2-BROMO-4-METHOXYPHENOL Chemical Properties

Melting point:

47°

Boiling point:

281.1±20.0 °C(Predicted)

Density 

1.585±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

9.49±0.18(Predicted)

Appearance

Light brown to black Solid

InChI

InChI=1S/C7H7BrO2/c1-10-7-3-2-5(9)4-6(7)8/h2-4,9H,1H3

InChIKey

NOJOUQQJSGRBMN-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

17332-12-6(CAS DataBase Reference)

Safety Information

HazardClass 

IRRITANT

HS Code 

2909500090

2-BROMO-4-METHOXYPHENOL Usage And Synthesis

Uses

3-Bromo-4-methoxyphenol is a malate dehyrogenase inhibitor.

Synthesis

General procedure for the synthesis of 3-bromo-4-methoxyphenol from 3-bromo-4-methoxyphenyl acetate: a solution of potassium hydroxide (290 mg, 5.19 mmol) in water (2.5 mL) was added to a solution of 3-bromo-4-methoxyphenyl acetate (1.2 g, 4.9 mmol) in methanol (18.5 mL). The reaction mixture was stirred at room temperature for 30 min, followed by removal of the solvent under reduced pressure. Water (40 mL) was added to the residue and 1.2 M aqueous hydrochloric acid (4.3 mL) was added dropwise until the mixture was acidic. The mixture was extracted with dichloromethane (2 x 40 mL), the organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated under reduced pressure to give 3-bromo-4-methoxyphenol (976 mg, 98% yield) as a light yellow solid.LCMS analysis (Method A): retention time (RT) = 2.11 min; no ionization was observed.TLC analysis: Rf = 0.28 (unfolding reagent ratio 1:4 ethyl acetate:hexane).

References

[1] Patent: WO2009/109743, 2009, A1. Location in patent: Page/Page column 37; 38
[2] Patent: CN105001107, 2016, B. Location in patent: Paragraph 0045; 0047
[3] Patent: WO2004/16621, 2004, A1. Location in patent: Page 31

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