(6-BROMO-NAPHTHALEN-2-YL)-METHANOL Chemical Properties

Melting point:

152-153℃

Boiling point:

374.6±17.0 °C(Predicted)

Density 

1.544±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DCM, DMSO. DMF, Ethyl Acetate

form 

Solids

pka

14.15±0.10(Predicted)

color 

White

(6-BROMO-NAPHTHALEN-2-YL)-METHANOL Usage And Synthesis

Uses

6-Bromo-2-naphthalenemethanol is an intermediate in the synthesis of Adapalene (A225000), an antiacne agent.

Synthesis

General procedure for the synthesis of 6-bromo-2-hydroxymethylnaphthalene from 6-bromo-2-naphthalenecarboxylic acid: To a solution of 6-bromo-2-naphthalenecarboxylic acid (1 g, 3.98 mmol) in tetrahydrofuran (THF, 20 ml) was added a tetrahydrofuran solution of 2M borane dimethyl sulphide (0.53 ml, 5.97 mmol) in batches at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred overnight. After completion of the reaction, the mixture was cooled to 0°C and the reaction was quenched by addition of methanol (MeOH). Subsequently, the solution was concentrated under reduced pressure. The crude product was purified by column chromatography (using ethyl acetate in heptane as eluent) to afford 6-bromo-2-hydroxymethylnaphthalene (0.4 g, 89% yield). lCMS analysis showed m/z 238 [M + H]+ .

References

[1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 1, p. 267 - 273
[2] Patent: WO2009/130475, 2009, A1. Location in patent: Page/Page column 31-32
[3] Patent: WO2016/40891, 2016, A2. Location in patent: Paragraph 00335
[4] Patent: WO2005/40157, 2005, A2. Location in patent: Page/Page column 83
[5] Patent: WO2016/112284, 2016, A1. Location in patent: Page/Page column 132; 133

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