(R)-(+)-Methyl 2-(2,4-dichlorophenoxy)propionate

Base Information

• Chemical Name: (R)-(+)-Methyl 2-(2,4-dichlorophenoxy)propionate
• CAS No.: 122674-96-8
• Molecular Formula: C10H10Cl2O3
• Molecular Weight: 249.094
• DSSTox Substance ID: DTXSID501034552
• Nikkaji Number: J365.245I
• Mol file: 122674-96-8.mol

Synonyms:122674-96-8;DTXSID501034552;(R)-(+)-Methyl 2-(2,4-dichlorophenoxy)propionate;Propanoic acid, 2-(2,4-dichlorophenoxy)-, methyl ester, (2R)-

Chemical Property of (R)-(+)-Methyl 2-(2,4-dichlorophenoxy)propionate

Chemical Property:

• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 248.0006996
• Heavy Atom Count: 15
• Complexity: 223

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)OC)OC1=C(C=C(C=C1)Cl)Cl
• Isomeric SMILES: C[C@H](C(=O)OC)OC1=C(C=C(C=C1)Cl)Cl

Technology Process of (R)-(+)-Methyl 2-(2,4-dichlorophenoxy)propionate

There total 4 articles about (R)-(+)-Methyl 2-(2,4-dichlorophenoxy)propionate 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: 99.0%

(S)-Methyl lactate (27871-49-4,2155-30-8) + 2,4-dichlorophenol (120-83-2,40477-79-0) → (R)-(+)-Methyl 2-(2,4-dichlorophenoxy)propionate (122674-96-8)

Guidance literature:

(S)-Methyl lactate; 2,4-dichlorophenol; With triphenylphosphine; In dichloromethane; at 0 ℃; for 0.166667h;

With diethylazodicarboxylate; In dichloromethane; at 0 - 20 ℃;

DOI:10.1371/journal.pone.0213552

Reference yield:

2-(2,4-dichlorophenoxy)propanoic acid methyl ester (23844-57-7) → (R)-dichlorprop (120-36-5,7547-66-2,15165-69-2,15165-67-0) + S-dichloprop (15165-67-0) + (R)-(+)-Methyl 2-(2,4-dichlorophenoxy)propionate (122674-96-8) + (S)-(-)-Methyl 2-(2,4-dichlorophenoxy)propionate (122674-95-7)

Guidance literature:

With phosphate buffer; α-chymotrypsin; In water; at 20 ℃; for 50h; Product distribution; hydrolyses catalysed with various enzymes;

Reference yield:

2-(2,4-dichlorophenoxy)propanoic acid methyl ester (23844-57-7) → (R)-(+)-Methyl 2-(2,4-dichlorophenoxy)propionate (122674-96-8) + (S)-(-)-Methyl 2-(2,4-dichlorophenoxy)propionate (122674-95-7)

Guidance literature:

With Candida rugosa lipase; In hexane; for 8.8h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature; phosphate buffer, pH 7.2;

DOI:10.1016/S0040-4020(98)00422-0

upstream raw materials:

diazomethane

(R)-dichlorprop

2-(2,4-dichlorophenoxy)propanoic acid methyl ester

(S)-Methyl lactate

Downstream raw materials:

(R)-dichlorprop

Refernces

• 1、 Cipiciani, Antonio,Cittadini, Massimiliano,Fringuelli, Francesco. "Improving the enantioselectivity of candida rugosa lipase in the kinetic resolution of racemic methyl 2-(2,4-dichlorophenoxy)propionate". . p. 7883 - 7890. Retrieved 2007/10/03.
• 2、 Chenevert, Robert,D'Astous, Linda. "Enzyme catalysed hydrolysis of chlorophenoxypropionates". . p. 1219 - 1222. Retrieved 2007/10/02.