| Identification | More | [Name]
3-Cyano-4-methylpyridine | [CAS]
5444-01-9 | [Synonyms]
3-CYANO-4-METHYLPYRIDINE
4-METHYLNICOTINONITRILE
3-Cyano-4-picoline
4-Methylnicotinotrile
4-Methylpyridine-3-carbonitrile | [EINECS(EC#)]
611-143-9 | [Molecular Formula]
C7H6N2 | [MDL Number]
MFCD00234272 | [Molecular Weight]
118.14 | [MOL File]
5444-01-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
41-44°C | [Boiling point ]
108-111°C 20mm | [density ]
1.08±0.1 g/cm3(Predicted) | [Fp ]
108-111°C/20mm | [storage temp. ]
Keep Cold | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
2.45±0.18(Predicted) | [color ]
White to Orange to Green | [BRN ]
112016 | [InChI]
InChI=1S/C7H6N2/c1-6-2-3-9-5-7(6)4-8/h2-3,5H,1H3 | [InChIKey]
XLAPHZHNODDMDD-UHFFFAOYSA-N | [SMILES]
C1=NC=CC(C)=C1C#N | [CAS DataBase Reference]
5444-01-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
3439 | [Hazard Note ]
Harmful | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Uses]
3-Cyano-4-methylpyridine, is an intermediate for the synthesis of various pharmaceutical compounds, including inhibitors and anticancer agents. It can be used for the preparation of a series of azaindenoisoquinoline topoisomerase I I inhibitors and potential anticancer agents. | [Synthesis]
General procedure for the synthesis of 3-cyano-4-methylpyridine (112) from 3-cyano-4-methyl-2,6-dichloropyridine (Ref. J. Org. Chem. 1960, 25, 560-564): palladium dichloride (50 mg, 0.3 mmol) was added to a degassed 3-cyano-4-methyl-2,6-dichloropyridine (5.0 g, 27 mmol) and sodium acetate (4.5 g, 55 mmol) in a methanol (100 mL) solution. The reaction mixture was stirred under hydrogen (1 atm) atmosphere for 14 hours at room temperature. After completion of the reaction, the precipitate was filtered and washed with methanol (3 x 20 mL). The filtrates were combined, the solvent was removed by evaporation under reduced pressure and chloroform (50 mL) was added to the residue. The chloroform solution was filtered through a thin silica gel pad and the silica gel pad was washed with additional chloroform. The filtrate was evaporated to dryness to afford 3-cyano-4-methylpyridine (112) (2.9 g, 93% yield) as a yellow oil. The product was characterized by 1H NMR (300 MHz, DMSO-d6): δ 8.77 (s, 1H), 8.63 (s, J = 6.0 Hz, 1H), 7.3 (d, J = 6.0 Hz, 1H), 2.56 (s, 3H). The resulting 3-cyano-4-methylpyridine (112) can be used in subsequent reactions without further purification. | [References]
[1] Journal of Medicinal Chemistry, 2012, vol. 55, # 4, p. 1682 - 1697
[2] Patent: US2014/18360, 2014, A1. Location in patent: Paragraph 0146
[3] Patent: EP1348706, 2003, A1. Location in patent: Page/Page column 36
[4] Letters in Organic Chemistry, 2016, vol. 13, # 6, p. 450 - 452 |
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Alfa Aesar
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Energy Chemical
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www.energy-chemical.com |
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