4-(4-BROMOPHENYL)BUTANOIC ACID Chemical Properties

Melting point:

67 °C

Boiling point:

176 °C / 3mmHg

Density 

1.463±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

4.74±0.10(Predicted)

color 

White to Light yellow to Light orange

InChIKey

AGIIMNQWNPUJPT-UHFFFAOYSA-N

CAS DataBase Reference

35656-89-4

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

29163990

4-(4-BROMOPHENYL)BUTANOIC ACID Usage And Synthesis

Physical form

Solid

Synthesis

General procedure for the synthesis of 4-(4-bromophenyl)butyric acid from 3-(4-bromobenzoyl)propionic acid: zinc powder (13.0 g, 200 mmol) was stirred with mercuric chloride (1.00 g, 4.80 mmol) in water (10 mL) and concentrated hydrochloric acid (0.6 mL) for 5 min. After decanting the liquid, toluene (20 mL), concentrated hydrochloric acid (20 mL) and water (8 mL) were added sequentially. 3-(4-Bromobenzoyl)propionic acid (2.55 g, 10.5 mmol) was added to the reaction system and heated at reflux at 100 °C for 24 h, during which concentrated hydrochloric acid (1 mL) was replenished every 6 hours. After completion of the reaction, it was cooled to room temperature, filtered, and the solvent was removed from the organic phase to give a clarified liquid, which precipitated as white crystals upon cooling. The product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane, 1:3, v/v) to afford 4-(4-bromophenyl)butanoic acid (2.33 g, 9.63 mmol, 91.4% yield). Mass spectrometry (ESI-quadrupole) m/z: calculated values of C10H11BrO2[M-H]-: 241.99, 243.99; measured values: 244.0 (10%), 243.0 (98%), 242.0 (11%), 241.0 (100%) (negative ion mode). High performance liquid chromatography (HPLC) retention time: 27.7 min. 1H NMR (300 MHz, CDCl3) δ (ppm): 7.40 (2H, d, J = 8.4 Hz, ArH), 7.06 (2H, d, J = 8.4 Hz, ArH), 2.63 (2H, t, J = 7.8 Hz, CH2), 2.36 (2H, t, J = 7.2 Hz, CH2), 1.97 (2H, dt, J = 7.2, 7.8 Hz, CH2), OH was not observed.

References

[1] Journal of the American Chemical Society, 2001, vol. 123, # 17, p. 3940 - 3952
[2] Journal of Organic Chemistry, 1992, vol. 57, # 1, p. 366 - 370
[3] Patent: WO2016/119017, 2016, A1. Location in patent: Page/Page column 22; 31
[4] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 22, p. 7434 - 7445
[5] Patent: WO2015/134973, 2015, A1. Location in patent: Page/Page column 123; 124

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