Methyl 4-bromo-3-methylbenzoate

Methyl 4-bromo-3-methylbenzoate Property

Melting point:

38-44 °C (lit.)

Boiling point:

287.4±20.0 °C(Predicted)

Density 

1.433±0.06 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

Low Melting Solid or Liquid

color 

White to yellow

BRN 

6593534

InChI

InChI=1S/C9H9BrO2/c1-6-5-7(9(11)12-2)3-4-8(6)10/h3-5H,1-2H3

InChIKey

GTZTYNPAPQKIIR-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

148547-19-7(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29163990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Methyl 4-bromo-3-methylbenzoate Chemical Properties,Usage,Production

Chemical Properties

Colorless low melting solid

Uses

Methyl 4-bromo-3-methylbenzoate may be used in the preparation of:

• 4-bromo-3-vinylbenzoic acid
• 4-bromo-3-(methylphenyl)methanol
• methyl (E)-4-bromo-3-[(phenylmethoxyimino)methyl]benzoate

General Description

Methyl 4-bromo-3-methylbenzoate, an aromatic ester, undergoes Suzuki coupling with 2-chloroboronic acid to afford the corresponding biaryl.

Synthesis

To a concentrated solution of 4-bromo-3-methylbenzoic acid (3 g, 13.19 mmol) in methanol (15 ml) was added concentrated sulfuric acid (catalytic amount). The reaction mixture was heated to reflux for 14 hours and subsequently cooled to 0°C. The reaction mixture was neutralized with saturated sodium bicarbonate solution and the precipitated solid product was collected by filtration. The crude product was purified by silica gel column chromatography to afford methyl 4-bromo-3-methylbenzoate (3.1 g, 97% yield) as a white solid.

References

[1] Patent: US2011/71150, 2011, A1. Location in patent: Page/Page column 33
[2] Angewandte Chemie - International Edition, 2008, vol. 47, # 44, p. 8482 - 8486
[3] Patent: WO2006/110173, 2006, A2. Location in patent: Page/Page column 78
[4] Chemical Communications, 2018, vol. 54, # 65, p. 9051 - 9054
[5] Patent: US2013/131016, 2013, A1. Location in patent: Paragraph 0189