| Identification | More | [Name]
2-FLUORO-3-FORMYLPYRIDINE | [CAS]
36404-90-7 | [Synonyms]
2-FLUORO-3-FORMYLPYRIDINE
2-FLUORO-3-PYRIDINECARBOXALDEHYDE
2-FLUORONICOTINALDEHYDE
2-FLUOROPYRIDINE-3-CARBALDEHYDE
2-FLUOROPYRIDINE-3-CARBOXALDEHYDE
3-Pyridinecarboxaldehyde,2-fluoro-(9CI)
3-Pyridinecarboxaldehyde, 2-fluoro- | [Molecular Formula]
C6H4FNO | [MDL Number]
MFCD03095270 | [Molecular Weight]
125.1 | [MOL File]
36404-90-7.mol |
| Chemical Properties | Back Directory | [Boiling point ]
50 °C/3 mmHg | [density ]
1.250 g/mL at 25 °C
| [refractive index ]
n20/D 1.520
| [Fp ]
164 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
liquid | [pka]
-2.23±0.10(Predicted) | [color ]
Clear, dark yellow | [InChIKey]
OFBVGDCXXGXDKU-UHFFFAOYSA-N | [CAS DataBase Reference]
36404-90-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
2933399990 |
| Hazard Information | Back Directory | [Uses]
Attachment of isoxazolinones by displacement of fluoride provide naphthyridines on hydrogenolysis and cyclization. | [Synthesis]
GENERAL STEPS: Lithium (trimethylsilylmethyl) (22 mL, 13.8 wt% hexane solution) was added to a 100 mL three-necked round-bottomed flask and the reaction system cooled to -50 °C. A mixed solution containing 2-fluoropyridine (2.0 g), THF (25 mL), and diisopropylamine (0.13 mL) was slowly added over 1 min while keeping the temperature below -50 °C. After 3 hours of reaction, 1-formylpiperidine (2.4 g) was added over 1 min, also at below -50 °C. Subsequently, the reaction mixture was gradually warmed to room temperature and stirring was continued overnight. Upon completion of the reaction, the reaction was quenched with acetic acid (3 mL) and water (7 mL). The aqueous layer was separated and washed with methyl tert-butyl ether (MTBE, 3 x 25 mL). All organic layers were combined, dried with anhydrous magnesium sulfate (MgSO?) and concentrated under reduced pressure to give 3.79 g of brown oil. Finally, the oily material was purified by silica gel column chromatography, using a hexane solution of 15% ethyl acetate as eluent, to give 2.24 g of 2-fluoro-3-pyridinecarboxaldehyde with a purity of 92.4% (90% yield, corrected for assay). | [References]
[1] Patent: WO2004/92125, 2004, A2. Location in patent: Page 7-8
[2] Journal of Organometallic Chemistry, 1991, vol. 406, # 1+2, p. 49 - 56 |
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