4-BROMO METHYLBENZYL ALCOHOL Chemical Properties

Melting point:

76-77℃

Boiling point:

287.9±20.0 °C(Predicted)

Density 

1.514±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

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

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

solid

pka

14.26±0.10(Predicted)

color 

Off-white

InChI

InChI=1S/C8H9BrO/c9-5-7-1-3-8(6-10)4-2-7/h1-4,10H,5-6H2

InChIKey

RDHSYXFAOVTAEH-UHFFFAOYSA-N

SMILES

C1(CO)=CC=C(CBr)C=C1

Safety Information

RIDADR 

2811

HazardClass 

6.1

PackingGroup 

Ⅱ

HS Code 

2906290090

4-BROMO METHYLBENZYL ALCOHOL Usage And Synthesis

Synthesis

The general procedure for the synthesis of 4-bromomethylbenzyl alcohol from methyl 4-bromomethylbenzoate was as follows: under nitrogen protection, methyl 4-bromomethylbenzoate (5.73 g, 25 mmol) was dissolved in anhydrous CH2Cl2 (150 mL), stirred and cooled to -78 °C. DIBAL-H solution (82.5 mL, 1.0 M THF solution) was added slowly and dropwise. The -78 °C reaction temperature was maintained and stirring was continued for 1.5 hours. Subsequently, the reaction mixture was slowly warmed to 0 °C and the reaction was quenched with H2O. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (2 x 100 mL). The organic extracts were combined, dried with MgSO4 and the solvent was evaporated under reduced pressure to afford the target product 4-bromomethylbenzyl alcohol (5.0 g, 100% yield) as a white solid. The product was characterized by 1H NMR (CDCl3): δ1.84 (br, 1H), 4.49 (s, 2H), 4.67 (s, 2H), 7.33 (d, 2H, J=8.2Hz), 7.38 (d, 2H, J=8.2Hz).

References

[1] Patent: US6506770, 2003, B1
[2] Patent: US6872714, 2005, B1
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 3, p. 1250 - 1260
[4] European Journal of Medicinal Chemistry, 2015, vol. 104, p. 127 - 138
[5] Journal of Labelled Compounds and Radiopharmaceuticals, 2017, vol. 60, # 10, p. 466 - 480

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