| Identification | More | [Name]
2-Fluoro-4-cyanobenzyl bromide | [CAS]
105942-09-4 | [Synonyms]
2-FLUORO-4-CYANO-BENZYLBROMIDE
4-(BROMOMETHYL)-3-FLUOROBENZONITRILE
4-CYANO-2-FLUOROBENZYL BROMIDE
BENZONITRILE, 4-(BROMOMETHYL)-3-FLUORO-
4-Cyano-2-fluorobenzylbromide97%
4-Cyano-2-fluorbenzylbromid | [Molecular Formula]
C8H5BrFN | [MDL Number]
MFCD07368341 | [Molecular Weight]
214.03 | [MOL File]
105942-09-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
77 °C | [Boiling point ]
276.4±30.0 °C(Predicted) | [density ]
1.59±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
soluble in Methanol | [form ]
Solid | [color ]
Off-white | [Sensitive ]
Lachrymatory | [InChI]
InChI=1S/C8H5BrFN/c9-4-7-2-1-6(5-11)3-8(7)10/h1-3H,4H2 | [InChIKey]
ZESZAIOGACKOMB-UHFFFAOYSA-N | [SMILES]
C(#N)C1=CC=C(CBr)C(F)=C1 | [CAS DataBase Reference]
105942-09-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
C | [RIDADR ]
3439 | [Hazard Note ]
Corrosive/Lachrymatory | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29269090 |
| Hazard Information | Back Directory | [Chemical Properties]
White to yellow fine crystalline powder | [Uses]
2-Fluoro-4-cyanobenzyl bromide can be used in organic synthesis. | [Synthesis]
General procedure for the synthesis of 4-cyano-2-fluorobenzyl bromide from 3-fluoro-4-methylbenzonitrile: 3-fluoro-4-methylbenzonitrile (40 g, 296 mmol), N-bromosuccinimide (NBS, 63.2 g, 356 mmol), and benzoyl peroxide (3.6 g, 14.8 mmol) were dissolved in carbon tetrachloride (490 mL), and the reaction was performed at reflux for 16 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered. The filtrate was concentrated and purified by fast column chromatography (eluent: 0-5% ethyl acetate/hexane) to afford the target product 4-(bromomethyl)-3-fluorobenzonitrile (35.4 g, 56% yield). | [References]
[1] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 12, p. 1647 - 1650
[2] Organic and Biomolecular Chemistry, 2004, vol. 2, # 9, p. 1339 - 1352
[3] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 12, p. 1203 - 1207
[4] Patent: WO2016/109361, 2016, A2. Location in patent: Paragraph 00144
[5] Patent: US2010/240719, 2010, A1. Location in patent: Page/Page column 11 |
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