 4) Isoamyl alcohol (C 5) 2-Methyl-1-butanol (C 5) Phenethyl alcohol (C 8) Tryptophol (C 10)
Secondary alcohols (2°)	Isopropanol (C 3) 2-Butanol (C 4) 2-Pentanol (C 5) 2-Hexanol (C 6) 2-Heptanol (C 7) Cyclohexanol (C 6) 2-Octanol (C 8)
Tertiary alcohols (3°)	tert-Butyl alcohol (C 4) tert-Amyl alcohol (C 5) 2-Methyl-2-pentanol (C 6) 2-Methylhexan-2-ol (C 7) 2-Methylheptan-2-ol (C 8) 3-Methyl-3-pentanol (C 6) 3-Methyloctan-3-ol (C 9)

v t e Antiseptics and disinfectants (D08)
Acridine derivatives	Ethacridine lactate 9-Aminoacridine Euflavine
Biguanides and amidines	Dibrompropamidine Chlorhexidine^# Propamidine Hexamidine Polihexanide
Phenol and derivatives	Hexachlorophene Policresulen Phenol Triclosan Triclocarban Chloroxylenol^# Biphenylol Fenticlor
Nitrofuran derivatives	Nitrofurazone
Iodine products	Iodine/octylphenoxypolyglycolether Povidone-iodine^# Diiodohydroxypropane
Quinoline derivatives	Dequalinium Chlorquinaldol Oxyquinoline Clioquinol
Quaternary ammonium compounds	Benzalkonium Benzethonium chloride Cetrimonium (bromide/chloride) Cetylpyridinium Cetrimide Benzoxonium chloride Didecyldimethylammonium chloride
Mercurial products	Mercuric amidochloride Phenylmercuric borate Mercuric chloride Merbromin Thiomersal Mercuric iodide
Silver compounds	Silver nitrate
Alcohols	Propanol (propyl alcohol) Isopropanol (isopropyl alcohol) Ethanol (ethyl alcohol)^#
Other	Potassium permanganate Sodium hypochlorite Hydrogen peroxide Eosin Tosylchloramide Octenidine dihydrochloride
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

v t e GABA_A receptor positive modulators
Alcohols	Brometone Butanol Chloralodol Chlorobutanol (cloretone) Ethanol (alcohol) (alcoholic drink) Ethchlorvynol Isobutanol Isopropanol Menthol Methanol Methylpentynol Pentanol Petrichloral Propanol tert-Butanol (2M2P) tert-Pentanol (2M2B) Tribromoethanol Trichloroethanol Triclofos Trifluoroethanol
Barbiturates	(-)-DMBB Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Butabarbital/Secbutabarbital Butalbital Buthalital Butobarbital Butallylonal Carbubarb Crotylbarbital Cyclobarbital Cyclopentobarbital Difebarbamate Enallylpropymal Ethallobarbital Eterobarb Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Metharbital Methitural Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenallymal Phenobarbital Phetharbital Primidone Probarbital Propallylonal Propylbarbital Proxibarbital Reposal Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Thiotetrabarbital Valofane Vinbarbital Vinylbital
Benzodiazepines	2-Oxoquazepam 3-Hydroxyphenazepam Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Brotizolam Camazepam Carburazepam Chlordiazepoxide Ciclotizolam Cinazepam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clonazolam Cloniprazepam Clorazepate Clotiazepam Cloxazolam CP-1414S Cyprazepam Delorazepam Demoxepam Diazepam Diclazepam Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam EVT-201 FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam Flunitrazolam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Haloxazolam Iclazepam Imidazenil Irazepine Ketazolam Lofendazam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitrazepam Nitrazepate Nitrazolam Nordazepam Nortetrazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam Pyrazolam QH-II-66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48-6791 Ro48-8684 SH-053-R-CH3-2′F Sulazepam Temazepam Tetrazepam Tolufazepam Triazolam Triflubazam Triflunordazepam (Ro5-2904) Tuclazepam Uldazepam Zapizolam Zolazepam Zomebazam
Carbamates	Carisbamate Carisoprodol Clocental Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Lorbamate Mebutamate Meprobamate Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate
Flavonoids	6-Methylapigenin Ampelopsin (dihydromyricetin) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Linarin Luteolin Rc-OMe Skullcap constituents (e.g., baicalin) Wogonin
Imidazoles	Etomidate Metomidate Propoxate
Kava constituents	10-Methoxyyangonin 11-Methoxyyangonin 11-Hydroxyyangonin Desmethoxyyangonin 11-Methoxy-12-hydroxydehydrokavain 7,8-Dihydroyangonin Kavain 5-Hydroxykavain 5,6-Dihydroyangonin 7,8-Dihydrokavain 5,6,7,8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin
Monoureides	Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride Ectylurea
Neuroactive steroids	Acebrochol Allopregnanolone (brexanolone) Alfadolone Alfaxalone 3α-Androstanediol Androstenol Androsterone Certain anabolic-androgenic steroids Cholesterol DHDOC 3α-DHP 5α-DHP 5β-DHP DHT Etiocholanolone Ganaxolone Hydroxydione Minaxolone ORG-20599 ORG-21465 P1-185 Pregnanolone (eltanolone) Progesterone Renanolone SAGE-105 SAGE-217 SAGE-324 SAGE-516 SAGE-689 SAGE-872 Testosterone THDOC
Nonbenzodiazepines	β-Carbolines: Abecarnil Gedocarnil Harmane SL-651,498 ZK-93423 Cyclopyrrolones: Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone Imidazopyridines: Alpidem DS-1 Necopidem Saripidem Zolpidem Pyrazolopyrimidines: Divaplon Fasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon Others: Adipiplon CGS-8216 CGS-9896 CGS-13767 CGS-20625 CL-218,872 CP-615,003 CTP-354 ELB-139 GBLD-345 Imepitoin JM-1232 L-838,417 Lirequinil (Ro41-3696) NS-2664 NS-2710 NS-11394 Pipequaline ROD-188 RWJ-51204 SB-205,384 SX-3228 TGSC01AA TP-003 TPA-023 TP-13 U-89843A U-90042 Viqualine Y-23684
Phenols	Fospropofol Propofol Thymol
Piperidinediones	Glutethimide Methyprylon Piperidione Pyrithyldione
Pyrazolopyridines	Cartazolate Etazolate ICI-190,622 Tracazolate
Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164
Volatiles/gases	Acetone Acetophenone Acetylglycinamide chloral hydrate Aliflurane Benzene Butane Butylene Centalun Chloral Chloral betaine Chloral hydrate Chloroform Cryofluorane Desflurane Dichloralphenazone Dichloromethane Diethyl ether Enflurane Ethyl chloride Ethylene Fluroxene Gasoline Halopropane Halothane Isoflurane Kerosine Methoxyflurane Methoxypropane Nitric oxide Nitrogen Nitrous oxide Norflurane Paraldehyde Propane Propylene Roflurane Sevoflurane Synthane Teflurane Toluene Trichloroethane (methyl chloroform) Trichloroethylene Vinyl ether
Others/unsorted	3-Hydroxybutanal α-EMTBL AA-29504 Avermectins (e.g., ivermectin) Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide) Carbamazepine Chloralose Chlormezanone Clomethiazole DEABL Dihydroergolines (e.g., dihydroergocryptine, dihydroergosine, dihydroergotamine, ergoloid (dihydroergotoxine)) DS2 Efavirenz Etazepine Etifoxine Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid) Fluoxetine Flupirtine Hopantenic acid Lanthanum Lavender oil Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol) Loreclezole Menthyl isovalerate (validolum) Monastrol Niacin Nicotinamide (niacinamide) Org 25,435 Phenytoin Propanidid Retigabine (ezogabine) Safranal Seproxetine Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal), tetronal, trional) Terpenoids (e.g., borneol) Topiramate Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, valerenol) Unsorted benzodiazepine site positive modulators: α-Pinene MRK-409 (MK-0343) TCS-1105 TCS-1205
See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators

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isopropanol