Methyl 3-(bromomethyl)-2-benzofurancarboxylate

Base Information

• Chemical Name: Methyl 3-(bromomethyl)-2-benzofurancarboxylate
• CAS No.: 58763-73-8
• Molecular Formula: C11H9 Br O3
• Molecular Weight: 269.095
• European Community (EC) Number: 261-428-3
• DSSTox Substance ID: DTXSID20207498
• Nikkaji Number: J297.022H
• Mol file: 58763-73-8.mol

Synonyms:58763-73-8;methyl 3-(bromomethyl)-1-benzofuran-2-carboxylate;Methyl 3-(bromomethyl)-2-benzofurancarboxylate;EINECS 261-428-3;SCHEMBL445085;3-Bromomethylbenzofuran-2-carboxylic acid methyl ester;DTXSID20207498;MFCD09971574;AKOS009222605;CS-0246183;methyl 3-bromomethylbenzofuran-2-carboxylate;EN300-31871;Methyl3-(bromomethyl)benzofuran-2-carboxylate;Methyl 3-(bromomethyl)benzofuran-2-carboxylate;methyl 3-(bromomethyl)-2-benzo[b]furancarboxylate;methyl 3-(bromomethyl)-1-benzo[b]furan-2-carboxylate;3-(Bromomethyl)benzofuran-2-carboxylic acid methyl ester;Z335575980

Chemical Property of Methyl 3-(bromomethyl)-2-benzofurancarboxylate

Chemical Property:

• Vapor Pressure: 2.74E-05mmHg at 25°C
• Boiling Point: 357.4°Cat760mmHg
• Flash Point: 169.9°C
• PSA: 39.44000
• Density: 1.548g/cm³
• LogP: 3.11430
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 267.97351
• Heavy Atom Count: 15
• Complexity: 244

Purity/Quality:

99% ^*data from raw suppliers

METHYL 3-(BROMOMETHYL)-1-BENZOFURAN-2-CARBOXYLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(C2=CC=CC=C2O1)CBr

Technology Process of Methyl 3-(bromomethyl)-2-benzofurancarboxylate

There total 2 articles about Methyl 3-(bromomethyl)-2-benzofurancarboxylate 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%

methyl 3-methylbenzofuran-2-carboxylate (2076-36-0) → 3-bromomethylbenzofuran-2-carboxylic acid methyl ester (58763-73-8)

Guidance literature:

With N-Bromosuccinimide; In tetrachloromethane;

DOI:10.1016/0960-894X(96)00288-0

Reference yield:

methanol (67-56-1) + 3-methyl-1-benzofuran-2-carboxylic acid (24673-56-1) → 3-bromomethylbenzofuran-2-carboxylic acid methyl ester (58763-73-8)

Guidance literature:

methanol; 3-methyl-1-benzofuran-2-carboxylic acid; With sulfuryl dichloride; for 12h; Reflux;

With N-Bromosuccinimide; dibenzoyl peroxide; In 1,2-dichloro-ethane; for 3h; Reflux;

DOI:10.1002/anie.202113464

Reference yield:

3-bromomethylbenzofuran-2-carboxylic acid methyl ester (58763-73-8) → C25H19NO4S

Guidance literature:

Multi-step reaction with 5 steps

1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere

2: ammonium hydroxide / tetrahydrofuran / 12 h / 20 °C

3: triethylamine / dichloromethane / 12 h / 20 °C

4: copper(I) bromide; potassium phosphate; N,N`-dimethylethylenediamine / toluene / 1.5 h / 80 °C

5: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C

With ammonium hydroxide; potassium phosphate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; copper(I) bromide; N,N`-dimethylethylenediamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1002/anie.202113464

upstream raw materials:

methyl 3-methylbenzofuran-2-carboxylate

methanol

3-methyl-1-benzofuran-2-carboxylic acid

Downstream raw materials:

3-dimethylaminomethylbenzofuran-2-carboxylic acid methyl ester

Refernces

• 1、 -. "BENZOFURAN ANILIDE HISTONE DEACETYLASE INHIBITORS". Page/Page column 29-30. . Retrieved 2009/07/18.
• 2、 -. "NOVEL SAFRAMYCIN ANALOGS AS THERAPEUTIC AGENTS". Page/Page column 81. . Retrieved 2010/02/15.