1193-17-5

Basic information

• Product Name: trans-3-Methylcyclohexylamine
• Synonyms: trans-3-Methylcyclohexylamine;Cyclohexanamine, 3-methyl-, trans-;(1R,3R)-3-methylcyclohexanamine;trans-3-MethylcyclohexanaMine;(1S,3S)-3-methylcyclohexan-1-amine
• CAS NO: 1193-17-5
• Molecular Formula: C₇H₁₅N
• Molecular Weight: 113.2007
• Mol File: 1193-17-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: -8.5°C (estimate)
• Boiling Point: 141.98°C (estimate)
• Flash Point: 22.2°C
• Appearance: /
• Density: 0.8572
• Refractive Index: 1.4547
• CAS DataBase Reference: trans-3-Methylcyclohexylamine(CAS DataBase Reference)
• NIST Chemistry Reference: trans-3-Methylcyclohexylamine(1193-17-5)
• EPA Substance Registry System: trans-3-Methylcyclohexylamine(1193-17-5)

Safety Data

• Hazardous Substances Data: 1193-17-5(Hazardous Substances Data)

Upstream product

• 77287-34-4 formamide 
• 591-24-2 3-Methylcyclohexanone 
• 108-44-1 1-amino-3-methylbenzene 
• 108-39-4 3-methyl-phenol 
• 37690-41-8 rac-cis-3-methylcyclohexyl p-toluenesulfonate 
• 5454-79-5 cis-3-methylcyclohexanol 
• 127818-60-4 1-methyl-3-nitro-cyclohexane 
• 13293-59-9 (+/-)-trans-3-methyl-cyclohexanecarboxylic acid 
• 537-92-8 3-Methylacetanilide 
• 99-08-1 1-methyl-3-nitrobenzene 
• 82166-21-0 methyl cyclohexane 

Downstream Products

• 19095-86-4 N-(trans-3-methyl-cyclohexyl)-N'-phenyl-urea 

Relevant articles and documents

Air Stable Iridium Catalysts for Direct Reductive Amination of Ketones

Half-sandwich iridium complexes bearing bidentate urea-phosphorus ligands were found to catalyze the direct reductive amination of aromatic and aliphatic ketones under mild conditions at 0.5 mol % loading with high selectivity towards primary amines. One of the complexes was found to be active in both the Leuckart–Wallach (NH4CO2H) type reaction as well as in the hydrogenative (H2/NH4AcO) reductive amination. The protocol with ammonium formate does not require an inert atmosphere, dry solvents, as well as additives and in contrast to previous reports takes place in hexafluoroisopropanol (HFIP) instead of methanol. Applying NH4CO2D or D2 resulted in a high degree of deuterium incorporation into the primary amine α-position.

The Rhodium Catalysed Direct Conversion of Phenols to Primary Cyclohexylamines

Cyclohexylamines are important intermediates in chemical industry, which are currently produced from petrochemical sources. Phenols, however, are an attractive sustainable feedstock. We here demonstrate the transformation of phenols with ammonia to primary cyclohexylamines. In contrast to previously reported chemistry which used palladium catalysts, we here show that rhodium is an excellent catalyst for the formation of primary cyclohexylamines. Different parameters were studied and it was shown that the reaction is applicable to a scope of phenolic compounds providing high selectivity.

HIGHLY STEREOSELECTIVE SYNTHESIS OF CYCLIC PRIMARY AMINES VIA HYDRIDE REDUCTIONS.

The reduction of p,p'-dimethoxybenzhydryl imines of substituted cyclohexanones with lithium tri-sec-butyl or tri-ethylborohydride and subsequent cleavage of the resulting secondary amines with formic acid affords the corresponding axial cyclohexyl primary amines with high stereoselectivity.