Methyl 2-bromomethylbenzoate Chemical Properties

Melting point:

32-32.5 °C

Boiling point:

114 °C(Press: 0.44 Torr)

Density 

1.460±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform (Sparingly), Hexane (Slightly)

form 

Solid

color 

White Low Melting

InChI

InChI=1S/C9H9BrO2/c1-12-9(11)8-5-3-2-4-7(8)6-10/h2-5H,6H2,1H3

InChIKey

QKASDIPENBEWBU-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=CC=C1CBr

CAS DataBase Reference

2417-73-4(CAS DataBase Reference)

Safety Information

HS Code 

2916310090

Methyl 2-bromomethylbenzoate Usage And Synthesis

Uses

Methyl 2-Bromomethylbenzoate is a reactant in the preparation of Methyl 2-((4-(2-(2-methylphenoxy)acetyl)piperazin-1-yl)methyl)benzoate with neuroprotective activity.

Synthesis

General procedure for the synthesis of methyl 2-bromomethylbenzoate from methyl o-toluate: (2) 1.50 g (10 mmol) of methyl o-toluate was added to a 250 mL round-bottom flask and dissolved in 80 mL of carbon tetrachloride. Subsequently 1.98 g (11 mmol) of N-bromosuccinimide (NBS) and 48 mg (0.2 mmol) of benzoyl peroxide (BPO) were added. The mixture was heated to reflux for 1.5 h to ensure complete reaction. Upon completion of the reaction, insoluble material was removed by filtration and the solvent was subsequently evaporated to give methyl 2-bromomethylbenzoate. The reaction was quantitative.

References

[1] Journal of Medicinal Chemistry, 2000, vol. 43, # 24, p. 4667 - 4677
[2] Chemical Communications, 2010, vol. 46, # 13, p. 2227 - 2229
[3] Patent: US2011/237786, 2011, A1. Location in patent: Page/Page column 7
[4] Zeitschrift fuer Naturforschung, B: Chemical Sciences, 1989, vol. 44, # 9, p. 1132 - 1148
[5] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 9, p. 1359 - 1360

Methyl 2-bromomethylbenzoate(2417-73-4)Related Product Information

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