1,2-ETHANEDIOL-(P-BROMOPHENYL)- Chemical Properties

Melting point:

100-101 °C

Boiling point:

356.6±27.0 °C(Predicted)

Density 

1.617±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

13.41±0.20(Predicted)

Appearance

White to off-white Solid

1,2-ETHANEDIOL-(P-BROMOPHENYL)- Usage And Synthesis

Uses

1-(4-Bromophenyl)ethane-1,2-diol is used as a reactant in the regioselective palladium-catalyzed O,S rearrangement of cyclic thiocarbonates.

Synthesis

The general procedure for the synthesis of 1-(4-bromophenyl)ethane-1,2-diol from 4-bromostyrene was as follows: 4-bromostyrene (1.00 g, 5.46 mmol) was dissolved in 25 mL of a 2:1 (v/v) water/acetone solvent mixture. Subsequently, 4-methylmorpholine N-oxide (0.704 g, 6.01 mmol) and osmium tetroxide (0.167 g, 0.061 mmol, dissolved in tert-butanol at a concentration of 2.5%) were sequentially added to this solution. The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the reaction solution was diluted with ethyl acetate (EtOAc) and washed sequentially with 1N aqueous hydrochloric acid solution and saturated sodium bicarbonate solution each. The organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. The resulting crude product was purified by fast column chromatography (Biotage 40M column, 100% ethyl acetate as eluent) to give 335 mg (28% yield) of 1-(4-bromophenyl)ethane-1,2-diol as a white solid.

References

[1] Organic Letters, 2005, vol. 7, # 22, p. 5071 - 5074
[2] Journal of the American Chemical Society, 2010, vol. 132, # 41, p. 14409 - 14411
[3] Journal of Organic Chemistry, 2015, vol. 79, # 23, p. 11431 - 11439
[4] Tetrahedron Letters, 2007, vol. 48, # 38, p. 6776 - 6778
[5] Chemical Research in Toxicology, 1998, vol. 11, # 1, p. 44 - 53

1,2-ETHANEDIOL-(P-BROMOPHENYL)-(92093-23-7)Related Product Information

• 3,6-DIBROMO-9,10-DIMETHYL-9,10-DIHYDROXY-9,10-DIHYDROPHENANTHRENE
• (R)-4-BROMOMANDELIC ACID
• Bromopropylate
• 4-Bromomandelic acid
• (R)-2-HYDROXY-2-METHYL(4-BROMOBENZENE)ACETIC ACID
• (S)-2-HYDROXY-2-METHYL(4-BROMOBENZENE)ACETIC ACID
• DIBROMOBENZILIC ACID
• [2-(4-BROMOPHENYL)-[1,3]DIOXOLAN-2-YL]METHANOL
• BROMOPROPYLATE D7
• 4-BROMO-2-FLUOROMANDELIC ACID
• 1,2-ETHANEDIOL-(P-BROMOPHENYL)-
• 2-(4-Bromophenyl)-2-hydroxypropionic acid