66909-36-2

Basic information

• Product Name: 6-chloro-2-methylnicotinonitrile
• Synonyms: 6-chloro-2-methylnicotinonitrile;6-CHLORO-2-METHYLPYRIDINE-3-CARBONITRILE;6-chloro-3-isocyano-2-methylpyridine;6-chloro-3-cyano-2-methylpyridine;6-Chloro-3-cyanopicoline;6-chloro-2-Methyl-3-pyridinecarbonitrile;2-Methyl pyridine-3-base-6-chlorine cyanide
• CAS NO: 66909-36-2
• Molecular Formula: C₇H₅ClN₂
• Molecular Weight: 152.58
• EINECS: -0
• Product Categories: Pyridine series
• Mol File: 66909-36-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 106-110 °C
• Boiling Point: 246.462 °C at 760 mmHg
• Flash Point: 102.857 °C
• Appearance: /
• Density: 1.269 g/cm³
• Vapor Pressure: 0.027mmHg at 25°C
• Refractive Index: 1.555
• Storage Temp.: 2-8°C
• PKA: -2.60±0.10(Predicted)
• CAS DataBase Reference: 6-chloro-2-methylnicotinonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 6-chloro-2-methylnicotinonitrile(66909-36-2)
• EPA Substance Registry System: 6-chloro-2-methylnicotinonitrile(66909-36-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 66909-36-2(Hazardous Substances Data)

Usage

General Description

6-chloro-2-methylnicotinonitrile is a chemical compound with the molecular formula C7H6ClN2. It is a nitrile derivative of 6-chloro-2-methylnicotinic acid, commonly used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. 6-chloro-2-methylnicotinonitrile is known for its versatile properties and is utilized in the production of various substances including drugs, insecticides, and herbicides. It is also used as a building block for more complex chemical structures due to its reactivity and stability. Additionally, 6-chloro-2-methylnicotinonitrile is considered to be a valuable precursor in organic synthesis due to its ability to undergo various chemical transformations.

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

Upstream product

• 41877-40-1 6-hydroxy-2-methylpyridine-3-carbonitrile 
• 824-72-6 P,P-dichlorophenylphosphine oxide 
• 1336-21-6 ammonium hydroxide 
• 41877-40-1 1,6-Dihydro-2-methyl-6-oxo-3-pyridinecarbonitrile 

Downstream Products

• 1150111-55-9 phenylmethyl 4-[(5-cyano-6-methyl-2-pyridinyl)oxy]benzoate 
• 1150100-29-0 C₁₄H₁₃N₃O₃S 
• 116986-12-0 2-(bromomethyl)nicotinonitrile 

Relevant articles and documents

A facile and green synthesis of a naphthyridine derivative: A novel hedgehog pathway modulator

A green and highly efficient synthesis of a naphthyridine derivative, a novel hedgehog pathway modulator, in high yield and purity from inexpensive starting materials is described. The key step involves an acid-promoted aryl amination reaction of aniline

One-Step Synthetic Access to Isosteric and Potent Anticancer Nitrogen Heterocycles with the Benzo[c]phenanthridine Scaffold

A versatile one-step two-component cyclization to build new tetracyclic nitrogen heterocycles is described. Ortho-methylhetarenecarbonitrile components were condensed with aldehydes to access a large library of differently substituted ring systems. The heterocyclic core can be easily modified by variation of the position of the endocyclic nitrogen atom in the o-methylhetarenecarbonitrile substrate. The manner of the nucleophilic attack that leads to the condensation can be triggered by different electron-density distribution in the molecule induced by the position of the nitrogen atom. Taking this into account, there is an electronic preference that leads to either pyridophenanthrolines or the corresponding pyridoazacarbazoles as the main products. We demonstrate the high antitumor potential of some of our synthesized heterocycles, which is strongly dependent on the substitution pattern introduced through the aldehyde component. The position and number of endocyclic nitrogen atoms play an important role regarding cytotoxicity of the studied compounds. Isosteric nitrogen heterocycles: A large library of heterocycles, some possessing promising anticancer properties, with different substitution patterns is accessible by a facile one-step cyclization method through application of different aldehydes and distinct o-methylhetarenecarbonitrile components with diverse numbers of nitrogen atoms at various positions in the ring (see scheme).

Azaindenoisoquinolines as topoisomerase i inhibitors and potential anticancer agents: A systematic study of structure-activity relationships

A comprehensive study of a series of azaindenoisoquinoline topoisomerase I (Top1) inhibitors is reported. The synthetic pathways have been developed to prepare 7-, 8-, 9-, and 10-azaindenoisoquinolines. The present study shows that 7-azaindenoisoquinolines possess the greatest Top1 inhibitory activity and cytotoxicity. Additionally, the introduction of a methoxy group into the D-ring of 7-azaindenoisoquinolines improved their biological activities, leading to new lead molecules for further development. A series of QM calculations were performed on the model "sandwich" complexes of azaindenoisoquinolines with flanking DNA base pairs from the Drug-Top1-DNA ternary complex. The results of these calculations demonstrate how changes in two forces contributing to the π-π stacking (dispersion and charge-transfer interactions) affect the binding of the drug to the Top1-DNA cleavage complex and thus modulate the drug's Top1 inhibitory activity.