Identification | Back Directory | [Name]
4-Pyridinecarbonitrile,2-formyl-(9CI) | [CAS]
116308-38-4 | [Synonyms]
2-forMylisonicotinonitrile 2-Formylpyridine-4-carbonitrile 2-forMyl-4-pyridinecarbonitrile 4-Cyanopyridine-2-carboxaldehyde 4-Cyano-2-pyridinecarboxaldehyde 4-Pyridinecarbonitrile, 2-formyl- 4-Pyridinecarbonitrile,2-formyl-(9CI) 4-Pyridinecarbonitrile,2-formyl-(9CI) ISO 9001:2015 REACH | [Molecular Formula]
C7H4N2O | [MDL Number]
MFCD12546404 | [MOL File]
116308-38-4.mol | [Molecular Weight]
132.12 |
Chemical Properties | Back Directory | [Boiling point ]
201.0±20.0℃ (760 Torr) | [density ]
1.24±0.1 g/cm3 (20 ºC 760 Torr) | [Fp ]
75.4±21.8℃ | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [pka]
-0.45±0.10(Predicted) | [Appearance]
Light yellow to yellow Solid |
Hazard Information | Back Directory | [Synthesis]
Oxalyl chloride (13.2 mL, 150 mmol) was dissolved in anhydrous dichloromethane (86 mL) under nitrogen protection and cooled to -78°C. Dimethyl sulfoxide (21.2 mL) was added slowly dropwise over 20 min and the reaction mixture was stirred at -78°C for 15 min. Subsequently, 4-cyanopyridine-2-methanol (4.0 g, 30 mmol) dissolved in anhydrous dichloromethane (60 mL) was added dropwise to the reaction mixture over a period of 5 min and stirring was continued for 2 h while maintaining -78°C and a nitrogen atmosphere. Formation of a white solid precipitate was observed during the reaction. The reaction temperature was raised to -55°C and triethylamine (6.15 mL, 450 mmol) was added dropwise over 15 minutes. The cooling bath was removed and the reaction mixture was allowed to warm naturally to room temperature over a period of 2 hours. Upon completion of the reaction, the mixture was diluted with dichloromethane (400 mL), washed successively with brine (2 x 50 mL), and the aqueous phase was then back-extracted with dichloromethane (3 x 50 mL). All organic layers were combined and concentrated under reduced pressure to give a light yellow solid product. The product did not require further purification and showed a single peak by LC-MS analysis with a retention time (RT) of 2.53 min and a mass spectrometry (M + H) peak located at m/z 133.0 in quantitative yield. | [References]
[1] Patent: WO2006/21801, 2006, A1. Location in patent: Page/Page column 65-66 [2] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458 [3] Patent: US6043248, 2000, A [4] Patent: WO2006/21801, 2006, A1. Location in patent: Page/Page column 46-47 [5] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 559 - 576 |
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