66399-59-5

Basic information

• Product Name: (S)-(-)-N-Cyclohexyl-1-(4-chlorophenyl)ethylamine
• Synonyms: (S)-(-)-N-Cyclohexyl-1-(4-chlorophenyl)ethylamine
• CAS NO: 66399-59-5
• Molecular Weight: 237.772
• Mol File: 66399-59-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-(-)-N-Cyclohexyl-1-(4-chlorophenyl)ethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-N-Cyclohexyl-1-(4-chlorophenyl)ethylamine(66399-59-5)
• EPA Substance Registry System: (S)-(-)-N-Cyclohexyl-1-(4-chlorophenyl)ethylamine(66399-59-5)

Safety Data

• Hazardous Substances Data: 66399-59-5(Hazardous Substances Data)

Upstream product

• 143969-36-2 2-[1-(4-chloro-phenyl)-ethyl]-benzo[1,3,2]dioxaborole 
• 108-91-8 cyclohexylamine 
• 1073-67-2 4-vinylbenzyl chloride 
• 52185-81-6 N-chlorocyclohexanamine 

Relevant articles and documents

Catalytic asymmetric hydroboration/amination and alkylamination with rhodium complexes of 1,1′-(2-diarylphosphino-1-naphthyl)isoquinoline

Catecholboronate esters formed by asymmetric hydroboration of arylalkenes are not directly converted to amines by reaction with hydroxylamine-O-sulfonic acid. Prior conversion to a trialkylborane by reaction with ZnEt2 or MeMgCl permits a subsequent amination reaction to occur with essentially complete retention of configuration, leading to a range of primary α-arylalkylamines in up to 97% enantiomeric excess (ee). Secondary, but not tertiary amines may be formed by a related pathway when in situ generated alkylchloramines are employed as the aminating agent. The catalytic asymmetric hydroboration, β-alkylation and amination steps may be combined in a single stage. Overall, this provides a practical procedure for the synthesis of enantiomerically enriched arylamines, exemplified inter alia by the synthesis of (S)-1,2,3,4-tetrahydro-1-naphthylamine in 95-97% ee and of (R)-N-(cyclohexyl)-1′-(4-methoxyphenyl)ethylamine in 93 % ee.