シクロヘキシルアミン
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2017/12/10 00:45:38」(JST)
[Wiki en表示]
Cyclohexylamine[1]
|
|
Names |
IUPAC name
Cyclohexanamine
|
Other names
Aminocyclohexane
Aminohexahydrobenzene
Hexahydroaniline
Hexahydrobenzenamine
|
Identifiers |
CAS Number
|
|
3D model (JSmol)
|
|
ChEBI |
|
ChemSpider |
|
ECHA InfoCard |
100.003.300 |
EC Number |
203-629-0 |
IUPHAR/BPS
|
|
KEGG |
|
|
|
RTECS number |
GX0700000 |
UNII |
|
InChI
-
InChI=1S/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2 Y
Key: PAFZNILMFXTMIY-UHFFFAOYSA-N Y
-
InChI=1/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2
Key: PAFZNILMFXTMIY-UHFFFAOYAP
|
|
Properties |
Chemical formula
|
C6H13N |
Molar mass |
99.17 |
Appearance |
clear to yellowish liquid |
Odor |
strong, fishy, amine odor |
Density |
0.8647 g/cm3 |
Melting point |
−17.7 °C (0.1 °F; 255.5 K) |
Boiling point |
134.5 °C (274.1 °F; 407.6 K) |
Solubility in water
|
Miscible |
Solubility |
very soluble in ethanol, oil
miscible in ethers, acetone, esters, alcohol, ketones |
Vapor pressure |
11 mmHg (20° C)[2] |
Acidity (pKa) |
10.64[3] |
Refractive index (nD)
|
1.4565 |
Hazards |
S-phrases (outdated) |
S36 S37 S39 |
R/S statement (outdated) |
R21 R23 R25 R36 R37 R38 R41 |
NFPA 704 |
|
Flash point |
28.6 °C (83.5 °F; 301.8 K) |
Autoignition
temperature
|
293 °C (559 °F; 566 K) |
Explosive limits |
1.5%-9.4%[2] |
Lethal dose or concentration (LD, LC): |
LD50 (median dose)
|
156 mg/kg (rat, oral) |
US health exposure limits (NIOSH): |
PEL (Permissible)
|
none[2] |
REL (Recommended)
|
TWA 10 ppm (40 mg/m3)[2] |
IDLH (Immediate danger)
|
N.D.[2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
Y verify (what is YN ?) |
Infobox references |
|
|
Cyclohexylamine is an organic compound, belonging to the aliphatic amine class. It is a colorless liquid, although like many amines, samples are often colored due to contaminants. It has a fishy odor and is miscible with water. Like other amines, it is a weak base, compared to strong bases such as NaOH, but it is a stronger base than its aromatic analog, aniline.
It is a useful intermediate in the production of many other organic compounds. It is a metabolite of cyclamate.
Contents
- 1 Preparation
- 2 Applications
- 3 Toxicity
- 4 Safety
- 5 References
Preparation
Cyclohexylamine is produced by two routes, the main one being hydrogenation of aniline using cobalt or nickel catalysts:[4]
Cyclohexylamine catalytical synthesis from aniline hydrogenation upon high pressure and temperature.
It is also prepared by alkylation of ammonia using cyclohexanol.
Applications
Cyclohexylamine is used as an intermediate in synthesis of other organic compounds. It is the precursor to sulfenamide-based reagents used as accelerators for vulcanization. It is a building block for pharmaceuticals (e.g., mucolytics, analgesics, and bronchodilators). The amine itself is an effective corrosion inhibitor. Some sweeteners are derived from this amine, notably cyclamate. The herbicide hexazinone is derived from cyclohexylamine.[4]
Toxicity
LD50 (rat; p.o.) = 0.71 ml/kg[5]
Safety
It is flammable, with flash point at 28.6 °C. It is toxic by both ingestion and inhalation; the inhalation itself may be fatal. It readily absorbs through skin, which it irritates. It is corrosive. Cyclohexylamine is listed as an extremely hazardous substance as defined by Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act. It has been used as a flushing aid in the printing ink industry.[6]
In regards to occupational exposures, the National Institute for Occupational Safety and Health has suggested workers not be exposed to a recommended exposure limit of over 10 ppm (40 mg/m3) over an eight-hour workshift.[2]
References
- ^ Merck Index, 11th Edition, 2735.
- ^ a b c d e f "NIOSH Pocket Guide to Chemical Hazards #0168". National Institute for Occupational Safety and Health (NIOSH).
- ^ H. K. Hall, J. Am. Chem. Soc. (1957) 79 5441.
- ^ a b Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a02_001
- ^ The Merck Index, 10th Ed. (1983) p.392, Rahway: Merck & Co.
- ^ Apps, E. A. (1958). Printing Ink Technology. London: Leonard Hill [Books] Limited. pp. ix.
English Journal
- Assessment of skin sensitization under REACH: A case report on vehicle choice in the LLNA and its crucial role preventing false positive results.
- Watzek N1, Berger F2, Kolle SN3, Kaufmann T3, Becker M3, van Ravenzwaay B3.
- Regulatory toxicology and pharmacology : RTP.Regul Toxicol Pharmacol.2017 Apr;85:25-32. doi: 10.1016/j.yrtph.2017.01.010. Epub 2017 Jan 31.
- PMID 28159477
- A Ni-Mg-Al layered triple hydroxide-supported Pd catalyst for heterogeneous acceptorless dehydrogenative aromatization.
- Jin X1, Taniguchi K1, Yamaguchi K1, Nozaki K2, Mizuno N1.
- Chemical communications (Cambridge, England).Chem Commun (Camb).2017 Mar 28. doi: 10.1039/c7cc01182b. [Epub ahead of print]
- PMID 28350410
- Development of New Benzenesulfonamides As Potent and Selective Nav1.7 Inhibitors for the Treatment of Pain.
- Wu YJ1, Guernon J1, Shi J1, Ditta J1, Robbins KJ1, Rajamani R1, Easton A1, Newton A1, Bourin C1, Mosure K1, Soars MG1, Knox RJ1, Matchett M1, Pieschl RL1, Post-Munson DJ1, Wang S1, Herrington J1, Graef J1, Newberry K1, Bristow LJ1, Meanwell NA1, Olson R1, Thompson LA1, Dzierba C1.
- Journal of medicinal chemistry.J Med Chem.2017 Mar 23;60(6):2513-2525. doi: 10.1021/acs.jmedchem.6b01918. Epub 2017 Mar 10.
- PMID 28234467
Japanese Journal
- Combination of Novozym 435-catalyzed Enantioselective Hydrolysis and Amidation for the Preparation of Optically Active δ-Hexadecalactone
- Shimotori Yasutaka,Hoshi Masayuki,Miyakoshi Tetsuo
- Journal of Oleo Science 64(5), 561-575, 2015
- … The addition of cyclohexylamine to lipase-catalyzed hydrolysis afforded the best results to give both enantiomers of 3 with more than 90% enantiomeric excess. …
- NAID 130005067210
- Spermidine-Analogous Triamines Suppressed the Growth of Candida albicans
- Takahashi Eizo,Oono Seiji,Yamamoto Shigeo [他],Arimoto Sakae,Negishi Tomoe,Okamoto Keinosuke
- Biological and Pharmaceutical Bulletin 36(9), 1440-1447, 2013
- … Subsequently, we investigated the synergistic effect of two compounds with triamine 4–8, cyclohexylamine and dl-α-difluoromethylornithine which are inhibitors of enzymes involving in the biosynthesis of physiological polyamines such as spermidine. …
- NAID 130003361514
- Polyamine metabolism is involved in adipogenesis of 3T3-L1 cells
- 石井 育美,池口 文彦,真野 博,和田 政裕,Pegg Anthony E.,白幡 晶
- Amino Acids 42(2-3), 619-626, 2012-02
- … The spermidine synthase inhibitor trans-4-methylcyclohexylamine (MCHA) increased spermine/spermidine ratios, whereas the spermine synthase inhibitor N-(3-aminopropyl)-cyclohexylamine (APCHA) decreased the ratios in the cells. …
- NAID 120005520696
Related Links
- Cyclohexylamine is an organic compound, belonging to the aliphatic amine class . It is a colorless liquid, although like many amines, samples are often colored due to contaminants. It has a fishy odor and is miscible with water. Like other ...
- Sigma-Aldrich offers Aldrich-Cyclohexylamine for your research needs. Find product specific information, including CAS, MSDS, protocols and references.
★リンクテーブル★
[★]
- 英
- cyclohexylamine
- 関
- チクロ