Methyl 5-amino-2-chloro-4-fluorobenzoate

Base Information

• Chemical Name: Methyl 5-amino-2-chloro-4-fluorobenzoate
• CAS No.: 141772-31-8
• Molecular Formula: C8H7ClFNO2
• Molecular Weight: 203.6
• DSSTox Substance ID: DTXSID10441400
• Wikidata: Q82258161
• Mol file: 141772-31-8.mol

Synonyms:Methyl 5-amino-2-chloro-4-fluorobenzoate;141772-31-8;5-Amino-2-chloro-4-fluoro-benzoic acid methyl ester;2-fluoro-4-chloro-5-methoxycarbonylaniline;Benzoic acid, 5-amino-2-chloro-4-fluoro-, methyl ester;SCHEMBL3528669;AMY6618;DTXSID10441400;GRQLIRSFYJTUQR-UHFFFAOYSA-N;MFCD17168708;AKOS012322561;DS-5865;SB33483;Methyl5-amino-2-chloro-4-fluorobenzoate;CS-0098660;O11946;EN300-3102230;Z1079174412

Chemical Property of Methyl 5-amino-2-chloro-4-fluorobenzoate

Chemical Property:

• PSA: 52.32000
• LogP: 2.42910
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 203.0149343
• Heavy Atom Count: 13
• Complexity: 203

Purity/Quality:

98% ^*data from raw suppliers

Methyl5-Amino-2-chloro-4-fluorobenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC(=C(C=C1Cl)F)N
• Uses: Methyl 5-Amino-2-chloro-4-fluorobenzoate is an intermediate of Saflufenacil (S081800), a herbicide of the pyrimidinedione chemical class used for the preplant burndown and selective preemergence dicot weed control in different field crops.

Technology Process of Methyl 5-amino-2-chloro-4-fluorobenzoate

There total 3 articles about Methyl 5-amino-2-chloro-4-fluorobenzoate 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: 86.0%

methyl 2-chloro-4-fluoro-5-nitrobenzoate (85953-30-6) → 2-fluoro-4-chloro-5-methoxycarbonylaniline (141772-31-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; for 12h; under 760.051 Torr; Reflux;

DOI:10.1016/j.bmc.2021.116165

Reference yield:

2-chloro-4-fluoro-5-nitrobenzoic acid (114776-15-7) → 2-fluoro-4-chloro-5-methoxycarbonylaniline (141772-31-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / 6 h / Reflux

2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 760.05 Torr / Reflux

With sulfuric acid; palladium 10% on activated carbon; hydrogen; In ethyl acetate;

DOI:10.1016/j.bmc.2021.116165

Reference yield:

→ 2-fluoro-4-chloro-5-methoxycarbonylaniline (141772-31-8)

Guidance literature:

upstream raw materials:

methyl 2-chloro-4-fluoro-5-nitrobenzoate

2-chloro-4-fluoro-5-nitrobenzoic acid

Downstream raw materials:

2-Chloro-5-ethoxycarbonylamino-4-fluoro-benzoic acid methyl ester

2-fluoro-4-chloro-5-methoxycarbonylphenyl isocyanate

Refernces

• 1、 -. "Herbicidal tricyclic heterocycles". . . Retrieved 2008/06/13.