Methyl 4-bromo-3-methylbenzoate Chemical Properties

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29163990

MSDS

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

Methyl 4-bromo-3-methylbenzoate Usage And Synthesis

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

It may be used as a starting material in the total synthesis of (-)-martinellic acid.

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

Methyl 4-bromo-3-methylbenzoate(148547-19-7)Related Product Information

• Methyl acetate
• Methyl benzoate
• METSULFURON METHYL
• Methyl 4-cyanobenzoate
• Tribenuron methyl
• 4-Bromomethylbenzoic acid
• Methyl 4-(bromomethyl)benzoate
• Methyl salicylate
• Methyl bromoacetate
• Methylparaben
• Kresoxim-methyl
• Methyl 4-bromo-2-fluorobenzoate
• Methyl 4-bromo-3-cyanobenzoate
• Methyl 4-bromo-3-nitrobenzoate
• Thiophanate-methyl
• Methyl
• METHYL 3-BROMO-4-METHYLBENZOATE
• methyl 5-bromo-2-methyl-benzoate