2,3-Dichlorobenzoyl cyanide Chemical Properties

Melting point:

52-53 °C(Solv: ligroine (8032-32-4))

Boiling point:

309°C

Density 

1.446

Flash point:

141°C

storage temp. 

Sealed in dry,Room Temperature

form 

solid

color 

Cream

InChI

InChI=1S/C8H3Cl2NO/c9-6-3-1-2-5(8(6)10)7(12)4-11/h1-3H

InChIKey

FIBBFBXFASKAON-UHFFFAOYSA-N

SMILES

C1(C(=O)C#N)=CC=CC(Cl)=C1Cl

CAS DataBase Reference

77668-42-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

RIDADR 

UN3439

Hazard Note 

Irritant

HazardClass 

6.1

HS Code 

2926907090

2,3-Dichlorobenzoyl cyanide Usage And Synthesis

Chemical Properties

White Solid

Uses

2,3-Dichlorobenzoyl cyanide is an impurity of Lamotrigine (L173250), an anticonvulsant that is used in the treatment of bipolar and depression.

Synthesis

1. Synthesis of 2,3-dichlorobenzoyl cyanide 2,3-Dichlorobenzoyl chloride (20.0 g, 100 mmol) and cuprous iodide (I) (0.90 g, 4.7 mmol) were suspended in acetonitrile (50 mL) and stirred at room temperature until a yellow homogeneous solution was formed. Solid sodium cyanide (5.15 g, 110 mmol) was added slowly with a controlled addition time of 5-8 hours. After addition, stirring of the reaction mixture was continued for 1 h. The reaction progress was monitored by HPLC. The resulting inorganic salt (mainly NaCl) was removed by filtration and the filter cake was washed with acetonitrile (15 mL). Acetonitrile was removed by distillation under reduced pressure (~150 mbar). Sodium metabisulfite (Na2S2O3, 0-4 g, 3 mmol) was added to remove trace iodine. Finally, the product was purified by vacuum distillation (jacket temperature 140°C, boiling point 115°C/2 mbar) to give 2,3-dichlorobenzoyl cyanide in >80% yield and 100% purity (as determined by analytical HPLC) with a melting point of 60°C.

References

[1] Patent: WO2008/19798, 2008, A1. Location in patent: Page/Page column 12

2,3-Dichlorobenzoyl cyanide (77668-42-9)Related Product Information

• 2-Chlorobenzoyl chloride
• Benzoyl cyanide
• 2,4-Dichlorobenzyl chloride
• 2,3-Dichlorobenzoic acid
• (Z)-[cyano(2,3-dichlorophenyl)methylene]carbazamidine
• 3-Dechloro-4-chloro Lamotrigine
• 1,3-Dichlorobenzene
• Lamotrigine
• LaMotrigine IMpurity D
• Lamotrigine N2-Oxide
• 2,4-Dichlorobenzoyl Cyanide
• Lamotrigine Impurity 3
• Lamotrigine N2-Glucuronide
• (E)-3-[cyano(2,3-dichlorophenyl)methylene]carbazamidine
• Dibenzoylmethane
• LaMotrigine Related CoMpound C
• Lamotrigine Impurity 6
• Lamotrigine Impurity 4