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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)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.003.300Edit 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 mass99.17
Appearanceclear to yellowish liquid
Odorstrong, fishy,amine odor
Density0.8647 g/cm3
Melting point−17.7 °C (0.1 °F; 255.5 K)
Boiling point134.5 °C (274.1 °F; 407.6 K)
Miscible
Solubilityvery soluble inethanol,oil
miscible inethers,acetone,esters,alcohol,ketones
Vapor pressure11 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)
Flash point28.6 °C (83.5 °F; 301.8 K)
293 °C (559 °F; 566 K)
Explosive limits1.5–9.4%[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 theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Cyclohexylamine is anorganic compound, belonging to thealiphaticamine 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 aweak base, compared tostrong bases such asNaOH, but it is a stronger base than itsaromatic 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 ofaniline using some cobalt- or nickel-based catalysts:[4]

C6H5NH2 + 3 H2 → C6H11NH2

It is also prepared byalkylation of ammonia usingcyclohexanol.

Applications

[edit]

Cyclohexylamine is used as an intermediate in synthesis of other organic compounds. It is the precursor tosulfenamide-based reagents used asaccelerators forvulcanization. The amine itself is an effectivecorrosion inhibitor. It has been used as a flushing aid in theprinting ink industry.[5]

Drugs List

[edit]

It is a building block for pharmaceuticals (e.g.,mucolytics,analgesics, andbronchodilators). 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 anextremely hazardous substance as defined by Section 302 of the U.S.Emergency Planning and Community Right-to-Know Act. TheNational Institute for Occupational Safety and Health has suggested workers not be exposed to arecommended exposure limit of over 10 ppm (40 mg/m3) over an eight-hour workshift.[2]

References

[edit]
  1. ^Merck Index, 11th Edition,2735.
  2. ^abcdefNIOSH 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. Retrieved10 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. Retrieved10 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. Retrieved10 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. Retrieved10 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.
  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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