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Chemical PropertiesBack Directory
[Appearance]

White to off-white Solid
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302
[Precautionary statements ]

P280-P305+P351+P338
[HS Code ]

2928009090
Spectrum DetailBack Directory
[Spectrum Detail]

Benzonitrile, 2-broMo-4-hydrazinyl-(263845-82-5)1HNMR
Hazard InformationBack Directory
[Synthesis]

2-Bromo-4-fluorobenzonitrile

36282-26-5

Benzonitrile, 2-broMo-4-hydrazinyl-

263845-82-5

Example 4a Preparation of 2-bromo-4-hydrazinobenzonitrile: Anhydrous hydrazine (10 mL) was slowly added to a solution of 2-bromo-4-fluorobenzonitrile (5.00 g, 25.00 mmol) in tetrahydrofuran (THF, 10 mL) through an addition funnel under dry conditions. After the addition was completed, the reaction mixture was stirred at room temperature for 24 hours. Upon completion of the reaction, water (20 mL) was added to the mixture to quench the reaction. The resulting white precipitate was collected by diafiltration and washed well with deionized water. Subsequently, the product was dried in a vacuum oven at 40 °C to afford 2-bromo-4-hydrazinylbenzonitrile (4.92 g, 93% yield) as a white solid. The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3): δ 8.05 (br s, 1H), 7.47 (d, J = 8.7 Hz, 1H), 7.06 (d, J = 2.0 Hz, 1H), 6.72 (dd, J = 8.7, 2.0 Hz, 1H), 4.37 (br s, 2H); ESI MS m/z 212 [M + H]+.

[References]

[1] Patent: US2008/119457, 2008, A1. Location in patent: Page/Page column 45
[2] Patent: WO2006/91963, 2006, A1. Location in patent: Page/Page column 83; 84; 96
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 14, p. 4288 - 4305
[4] Patent: US2007/207984, 2007, A1. Location in patent: Page/Page column 24
[5] Patent: US2015/329493, 2015, A1. Location in patent: Paragraph 0228; 0242; 0243
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