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a white crystalline compound used as an analgesic and also as an antipyretic (同)acetanilid, phenylacetamide

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アセトアニリド(下熱・鎮痛剤)

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/11/08 13:13:49」(JST)

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Drying acetanilide

Acetanilide^[5] is an odourless solid chemical of leaf or flake-like appearance. It is also known as N-phenylacetamide, acetanil, or acetanilid, and was formerly known by the trade name Antifebrin.

Preparation and properties

Acetanilide can be produced by reacting acetic anhydride with aniline:

C₆H₅NH₂ + (CH₃CO)₂O → C₆H₅NHCOCH₃ + CH₃COOH

The preparation used to be a traditional experiment in introductory organic chemistry lab classes,^[6] but it has now been widely replaced by the preparation of either paracetamol or aspirin, both of which teach the same practical techniques (especially recrystallization of the product) but which avoid the use of aniline, a suspected carcinogen.

Acetanilide is slightly soluble in water, and stable under most conditions.^[4] Pure crystals are plate shaped and colorless to white.

Applications

Acetanilide is used as an inhibitor of hydrogen peroxide decomposition and is used to stabilize cellulose ester varnishes. It has also found uses in the intermediation in rubber accelerator synthesis, dyes and dye intermediate synthesis, and camphor synthesis. Acetanilide is used for the production of 4-acetamidobenzenesulfonyl chloride, a key intermediate for the manufacture of the sulfa drugs.^[7] It is also a precursor in the synthesis of penicillin and other pharmaceuticals.^[2]

In the 19th century acetanilide was one of a large number of compounds used as experimental photographic developers.

Pharmaceutical use

Acetanilide was the first aniline derivative serendipitously found to possess analgesic as well as antipyretic properties, and was quickly introduced into medical practice under the name of Antifebrin by A. Cahn and P. Hepp in 1886.^[8] But its (apparent) unacceptable toxic effects, the most alarming being cyanosis due to methemoglobinemia, prompted the search for supposedly less toxic aniline derivatives such as phenacetin.^[9] After several conflicting results over the ensuing fifty years, it was established in 1948 that acetanilide was mostly metabolized to paracetamol (USAN: acetaminophen) in the human body, and that it was the paracetamol that was responsible for the analgesic and antipyretic properties.^[10]^[11]^[12]^[13] The observed methemoglobinemia after acetanilide administration was ascribed to the small proportion of acetanilide that is hydrolyzed to aniline in the body.^{[note 1]} Acetanilide is no longer used as a drug in its own right, although the success of its metabolite – paracetamol (acetaminophen) – is well known.

Notes

^ The presence of aniline as an impurity in 19th century batches of acetanilide drugs cannot be ruled out. In this sense as well, paracetamol (acetaminophen) is safer than acetanilide, as (1) the corresponding impurity would be 4-aminophenol, which is less toxic than aniline; and (2) in vivo hydrolysis of the amide group in paracetamol appears to be negligible.

References

^ Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-67. ISBN 0-8493-0462-8. .
^ ^a ^b Acetanilide (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, September 2003 .
^ HSNO Chemical Classification Information Database, New Zealand Environmental Risk Management Authority, retrieved 2009-08-26 .
^ ^a ^b Safety data for acetanilide, Physical Chemistry Laboratory, University of Oxford .
^ Acetanilide .
^ See, e.g., The preparation of acetanilide from aniline, Department of Chemistry, University of the West Indies at Mona, Jamaica, retrieved 2009-08-26 ; Reeve, Wilkins; Lowe, Valerie C. (1979), "Preparation of Acetanilide from Nitrobenzene", J. Chem. Educ. 56 (7): 488, doi:10.1021/ed056p488 : the latter preparation includes the reduction of nitrobenzene to aniline.
^ Ashford's Dictionary of Industrial Chemicals (PDF) (Third ed.). 2011. p. 33.
^ Cahn, A.; Hepp, P. (1886), "Das Antifebrin, ein neues Fiebermittel", Centralbl. Klin. Med. 7: 561–64 .
^ Bertolini, A.; Ferrari, A.; Ottani, A.; Guerzoni, S.; Tacchi, R.; Leone, S. (2006), "Paracetamol: new vistas of an old drug", CNS Drug Reviews 12 (3–4): 250–75, doi:10.1111/j.1527-3458.2006.00250.x, PMID 17227290 .
^ Lester, D.; Greenberg, L. A. (1947), "Metabolic fate of acetanilide and other aniline derivatives. II. Major metabolites of acetanilide in the blood", J. Pharmacol. Exp. Ther. 90 (1): 68, PMID 20241897 .
^ Brodie, B. B.; Axelrod, J. (1948), "The estimation of acetanilide and its metabolic products, aniline, N-acetyl p-aminophenol and p-aminophenol (free and total conjugated) in biological fluids and tissues", J. Pharmacol. Exp. Ther. 94 (1): 22–28, PMID 18885610 .
^ Brodie, B. B.; Axelrod, J. (1948), "The fate of acetanilide in man" (PDF), J. Pharmacol. Exp. Ther. 94 (1): 29–38, PMID 18885611
^ Flinn, Frederick B.; Brodie, Bernard B. (1948), "The effect on the pain threshold of N-acetyl p-aminophenol, a product derived in the body from acetanilide", J. Pharmacol. Exp. Ther. 94 (1): 76–77, PMID 18885618 .

English Journal

Palladium-catalysed directed C-H activation by anilides and ureas; water participation in a general base mechanism.

Rauf W1, Brown JM.
Organic & biomolecular chemistry.Org Biomol Chem.2016 Jun 21;14(23):5251-7. doi: 10.1039/c6ob00897f. Epub 2016 May 17.
C-H activation plays a central role in organometallic catalysis. Concerted metallation-deprotonation (CMD) has been dominant as the pathway for C-H bond cleavage. In the course of studying the mechanism of C-H activation of arylamides and arylureas with Pd complexes as part of catalytic oxidative He
PMID 27184358

Chelation-Assisted Copper-Mediated Direct Acetylamination of 2-Arylpyridine C-H Bonds with Cyanate Salts.

Kianmehr E, Amiri Lomedasht Y, Faghih N, Khan KM.
The Journal of organic chemistry.J Org Chem.2016 Jun 13. [Epub ahead of print]
In this study, the coupling of 2-phenylpyridine derivatives and potassium cyanate through C-H bond functionalization in the presence of a copper salt is developed for the first time. By this protocol, various heteroarylated acetanilide derivatives are synthesized in good yields. 2-phenylpyridines co
PMID 27295365

Human metabolism and excretion kinetics of aniline after a single oral dose.

Modick H1, Weiss T1, Dierkes G1, Koslitz S1, Käfferlein HU1, Brüning T1, Koch HM2.
Archives of toxicology.Arch Toxicol.2016 Jun;90(6):1325-33. doi: 10.1007/s00204-015-1566-x. Epub 2015 Aug 2.
Aniline is an important source material in the chemical industry (e.g., rubber, pesticides, and pharmaceuticals). The general population is known to be ubiquitously exposed to aniline. Thus, assessment of aniline exposure is of both occupational and environmental relevance. Knowledge on human metabo
PMID 26233686

Japanese Journal

Chemoselective and Kilogram-Scale Synthesis of Acetanilide β₃-Adrenergic Receptor Agonist

, , [他], , , ,
Bulletin of the Chemical Society of Japan 88(1), 139-145, 2015
… We describe an alternative route for the synthesis of β3-adrenergic receptor agonist (S)-2-(2-phenylamino-1,3-thiazol-4-yl)-4′-{2-[(2-hydroxy-3-phenoxypropyl)amino]ethyl}acetanilide (1). …
NAID 130004801806

Chemoselective and Kilogram-scale Synthesis of Acetanilide β3-Adrenergic Receptor Agonist

, , , , , ,
Bulletin of the Chemical Society of Japan, 2014
… We describe an alternative route for the synthesis of β3-adrenergic receptor agonist (S)-2- (2-phenyl-amino-1,3-thiazol-4-yl)-4'-{2-[(2-hydroxy-3-phenoxypropyl)amino]ethyl}acetanilide (1). …
NAID 130004690770

Discovery of a Novel Acyl-CoA: Cholesterol Acyltransferase Inhibitor: The Synthesis, Biological Evaluation, and Reduced Adrenal Toxicity of (4-Phenylcoumarin)acetanilide Derivatives with a Carboxylic Acid Moiety

, , [他], , , , , , ,
Chemical and Pharmaceutical Bulletin 59(11), 1369-1375, 2011
… As a part of our research for novel potent and orally available acyl-CoA: cholesterol acyltransferase (ACAT) inhibitors that can be used as anti-atherosclerotic agents, we recently reported the discovery of the (4-phenylcoumarine)acetanilide derivative 1. …
NAID 130001274812

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リンク元	「アセトアニリド」
拡張検索	「acetanilide poisoning」

「アセトアニリド」

Acetanilide
Names
	IUPAC names N-phenylacetamide; N-phenylethanamide
Identifiers
CAS Registry Number	103-84-4
ChEBI	CHEBI:28884
ChEMBL	ChEMBL269644
ChemSpider	880
EC number	203-150-7
	InChI InChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10) ; Key: FZERHIULMFGESH-UHFFFAOYSA-N ; InChI=1/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10); Key: FZERHIULMFGESH-UHFFFAOYAA ;
Jmol-3D images	Image
KEGG	C07565
	SMILES O=C(Nc1ccccc1)C ;
UNII	SP86R356CC
Properties
Chemical formula	C8H9NO
Molar mass	135.17 g·mol−1
Odor	Odorless
Density	1.219 g/cm3
Melting point	114.3 °C (237.7 °F; 387.4 K)
Boiling point	304 °C (579 °F; 577 K)
Solubility in water	<0.56 g/100 mL (25 °C)
Solubility	Soluble in ethanol, diethyl ether, acetone, benzene
log P	1.16 (23 °C)
Vapor pressure	2 Pa (20 °C)
Dipole moment	2.71
Hazards
Safety data sheet	External MSDS
GHS pictograms
GHS signal word	WARNING
GHS hazard statements	H302
GHS precautionary statements	P264, P270, P301+312, P330, P501
Flash point	174 °C (345 °F; 447 K)
Autoignition; temperature	545 °C (1,013 °F; 818 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

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英: acetanilide
同: アンチフェブリン antifebrin

「acetanilide poisoning」

　　[★] アセトアニリド中毒

[14] The presence of aniline as an impurity in 19th century batches of acetanilide drugs cannot be ruled out. In this sense as well, paracetamol (acetaminophen) is safer than acetanilide, as (1) the corresponding impurity would be 4-aminophenol, which is less toxic than aniline; and (2) in vivo hydrolysis of the amide group in paracetamol appears to be negligible.

[1] Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-67. ISBN 0-8493-0462-8. .

[SIDS-2] Acetanilide (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, September 2003 .

[3] HSNO Chemical Classification Information Database, New Zealand Environmental Risk Management Authority, retrieved 2009-08-26 .

[MSDS-4] Safety data for acetanilide, Physical Chemistry Laboratory, University of Oxford .

[5] Acetanilide .

[6] See, e.g., The preparation of acetanilide from aniline, Department of Chemistry, University of the West Indies at Mona, Jamaica, retrieved 2009-08-26 ; Reeve, Wilkins; Lowe, Valerie C. (1979), "Preparation of Acetanilide from Nitrobenzene", J. Chem. Educ. 56 (7): 488, doi:10.1021/ed056p488 : the latter preparation includes the reduction of nitrobenzene to aniline.

[7] Ashford's Dictionary of Industrial Chemicals (PDF) (Third ed.). 2011. p. 33.

[8] Cahn, A.; Hepp, P. (1886), "Das Antifebrin, ein neues Fiebermittel", Centralbl. Klin. Med. 7: 561–64 .

[pmid17227290-9] Bertolini, A.; Ferrari, A.; Ottani, A.; Guerzoni, S.; Tacchi, R.; Leone, S. (2006), "Paracetamol: new vistas of an old drug", CNS Drug Reviews 12 (3–4): 250–75, doi:10.1111/j.1527-3458.2006.00250.x, PMID 17227290 .

[10] Lester, D.; Greenberg, L. A. (1947), "Metabolic fate of acetanilide and other aniline derivatives. II. Major metabolites of acetanilide in the blood", J. Pharmacol. Exp. Ther. 90 (1): 68, PMID 20241897 .

[11] Brodie, B. B.; Axelrod, J. (1948), "The estimation of acetanilide and its metabolic products, aniline, N-acetyl p-aminophenol and p-aminophenol (free and total conjugated) in biological fluids and tissues", J. Pharmacol. Exp. Ther. 94 (1): 22–28, PMID 18885610 .

[12] Brodie, B. B.; Axelrod, J. (1948), "The fate of acetanilide in man" (PDF), J. Pharmacol. Exp. Ther. 94 (1): 29–38, PMID 18885611

[13] Flinn, Frederick B.; Brodie, Bernard B. (1948), "The effect on the pain threshold of N-acetyl p-aminophenol, a product derived in the body from acetanilide", J. Pharmacol. Exp. Ther. 94 (1): 76–77, PMID 18885618 .

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acetanilide