2-BROMO-4-HYDROXYMETHYL-PHENOL Chemical Properties

Melting point:

128-132℃

Boiling point:

307.8±27.0 °C(Predicted)

Density 

1.722±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

solid

pka

8.21±0.18(Predicted)

color 

Yellow

CAS DataBase Reference

29922-56-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2908190090

2-BROMO-4-HYDROXYMETHYL-PHENOL Usage And Synthesis

Chemical Properties

off-white crystalline

Synthesis

Methyl 3-bromo-4-hydroxybenzoate (12, 0.185 g, 0.80 mmol) in anhydrous CH2Cl2 (14 mL) was added slowly to a THF solution of DIBAL-H (1.0 M, 1.92 mL, 1.92 mmol) at -78 °C. The reaction mixture was stirred at -78 °C for 1 h before the reaction was quenched by addition of MeOH and water. Subsequently, saturated potassium sodium tartrate solution was added and stirring was continued for 1 hour. The aqueous layer was extracted with ethyl acetate (3 x 20 mL), the organic layers were combined, washed sequentially with 10% aqueous NaHCO3 and water, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by fast column chromatography (eluent: ethyl acetate/hexane, 1:1) to afford the target product 3-bromo-4-hydroxybenzenemethanol (13, 0.111 g, 68% yield) as a white solid. The product characterization data were as follows: melting point 125 °C; elemental analysis (measured value: C, 41.45; H, 3.42. theoretical value of C7H7BrO2: C, 41.41; H, 3.48); thin-layer chromatography Rf-value of 0.6 (unfolding reagent: ethyl acetate/hexanes, 65:35); IR (Nujol) νmax 3510, 3060, 2982, 1610 , 1505, 1425, 1270, 905, 750, 710 cm-1; 1H NMR (300MHz, DMSO-d6) δ: 7.38 (d, J=2.0Hz, 1H), 7.08 (dd, J=2.0,8.2Hz, 1H), 6.87 (d, J=8.2Hz, 1H), 5.07 (t, J=5.7 Hz, 1H), 4.34 (d, J=5.7Hz, 2H); 13C NMR (75MHz, DMSO-d6) δ: 153.3, 135.4, 131.6, 127.6, 116.5, 109.4, 62.5.

References

[1] Tetrahedron, 2011, vol. 67, # 34, p. 6300 - 6307

2-BROMO-4-HYDROXYMETHYL-PHENOL(29922-56-3)Related Product Information

• 4',5'-DIBROMOFLUORESCEIN
• 3-BROMO-4-HYDROXYBENZOIC ACID HYDRATE
• 3,5-Dibromo-4-hydroxybenzoic acid
• Bromocresol green
• Bromophenol Blue
• Acid Red 87
• Bromocresol Purple
• 5-BROMO-2,4-DIHYDROXYBENZOIC ACID
• Bromochlorophenol Blue sodium salt
• Bromophenol Red sodium salt
• 3',3'',5',5''-TETRABROMOPHENOLPHTHALEIN
• 3-BROMO-4-METHOXYBENZOIC ACID
• METHYL 3,5-DIBROMO-4-HYDROXYBENZOATE
• Bromoxylenol Blue
• BTB
• Tetrabromophenol Blue
• EOSIN DIACETATE
• 3,5-DIBROMO-4-METHOXYBENZOIC ACID