METHYL 2-BROMOMETHYL-3-CHLORO-BENZOATE

METHYL 2-BROMOMETHYL-3-CHLORO-BENZOATE Property

Boiling point:

331.0±32.0 °C(Predicted)

Density 

1.561±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C9H8BrClO2/c1-13-9(12)6-3-2-4-8(11)7(6)5-10/h2-4H,5H2,1H3

InChIKey

BZXFVKQUKUJTIM-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=CC(Cl)=C1CBr

Safety

RIDADR 

3261

HazardClass 

8

PackingGroup 

Ⅱ

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.

METHYL 2-BROMOMETHYL-3-CHLORO-BENZOATE Chemical Properties,Usage,Production

Synthesis

Methyl 3-chloro-2-methylbenzoate (1 g, 5.42 mmol) was used as a raw material, which was mixed with carbon tetrachloride (13.3 ml), N-bromosuccinimide (1.06 g, 5.96 mmol) and benzoyl peroxide (3.5 mg, 0.0108 mmol) to form a suspension. The reaction mixture was heated in an oil bath at 90°C under nitrogen protection. After the reaction was carried out for 3 hours and 45 minutes, the heating was stopped. The reaction solution was sequentially diluted with water, ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was separated, washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered and concentrated to afford the target product methyl 2-bromomethyl-3-chloro-benzoate (1.43 g, yield: 100%). The product was characterized by 1H-NMR (400 MHz, CDCl3) with chemical shifts δppm of 4.00 (3H, s), 5.12 (2H, s), 7.32 (1H, t, J = 8 Hz), 7.58 (1H, dd, J = 2,8 Hz), 7.86 (1H, dd, J = 2,8 Hz), respectively.

References

[1] Patent: US2013/65925, 2013, A1. Location in patent: Paragraph 0338; 0339
[2] Patent: EP2757103, 2014, A1. Location in patent: Paragraph 0215
[3] Patent: US5958968, 1999, A
[4] Patent: WO2004/58717, 2004, A1. Location in patent: Page 77
[5] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 360 - 365