Cyclohexylamine is an organic compound with the chemical formula or , 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 Cyclohexylamine is produced by two routes, the main one being the complete hydrogenation of aniline using some cobalt- or nickel-based catalysts:
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.
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 BrovanexineMoga Antonio Carmelo Dr Marin, Barra Emilia Francia, DE2440596 (1975 to Uriach & Cia Sa J ). CGP-11112 (not actually made from CyNH2 but CyN containing). Cilostazol Clorexolone Cyclamate EnpromateDonald R Cassady, Robert D Dillard, Nelson R Easton, (1966 to Lilly Co Eli)., GB772721 (1957 to Bayer Pharma AG). EsaprazoleDE2702537 idem Camillo Corvi-Mora, (1978 both to Camillo Corvi S.P.A.). Glibenclamide Glicaramide Gliquidone Glipizide GlisindamideGB2024221 idem Rudi Weyer, Volker Hitzel, Karl Geisen, Gunter Regitz, (1981 to Hoechst Aktiengesellschaft). GlisolamideGiorgio D Alo, FR2459237 (1983 to WASSERMANN SpA A). Glycyclamide Patent (beispiel 5):Dr. Walter Aumüller und Heinz Herr, DE1075588B (1960 to Farbwerke Hoechst Aktiengesellschaft vormals Meister Lucius & Brüning,). GlyhexamideBreuer, H. et al, Chim. Ther., 1973, 8, 659.Hoehn Hans, Breuer Hermann, U.S. patent 3,097,242 (1963 to Olin Corp). Hexazinone Hexylcaine Hydroxyhexamide Lomustine Metahexamide TimegadineSchneur Vaerloese Dk Rachlin, Edoardo Farum Dk Arrigoni-Martelli, DE2847792 (1988 to Leo Pharmaceutical Products Ltd. A/S (Loevens Kemiske Fabrik Produktionsaktieselskab), Ballerup, Dk). Thiohexamide U-37883A HCl: [57568-80-6]Donald W. DuCharme & Louis L. Skaletzky, (1977 to Upjohn Co). Hair Growth Inhibition:Kaushik D. Meisheri & Loretta A. Cipkus, WO1988008295 (to Pharmacia and Upjohn Co). Pharmacol:
Toxicity Cyclohexylamine has a low acute toxicity with LD50 (rat; p.o.) = 0.71 ml/kgThe Merck Index, 10th Ed. (1983) p.392, Rahway: Merck & Co. 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.
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