4-Bromomethylbenzoic acid Chemical Properties

Melting point:

224-229 °C(lit.)

Boiling point:

252.95°C (rough estimate)

Density 

1.5313 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

Store below +30°C.

pka

4.10±0.10(Predicted)

form 

Crystalline Powder

color 

White to beige

Water Solubility 

Soluble in water.

BRN 

1862870

InChI

InChI=1S/C8H7BrO2/c9-5-6-1-3-7(4-2-6)8(10)11/h1-4H,5H2,(H,10,11)

InChIKey

CQQSQBRPAJSTFB-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=C(CBr)C=C1

CAS DataBase Reference

6232-88-8(CAS DataBase Reference)

EPA Substance Registry System

Benzoic acid, 4-(bromomethyl)- (6232-88-8)

Safety Information

Hazard Codes 

Xi,C

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

3261

WGK Germany 

3

F 

19-21

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29163900

MSDS

• Language:English Provider:4-Bromomethylbenzoic acid
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Bromomethylbenzoic acid Usage And Synthesis

Chemical Properties

white to beige crystalline powder

Uses

4-(Bromomethyl)benzoic Acid is an intermediate in the synthesis of Eprosartan (E590100), a prototype of the imidazoleacrylic acid angiotensin II receptor antagonists used as an antihypertensive agent.

Uses

4-(Bromomethyl)benzoic acid acts as an intermediate in the synthesis of eprosartan, which is used as an antihypertensive agent. Further, it is used in the preparation of 5,10,15,20-tetra(m-hydroxyphenyl)chlorin (temoporfin), which is a second generation photosensitizer. In addition to this, it is used in the preparation of 4-(5-arylidene-2,4-dioxothiazolidin-3-yl) methylbenzoic acids.

Uses

4-(Bromomethyl)benzoic acid was used in the chemical modification of 5,10,15,20-tetra(m-hydroxyphenyl)chlorin (temoporfin), second generation photosensitizer. It was also used in the synthesis of 4-(5-arylidene-2,4-dioxothiazolidin-3-yl) methylbenzoic acids.

Synthesis

In a 100 mL round-bottomed flask, 40 mL of carbon tetrachloride was added as solvent, 3.00 g of p-methylbenzoic acid as starting material, 4.00 g of N-bromosuccinimide (NBS) as bromination reagent, and 0.1 g of azobisisobutyronitrile (AIBN) as initiator. The reaction mixture was stirred and refluxed at 90 °C and the reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was cooled to room temperature followed by filtration. The filter cake was washed with warm water to remove the succinimide by-products generated in the reaction. After drying, 4.02 g of p-bromomethylbenzoic acid was obtained with a melting point of 231-232°C in 84% yield.

Purification Methods

Crystallise the acid from pKEst Me2CO. [Beilstein 9 IV 1745.]

References

[1] Chemistry - A European Journal, 2018, vol. 24, # 7, p. 1619 - 1630
[2] Organic Process Research and Development, 1998, vol. 2, # 4, p. 261 - 269
[3] Patent: CN108570012, 2018, A. Location in patent: Paragraph 0020; 0024; 0025
[4] Patent: CN108623537, 2018, A. Location in patent: Paragraph 0046; 0047; 0048
[5] Journal of Organic Chemistry, 1998, vol. 63, # 17, p. 6023 - 6026

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