2-Chloro-6-methyl-3-pyridinecarbonitrile Chemical Properties

Melting point:

114-116 °C (lit.)

Boiling point:

140-145 °C (lit.)

Density 

1.2763 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol

form 

Solid

pka

-1.21±0.10(Predicted)

color 

Pale Yellow

BRN 

120414

InChI

InChI=1S/C7H5ClN2/c1-5-2-3-6(4-9)7(8)10-5/h2-3H,1H3

InChIKey

YSBNBAYNISAUIT-UHFFFAOYSA-N

SMILES

C1(Cl)=NC(C)=CC=C1C#N

CAS DataBase Reference

28900-10-9(CAS DataBase Reference)

NIST Chemistry Reference

2-Chloro-3-cyano-6-methylpyridine(28900-10-9)

Safety Information

Hazard Codes 

Xn,T

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-37/39-36/37/39-22

RIDADR 

3276

WGK Germany 

3

Hazard Note 

Toxic

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Chloro-6-methyl-3-pyridinecarbonitrile Usage And Synthesis

Uses

2-Chloro-6-methyl-3-pyridinecarbonitrile, is a building block used for the synthesis of various biologically active compounds. It can be used for the preparation of 2-(Alkoxycarbonyl)-3-Anilinobenzo[b]thiophenes and Thieno[2,3-b]pyridines as new potent anticancer agents.

Chemical Properties

light yellow to brown cryst. flakes or needles

Uses

2-Chloro-6-methyl-3-pyridinecarbonitrile, is a building block used for the synthesis of various biologically active compounds. It can be used for the preparation of 2-(Alkoxycarbonyl)-3-Anilinobenzo[b]thiophenes and Thieno[2,3-b]pyridines as new potent anticancer agents.

Uses

2-Chloro-6-methyl-3-pyridinecarbonitrile (2-chloro-6-methylnicotinonitrile) may be used in the preparation of methyl-2-nitropyridinecarboxamides.

Synthesis

Step 1: 6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (45.0 g, 335 mmol) was added to phosphorochloridic acid (652 g, 4250 mmol) and the reaction was stirred at 130°C for 2 hours. After the reaction was completed, the reaction solution was concentrated and the resulting residue was dissolved in dichloromethane and the pH was adjusted to 8 by slowly adding 4 M aqueous sodium hydroxide.The organic layer was separated, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to give 2-chloro-6-methylnicotinonitrile (51.0 g, 99% yield).1H NMR (400 MHz, CDCl3) δ 2.65 (s, 3H), 7.24 (d, J = 8.0 Hz, 1H), 7.89 (d, J = 8.0 Hz, 1H).

References

[1] Patent: US2017/145005, 2017, A1. Location in patent: Paragraph 0149; 0150; 0151; 0152
[2] Heterocycles, 1995, vol. 41, # 6, p. 1307 - 1318
[3] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 2206 - 2210
[4] Polish Journal of Chemistry, 1982, vol. 56, # 2, p. 419 - 423
[5] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2014, vol. 69, # 5, p. 509 - 518

2-Chloro-6-methyl-3-pyridinecarbonitrile(28900-10-9)Related Product Information

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• 2,6-Lutidine
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• Basic Violet 1
• 2,4,6-Collidine
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