| Identification | Back Directory | [Name]
6-Bromomethyl-nicotinonitrile | [CAS]
158626-15-4 | [Synonyms]
6-Bromomethyl-nicotinonitrile
6-Bromomethy1-micotinonitrile
2-(Bromomethyl)-5-cyanopyridine
2-(Bromomethyl)pyridine-5-carbonitrile
6-(bromomethyl)pyridine-3-carbonitrile
3-Pyridinecarbonitrile, 6-(bromomethyl)-
6-Bromomethyl-nicotinonitrile ISO 9001：2015 REACH | [Molecular Formula]
C7H5BrN2 | [MDL Number]
MFCD11227190 | [MOL File]
158626-15-4.mol | [Molecular Weight]
197.03 |
| Chemical Properties | Back Directory | [Boiling point ]
286.5±30.0 °C(Predicted) | [density ]
1.60±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [form ]
solid | [pka]
0.00±0.22(Predicted) | [color ]
Red |
| Hazard Information | Back Directory | [Uses]
6-(Bromomethyl)nicotinonitrile has been used as a reactant in the synthesis of oxadiazoles as selective S1P receptor agonists that may be used in the treatment of relapsing forms of MS. | [Synthesis]
Example 50 General procedure for the preparation of 6-bromomethylnicotinonitrile (11-2): to a solution of 6-methylnicotinonitrile (11-1) (15 g, 127 mmol) in carbon tetrachloride (300 mL) was added N-bromosuccinimide (27.12 g, 152.4 mmol). The reaction mixture was degassed and displaced three times with nitrogen, followed by the addition of AIBN (2,2'-azobisisobutyronitrile) (2.08 g, 12.6 mmol). After stirring the reaction at 85 °C for 7 h, AIBN (1.04 g) was added and the reaction was continued for 1 h. The reaction was completed with the addition of AIBN (2,2'-Azobisisobutyronitrile). After completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography with the eluent being a mixed solvent of ethyl acetate/hexane to give 10 g of the target product 6-bromomethylnicotinonitrile in 40% yield. | [References]
[1] Patent: WO2007/28083, 2007, A2. Location in patent: Page/Page column 74-75
[2] Inorganic Chemistry, 2014, vol. 53, # 15, p. 7824 - 7836
[3] Patent: WO2016/201052, 2016, A1. Location in patent: Page/Page column 265
[4] Patent: WO2013/102145, 2013, A1. Location in patent: Paragraph 0351
[5] Patent: US2015/344483, 2015, A1. Location in patent: Paragraph 0649; 0650 |
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