tert-Butyl 4-(bromomethyl)benzoate Chemical Properties

Melting point:

53-55 °C

Boiling point:

320.9±25.0 °C(Predicted)

Density 

1.313±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 30 mg/ml; Ethanol:PBS (pH 7.2)(1:3): .25 mg/ml

form 

A crystalline solid

InChI

InChI=1S/C12H15BrO2/c1-12(2,3)15-11(14)10-6-4-9(8-13)5-7-10/h4-7H,8H2,1-3H3

InChIKey

GSIBTIUXYYFCPU-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

108052-76-2(CAS DataBase Reference)

Safety Information

HS Code 

2916399090

tert-Butyl 4-(bromomethyl)benzoate Usage And Synthesis

Description

tert-butyl p-(bromomethyl) Benzoate is a synthetic intermediate useful for pharmaceutical synthesis.WARNING This product is not for human or veterinary use.

Synthesis

To a solution of substituted toluene in carbon tetrachloride were added N-bromosuccinimide (1.1 equiv) and 2,2'-azobis(isobutyronitrile) (0.15 equiv). The mixture was refluxed, then filtered and concentrated. The residue was purified by silica gel column chromatography to give tert-Butyl 4-(bromomethyl)benzoate.

References

[1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 10, p. 3156 - 3172
[2] Angewandte Chemie - International Edition, 2007, vol. 46, # 46, p. 8869 - 8871
[3] Journal of Medicinal Chemistry, 1989, vol. 32, # 3, p. 709 - 715
[4] Patent: CN108329259, 2018, A. Location in patent: Paragraph 0047; 0052
[5] European Journal of Medicinal Chemistry, 2018, vol. 152, p. 175 - 194

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