Methyl 2-(bromomethyl)-5-nitrobenzoate

Base Information

• Chemical Name: Methyl 2-(bromomethyl)-5-nitrobenzoate
• CAS No.: 90725-68-1
• Molecular Formula: C9H8 Br N O4
• Molecular Weight: 274.071
• Hs Code.: 2916310090
• European Community (EC) Number: 822-866-6
• DSSTox Substance ID: DTXSID60561622
• Wikidata: Q72488731
• Mol file: 90725-68-1.mol

Synonyms:90725-68-1;Methyl 2-(bromomethyl)-5-nitrobenzoate;METHYL 2-BROMOMETHYL-5-NITROBENZOATE;Methyl 2-bromomethyl-5-nitro-benzoate;SCHEMBL1318195;DTXSID60561622;OAEABYNRBPCSQB-UHFFFAOYSA-N;AMY12033;CS-D0234;Methyl 6-Bromomethyl-3-nitrobenzoate;MFCD04114313;AKOS016004579;Methyl2-(bromomethyl)-5-nitrobenzoate;AB18048;DS-11190;2-bromomethyl-5-nitrobenzoic acid methyl ester;A843623;J-521974;methyl 2-(bromomethyl)-5-nitro-benzoate

Chemical Property of Methyl 2-(bromomethyl)-5-nitrobenzoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 76-77 °C
• Boiling Point: 397.253°C at 760 mmHg
• Flash Point: 194.052°C
• PSA: 72.12000
• Density: 1.625g/cm³
• LogP: 2.79950
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 272.96367
• Heavy Atom Count: 15
• Complexity: 253

Purity/Quality:

98%min ^*data from raw suppliers

Methyl2-(Bromomethyl)-5-nitrobenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(C=CC(=C1)[N+](=O)[O-])CBr
• Uses: Methyl 2-(Bromomethyl)-5-nitrobenzoate is used in the synthetic preparation of novel and reversible inhibitors for severe acute respiratory syndrome-coronavirus papain-like protease.

Technology Process of Methyl 2-(bromomethyl)-5-nitrobenzoate

There total 6 articles about Methyl 2-(bromomethyl)-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%

methyl 2-methyl-5-nitrobenzoate (77324-87-9) → methyl 2-(bromomethyl)-5-nitrobenzoate (90725-68-1)

Guidance literature:

With N-Bromosuccinimide; dibenzoyl peroxide; In benzene; at 65 ℃; for 24h; Inert atmosphere;

DOI:10.1039/c7ob02415k

Reference yield:

N-Bromosuccinimide (128-08-5) + methyl 2-methyl-5-nitrobenzoate (77324-87-9) → methyl 2-(bromomethyl)-5-nitrobenzoate (90725-68-1)

Guidance literature:

With dibenzoyl peroxide; In tetrachloromethane; water;

Reference yield:

5-nitro-o-toluic acid (1975-52-6) → methyl 2-(bromomethyl)-5-nitrobenzoate (90725-68-1)

Guidance literature:

Multi-step reaction with 2 steps

1: AcCl / Heating

2: N-bromosuccinimide (NBS), benzoyl peroxide / CCl₄ / 20 h / Heating

With N-Bromosuccinimide; Perbenzoic acid; acetyl chloride; In tetrachloromethane;

DOI:10.1016/0223-5234(91)90119-8

upstream raw materials:

methyl 2-methyl-5-nitrobenzoate

5-nitro-o-toluic acid

N-Bromosuccinimide

ortho-methylbenzoic acid

Downstream raw materials:

methyl 2-{[bromo(triphenyl)phosphoranyl]methyl}-5-nitrobenzoate

methyl 2-((diethoxyphosphoryl)methyl)-5-nitrobenzoate

(R)-methyl 2-(2-formyloctyl)-5-nitrobenzoate

2-[(bis-pyridin-2-ylmethylamino)methyl]-5-nitrobenzoic acid

Refernces

• 1、 Lai, Huifang,Lin, Jin,Xu, Jiexin,Zha, Daijun. "Copper-promoted direct amidation of isoindolinone scaffolds by sodium persulfate". supporting information. p. 7621 - 7626. Retrieved 2021/09/22.
• 2、 Pillow, Thomas H.,Adhikari, Pragya,Blake, Robert A.,Chen, Jinhua,Del Rosario, Geoffrey,Deshmukh, Gauri,Figueroa, Isabel,Gascoigne, Karen E.,Kamath, Amrita V.,Kaufman, Susan,Kleinheinz, Tracy,Kozak, Katherine R.,Latifi, Brandon,Leipold, Douglas D.,Sing Li, Chun,Li, Ruina,Mulvihill, Melinda M.,O'Donohue, Aimee,Rowntree, Rebecca K.,Sadowsky, Jack D.,Wai, John,Wang, Xinxin,Wu, Cong,Xu, Zijin,Yao, Hui,Yu, Shang-Fan,Zhang, Donglu,Zang, Richard,Zhang, Hongyan,Zhou, Hao,Zhu, Xiaoyu,Dragovich, Peter S.. "Antibody Conjugation of a Chimeric BET Degrader Enables in vivo Activity". supporting information. p. 17 - 25. Retrieved 2019/11/20.