6-Methoxyquinoline-2-carbonitrile

Base Information

• Chemical Name: 6-Methoxyquinoline-2-carbonitrile
• CAS No.: 5467-79-8
• Molecular Formula: C11H8N2O
• Molecular Weight: 184.197
• Hs Code.: 2933499090
• European Community (EC) Number: 624-716-3
• NSC Number: 25415
• DSSTox Substance ID: DTXSID30282317
• Nikkaji Number: J836.244K
• Wikidata: Q82016558
• ChEMBL ID: CHEMBL223702
• Mol file: 5467-79-8.mol

Synonyms:6-methoxyquinoline-2-carbonitrile;5467-79-8;6-Methoxy-2-quinolinecarbonitrile;6-Methoxy-quinoline-2-carbonitrile;NSC-25415;CHEMBL223702;6-Methoxyquinaldonitrile;2-Cyano-6-methoxyquinoline;NSC25415;SCHEMBL906879;DTXSID30282317;BDBM50195864;NSC 25415;AKOS009098554;SB67550;6-Methoxy-2-quinolinecarbonitrile, 97%;NCGC00335416-01;AS-82935;FT-0714045;EN300-25443;AB01328499-02;SR-02000001213;SR-02000001213-1;Z204020258

Chemical Property of 6-Methoxyquinoline-2-carbonitrile

Chemical Property:

• Vapor Pressure: 1.96E-05mmHg at 25°C
• Melting Point: 175-179 °C
• Refractive Index: 1.627
• Boiling Point: 362.2 °C at 760 mmHg
• PKA: -0.61±0.43(Predicted)
• Flash Point: 172.9 °C
• PSA: 45.91000
• Density: 1.23 g/cm³
• LogP: 2.11508
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 184.063662883
• Heavy Atom Count: 14
• Complexity: 245

Purity/Quality:

98%,99%, ^*data from raw suppliers

6-Methoxyquinoline-2-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)N=C(C=C2)C#N

Technology Process of 6-Methoxyquinoline-2-carbonitrile

There total 15 articles about 6-Methoxyquinoline-2-carbonitrile 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%

6-methoxyquinoline N-oxide (6563-13-9) + trimethylsilyl cyanide (7677-24-9) → 2-cyano-6-methoxyquinoline (5467-79-8)

Guidance literature:

In neat (no solvent); at 130 ℃; for 1h; regioselective reaction; Sealed tube; Inert atmosphere;

DOI:10.1002/adsc.201901103

Reference yield: 88.0%

6-hydroxyquinoline-2-carbonitrile (52313-34-5) + methyl iodide (74-88-4) → 2-cyano-6-methoxyquinoline (5467-79-8)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 15h;

DOI:10.1021/acs.jmedchem.5b01066

Reference yield: 82.0%

6-methoxyquinoline N-oxide (6563-13-9) + silver(I) cyanide (506-64-9) → 2-cyano-6-methoxyquinoline (5467-79-8)

Guidance literature:

With benzoyl chloride; In chloroform; at 20 ℃; for 18h; Heating / reflux;

upstream raw materials:

6-methoxyquinoline N-oxide

potassium cyanide

benzoyl chloride

6-methoxy quinoline

Downstream raw materials:

N-(6-methoxy-2-methylquinolin-7-yl)-N-(phenylsulfonyl)benzenesulfonamide

N,N'-(6-methoxy-2-methylquinoline-5,7-diyl)bis(N-(phenylsulfonyl)benzenesulfonamide)

(S)-2-(6-hydroxyquinolin-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

2-Cyan-7-methoxy-benz-(1,3)-oxazepin

Refernces

• 1、 Spadoni, Gilberto,Bedini, Annalida,Lucarini, Simone,Mari, Michele,Caignard, Daniel-Henri,Boutin, Jean A.,Delagrange, Philippe,Lucini, Valeria,Scaglione, Francesco,Lodola, Alessio,Zanardi, Franca,Pala, Daniele,Mor, Marco,Rivara, Silvia. "Highly Potent and Selective MT2 Melatonin Receptor Full Agonists from Conformational Analysis of 1-Benzyl-2-acylaminomethyl-tetrahydroquinolines". . p. 7512 - 7525. Retrieved 2015.
• 2、 Sarmah, Bikash Kumar,Konwar, Monuranjan,Bhattacharyya, Dipanjan,Adhikari, Priyanka,Das, Animesh. "Regioselective Cyanation of Six-Membered N-Heteroaromatic Compounds Under Metal-, Activator-, Base- and Solvent-Free Conditions". . p. 5616 - 5625. Retrieved 2019/11/22.
• 3、 Ma, Wenpeng,Zhang, Jianwei,Xu, Cong,Chen, Fei,He, Yan-Mei,Fan, Qing-Hua. "Highly Enantioselective Direct Synthesis of Endocyclic Vicinal Diamines through Chiral Ru(diamine)-Catalyzed Hydrogenation of 2,2′-Bisquinoline Derivatives". . p. 12891 - 12894. Retrieved 2016/10/04.