Methyl 2-amino-5-bromobenzoate

Base Information

• Chemical Name: Methyl 2-amino-5-bromobenzoate
• CAS No.: 52727-57-8
• Molecular Formula: C8H8BrNO2
• Molecular Weight: 230.061
• Hs Code.: 29224999
• European Community (EC) Number: 610-890-8
• DSSTox Substance ID: DTXSID90352969
• Nikkaji Number: J1.053.015F
• Wikidata: Q72486730
• Mol file: 52727-57-8.mol

Synonyms:methyl 2-amino-5-bromobenzoate

Chemical Property of Methyl 2-amino-5-bromobenzoate

Chemical Property:

• Appearance/Colour: White to light yellow crystal powder
• Vapor Pressure: 0.00266mmHg at 25°C
• Melting Point: 72-74 °C(lit.)
• Refractive Index: 1.601
• Boiling Point: 286.3 °C at 760 mmHg
• PKA: 1.76±0.10(Predicted)
• Flash Point: 126.9 °C
• PSA: 52.32000
• Density: 1.578 g/cm³
• LogP: 2.39910
• Storage Temp.: Room temperature.
• Solubility.: DMSO, Methanol
• Water Solubility.: Soluble in water.
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 228.97384
• Heavy Atom Count: 12
• Complexity: 174

Purity/Quality:

98% ^*data from raw suppliers

Methyl 2-amino-5-bromobenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36:Wear suitable prot

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C1=C(C=CC(=C1)Br)N
• Uses: Methyl 2-amino-5-bromobenzoate acts as a potential PqsD inhibitor against pseudomonas aeruginosa infections. It is also used in the preparation of hepatitis C virus NS5b RNA polymerase inhibitors. It is involved in plant growth-regulator activity.

Technology Process of Methyl 2-amino-5-bromobenzoate

There total 14 articles about Methyl 2-amino-5-bromobenzoate 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: 98.0%

2-carbomethoxyaniline (134-20-3) → 5-bromo-2-aminobenzoic acid methyl ester (52727-57-8)

Guidance literature:

With tetrabutylammomium bromide; copper(ll) bromide; In ethanol; at 45 ℃; regioselective reaction;

DOI:10.1080/00397911.2019.1598558

Reference yield: 98.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 5-Bromo-2-aminobenzoic acid (5794-88-7) → 5-bromo-2-aminobenzoic acid methyl ester (52727-57-8)

Guidance literature:

In 2-methyltetrahydrofuran; diethyl ether; at 20 ℃; for 0.358333h; Flow reactor;

DOI:10.1039/c6gc03066a

Reference yield: 90.8%

methanol (67-56-1) + 5-Bromo-2-aminobenzoic acid (5794-88-7) → 5-bromo-2-aminobenzoic acid methyl ester (52727-57-8)

Guidance literature:

With sulfuric acid; Reflux;

DOI:10.1016/j.bmc.2017.09.006

upstream raw materials:

chloral

2-carbomethoxyaniline

methanol

5-Bromo-1H-indole-2,3-dione

Downstream raw materials:

2-amino-5-bromo-3-chloro-benzoic acid methyl ester

2-amino-3,5-dibromo-benzoic acid methyl ester

5-Bromo-2-aminobenzoic acid

methyl N-(4-bromo-2-carbomethoxyphenyl)propionimidate

Refernces

• 1、 Takahashi, Yusuke,Seki, Masahiko. "A Practical Procedure for Regioselective Bromination of Anilines". . p. 1828 - 1832. Retrieved 2021/04/15.
• 2、 Caspers, Lucien D.,Spils, Julian,Damrath, Mattis,Lork, Enno,Nachtsheim, Boris J.. "One-Pot Synthesis and Conformational Analysis of Six-Membered Cyclic Iodonium Salts". . p. 9161 - 9178. Retrieved 2020/08/14.