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188187-03-3

188187-03-3 Structure

188187-03-3 Structure
IdentificationBack Directory
[Name]

METHYL 2-BROMOMETHYL-3-CHLORO-BENZOATE
[CAS]

188187-03-3
[Synonyms]

METHYL 2-BROMOMETHYL-3-CHLORO-BENZOATE
2-(BroMoMethyl)-3-chloro-benzoic acid Methyl ester
Benzoic acid, 2-(bromomethyl)-3-chloro-, methyl ester
[Molecular Formula]

C9H8BrClO2
[MDL Number]

MFCD04114322
[MOL File]

188187-03-3.mol
[Molecular Weight]

263.52
Chemical PropertiesBack Directory
[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 DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319
[Precautionary statements ]

P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
[RIDADR ]

3261
[HazardClass ]

8
[PackingGroup ]

Ⅱ
Hazard InformationBack Directory
[Synthesis]

Methyl 3-chloro-2-methylbenzoate

99586-84-2

METHYL 2-BROMOMETHYL-3-CHLORO-BENZOATE

188187-03-3

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
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