Ethyl 4-(bromomethyl)benzoate Chemical Properties

Melting point:

40°C

Boiling point:

145°C 5mm

Density 

1.402±0.06 g/cm3(Predicted)

refractive index 

1.5494

Flash point:

145°C/5mm

storage temp. 

2-8°C

form 

fused solid

color 

White

BRN 

1869569

InChI

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

InChIKey

TWQLMAJROCNXEA-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

26496-94-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

22-34

Safety Statements 

26-36/37/39-45

RIDADR 

1759

HazardClass 

8

PackingGroup 

II

HS Code 

2916399090

MSDS

• Language:English Provider:ALFA

Ethyl 4-(bromomethyl)benzoate Usage And Synthesis

Uses

4-​(bromomethyl)​-​Benzoic acid ethyl ester is a brominated aromatic building block used in various syntheses such as the preparation of imidazoles and imidazo-fused heterocycles.

Uses

4-?(bromomethyl)?-?Benzoic acid ethyl ester is a brominated aromatic building block used in various syntheses such as the preparation of imidazoles and imidazo-fused heterocycles.

Synthesis

General procedure for the synthesis of ethyl 4-(bromomethyl)benzoate from ethyl p-methylbenzoate: to a stirred solution of ethyl 4-methylbenzoate (5 g, 30.49 mmol) in carbon tetrachloride (35 ml) was added sequentially N-bromosuccinimide (5.90 g, 33.53 mmol) and benzoyl peroxide (720 mg, 1.52 mmol). The reaction mixture was heated under reflux conditions for 4 h. The progress of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was cooled to room temperature and subsequently filtered. The filtrate was concentrated by vacuum evaporation to give the colorless oily product ethyl 4-(bromomethyl)benzoate (7.25 g, 98% yield).

References

[1] Chinese Journal of Chemistry, 2012, vol. 30, # 8, p. 1906 - 1908
[2] Patent: WO2009/109999, 2009, A1. Location in patent: Page/Page column 68
[3] Organic Process Research and Development, 1998, vol. 2, # 4, p. 261 - 269
[4] Synthesis (Germany), 2018, vol. 50, # 24, p. 4933 - 4939
[5] Tetrahedron, 2007, vol. 63, # 36, p. 8891 - 8901

Ethyl 4-(bromomethyl)benzoate(26496-94-6)Related Product Information

• Ethylparaben
• Benzyl benzoate
• ETHYL ANTHRANILATE
• Ethyl 2-chloromethylbenzoate
• Ethyl benzoate
• Bromotrimethylsilane
• Ethanol
• 4-Bromomethylbenzoic acid
• Ethyl 4-methylbenzoate
• Ethyl acetate
• Ethyl 4-hydroxybenzoate,sodium salt
• Tris(trimethylsilyl)phosphate
• Sodium benzoate
• Emamectin benzoate
• Denatonium Benzoate Anhydrous
• Methyl 4-(bromomethyl)benzoate
• 4-(BROMOMETHYL)-BENZOIC ACID, 1,1-DIMETHYLETHYL ESTER
• Methyl bromide