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ChemicalBook--->CAS DataBase List--->89642-49-9

89642-49-9

89642-49-9 Structure

89642-49-9 Structure
IdentificationBack Directory
[Name]

4-BROMO-3-NITROBENZONITRILE
[CAS]

89642-49-9
[Synonyms]

4-BROMO-3-NITROBENZONITRILE
2-Bromo-5-cyanonitrobenzene
3-nitro-4-broMobenzonitrile
Benzonitrile, 4-bromo-3-nitro-
4-Bromo-3-nitrobenzonitrile 97%
4-BROMO-3-NITROBENZONITRILE ISO 9001:2015 REACH
[Molecular Formula]

C7H3BrN2O2
[MDL Number]

MFCD00982006
[MOL File]

89642-49-9.mol
[Molecular Weight]

227.01
Chemical PropertiesBack Directory
[Melting point ]

116-120 °C
[Boiling point ]

269℃
[density ]

1.81
[Fp ]

116℃
[storage temp. ]

2-8°C
[form ]

powder to crystal
[color ]

White to Light yellow to Light orange
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302
[Precautionary statements ]

P280-P305+P351+P338
[WGK Germany ]

3
[HS Code ]

2926907090
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethyl acetate-->Sodium bicarbonate-->Ammonium nitrate-->PERCHLORIC ACID-->3-Bromobenzonitrile-->K-CATALYST-->4-Bromobenzonitrile
[Preparation Products]

4-HYDRAZINO-3-NITROBENZONITRILE
Spectrum DetailBack Directory
[Spectrum Detail]

4-BROMO-3-NITROBENZONITRILE(89642-49-9)1HNMR
4-BROMO-3-NITROBENZONITRILE(89642-49-9)FT-IR
Hazard InformationBack Directory
[Synthesis]

4-Bromobenzonitrile

623-00-7

4-BROMO-3-NITROBENZONITRILE

89642-49-9

General procedure for the synthesis of 4-bromo-3-nitrobenzonitrile from 4-bromobenzonitrile: To a concentrated solution of 4-bromobenzonitrile (4.0 g, 22 mmol) was added concentrated sulfuric acid (10 mL) and nitric acid (6 mL) slowly and dropwise at 0 °C. The reaction mixture was kept stirred at 0 °C for 30 min, then warmed up to room temperature and continued stirring for 2.5 h. The reaction was carried out at room temperature. Upon completion of the reaction, the mixture was slowly poured into ice water. The resulting white precipitate was collected by filtration and washed with water until the washings were neutral. The resulting solid was recrystallized twice by ethanol/water solvent mixture (1:1, 20 mL) to finally obtain 4-bromo-3-nitrobenzonitrile as a white crystalline solid (2.8 g, 56% yield). The product was identified by 1H NMR (300 MHz, DMSO-d6): δ8.54 (s, 1H), 8.06 (d, J = 8.4 Hz, 1H), 7.99 (d, J = 8.4 Hz, 1H); 13C NMR (75 MHz, DMSO-d6) δ150.4,137.4,136.6,129.6,119.6, 117.0,112.6; HPLC retention time 1.96 min (10-100% CH3CN, gradient 5 min); ESI-MS m/z 227.1 ([MH]+).

[References]

[1] Patent: US2015/231142, 2015, A1. Location in patent: Paragraph 0673
[2] Recueil des Travaux Chimiques des Pays-Bas, 1922, vol. 41, p. 36
[3] Recueil des Travaux Chimiques des Pays-Bas, 1922, vol. 41, p. 106,107
[4] Chemische Berichte, 1916, vol. 49, p. 2224
[5] Chemische Berichte, 1890, vol. 23, p. 3442
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