3-(4-BROMOBENZOYL)PROPIONIC ACID Chemical Properties

Melting point:

148-152 °C (lit.)

Boiling point:

147-150 °C

Density 

1.5943 (rough estimate)

refractive index 

1.4620 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

Shiny Crystalline Flakes or Powder

pka

4.44±0.17(Predicted)

color 

White to light beige

BRN 

2104410

InChI

InChI=1S/C10H9BrO3/c11-8-3-1-7(2-4-8)9(12)5-6-10(13)14/h1-4H,5-6H2,(H,13,14)

InChIKey

ZODFRCZNTXLDDW-UHFFFAOYSA-N

SMILES

C1(C=CC(Br)=CC=1)C(=O)CCC(=O)O

CAS DataBase Reference

6340-79-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29183000

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-(4-BROMOBENZOYL)PROPIONIC ACID Usage And Synthesis

Chemical Properties

white to light beige shiny crystalline flakes

Synthesis

The general procedure for the synthesis of 3-(4-bromobenzoyl)propionic acid from butanedioic anhydride and bromobenzene was as follows: butanedioic anhydride (5.0 g, 50 mmol) and bromobenzene (48 g, 300 mmol) were cooled to 0 °C. Anhydrous aluminum chloride (13.3 g, 100 mmol) was added to the reaction mixture under nitrogen protection and stirred at 0 °C for 4 hours. Subsequently, the reaction mixture was slowly warmed to room temperature and stirring was continued for 96 hours under nitrogen protection. Upon completion of the reaction, the mixture was cooled again to 0 °C, concentrated hydrochloric acid (125 mL) was slowly added and stirred under nitrogen protection for 1 hour. The reaction mixture was filtered and washed with water (1 L) to give a light yellow solid. The solid was purified by recrystallization from toluene to give 4-(4-bromophenyl)-4-oxobutanoic acid (12 g, 46.68 mmol, 93.4% yield). Mass spectrometry (ESI-quadrupole) m/z: calculated values of C10H9BrO3 were 255.97, 257.97; measured values: 258.0 (11), 257.0 (98), 256.0 (12), 255.0 (100), 213.0 (18), 211.0 (17) (in negative ion mode). High performance liquid chromatography (HPLC) retention time: 24.4 min. 1H NMR (500 MHz, DMSO-d6) δ: 2.59 (2H, triple peaks, J=6.5 Hz, CH2), 3.21 (2H, triple peaks, J=6.5 Hz, CH2), 7.88 (2H, double peaks, J=8.8 Hz, ArH), 7.96 (2H. double peak, J=8.8Hz, ArH), 12.19 (1H, broad single peak, OH).

References

[1] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2001, vol. 365, p. 181 - 188
[2] Journal of Organic Chemistry, 2001, vol. 66, # 22, p. 7283 - 7286
[3] Organic Syntheses, 2002, vol. 79, p. 204 - 204
[4] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 13, p. 4345 - 4359
[5] Organic Process Research and Development, 2014, vol. 18, # 1, p. 215 - 227

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