4-Bromo-pyridine-2-carbonitrile
4-Bromo-pyridine-2-carbonitrile
CAS: 62150-45-2
Molecular Formula: C6H3BrN2
4-Bromo-pyridine-2-carbonitrile - Names and Identifiers
| Name | 4-Bromo-pyridine-2-carbonitrile |
| Synonyms | AURORA 23233 OTAVA-BB BB7110952495 4-Bromopicolinonitrile 4-BROMO-2-CYANOPYRIDINE 4-Bromopyridine-2-carbonitrile 4-BroMo-2-pyridinecarbonitrile 4-Bromo-pyridine-2-carbonitrile 4-BROMO-PYRIDINE-2-CARBONITRILE 2-pyridinecarbonitrile, 4-bromo- 4-Bromo-2-cyanopyridine, 4-Bromopicolinonitrile |
| CAS | 62150-45-2 |
| EINECS | 688-035-3 |
| InChI | InChI=1/C8H8BrNO2/c1-2-12-8(11)7-5-6(9)3-4-10-7/h3-5H,2H2,1H3 |
4-Bromo-pyridine-2-carbonitrile - Physico-chemical Properties
| Molecular Formula | C6H3BrN2 |
| Molar Mass | 183.01 |
| Density | 1.72±0.1 g/cm3(Predicted) |
| Melting Point | 82-84°C |
| Boling Point | 265.3±20.0 °C(Predicted) |
| Solubility | Chloroform (Slightly), Ethyl Acetate (Slightly) |
| Appearance | Solid |
| Color | Off-White to Light Beige |
| pKa | -2.73±0.10(Predicted) |
| Storage Condition | under inert gas (nitrogen or Argon) at 2-8°C |
| Refractive Index | 1.544 |
| MDL | MFCD04065805 |
4-Bromo-pyridine-2-carbonitrile - Risk and Safety
| UN IDs | 3439 |
| Hazard Class | 6.1 |
| Packing Group | Ⅲ |
4-Bromo-pyridine-2-carbonitrile - Reference Information
| Application | 4-bromopyridine-2-carbonitrile, 4-bromo-2-cyanopyridine. 4-bromopyridine-2-carbonitrile 4-bromopyridine 1-oxide can be prepared from 4-bromopyridine hydrochloride by first oxidation and then cyano substitution to give 4-bromopyridine-2-carbonitrile. 4-bromopyridine-2-carbonitrile can be used as a starting material for the synthesis of the antitumor drug sorafenib. |
| preparation | A. 4-bromopyridine 1-oxide at room temperature. To a suspension of 4-bromopyridine hydrochloride (5.0g,25.9mmol) in dichloromethane (50ml) was added triethylamine (2.62g,25.9mmol). After stirring for 0.5H, 3-chloroperoxybenzoic acid (4.46g,25.9mmol) was added portionwise and the reaction mixture was stirred for 5h at room temperature. The solution was washed with saturated aqueous sodium thiosulfate (30ml), saturated aqueous sodium carbonate (30ml) and brine (30ml) and dried over sodium sulfate. The solvent was removed under reduced pressure to give the crude product, which was purified by chromatography on silica gel (eluting with 50-100% ethyl acetate in methanol) to give 4-bromopyridine 1-oxide as a solid (2.1g,44.8% yield).. B .4-bromopyridine-2-carbonitrile. 4-bromopyridine 1-oxide (2.0g,11.56mmol), trimethylsilyl cyanide (3.43g,34.68mmol) and triethylamine (2.34g,23.12mmol) in acetonitrile (10ml) the mixture was stirred at 110 °c for 3H under nitrogen. The reaction mixture was concentrated under reduced pressure and the residue was purified on a silica gel column eluting with 20% ethyl acetate in petroleum ether to give 4-bromopyridine-2-carbonitrile (1.52g,72.4% yield). |
Last Update：2024-04-09 15:16:52
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