Ethyl 4-bromophenylacetate Chemical Properties

Melting point:

29-33 °C(lit.)

Boiling point:

88-90°C 0,35mm

Density 

1.389±0.06 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

form 

Liquid or Low Melting Solid

color 

Clear colorless to pale yellow

InChI

InChI=1S/C10H11BrO2/c1-2-13-10(12)7-8-3-5-9(11)6-4-8/h3-6H,2,7H2,1H3

InChIKey

ZFDCWHPNBWPPHG-UHFFFAOYSA-N

SMILES

C1(CC(OCC)=O)=CC=C(Br)C=C1

CAS DataBase Reference

14062-25-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22

Safety Statements 

36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29163990

MSDS

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

Ethyl 4-bromophenylacetate Usage And Synthesis

Chemical Properties

Clear colorless to pale yellow liquid

Uses

4-Bromo-benzeneacetic Acid Ethyl Ester is used to prepare highly selective and orally active Lysophosphatidic Acid (LPA) receptor-1 antagonists with potent activity on human lung fibroblasts.

Synthesis

Preparation of the intermediate 1-bromo-4-(2-methoxy-2-methyldienyl)benzene (1AG-1): 2-(4-bromophenyl)acetic acid (75 g, 340 mmol) was suspended in ethanol (341 mL). Concentrated sulfuric acid (0.682 mL, 12.79 mmol) was added slowly and the reaction mixture was subsequently heated to reflux and maintained for 24 hours. Upon completion of the reaction, the mixture was concentrated to remove the solvent. The residue was diluted with ether and saturated sodium bicarbonate solution for acid-base neutralization. The organic and aqueous layers were carefully separated and the organic layer was subsequently washed with brine and dried over sodium sulfate. The dried organic phase was filtered and the filtrate was concentrated to give ethyl 2-(4-bromophenyl)acetate (80.2 g, 97% yield) as an off-white solid.

References

[1] Patent: WO2010/86820, 2010, A1. Location in patent: Page/Page column 53
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 21, p. 6665 - 6681
[3] Patent: US2013/79320, 2013, A1. Location in patent: Paragraph 0473; 0474
[4] Patent: WO2013/45451, 2013, A1. Location in patent: Paragraph 51
[5] European Journal of Medicinal Chemistry, 2014, vol. 86, p. 714 - 723

Ethyl 4-bromophenylacetate(14062-25-0)Related Product Information

• Ethyl 4-bromobutyrate
• Ethyl propionate
• 2-Ethoxyethanol
• ISOXADIFEN-ETHYL
• Ethyl formate
• Ethyl chloroacetate
• 3-Bromofluorobenzene
• 1,4-Dibromobenzene
• 1,2-Dibromobenzene
• Brompheniramine hydrogen maleate
• Tris(trimethylsilyl)phosphate
• 4-Bromoanisole
• Brompheniramine
• Trinexapac-ethyl
• Bromoxynil
• 4-Bromobenzaldehyde
• 4-Bromobenzotrifluoride
• 1-Bromo-4-nitrobenzene