101617-91-8

Basic information

• Product Name: 2-CHLORO-6-METHOXYQUINOLINE-3-CARBONITRILE
• Synonyms: AKOS BB-7576;2-CHLORO-6-METHOXYQUINOLINE-3-CARBONITRILE
• CAS NO: 101617-91-8
• Molecular Formula: C₁₁H₇ClN₂O
• Molecular Weight: 218.63908
• Mol File: 101617-91-8.mol
• Article Data: 9

Chemical Properties

• Melting Point: 157-160 °C
• Boiling Point: 396.5°Cat760mmHg
• Flash Point: 193.6°C
• Appearance: /
• Density: 1.36g/cm³
• Vapor Pressure: 1.71E-06mmHg at 25°C
• Refractive Index: 1.64
• PKA: -2.94±0.50(Predicted)
• CAS DataBase Reference: 2-CHLORO-6-METHOXYQUINOLINE-3-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-6-METHOXYQUINOLINE-3-CARBONITRILE(101617-91-8)
• EPA Substance Registry System: 2-CHLORO-6-METHOXYQUINOLINE-3-CARBONITRILE(101617-91-8)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25-41
• Safety Statements: 45-39-26
• Hazardous Substances Data: 101617-91-8(Hazardous Substances Data)

Usage

General Description

2-Chloro-6-methoxyquinoline-3-carbonitrile is a chemical compound with the molecular formula C11H7ClN2O. It is a quinoline derivative that contains a chlorine atom, a methoxy group, and a carbonitrile group. 2-CHLORO-6-METHOXYQUINOLINE-3-CARBONITRILE is used in organic synthesis and pharmaceutical research as a building block for the development of new drugs and functional materials. It has potential applications in the pharmaceutical industry as a key intermediate in the synthesis of various bioactive molecules. Additionally, it may also have uses in the field of agrochemicals and materials science.

InChI:InChI=1/C11H7ClN2O/c1-15-9-2-3-10-7(5-9)4-8(6-13)11(12)14-10/h2-5H,1H3

Upstream product

• 73568-29-3 2-chloro-6-methoxyquinolin-3-carboxaldehyde 
• 51-66-1 4-methoxyacetanilide 

Downstream Products

• 95733-92-9 (2-Chloro-6-methoxy-quinolin-3-yl)-phenyl-methanone 
• 1415354-59-4 1-benzyl-7-methoxy-1H-pyrimido[4,5-b]quinolin-4-one 
• 1415354-69-6 2-(benzylamino)-6-methoxyquinoline-3-carbonitrile 
• 1371588-07-6 4-(3-cyano-6-hydroxyquinolin-2-yl)benzoic acid 
• 1371588-96-3 4-(3-cyano-6-methoxyquinolin-2-yl)benzoic acid 
• 125918-13-0 C₁₈H₁₆N₄O₂S 
• 123990-79-4 6-methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile 

Relevant articles and documents

An alternate route to the synthesis of imidazo[1,2-a]quinolines using I2-NaI reagent

A new and a facile route to the synthesis of imidazo[1,2-a]quinolines has been described via iodocyclization reaction of 2-allylaminoquinoline derivatives using I2-NaI reagent.

lH-Pyrazolo[3,4-b]quinolin-3-amine derivatives inhibit growth of colon cancer cells via apoptosis and sub G1 cell cycle arrest

A series of lH-pyrazolo[3,4-b]quinolin-3-amine derivatives were synthesized and evaluated for anticancer efficacy in a panel of ten cancer cell lines, including breast (MDAMB-231 and MCF-7), colon (HCT-116, HCT-15, HT-29 and LOVO), prostate (DU-145 and PC3), brain (LN-229), ovarian (A2780), and human embryonic kidney (HEK293) cells, a non-cancerous cell line. Among the eight derivatives screened, compound QTZ05 had the most potent and selective antitumor efficacy in the four colon cancer cell lines, with IC50 values ranging from 2.3 to 10.2 μM. Furthermore, QTZ05 inhibited colony formation in HCT-116 cells in a concentration-dependent manner. Cell cycle analysis data indicated that QTZ05 caused an arrest in the sub G1 cell cycle in HCT-116 cells. QTZ05 induced apoptosis in HCT-116 cells in a concentration-dependent manner that was characterized by chromatin condensation and increase in the fluorescence of fluorochrome-conjugated Annexin V. The findings from our study suggest that QTZ05 may be a valuable prototype for the development of chemotherapeutics targeting apoptotic pathways in colorectal cancer cells.

A one pot method of conversion of aldehydes into nitriles using iodine in ammonia water: Synthesis of 2-chloro-3-cyanoquinolines

One pot rapid transformations of heteroaromatic carbaldehyde to cyano group using cheap and easily available iodine in aqueous ammonia has been described.