3-BROMO-5-METHYL-BENZOIC ACID METHYL ESTER

3-BROMO-5-METHYL-BENZOIC ACID METHYL ESTER Property

Boiling point:

271.8±20.0℃ (760 Torr)

Density 

1.433±0.06 g/cm3 (20 ºC 760 Torr)

Flash point:

118.2±21.8℃

storage temp. 

Sealed in dry,Room Temperature

form 

solid

color 

Yellow

InChI

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

InChIKey

OAOZBFUAVJUPED-UHFFFAOYSA-N

SMILES

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

Safety

HS Code 

2916310090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

3-BROMO-5-METHYL-BENZOIC ACID METHYL ESTER Chemical Properties,Usage,Production

Chemical Properties

off-white powder

Synthesis

Methanol (1.104 g, 0.035 mol) was slowly added to a solution of 3-bromo-5-methylbenzoic acid (5 g, 0.023 mol) in dichlorosulfoxide (30 mL) at 0 °C. The reaction mixture was warmed to 80 °C and stirred for 2 hours. Upon completion of the reaction, the mixture was cooled to 18 °C and concentrated by rotary evaporation to remove the solvent. The residue was washed with water (20 mL) and subsequently extracted with ethyl acetate (100 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated to afford methyl 3-bromo-5-methylbenzoate (5.3 g, 93.8% yield).LC-MS (mass spectrometry) analysis showed the molecular ion peak of the target product to be 229 [M + 1].

References

[1] Patent: US2015/197493, 2015, A1. Location in patent: Paragraph 0871; 0872; 0873; 0874
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 16, p. 7358 - 7373
[3] Patent: US2015/225355, 2015, A1. Location in patent: Paragraph 0868; 0869