METHYL 4'-BROMO[1,1'-BIPHENYL]-4-CARBOXYLATE Chemical Properties

Melting point:

146-148°C

Boiling point:

382.7±25.0 °C(Predicted)

Density 

1.394±0.06 g/cm3(Predicted)

storage temp. 

Store at room temperature

form 

solid

Appearance

White to off-white Solid

Water Solubility 

Slightly soluble in water.

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

36/37/38-50/53-41

Safety Statements 

26-36/37/39-61-60-39

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

2

HazardClass 

IRRITANT

HS Code 

2916399090

METHYL 4'-BROMO[1,1'-BIPHENYL]-4-CARBOXYLATE Usage And Synthesis

Uses

It is employed in the design, synthesis, and biological evaluation of novel nonsteroidal farnesoid x receptor (fxr) antagonists.

Synthesis

Methyl 4-iodobenzoate (9.38 g, 35.8 mmol) and 4-bromophenylboronic acid (7.18 g, 35.8 mmol) were added to Pd(PPh3)4 (2.07 g, 1.79 mmol) in a solvent mixture of toluene (180 mL) and ethanol (100 mL) to form a clarified solution. To this solution was added 4.0 M aqueous sodium carbonate (30 mL). The reaction mixture was refluxed at 80°C for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature and diluted with ethyl acetate (300 mL). The organic layer was washed sequentially with water (2 x 300 mL), saturated aqueous NaHCO3 (2 x 300 mL) and saturated aqueous NaCl, and then dried over MgSO4. After concentrating the organic phase, the residue was purified by column chromatography (eluent: 7% ethyl acetate-heptane) to afford the white solid product methyl 4'-bromo[1,1'-biphenyl]-4-carboxylate (7.8 g, 78% yield).1H NMR (CDCl3) δ: 8.10 (d, 2H, J = 9.0 Hz), 7.62 (d, 2H, J = 9.0 Hz), 7.59 (d, 2H, J = 9.0 Hz), 7.59 (d, 2H, J = 9.0 Hz), 7.59 (d, 2H, J = 9.0 Hz) 7.59 (d, 2H, J = 9.3 Hz), 7.48 (d, 2H, J = 9.3 Hz), 3.95 (s, 3H).

References

[1] Patent: WO2004/99170, 2004, A2. Location in patent: Page 57
[2] Patent: WO2006/55625, 2006, A2. Location in patent: Page/Page column 94-95
[3] Patent: WO2006/55725, 2006, A2. Location in patent: Page/Page column 179
[4] Patent: WO2004/99171, 2004, A2. Location in patent: Page 116-117

METHYL 4'-BROMO[1,1'-BIPHENYL]-4-CARBOXYLATE(89901-03-1)Related Product Information

• METHYL 4'-HYDROXY[1,1'-BIPHENYL]-4-CARBOXYLATE
• BIFENAZATE
• Methyl 4-phenylbenzoate
• METHYL 4'-BROMO[1,1'-BIPHENYL]-4-CARBOXYLATE
• 4-Bromo-4'-methylbiphenyl
• 4'-BROMO-4-BIPHENYL CARBOXYLIC ACID
• 4-Bromobiphenyl
• 4-Biphenylcarboxylic acid