87392-12-9

Basic information

• Product Name: (S)-Metolachlor
• Synonyms: S-METOLACHLOR;2-CHLORO-N-(2-ETHYL-6-METHYLPHENYL)-N-[(1S)-2-METHOXY-1-METHYLETHYL]ACETAMIDE;dualgold;metolachlor(alpha);S-METOLACHLOR 10 NG/UL PESTANAL;S-Metolachlor, Pestanal;Acetamide, 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1S)-2-methoxy-1-methylethyl-;cga77102
• CAS NO: 87392-12-9
• Molecular Formula: C₁₅H₂₂ClNO₂
• Molecular Weight: 283.79
• EINECS: 203-625-9
• Mol File: 87392-12-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: -39.9°C
• Boiling Point: 282°C (rough estimate)
• Flash Point: 4 °C
• Appearance: /
• Density: 1.0858 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: 0-6°C
• PKA: 1.45±0.50(Predicted)
• BRN: 6483536
• CAS DataBase Reference: (S)-Metolachlor(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Metolachlor(87392-12-9)
• EPA Substance Registry System: (S)-Metolachlor(87392-12-9)

Safety Data

• Hazard Codes: Xi,N,Xn,F
• Statements: 43-50/53-67-65-63-48/20-38-11
• Safety Statements: 24-37-60-61-62-36/37
• RIDADR: UN 3077
• WGK Germany: 2
• Hazardous Substances Data: 87392-12-9(Hazardous Substances Data)

Usage

Uses

Herbicide.

Definition

ChEBI: The (S)-enantiomer of 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide.

InChI:InChI=1/C15H22ClNO2/c1-5-13-8-6-7-11(2)15(13)17(14(18)9-16)12(3)10-19-4/h6-8,12H,5,9-10H2,1-4H3/t12-/m0/s1

Upstream product

• 118604-70-9 (S)-2-ethyl-N-(1-methoxypropan-2-yl)-6-methylaniline 
• 79-04-9 chloroacetyl chloride 
• 77-76-9 2,2-dimethoxy-propane 
• 82508-03-0 (S)-(-)-N-(2-Ethyl-6-methyl-phenyl)-alanin 
• 51219-00-2 2-methyl-6-ethyl-N-(1-methyl-2-methoxyethyl)aniline 
• 82508-08-5 (S)-(-)-N-(1'-Methyl-2'-hydroxyethyl)-2-ethyl-6-methylanilin 
• 69516-03-6 N-(1'-methoxy-carbonyl-ethyl)-2-methyl-6-ethyl-aniline 
• 24549-06-2 6-ethyl-o-toluidine 
• 87392-11-8 (aRS,1'S)-(+)-N-(1'-Methyl-2'-hydroxyethyl)-N-chloracetyl-2-ethyl-6-methylanilin 

Relevant articles and documents

Enantioselective Catalysis for Agrochemicals: Synthetic Routes to (S)-Metolachlor, (R)-Metalaxyl and (αS,3R)-Clozylacon

The application of enantioselective catalytic methods for the technical preparation of chiral agrochemicals is illustrated for three active ingredients of the acylanilide type. The key step for the technical synthesis of the herbicide (S)-metolachlor is the enantioselective hydrogenation of an imine intermediate using a novel iridium ferrocenyldiphosphine catalyst with an unprecedented high activity and 80 percent ee. (R)-metalaxyl and (αS,3R)-clozylacon were synthesized via the enantioselective hydrogenation of corresponding enamide precursors with Rh and Ru/binap catalysts with >95 percent and 99 percent enantiomeric purity, respectively.

Method for synthesizing chiral amine compound through catalyzing asymmetric hydrogenated imine by using iridium

The invention relates to a method for synthesizing a chiral amine compound through catalyzing high-activity high-selectivity asymmetric hydrogenated imine by using iridium. An adopted catalyst is generated in situ by an iridium-cyclooctadiene complex and a chiral phosphine-amino phosphine ligand. (S)-N-(1-methoxy-2-propyl)-2-methyl-6-ethylaniline [(S)-NAA] can be obtained by catalyzing a hydrogenation reaction of 2-methyl-6-ethyl-N-methylene aniline (EMA-imine) by using the catalyst, wherein the enantiomeric excess (ee) can reach 90%, and the molar ratio of the EMA-imine to the catalyst can beup to 1000000. Refined metolachlor with an S-configuration effective content of 94% can be obtained by carrying out an acylation reaction on the (S)-NAA with chloroacetyl chloride. Therefore, the ligand provided by the invention can be used for synthesizing the chiral herbicide metolachlor.

Optimized Synthetic Route for Enantioselective Preparation of (S)-Metolachlor from Commercially Available (R)-Propylene Oxide

An enantioselective preparation of (S)-metolachlor has been accomplished. The synthetic route featured the asymmetric preparation of chiral intermediates and the final (S)-metolachlor from commercially available (R)-propylene oxide and a key Fukuyama's process. The key steps, control points, separation purifications, and the whole process are optimized, and the target compound has been successfully prepared in five steps in 51-55% overall yield with excellent enantioselectivity (99% ee) up to a 30 g scale. By judicious choice of synthetic route and selection of starting materials and intermediates, no column chromatographic methods are needed for the separation and purification of the intermediates and the final products. The same strategy was extended as a general method for a series of pesticides and herbicide analogs of Metalaxyl-M and Dimethenamid-P.