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Cyclohexylamine

Aminohexahydrobenzene Hexahydroaniline Hexahydrobenzenamine miscible in ethers, acetone, esters, alcohol, ketones | NFPA-H = 3 | NFPA-F = 3 | NFPA-R = 0 | NFPA-S =

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 (e.g. cyclamate)

Preparation

Cyclohexylamine is produced by two routes, the main one being the complete hydrogenation of aniline using some cobalt- or nickel-based catalysts: :C6H5NH2 + 3 H2 → C6H11NH2 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. The amine itself is an effective corrosion inhibitor. It has been used as a flushing aid in the printing ink industry. | url-access = registration

Drugs List

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:

  • Acetohexamide
  • Amesergide
  • Bromhexine
  • Brovanexine
  • CGP-11112 (not actually made from CyNH2 but CyN containing).
  • Cilostazol
  • Clorexolone
  • Cyclamate
  • Enpromate
  • Esaprazole
  • Glibenclamide
  • Glicaramide
  • Gliquidone
  • Glipizide
  • Glisindamide
  • Glisolamide
  • Glycyclamide Patent (beispiel 5):
  • Glyhexamide
  • Hexazinone
  • Hexylcaine
  • Hydroxyhexamide
  • Lomustine
  • Metahexamide
  • Timegadine
  • Thiohexamide
  • U-37883A HCl: [57568-80-6] Hair Growth Inhibition: Pharmacol:

Toxicity

Cyclohexylamine has a low acute toxicity with LD50 (rat; p.o.) = 0.71 ml/kg 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.

References

References

  1. ''Merck Index'', 11th Edition, '''2735'''.
  2. H. K. Hall, ''J. Am. Chem. Soc.'' (1957) '''79''' 5441.
  3. {{PGCH. 0168
  4. (2005). "Amines, Aliphatic".
  5. Moga Antonio Carmelo Dr Marin, Barra Emilia Francia, DE2440596 (1975 to Uriach & Cia Sa J ).
  6. (1 January 1967). "Acetylenic Carbamates. A New Class of Potential Oncolytic Agents". Journal of Medicinal Chemistry.
  7. Donald R Cassady, Robert D Dillard, Nelson R Easton, {{US patent. 3436402 (1966 to Lilly Co Eli).
  8. , GB772721 (1957 to Bayer Pharma AG).
  9. (1986). "Esaprazole hydrochloride". Drugs of the Future.
  10. DE2702537 idem Camillo Corvi-Mora, {{US patent. 4123530 (1978 both to Camillo Corvi S.P.A.).
  11. (1988). "Experimental antiulcer agents: N-substituted 2-(4-methyl-1-piperazinyl)acetamides as pirenzepine models and some related compounds". Collection of Czechoslovak Chemical Communications.
  12. GB2024221 idem Rudi Weyer, Volker Hitzel, Karl Geisen, Gunter Regitz, {{US patent. 4282239 (1981 to Hoechst Aktiengesellschaft).
  13. (March 1974). "[Isoxazolecarboxamidoalkylbenzolesulfonylurea, -semicarbazide and -aminopyrimidine as well as related compounds and their blood sugar reducing activity]". Arzneimittel-Forschung.
  14. Giorgio D Alo, FR2459237 (1983 to WASSERMANN SpA A).
  15. Dr. Walter Aumüller und Heinz Herr, DE1075588B (1960 to Farbwerke Hoechst Aktiengesellschaft vormals Meister Lucius & Brüning,).
  16. Breuer, H. et al, Chim. Ther., 1973, 8, 659.
  17. Hoehn Hans, Breuer Hermann, U.S. patent 3,097,242 (1963 to Olin Corp).
  18. (January 1963). "Further Studies on N-Arylsulfonyl-N'-alkylureas". Journal of Medicinal Chemistry.
  19. (December 1998). "Determination of absolute configuration of a metabolite (−)-hydroxyhexamide from acetohexamide, syntheses of (−)- and (+)-hydroxyhexamides and (−)- and (+)-acetoxyhexamides". Tetrahedron: Asymmetry.
  20. (1981). "Timegadine". Drugs of the Future.
  21. (January 1980). "Basic antiinflammatory compounds. N,N',N''-Trisubstituted guanidines". Journal of Medicinal Chemistry.
  22. Schneur Vaerloese Dk Rachlin, Edoardo Farum Dk Arrigoni-Martelli, DE2847792 (1988 to Leo Pharmaceutical Products Ltd. A/S (Loevens Kemiske Fabrik Produktionsaktieselskab), Ballerup, Dk).
  23. (June 1958). "Notes - Some N-Arylculfonyl-N '-alkylureas". The Journal of Organic Chemistry.
  24. Donald W. DuCharme & Louis L. Skaletzky, {{US patent. 4007181 (1977 to Upjohn Co).
  25. Kaushik D. Meisheri & Loretta A. Cipkus, WO1988008295 (to Pharmacia and Upjohn Co).
  26. (2006). "Pharmacological Profile of U-37883A, a Channel Blocker of Smooth Muscle-Type ATP-Sensitive K Channels". Cardiovascular Drug Reviews.
  27. ''The Merck Index, 10th Ed.'' (1983) p.392, Rahway: Merck & Co.
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