(R)-Metolachlor

Base Information

• Chemical Name: (R)-Metolachlor
• CAS No.: 178961-20-1
• Molecular Formula: C15H22ClNO2
• Molecular Weight: 283.798
• European Community (EC) Number: 257-060-8
• UNII: 01UCU472ZD
• DSSTox Substance ID: DTXSID00897437
• Nikkaji Number: J1.315.287J
• Wikidata: Q27157049
• Mol file: 178961-20-1.mol

Synonyms:(R)-Metolachlor;178961-20-1;R-Metolachlor;Metolachlor, R-;UNII-01UCU472ZD;01UCU472ZD;2-chloro-N-(2-ethyl-6-methylphenyl)-N-[(2R)-1-methoxypropan-2-yl]acetamide;Acetamide, 2-chloro-N-(2-ethyl-6-methylphenyl)-N-((1R)-2-methoxy-1-methylethyl)-;Acetamide, 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)-, (R)-;Acetamide, 2-chloro-N-(2-ethyl-6-methylphenyl)-N-[(1R)-2-methoxy-1-methylethyl]-;2-Chloro-2'-ethyl-N-(2-methoxy-1-methylethyl)-6'-methylacetanilide;2-Chloro-N-(2-ethyl-6-methylphenyl)-N-[(1S)-2-methoxy-1-methylethyl]acetamide;METOLACHLOR, (R)-;2-CHLORO-N-(2-ETHYL-6-METHYLPHENYL)-N-[(1R)-2-METHOXY-1-METHYLETHYL]ACETAMIDE;SCHEMBL338302;CHEBI:83646;DTXSID00897437;Q27157049;(r)-2-chloro-n-(2-ethyl-6-methylphenyl)-n-(2-methoxy-1-methylethyl)acetamide

Chemical Property of (R)-Metolachlor

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.533
• Boiling Point: 670.9 °C at 760 mmHg
• PKA: 1.45±0.50(Predicted)
• Flash Point: 359.6 °C
• PSA: 29.54000
• Density: 1.100 g/cm³
• LogP: 3.16410
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 283.1339066
• Heavy Atom Count: 19
• Complexity: 285

Purity/Quality:

99% ^*data from raw suppliers

2-Chloro-N-(2-ethyl-6-methylphenyl)-N-[(1R)-2-methoxy-1-methylethyl]acetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R43:; R50/53:
• Hazard Codes: Xi:Irritant;; <
• Statements: R43:; R50/53:
• Safety Statements: S24:; S37:; S60:; S61:

MSDS Files:

Useful:

• Canonical SMILES: CCC1=CC=CC(=C1N(C(C)COC)C(=O)CCl)C
• Isomeric SMILES: CCC1=CC=CC(=C1N([C@H](C)COC)C(=O)CCl)C
• Uses: (R)-Metolachlor is the R-enantiomer of Metolachlor (M338700(P)), which is an acyanilide herbicide similar to selective pre-emergence herbicides. It is a contaminant in the groundwater and potential pollutant. This compound is a contaminant of emerging concern (CECs). Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.

Technology Process of (R)-Metolachlor

There total 8 articles about (R)-Metolachlor which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(S)-2-ethyl-N-(1-methoxypropan-2-yl)-6-methylaniline (118604-70-9,786711-55-5) + chloroacetyl chloride (79-04-9) → (aRS,1'R)-(+)-N-(1'-Methyl-2'-methoxyethyl)-N-chloracetyl-2-ethyl-6-methylanilin (178961-20-1) + (S)-metolachlor (87392-12-9)

Guidance literature:

With sodium carbonate; In diethyl ether;

DOI:10.1016/S0957-4166(00)80268-2

Reference yield:

2-methyl-6-ethyl-N-(1-methyl-2-methoxyethyl)aniline (51219-00-2,118604-69-6,118604-70-9,786711-55-5) + chloroacetyl chloride (79-04-9) → (aRS,1'R)-(+)-N-(1'-Methyl-2'-methoxyethyl)-N-chloracetyl-2-ethyl-6-methylanilin (178961-20-1) + (S)-metolachlor (87392-12-9)

Guidance literature:

With pyridine; In toluene; at 0 - 20 ℃;

Reference yield:

chloroacetyl chloride (79-04-9) + 2,2-dimethoxy-propane (77-76-9) + (S)-(-)-N-(2-Ethyl-6-methyl-phenyl)-alanin (82508-03-0) → (aRS,1'R)-(+)-N-(1'-Methyl-2'-methoxyethyl)-N-chloracetyl-2-ethyl-6-methylanilin (178961-20-1) + (S)-metolachlor (87392-12-9)

Guidance literature:

(S)-(-)-N-(2-Ethyl-6-methyl-phenyl)-alanin; With sodium tetrahydroborate; sulfuric acid; In tetrahydrofuran; at 20 ℃;

chloroacetyl chloride; With sodium carbonate; In benzene; at 20 ℃; for 3h;

2,2-dimethoxy-propane; With toluene-4-sulfonic acid; In methanol; for 36h; Title compound not separated from byproducts; Heating;

DOI:10.1139/V06-129

upstream raw materials:

(S)-2-ethyl-N-(1-methoxypropan-2-yl)-6-methylaniline

chloroacetyl chloride

2,2-dimethoxy-propane

(S)-(-)-N-(2-Ethyl-6-methyl-phenyl)-alanin

Refernces

• 1、 -. "PROCESS FOR PREPARING AMINES AND A CARBOXAMIDE THEREOF". Page/Page column 23. . Retrieved 2010/02/15.
• 2、 Moser,Rihs,Sauter. "The influence of atropisomerism and chiral centre on the biological activity of metolachlor". . p. 451 - 462. Retrieved 2007/10/02.