32710-65-9

Basic information

• Product Name: 2,6-Dichloroisonicotinonitrile
• Synonyms: 2,6-DICHLOROISONICOTINONITRILE;2,6-DICHLORO-4-CYANO-PYRIDINE;4-CYANO-2,6-DICHLOROPYRIDINE;4-PYRIDINECARBONITRILE,2,6-DICHLORO;2,6-DICHLOROPYRIDINE-4-CARBONITRILE;2,6-Dichloro-4-pyridinecarbonitrile;2,6-Dichloropyridine-4-carbonitrile, 4-Cyano-2,6-dichloropyridine;2,6-dichloro-2-cyano-1,2-dihydropyridine-4-carboxylic acid
• CAS NO: 32710-65-9
• Molecular Formula: C₆H₂Cl₂N₂
• Molecular Weight: 173
• EINECS: 604-596-9
• Product Categories: Pyridines
• Mol File: 32710-65-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 96 °C
• Boiling Point: 239.4 °C at 760 mmHg
• Flash Point: 98.6 °C
• Appearance: /
• Density: 1.5 g/cm³
• Vapor Pressure: 0.0403mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -4.76±0.10(Predicted)
• CAS DataBase Reference: 2,6-Dichloroisonicotinonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dichloroisonicotinonitrile(32710-65-9)
• EPA Substance Registry System: 2,6-Dichloroisonicotinonitrile(32710-65-9)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22
• Safety Statements: 26-36/37/39
• RIDADR: 3439
• Hazardous Substances Data: 32710-65-9(Hazardous Substances Data)

Usage

General Description

2,6-Dichloroisonicotinonitrile, also known as DCI or compound C-1305, is a chemical compound with the molecular formula C7H2Cl2N2. It has a molar mass of 191.01 grams per mole. 2,6-Dichloroisonicotinonitrile belongs to a class of organic compounds known as isocyanides or isonitriles, characterized by a carbon-nitrogen triple bond. The specific name "dichloroisonicotinonitrile" indicates that it is derived from isonicotinic acid and contains two chlorine atoms. This chemical is commonly used in research, including as a precursor in chemical syntheses, and can be hazardous if improperly handled, necessitating careful storage and handling procedures. Its appearance is typically a light yellow or colorless solid.

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

Upstream product

• 7719-09-7 thionyl chloride 
• 2464-63-3 2,6-dibromo-4-amidopyridine 
• 557-21-1 zinc(II) cyanide 
• 408492-27-3 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 
• 2402-78-0 2,6-dichloropyridine 
• 5398-44-7 2,6-dichloropyridine-4-carboxylic acid 
• 89281-13-0 2,6-dichloropyridine-4-carboxamide 
• 2587-02-2 2,6-dichloro-[4]pyridylamine 
• 151-50-8 potassium cyanide 
• 42521-08-4 2,6-dichloroisonicotinoyl chloride 

Downstream Products

• 88579-63-9 (2,6-dichloropyridin-4-yl)methanamine 
• 101990-69-6 (2,6-dichloropyridin-4-yl)methanol 
• 848499-11-6 2-chloro-6-(4-oxopiperidin-1-yl)isonicotinonitrile 
• 175421-96-2 4-cyano-2,6-di(meta-trifluoromethylphenoxy)-pyridine 
• 1367127-68-1 C₁₈H₁₀ClFN₂O 
• 1367127-70-5 C₃₀H₁₈F₂N₂O₂ 

Relevant articles and documents

Synthesis of novel pyridine and pyrimidine derivatives as potential inhibitors of HIV-1 reverse transcriptase using palladium-catalysed C-N cross-coupling and nucleophilic aromatic substitution reactions

Palladium-mediated cross-coupling reactions are used in the successful construction of a small library of flexible heteroatom-linked diarylpyridine target compounds, including pyridines bearing a secondary amide substituent. Heteroatom-linked diarylpyrimidine derivatives bearing a chlorine substituent are prepared by base-catalysed nucleophilic aromatic substitution reactions without the need for palladium catalysis.

Cyanation of arenes via iridium-catalyzed borylation

We report a method to conduct one-pot meta cyanation of arenes by iridium-catalyzed C-H borylation and copper-mediated cyanation of the resulting arylboronate esters. This process relies on a method to conduct the cyanation of arylboronic esters, and conditions for this new transformation are reported. Conditions for the copper-mediated cyanation of arylboronic acids are also reported. By the resulting sequence of borylation and cyanation, 1,3-disubstituted and 1,2,3-trisubstituted arenes and heteroarenes containing halide, ketone, ester, amide, and protected alcohol functionalities are converted to the corresponding meta-substituted aryl nitriles. The utility of this methodology is demonstrated through the conversion of a protected 2,6-disubstituted phenol to 4-cyano-2,6-dimethylphenol, which is an intermediate in the synthesis of the pharmaceutical etravirine. The utility of the method is further demonstrated by the conversion of 3-chloro-5-methylbenzonitrile, produced through the one-pot C-H borylation and cyanation sequence, to the corresponding 3,5-disubstituted aldehydes, ketones, amides, carboxylic acids, tetrazoles, and benzylamines.