Methyl 2-bromo-4-fluoro-5-nitrobenzoate

Base Information

• Chemical Name: Methyl 2-bromo-4-fluoro-5-nitrobenzoate
• CAS No.: 85953-31-7
• Molecular Formula: C₈H₅BrFNO₄
• Molecular Weight: 278.034
• DSSTox Substance ID: DTXSID601214432
• Mol file: 85953-31-7.mol

Synonyms:methyl 2-bromo-4-fluoro-5-nitrobenzoate;85953-31-7;2-Bromo-4-fluoro-5-nitrobenzoic Acid Methyl Ester;2-bromo-4-fluoro-5-nitro-benzoic acid methyl ester;SCHEMBL1721669;Benzoic acid, 2-bromo-4-fluoro-5-nitro-, methyl ester;UYTRUAPOXQRIMA-UHFFFAOYSA-N;DTXSID601214432;methyl2-bromo-4-fluoro-5-nitrobenzoate;BS-29761;CS-0142690;D86072;2-Bromo4-fluoro-5-nitro-benzoic acid methyl ester

Chemical Property of Methyl 2-bromo-4-fluoro-5-nitrobenzoate

Chemical Property:

• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 276.93860
• Heavy Atom Count: 15
• Complexity: 270

Purity/Quality:

99%min. ^*data from raw suppliers

2-Bromo-4-fluoro-5-nitrobenzoic Acid Methyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1=CC(=C(C=C1Br)F)[N+](=O)[O-]
• Uses: 2-Bromo-4-fluoro-5-nitrobenzoic Acid Methyl Ester is used in the preparation of quinoxaline as PDE9 inhibitors.

Technology Process of Methyl 2-bromo-4-fluoro-5-nitrobenzoate

There total 4 articles about Methyl 2-bromo-4-fluoro-5-nitrobenzoate 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%

methanol (67-56-1) + 2-bromo-4-fluoro-5-nitrobenzoic acid (1036389-83-9) → 2-bromo-4-fluoro-5-nitrobenzoic acid methyl ester (85953-31-7)

Guidance literature:

With thionyl chloride; at 60 ℃; for 18h;

Reference yield: 43.0%

methyl 2-bromo-4-fluorobenzoate (653-92-9) → 2-bromo-4-fluoro-5-nitrobenzoic acid methyl ester (85953-31-7)

Guidance literature:

With sulfuric acid; nitric acid; at 0 - 20 ℃; for 18.5h;

Reference yield:

2-bromo-4-fluorobenzoic acid (1006-41-3) → 2-bromo-4-fluoro-5-nitrobenzoic acid methyl ester (85953-31-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium nitrate; sulfuric acid / 3.17 h / 0 - 20 °C

2.1: thionyl chloride / 0.5 h / 0 °C / Inert atmosphere

2.2: 18 h / 60 °C / Inert atmosphere

With thionyl chloride; sulfuric acid; potassium nitrate;

DOI:10.1021/acsmedchemlett.6b00282

upstream raw materials:

methyl 2-bromo-4-fluorobenzoate

methanol

2-bromo-4-fluoro-5-nitrobenzoic acid

2-bromo-4-fluorobenzoic acid

Downstream raw materials:

6-amino-5-fluoro-isoindolin-1-one