Cinnoline

Base Information

• Chemical Name: Cinnoline
• CAS No.: 253-66-7
• Molecular Formula: C8H6 N2
• Molecular Weight: 130.149
• Hs Code.: 2933990090
• European Community (EC) Number: 205-964-8
• NSC Number: 58374
• UNII: N5KD6I506O
• DSSTox Substance ID: DTXSID60179943
• Nikkaji Number: J5.441K
• Wikipedia: Cinnoline
• Wikidata: Q413130
• Metabolomics Workbench ID: 55434
• ChEMBL ID: CHEMBL479792
• Mol file: 253-66-7.mol

Synonyms:cinnoline;hexahydrocinnoline

Chemical Property of Cinnoline

Chemical Property:

• Vapor Pressure: 0.0168mmHg at 25°C
• Melting Point: 38°; mp 40-41° (Morley); mp 24-25°
• Refractive Index: 1.6231 (estimate)
• Boiling Point: 263.4°Cat760mmHg
• PKA: 2.37(at 20℃)
• Flash Point: 120.7°C
• PSA: 25.78000
• Density: 1.183g/cm³
• LogP: 1.62980
• Storage Temp.: 2-8°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 130.053098200
• Heavy Atom Count: 10
• Complexity: 114

Purity/Quality:

99% ^*data from raw suppliers

Cinnoline 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CN=N2

Technology Process of Cinnoline

There total 22 articles about Cinnoline 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: 99.0%

N,N-diethyl-N'-(2-ethynylphenyl)triazene → Cinnoline (253-66-7)

Guidance literature:

In 1,2-dichloro-benzene; at 200 ℃;

DOI:10.1021/ol006517x

Reference yield: 93.0%

3,3-diethyl-1-(2-ethynylphenyl)triaz-1-ene (265670-91-5) → Cinnoline (253-66-7)

Guidance literature:

In 1,2-dichloro-benzene; at 200 ℃; Sealed tube; Inert atmosphere;

DOI:10.1002/jhet.4111

Reference yield: 62.0%

C18H17N3 (477909-61-8) → Cinnoline (253-66-7)

Guidance literature:

In 1,2-dichloro-benzene; at 200 ℃; for 24h;

DOI:10.1021/ja027809r

upstream raw materials:

cinnoline

4(1H)-cinnolon

cinnoline-4-carboxylic acid

pyridazine-3,4-dicarboxylic acid anhydride

Downstream raw materials:

8-nitrocinnoline

5-nitrocinnoline

4-isopropylidene-1,1-dimethyl-[1,3,4]oxadiazino[4,3-a]cinnolin-2-one

1,2-dibenzoyl-4-cyano-1,2-dihydrocinnoline

Refernces

• 1、 Ucar, Sefa,Dastan, Arif. "One-pot homo- and cross-coupling of diazanaphthalenes via C-H substitution: Synthesis of Bis- and Tris-diazanaphthalenes". . p. 4013 - 4022. Retrieved 2020/09/21.
• 2、 Kimball, David B.,Weakley, Timothy J. R.,Haley, Michael M.. "Cyclization of 1-(2-alkynylphenyl)-3,3-dialkyltriazenes: A convenient, high-yield synthesis of substituted cinnolines and isoindazoles". . p. 6395 - 6405. Retrieved 2007/10/03.