3-Quinolinecarbonitrile

Base Information

• Chemical Name: 3-Quinolinecarbonitrile
• CAS No.: 34846-64-5
• Molecular Formula: C10H6 N2
• Molecular Weight: 154.171
• Hs Code.: 2933499090
• European Community (EC) Number: 252-248-6
• NSC Number: 44644
• UNII: 6GHZ8PDL63
• DSSTox Substance ID: DTXSID70188400
• Nikkaji Number: J289.851I
• Wikidata: Q72459195
• ChEMBL ID: CHEMBL4524183
• Mol file: 34846-64-5.mol

Synonyms:3-Quinolinecarbonitrile;Quinoline-3-carbonitrile;34846-64-5;3-Cyanoquinoline;CHEMBL4524183;EINECS 252-248-6;MFCD00006766;NSC 44644;NSC-44644;NSC44644;Quinoline-3-nitrile;Quinolin-3-carbonitrile;6GHZ8PDL63;SCHEMBL63442;3-Quinolinecarbonitrile, 98%;DTXSID70188400;BBL103644;BDBM50526481;STL557454;AKOS004910368;AC-8732;CS-W010935;SB36763;TS-02059;FT-0639216;EN300-51131;J-019781;Z609090814;KDV

Chemical Property of 3-Quinolinecarbonitrile

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.000258mmHg at 25°C
• Melting Point: 108-110 ºC
• Boiling Point: 323.7 °C at 760 mmHg
• PKA: 1.72±0.11(Predicted)
• Flash Point: 115.5 °C
• PSA: 36.68000
• Density: 1.21 g/cm³
• LogP: 2.10648
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 154.053098200
• Heavy Atom Count: 12
• Complexity: 203

Purity/Quality:

99%, ^*data from raw suppliers

Quinoline-3-carbonitrile ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(C=N2)C#N
• General Description: 3-Cyanoquinoline derivatives, including 3-Cyanoquinoline (NSC 44644), have demonstrated promising cytotoxic activity against various cancer cell lines, particularly showing selective potency against the SMMC-7721 liver cancer cell line. These compounds, designed as analogs of Gefitinib with a modified quinoline-3-carbonitrile scaffold, exhibit potential as anti-tumor agents, with structure-activity relationship studies indicating their viability for further development in cancer therapy.

Technology Process of 3-Quinolinecarbonitrile

There total 44 articles about 3-Quinolinecarbonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

potassium cyanide + 3-bromoquinoline (5332-24-1) → 3-cyanoquinoline (34846-64-5)

Guidance literature:

potassium cyanide; With acetic acid; In ethylene glycol; at 20 ℃; Sealed tube;

3-bromoquinoline; With P(t-Bu)3 Palladacycle Gen_. 3; potassium acetate; In 1,4-dioxane; water; at 60 ℃; for 16h; Sealed tube;

DOI:10.1039/c7sc03912c

Reference yield: 96.0%

3-bromoquinoline (5332-24-1) + potassium cyanide (151-50-8) → 3-cyanoquinoline (34846-64-5)

Guidance literature:

With tributyltin chloride; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In acetonitrile; at 80 ℃; for 17h;

DOI:10.1021/ol049621d

Reference yield: 95.0%

3-bromoquinoline (5332-24-1) + dicyanozinc (557-21-1) → 3-cyanoquinoline (34846-64-5)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; polymethylhydrosiloxane; palladium diacetate; In water; at 80 ℃; for 3h;

DOI:10.1016/j.tetlet.2007.02.018

upstream raw materials:

2,4-Dichloroquinoline-3-carbonitrile

3-bromoquinoline

copper(I) cyanide

potassium cyanide

Downstream raw materials:

3-quinolylcarboxaldehyde

quinoline-3-carboxylic acid

N-benzyl-3-cyanoquinolinium bromide

3-Cyano-1-(4-trifluoromethyl-benzyl)-quinolinium; bromide

Refernces

Synthesis and cytotoxicity studies of quinoline-3-carbonitrile derivatives

10.1016/j.cclet.2010.03.016

The study focuses on the design, synthesis, and in vitro cytotoxicity evaluation of a series of quinoline-3-carbonitrile derivatives against four cancer cell lines: A549 (lung), HT-29 (colon), MDA-MB-231 (breast), and SMMC-7721 (liver). The research aimed to develop potent and selective anti-tumor agents by replacing the quinazoline scaffold of Gefitinib, an EGFR tyrosine kinase inhibitor, with a quinoline-3-carbonitrile scaffold. The synthesized compounds were tested for their cytotoxic effects using the MTT assay, and the results showed that several of these derivatives exhibited superior selective cytotoxicity against the SMMC-7721 cell line compared to Gefitinib, with compound 11g being the most potent among them. The study also provided preliminary insights into the structure-activity relationships of these compounds, suggesting their potential as anti-cancer agents. Further research on their anti-tumor activities and detailed structure-activity relationships is ongoing.

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