87392-11-8

Basic information

• Product Name: (aRS,1'S)-(+)-N-(1'-Methyl-2'-hydroxyethyl)-N-chloracetyl-2-ethyl-6-methylanilin
• Synonyms: (aRS,1'S)-(+)-N-(1'-Methyl-2'-hydroxyethyl)-N-chloracetyl-2-ethyl-6-methylanilin
• CAS NO: 87392-11-8
• Molecular Weight: 269.771
• Mol File: 87392-11-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (aRS,1'S)-(+)-N-(1'-Methyl-2'-hydroxyethyl)-N-chloracetyl-2-ethyl-6-methylanilin(CAS DataBase Reference)
• NIST Chemistry Reference: (aRS,1'S)-(+)-N-(1'-Methyl-2'-hydroxyethyl)-N-chloracetyl-2-ethyl-6-methylanilin(87392-11-8)
• EPA Substance Registry System: (aRS,1'S)-(+)-N-(1'-Methyl-2'-hydroxyethyl)-N-chloracetyl-2-ethyl-6-methylanilin(87392-11-8)

Safety Data

• Hazardous Substances Data: 87392-11-8(Hazardous Substances Data)

Upstream product

• 79-04-9 chloroacetyl chloride 
• 82508-03-0 (S)-(-)-N-(2-Ethyl-6-methyl-phenyl)-alanin 
• 69516-03-6 N-(1'-methoxy-carbonyl-ethyl)-2-methyl-6-ethyl-aniline 
• 24549-06-2 6-ethyl-o-toluidine 
• 82508-08-5 (S)-(-)-N-(1'-Methyl-2'-hydroxyethyl)-2-ethyl-6-methylanilin 

Downstream Products

• 87392-12-9 (S)-metolachlor 

Relevant articles and documents

Chemoenzymatic synthesis of the chiral herbicide: (S)-metolachlor

A chemoenzymatic approach for the production of (5)-metolachlor, one of the most widely used herbicides, has been developed. The starting material (S)-N-(2-ethyl-6-methylphenyl)alanine was obtained by the use of lipase-catalyzed hydrolytic kinetic resolution. Under the optimal conditions, the good activity and excellent enantioselectivity of lipase B from Candida antarctica (CAL-B, E > 100) are achieved in diethyl ether - water (15% v/v), which is about 9.7-fold more enantioselective than that in a pure buffered aqueous solution (E = 12.1). After a simple extraction procedure is used to separate the acid product from the remaining ester, the remaining ester is racemized, providing the basis for the continuous resolution process. Then (S)-metolachlor is synthesized by a simple chemical method using the enantiomerically pure (S)-acid.