128259-63-2

Basic information

• Product Name: 2-CHLORO-7-METHOXYQUINOLINE-3-CARBONITRILE
• Synonyms: 2-CHLORO-7-METHOXYQUINOLINE-3-CARBONITRILE;AKOS BB-7574;OTAVA-BB 1049560
• CAS NO: 128259-63-2
• Molecular Formula: C₁₁H₇ClN₂O
• Molecular Weight: 218.63908
• Mol File: 128259-63-2.mol

Chemical Properties

• Boiling Point: 396.5°C at 760 mmHg
• Flash Point: 193.6°C
• Appearance: /
• Density: 1.36g/cm³
• Vapor Pressure: 1.71E-06mmHg at 25°C
• Refractive Index: 1.64
• CAS DataBase Reference: 2-CHLORO-7-METHOXYQUINOLINE-3-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-7-METHOXYQUINOLINE-3-CARBONITRILE(128259-63-2)
• EPA Substance Registry System: 2-CHLORO-7-METHOXYQUINOLINE-3-CARBONITRILE(128259-63-2)

Safety Data

• Hazard Codes: T
• Statements: 25-41
• Safety Statements: 26-39-45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 128259-63-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-7-methoxyquinoline-3-carbonitrile is used as an intermediate in the synthesis of various drugs for its ability to be chemically modified and incorporated into complex molecular structures. Its unique functional groups allow for a wide range of reactions, facilitating the development of new therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, 2-chloro-7-methoxyquinoline-3-carbonitrile serves as a key intermediate in the production of pesticides and other crop protection agents. Its chemical properties enable the creation of compounds that can effectively target and control pests, thereby enhancing crop yields and quality.

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

Upstream product

• 91818-29-0 2-cyano-N-(3-methoxyphenyl)acetamide 
• 588-16-9 m-methoxyacetanilide 
• 536-90-3 m-Anisidine 
• 68236-20-4 2-chloro-7-methoxyquinoline-3-carbaldehyde 
• 128259-57-4 (E)-2-Cyano-3-dimethylamino-N-(3-methoxy-phenyl)-acrylamide 

Downstream Products

• 158583-97-2 (E)-1-(3-Amino-7-methoxy-thieno[2,3-b]quinolin-2-yl)-3-phenyl-propenone 
• 158584-00-0 (E)-1-(3-Amino-7-methoxy-thieno[2,3-b]quinolin-2-yl)-3-(4-methoxy-phenyl)-propenone 
• 1415354-61-8 1-benzyl-8-methoxy-1H-pyrimido[4,5-b]quinolin-4-one 
• 485335-41-9 2-(benzylamino)-7-methoxyquinoline-3-carbonitrile 
• 1100051-07-7 7-methoxy-2-phenylethynyl-quinoline-3-carbonitrile 
• 116705-02-3 7-Methoxy-2-thioxo-1,2-dihydro-quinoline-3-carbonitrile 

Relevant articles and documents

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.

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.

Base-catalyzed cyclization reaction of 2-chloroquinoline-3-carbonitriles and guanidine hydrochloride: A rapid synthesis of 2-amino-3H-pyrimido[4,5-b] quinolin-4-ones

t-BuOK-catalyzed cyclization of 2-chloroquinoline-3-carbonitriles with guanidine hydrochloride provided simple and rapid synthesis of 2-amino-3H-pyrimido[4,5-b]quinolin-4-ones in very short reaction time with good yield. Other 1,3-binucleophiles are found to react at the same rate. This methodology could be extended with their 3-formyl and 3-ester derivatives for the synthesis of pyrimido annulated quinolines.

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.

Pyrazolo-fused quinoline analogues: Synthesis of 1H-pyrazolo [3, 4-b] quinolines and 3-amino-1H-pyrazolo [3, 4-b] quinolines from 3-formyl and 3-cyano-2-chloroquinolines

Stepwise synthesis of 1H-pyrazolo [3, 4-b] quinolines 6 has been described from the reactions of 2-chloro-3-formylquinolines 1 with ethyleneglycol and hydrazine hydrate reagents in sequence followed by hydrolysis with BiCl 3. However, 3-amino-1H-pyrazolo[3, 4-b]quinolines 7 have been synthesized from 2-chloro-3-cyanoquinolines 2 with excess of hydrazine hydrate in one step. The functional group manipulation of amino group in compounds 7 has also been studied.

Synthesis of 2-aryl-1,2,3,4-tetrahydropyridothienoquinolin-4-ones

The synthesis of a new tetracyclic condensed quinoline system is reported by a novel method.The method involves β-enamino carbonyl compound as starting material to get 1-quinolin-2-yl>-3-aryl-2-propen-1-one, which in turn is cyclised

Pyrazolo[3,4-b]quinolines and their use as antiviral agents

Pyrazolo[3,4-b]quinolines having the formula STR1 where R is hydrogen, hydroxy or alkoxy; R2 is halogen, cyano, carbamyl, carboxy, lower-alkylcarbonyl, amino or aminomethyl; and R1 is hydrogen or selected substituents as defined herein, are useful as antiviral agents and/or as vasodilators.

Synthesis of Quinolines via Cyclization of 2-Cyano-3-dimethylamino-N-(aryl)acrylamides

A simple synthesis of 2-cyano-3-dimethylamino-N-(aryl)-acrylamides and their subsequent conversion to 2-chloro-3-cyanoquinolines is presented.