| Identification | More | [Name]
2-Chloro-4-cyanopyridine | [CAS]
33252-30-1 | [Synonyms]
2-CHLORO-4-CYANOPYRIDINE
2-CHLORO-4-PYRIDINECARBONITRILE
2-CHLOROISONICOTINONITRILE
2-CHLOROPYRIDINE-4-CARBONITRILE
4-CYANO-2-CHLORO PYRIDINE
BUTTPARK 43\57-01
2-CHLORO-4-CYANOPYRIDINE 99+%
2-CHLORO-4-CYANOPYRIDINE 2-CHLORO-ISONICOTINONITRILE
2-Chloro-4-Cyano Pyridine 99%
2-Chloro-4-cyanopyridine ,98% | [EINECS(EC#)]
608-852-0 | [Molecular Formula]
C6H3ClN2 | [MDL Number]
MFCD00174318 | [Molecular Weight]
138.55 | [MOL File]
33252-30-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
69-73 °C(lit.)
| [Boiling point ]
104-106°C 15mm | [density ]
1.33±0.1 g/cm3(Predicted) | [Fp ]
104-106°C/15mm | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
-1.60±0.10(Predicted) | [color ]
White to Almost white | [Detection Methods]
HPLC,NMR | [BRN ]
113927 | [InChI]
InChI=1S/C6H3ClN2/c7-6-3-5(4-8)1-2-9-6/h1-3H | [InChIKey]
QRXBTPFMCTXCRD-UHFFFAOYSA-N | [SMILES]
C1(Cl)=NC=CC(C#N)=C1 | [CAS DataBase Reference]
33252-30-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
3276 | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white solid | [Uses]
2-Chloro-4-cyanopyridine is an intermediate used to prepare pyrrolopyridine inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2). It is also used to synthesize pyridinyl-tetrazoles as scaffold to identify matrix MMP-13 inhibitors for treatment of osteoarthritis. | [Synthesis]
The general procedure for the synthesis of 2-chloro-4-cyanopyridine from 4-cyanopyridine N-oxide was as follows: 120 g of 4-cyanopyridine-N-oxide, 360 mL of 1,2-dichloroethane, and 183.6 g of phosphorochloridic acid were added sequentially in a 1000 mL three-necked reaction flask. After the reaction system was cooled to -2±2°C, 151.5 g of triethylamine was added slowly dropwise for a controlled dropwise time of 2 hours. After the dropwise addition, the reaction was continued at the same temperature with stirring for 2 hours. Upon completion of the reaction, the reaction solution was concentrated by reduced pressure distillation until no fractions flowed out. 240 mL of water was added to the concentrated solution and a large amount of solid was precipitated after thorough stirring. The solid was collected by filtration and the filter cake was washed with appropriate amount of water to obtain 117.5 g of white solid product 2-chloro-4-cyanopyridine. | [References]
[1] Tetrahedron Letters, 2001, vol. 42, # 39, p. 6815 - 6818
[2] Patent: CN104945383, 2017, B. Location in patent: Paragraph 0031; 0035; 0036 |
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