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Cyclohexylamine

From Wikipedia, the free encyclopedia
Cyclohexylamine[1]
Names
Preferred IUPAC name
Cyclohexanamine
Other names
Aminocyclohexane
Aminohexahydrobenzene
Hexahydroaniline
Hexahydrobenzenamine
Identifiers
3D model (JSmol)
Abbreviations CyNH2
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.300 Edit this at Wikidata
EC Number
  • 203-629-0
KEGG
RTECS number
  • GX0700000
UNII
  • InChI=1S/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2 checkY
    Key: PAFZNILMFXTMIY-UHFFFAOYSA-N checkY
  • InChI=1/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2
    Key: PAFZNILMFXTMIY-UHFFFAOYAP
  • NC1CCCCC1
Properties
C6H13N
Molar mass 99.177 g·mol−1
Appearance Colorless 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)
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]
1.4565
Hazards
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
Danger
H226, H302, H312, H314, H361
P201, P202, P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P281, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P322, P330, P363, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
3
0
Flash point 28.6 °C (83.5 °F; 301.8 K)
293 °C (559 °F; 566 K)
Explosive limits 1.5–9.4%[2]
Lethal dose or concentration (LD, LC):
156 mg/kg (rat, oral)
NIOSH (US health exposure limits):
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).
checkY verify (what is checkYX markN ?)

Cyclohexylamine is an organic compound with the chemical formula C6H13N or C6H11NH2, belonging to the aliphatic amine class. It is a colorless liquid, although, like many amines, samples are often yellowish 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 (e.g. cyclamate)

Preparation

[edit]

Cyclohexylamine is produced by two routes, the main one being the complete hydrogenation of aniline using some cobalt- or nickel-based catalysts:[4]

C6H5NH2 + 3 H2 → C6H11NH2

It is also prepared by alkylation of ammonia using cyclohexanol.

Applications

[edit]

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. The amine itself is an effective corrosion inhibitor. It has been used as a flushing aid in the printing ink industry.[5]

Drugs List

[edit]

It is a building block for pharmaceuticals (e.g., mucolytics, analgesics, and bronchodilators). Most of the drugs in the following list fall into the arena of sulfonamide hypoglycemics though:

U-37883A

Toxicity

[edit]

Cyclohexylamine has a low acute toxicity with LD50 (rat; p.o.) = 0.71 ml/kg[28] Like other amines, 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. 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

[edit]
  1. ↑ Merck Index, 11th Edition, 2735.
  2. 1 2 3 4 5 6 NIOSH Pocket Guide to Chemical Hazards. "#0168". National Institute for Occupational Safety and Health (NIOSH).
  3. ↑ H. K. Hall, J. Am. Chem. Soc. (1957) 79 5441.
  4. ↑ Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2005). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001. ISBN 978-3-527-30673-2.
  5. ↑ Apps, E. A. (1958). Printing Ink Technology. London: Leonard Hill [Books] Limited. pp. ix.
  6. ↑ Moga Antonio Carmelo Dr Marin, Barra Emilia Francia, DE2440596 (1975 to Uriach & Cia Sa J ).
  7. ↑ Dillard, R. D., Poore, Gerald., Cassady, D. R., Easton, N. R. (1 January 1967). "Acetylenic Carbamates. A New Class of Potential Oncolytic Agents". Journal of Medicinal Chemistry. 10 (1): 40–44. doi:10.1021/jm00313a008. ISSN 1520-4804 0022-2623, 1520-4804. PMID 5233161. Retrieved 10 December 2025. {{cite journal}}: Check |issn= value (help)
  8. ↑ Donald R Cassady, Robert D Dillard, Nelson R Easton, U.S. patent 3,436,402 (1966 to Lilly Co Eli).
  9. ↑ , GB772721 (1957 to Bayer Pharma AG).
  10. ↑ De Angelis, L. (1986). "Esaprazole hydrochloride". Drugs of the Future. 11 (4): 263. doi:10.1358/dof.1986.011.04.64815. ISSN 0377-8282. Retrieved 10 December 2025.
  11. ↑ DE2702537 idem Camillo Corvi-Mora, U.S. patent 4,123,530 (1978 both to Camillo Corvi S.P.A.).
  12. ↑ Hulinská, H., Polívka, Z., Jílek, J., Šindelář, K., Holubek, J., Svátek, E., Matoušová, O., Buděšínský, M., Frycová, H., Protiva, M. (1988). "Experimental antiulcer agents: N-substituted 2-(4-methyl-1-piperazinyl)acetamides as pirenzepine models and some related compounds". Collection of Czechoslovak Chemical Communications. 53 (8): 1820–1844. doi:10.1135/cccc19881820.
  13. ↑ GB2024221 idem Rudi Weyer, Volker Hitzel, Karl Geisen, Gunter Regitz, U.S. patent 4,282,239 (1981 to Hoechst Aktiengesellschaft).
  14. ↑ Plümpe H, Horstmann H, Puls W (March 1974). "[Isoxazolecarboxamidoalkylbenzolesulfonylurea, -semicarbazide and -aminopyrimidine as well as related compounds and their blood sugar reducing activity]". Arzneimittel-Forschung (in German). 24: 363–74. PMID 4408067.
  15. ↑ Giorgio D Alo, FR2459237 (1983 to WASSERMANN SpA A).
  16. ↑ Dr. Walter Aumüller und Heinz Herr, DE1075588B (1960 to Farbwerke Hoechst Aktiengesellschaft vormals Meister Lucius & Brüning,).
  17. ↑ Breuer, H. et al, Chim. Ther., 1973, 8, 659.
  18. ↑ Hoehn Hans, Breuer Hermann, U.S. patent 3,097,242 (1963 to Olin Corp).
  19. ↑ Marshall, F. J., Sigal, M. V., Sullivan, H. R., Cesnik, C., Root, M. A. (January 1963). "Further Studies on N-Arylsulfonyl-N'-alkylureas". Journal of Medicinal Chemistry. 6 (1): 60–63. doi:10.1021/jm00337a014. ISSN 1520-4804 0022-2623, 1520-4804. PMID 14175624. Retrieved 10 December 2025. {{cite journal}}: Check |issn= value (help)
  20. ↑ Akita, H., Kurashima, K., Nozawa, M., Yamamura, S., Seri, K., Imamura, Y. (December 1998). "Determination of absolute configuration of a metabolite (−)-hydroxyhexamide from acetohexamide, syntheses of (−)- and (+)-hydroxyhexamides and (−)- and (+)-acetoxyhexamides". Tetrahedron: Asymmetry. 9 (24): 4331–4340. doi:10.1016/S0957-4166(98)00436-4.
  21. ↑ Castañer, J., Arrigoni-Martelli, E. (1981). "Timegadine". Drugs of the Future. 6 (6): 369. doi:10.1358/dof.1981.006.06.67124. ISSN 0377-8282. Retrieved 10 December 2025.
  22. ↑ Rachlin, S., Bramm, E., Ahnfelt-Roenne, I., Arrigoni-Martelli, E. (January 1980). "Basic antiinflammatory compounds. N,N',N''-Trisubstituted guanidines". Journal of Medicinal Chemistry. 23 (1): 13–20. doi:10.1021/jm00175a004. PMID 6965727.
  23. ↑ Schneur Vaerloese Dk Rachlin, Edoardo Farum Dk Arrigoni-Martelli, DE2847792 (1988 to Leo Pharmaceutical Products Ltd. A/S (Loevens Kemiske Fabrik Produktionsaktieselskab), Ballerup, Dk).
  24. ↑ Marshall, F., Sigal, Jr., M. (June 1958). "Notes - Some N-Arylculfonyl-N '-alkylureas". The Journal of Organic Chemistry. 23 (6): 927–929. doi:10.1021/jo01100a622.
  25. ↑ Donald W. DuCharme & Louis L. Skaletzky, U.S. patent 4,007,181 (1977 to Upjohn Co).
  26. ↑ Kaushik D. Meisheri & Loretta A. Cipkus, WO1988008295 (to Pharmacia and Upjohn Co).
  27. ↑ Teramoto N (2006). "Pharmacological Profile of U-37883A, a Channel Blocker of Smooth Muscle-Type ATP-Sensitive K Channels". Cardiovascular Drug Reviews. 24 (1): 25–32. doi:10.1111/j.1527-3466.2006.00025.x. PMID 16939631.
  28. ↑ The Merck Index, 10th Ed. (1983) p.392, Rahway: Merck & Co.
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