2,6-Dichloro-4-methylnicotinonitrile Chemical Properties

Melting point:

108-112 °C(lit.)

Boiling point:

118 °C / 5mmHg

Density 

1.42±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

0.4g/l

pka

-4.53±0.10(Predicted)

form 

solid

PH

3.5 (H2O, 20℃)(aqueous suspension)

Appearance

White to light brown Solid

InChI

InChI=1S/C7H4Cl2N2/c1-4-2-6(8)11-7(9)5(4)3-10/h2H,1H3

InChIKey

LSPMHHJCDSFAAY-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

875-35-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xi

Risk Statements 

20/21-25-37/38-41-43-36/37/38

Safety Statements 

26-36/37/39-45-36

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333990

MSDS

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

2,6-Dichloro-4-methylnicotinonitrile Usage And Synthesis

Chemical Properties

White to light brown powder

Uses

2,6-Dichloro-4-methylnicotinonitrile is a pharmaceutical intermediate compound of Nevirapine, a non-nucleoside reverse transcriptase inhibitor (NNRTI) used in the treatment of human immunodeficiency virus (HIV).

Synthesis

General procedure for the synthesis of 3-cyano-4-methyl-2,6-dichloropyridine from 6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile: 6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (28.0 g, 195.2 mmol) was dissolved in phosphorus triclosan (60.0 mL). The reaction mixture was transferred to a pressure tube, sealed and heated to 180 °C for 6 hours. Upon completion of the reaction, it was cooled to room temperature and excess phosphorous trichloride was removed by distillation under reduced pressure. Crushed ice was slowly added to the residue and a solid was precipitated. The solid was collected by filtration and dried under vacuum to afford the target product 3-cyano-4-methyl-2,6-dichloropyridine in 92% yield without further purification.

References

[1] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 3, p. 979 - 984
[2] Patent: WO2014/165232, 2014, A1. Location in patent: Paragraph 0174; 0175
[3] Patent: US2015/119387, 2015, A1. Location in patent: Paragraph 0175; 0176
[4] Patent: JP2017/95498, 2017, A. Location in patent: Paragraph 0079; 0080
[5] Patent: CN104530042, 2017, B. Location in patent: Paragraph 0171; 0177; 0178; 0179

2,6-Dichloro-4-methylnicotinonitrile(875-35-4)Related Product Information

• Basic Violet 1
• 2-Chloro-5-chloromethylpyridine
• 2,6-Dichloropyridine
• Methyl acrylate
• Methyl salicylate
• Methanol
• Tribenuron methyl
• 4-Methylpyridine
• 3-Cyanopyridine
• 2,6-Lutidine
• Clopyralid
• 3-Cyano-4-methylpyridine
• Methylparaben
• Kresoxim-methyl
• Methyl
• 2-Chloro-3-picoline
• 2-Chloro-5-methylpyridine
• 2-Chloro-4-picoline