3,5-Dichloro-2-cyanopyridine Chemical Properties

Melting point:

101-103°C

Boiling point:

271.9±35.0 °C(Predicted)

Density 

1.49±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

-4.61±0.10(Predicted)

form 

powder to crystal

color 

White to Light yellow

BRN 

4390101

InChI

InChI=1S/C6H2Cl2N2/c7-4-1-5(8)6(2-9)10-3-4/h1,3H

InChIKey

ATUOLSDAAPMVJJ-UHFFFAOYSA-N

SMILES

C1(C#N)=NC=C(Cl)C=C1Cl

CAS DataBase Reference

85331-33-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

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

RIDADR 

3439

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

2933399990

MSDS

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3,5-Dichloro-2-cyanopyridine Usage And Synthesis

Chemical Properties

Yellow to light brown crystalline powder

Uses

3,5-Dichloro-2-cyanopyridine is an intermediate in the industrial synthesis of nicotinic acid and nicotinamide.

Synthesis

General procedure for the synthesis of 2-cyano-3,5-dichloropyridine from 3,5-dichloropyridine 1-oxide and trimethylcyanosilane: 21.8 mL (0.174 mol) of trimethylcyanosilane and 14.6 mL (0.158 mol) of dimethylcarbamoyl chloride were sequentially added to 26 g (0.158 mol) of 3,5-dichloropyridine 1-oxide in an 80-mL dichloromethane solution. The reaction mixture was stirred at room temperature for 48 hours. After the reaction was completed, 100 mL of 10% aqueous NaHCO3 solution was added and stirred vigorously for 10 minutes. After separating the organic and aqueous phases, the aqueous phase was extracted once with dichloromethane. All organic phases were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane as eluent. The target fraction was collected, concentrated and recrystallized from a small amount of methanol to give 11 g (40.2% yield) of 2-cyano-3,5-dichloropyridine with a melting point of 102 °C. The target fraction was collected, concentrated and recrystallized from a small amount of methanol.

References

[1] Patent: US2003/232842, 2003, A1. Location in patent: Page 8

3,5-Dichloro-2-cyanopyridine(85331-33-5)Related Product Information

• 2,3-Dichloropyridine
• 2,5-Dichloropyridine
• 2-Cyanopyridine
• 3-Aminopyridine
• Clopyralid
• 2-Chloro-5-chloromethylpyridine
• 3,5-Dichloropyridine
• 5-Bromo-3-nitropyridine-2-carbonitrile
• 2-Cyano-3-fluoropyridine
• 5-bromo-3-methylpicolinonitrile
• 2-Cyano-3-chloropyridine
• 2-Cyano-3,5-difluoropyridine
• 3-bromo-5-chloropyridine-2-carbonitrile
• 5-bromo-3-chloropyridine-2-carbonitrile
• 2-Cyano-3-trifluoromethylpyridine
• 5-Chloro-3-nitropyridine-2-carbonitrile
• 5-Bromo-3-fluoro-pyridine-2-carbonitrile
• 3-Bromo-5-methylpyridine-2-carbonitrile