Methyl 3,4-bis(bromomethyl)benzoate

Base Information

• Chemical Name: Methyl 3,4-bis(bromomethyl)benzoate
• CAS No.: 20896-23-5
• Molecular Formula: C10H10Br2O2
• Molecular Weight: 321.996
• Hs Code.: 2916399090
• European Community (EC) Number: 673-066-7
• DSSTox Substance ID: DTXSID40371625
• Wikidata: Q82159018
• Mol file: 20896-23-5.mol

Synonyms:methyl 3,4-bis(bromomethyl)benzoate;20896-23-5;Benzoic acid, 3,4-bis(bromomethyl)-, methyl ester;methyl 3,4-bis-(bromomethyl)benzoate;METHYL3,4-BIS(BROMOMETHYL)BENZOATE;SCHEMBL1028046;DTXSID40371625;PZOQMRZOUBBQFO-UHFFFAOYSA-N;MFCD00219865;AKOS002254645;PS-9916;AM803495;CS-0037224;FT-0754219;3,4-bis-bromomethyl-benzoic acid methyl ester;A815008

Chemical Property of Methyl 3,4-bis(bromomethyl)benzoate

Chemical Property:

• Vapor Pressure: 1.18E-05mmHg at 25°C
• Boiling Point: 369.5oC at 760 mmHg
• Flash Point: 177.3oC
• PSA: 26.30000
• Density: 1.728g/cm3
• LogP: 3.26300
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 321.90271
• Heavy Atom Count: 14
• Complexity: 197

Purity/Quality:

98% ^*data from raw suppliers

Methyl3,4-bis(bromomethyl)benzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC(=C(C=C1)CBr)CBr
• Uses: Methyl 3,4-bis(bromomethyl)benzoate is a reagent used in the preparation of sulfones through oxidation of 1,3-dihydrobenzo[c]thiophenes. Also is used in the synthesis of potent histone deacetylase inhibitors.

Technology Process of Methyl 3,4-bis(bromomethyl)benzoate

There total 4 articles about Methyl 3,4-bis(bromomethyl)benzoate 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: 90.0%

methyl 3,4-dimethylbenzoate (38404-42-1) → methyl 3,4-bis(bromomethyl)benzoate (20896-23-5)

Guidance literature:

With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 80 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.9b01987

Reference yield:

tetrachloromethane (56-23-5) + methyl 3,4-dimethylbenzoate (38404-42-1) → methyl 2,3-dihydro-2-(phenylmethyl)-1H-isoindole-5-carboxylate (127168-94-9) + methyl 3,4-bis(bromomethyl)benzoate (20896-23-5)

Guidance literature:

With N-Bromosuccinimide; dibenzoyl peroxide;

Reference yield:

3,4-dimethylbenzoic acid (619-04-5) → methyl 3,4-bis(bromomethyl)benzoate (20896-23-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / 16 h / 70 °C

2: potassium bromide; oxone||potassium monopersulfate triple salt / dichloromethane; water / 14 h / 0 - 25 °C

With oxone||potassium monopersulfate triple salt; sulfuric acid; potassium bromide; In dichloromethane; water;

upstream raw materials:

methyl 3,4-dimethylbenzoate

tetrachloromethane

3,4-dimethylbenzoic acid

Downstream raw materials:

methyl 3,4-bis(azidomethyl)benzoate

methyl (2R)-4'-chloro-6'-oxo-1,3,6',7'-tetra-hydrospiro[indene-2,5'-pyrrolo[2,3-d]pyrimidine]-5-carboxylate

methyl (6,7)-[6,6]-C₆₀-fullerene-(5,8)-dihydronapthyl-2-formic acid ester

(2R)-N-[(5R,6S,8S)-3-(2-hydroxypopan-2-yl)-5-methyl-6-phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-8-yl]-6'-oxo-1,3',6',7'-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-d]pyrimidine]-5-carboxamide

Refernces

• 1、 Hughes, Jonathan M. E.,Fier, Patrick S.. "Desulfonylative Arylation of Redox-Active Alkyl Sulfones with Aryl Bromides". supporting information. p. 5650 - 5654. Retrieved 2019/08/01.
• 2、 -. "Substituted Spiroamide Compounds". Page/Page column 20. . Retrieved 2010/09/18.