| Identification | Back Directory | [Name]
4-(BROMOMETHYL)-2-FLUOROBENZONITRILE | [CAS]
222978-03-2 | [Synonyms]
4-CYANO-3-FLUOROBENZYL BROMIDE
4-Cyano-3-fluorobenzylbromide98%
4-Cyano-3-fluorobenzyl bromide 98%
4-(BROMOMETHYL)-2-FLUOROBENZONITRILE
Benzonitrile, 4-(bromomethyl)-2-fluoro-
4-(Bromomethyl)-2-fluorobenzonitrile 98%
4-Cyano-3-fluorobenzyl bromide, alpha-Bromo-2-fluoro-p-tolunitrile | [Molecular Formula]
C8H5BrFN | [MDL Number]
MFCD03094323 | [MOL File]
222978-03-2.mol | [Molecular Weight]
214.03 |
| Chemical Properties | Back Directory | [Melting point ]
44-45 °C | [Boiling point ]
275.6±30.0 °C(Predicted) | [density ]
1.59±0.1 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [solubility ]
Methanol (Slightly) | [form ]
Solid | [color ]
Off-White | [Sensitive ]
Lachrymatory |
| Hazard Information | Back Directory | [Uses]
4-(Bromomethyl)-2-fluorobenzonitrile is a useful building block for the preparation and optimization of the highly selective GLUT1 inhibitor, BAY-876. | [Synthesis]
2-Fluoro-4-methylbenzonitrile (10 g, 74.07 mmol) was used as a raw material, which was dissolved in 200 mL of chloroform, 1 g of benzoyl peroxide (BPO) was added, and stirred until completely dissolved. Subsequently, N-bromosuccinimide (NBS, 19.77 g, 11.11 mmol) was added in batches and the reaction mixture was refluxed for 12 hours. After completion of the reaction, it was cooled to room temperature and washed three times with saturated aqueous sodium bicarbonate solution, then three times with appropriate amount of water and finally three times with saturated brine. The solvent was removed by evaporation under reduced pressure and purified by column chromatography to give the light yellow liquid product 4-cyano-3-fluorobenzyl bromide (14.00 g) in 88.79% yield. | [References]
[1] Patent: CN106810552, 2017, A. Location in patent: Paragraph 0068; 0070; 0071
[2] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 1325 - 1344
[3] Organic and Biomolecular Chemistry, 2004, vol. 2, # 9, p. 1339 - 1352
[4] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 20, p. 2925 - 2930
[5] Journal of the American Chemical Society, 2001, vol. 123, # 9, p. 2107 - 2108 |
|
|