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263159-64-4

263159-64-4 Structure

263159-64-4 Structure
IdentificationBack Directory
[Name]

2-BROMO-3-METHYLBENZONITRILE
[CAS]

263159-64-4
[Synonyms]

2-BROMO-3-METHYLBENZONITRILE
Benzonitrile, 2-bromo-3-methyl-
2-BroMo-3-Methylbenzonitrile 97%
[Molecular Formula]

C8H6BrN
[MDL Number]

MFCD09025664
[MOL File]

263159-64-4.mol
[Molecular Weight]

196.04
Chemical PropertiesBack Directory
[Melting point ]

67-71 °C
[Boiling point ]

286.8±28.0 °C(Predicted)
[density ]

1.51±0.1 g/cm3(Predicted)
[storage temp. ]

Inert atmosphere,Room Temperature
[form ]

powder
[Appearance]

White to off-white Solid
[InChI]

1S/C8H6BrN/c1-6-3-2-4-7(5-10)8(6)9/h2-4H,1H3
[InChIKey]

RNHZLKDKPMISMY-UHFFFAOYSA-N
[SMILES]

Cc1cccc(C#N)c1Br
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302
[Precautionary statements ]

P264-P270-P301+P312-P501
[Hazard Codes ]

Xn
[Risk Statements ]

22
[WGK Germany ]

3
[HazardClass ]

IRRITANT
[HS Code ]

2926907090
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
Spectrum DetailBack Directory
[Spectrum Detail]

2-BROMO-3-METHYLBENZONITRILE(263159-64-4)1HNMR
Hazard InformationBack Directory
[Synthesis]

2-BROMO-3-METHYLBENZAMIDE

101421-85-6

2-BROMO-3-METHYLBENZONITRILE

263159-64-4

Step 2: To a solution of 2-bromo-3-methylbenzamide (12 g, 56.1 mmol) in N,N-dimethylformamide (DMF, 100 mL) was slowly added a solution of cyanuric chloride (15.47 g, 84.1 mmol) in DMF (50 mL) at 0 °C and under nitrogen protection. After addition, the reaction mixture was brought to room temperature and stirred overnight. Thin layer chromatography (TLC, unfolding agent: petroleum ether/ethyl acetate = 1:1) was monitored to show complete reaction. The reaction mixture was poured into water (500 mL) and extracted with ethyl acetate (EtOAc, 200 mL x 2). The organic phases were combined and washed sequentially with saturated aqueous sodium carbonate (200 mL × 2), saturated saline (200 mL × 4), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 2-bromo-3-methylbenzonitrile (11 g, 100% yield) as an off-white solid.1H NMR (400 MHz, CDCl3): δ 7.51-7.45 (m, 2H), 7.33 -7.29 (m, 1H), 2.47 (s, 3H).

[References]

[1] Patent: WO2013/132376, 2013, A1. Location in patent: Page/Page column 226
[2] Organic Letters, 2018, vol. 20, # 3, p. 728 - 731
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 2, p. 644 - 651
[4] Patent: WO2011/22337, 2011, A1. Location in patent: Page/Page column 73-74
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