3-Isoquinolinecarbonitrile

Base Information

• Chemical Name: 3-Isoquinolinecarbonitrile
• CAS No.: 26947-41-1
• Molecular Formula: C10H6N2
• Molecular Weight: 154.171
• Hs Code.: 29334900
• European Community (EC) Number: 620-659-3
• DSSTox Substance ID: DTXSID10408098
• Nikkaji Number: J1.467.094G
• Wikidata: Q72486422
• Mol file: 26947-41-1.mol

Synonyms:3-Isoquinolinecarbonitrile;26947-41-1;isoquinoline-3-carbonitrile;3-Cyanoisoquinoline;MFCD00075136;3-cyano-isoquinoline;SCHEMBL507331;3-Isoquinolinecarbonitrile, 99%;DTXSID10408098;CHEBI:194843;AKOS005206756;AC-7699;SY062299;TS-02060;A5281;AM20051013;CS-0043954;FT-0627509;J-016629

Chemical Property of 3-Isoquinolinecarbonitrile

Chemical Property:

• Vapor Pressure: 4.88E-05mmHg at 25°C
• Melting Point: 126-128 °C(lit.)
• Refractive Index: 1.654
• Boiling Point: 348.9 °C at 760 mmHg
• PKA: 0.57±0.30(Predicted)
• Flash Point: 121.6 °C
• PSA: 36.68000
• Density: 1.21 g/cm³
• LogP: 2.10648
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water.
• XLogP3: 2.2
• 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:

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

3-Isoquinolinecarbonitrile 95% ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C=NC(=CC2=C1)C#N
• Uses: 3-Isoquinolinecarbonitrile was employed as analytical standard to study the thermal degradation of 2-chlorobenzylidenemalononitrile (CS riot control agent) at elevated temperatures.

Technology Process of 3-Isoquinolinecarbonitrile

There total 8 articles about 3-Isoquinolinecarbonitrile 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: 92.0%

isoquinoline-3(S)-carboxamide (50458-77-0) → 3-cyanoisoquinoline (26947-41-1)

Guidance literature:

With triethylamine; trifluoroacetic anhydride; In dichloromethane; at 0 ℃; for 0.0333333h;

Reference yield: 40.0%

2-aminoacetonitrile (540-61-4) + o-phthalic dicarboxaldehyde (643-79-8) → 3-cyanoisoquinoline (26947-41-1)

Guidance literature:

With sodium ethanolate; magnesium sulfate; In ethanol; for 4h; Heating;

DOI:10.1016/S0040-4039(00)02128-6

Reference yield:

(R,S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (67123-97-1) → 3-cyanoisoquinoline (26947-41-1)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂SO₄

2: Pd/C / xylene / Heating

3: 98 percent / methanolic NH₃ / Ambient temperature

4: 92 percent / triethylamine, trifluoroacetic anhydride / CH₂Cl₂ / 0.03 h / 0 °C

With palladium on activated charcoal; sulfuric acid; ammonia; triethylamine; trifluoroacetic anhydride; In dichloromethane; xylene;

upstream raw materials:

isoquinoline-3(S)-carboxamide

isoquinoline-3-aldoxime

2-aminoacetonitrile

o-phthalic dicarboxaldehyde

Downstream raw materials:

3-acetylisoquinoline

3-isoquinolinecarbothioamide

3-(aminomethyl)isoquinoline dihydrochloride

2-amino-3-(4-chlorobenzoyl)isoquinolinium tosylate

Refernces

• 1、 Ameur Meziane, Mohamed A?t,Royer, Sylvain,Bazureau, Jean Pierre. "A practical 'one-pot' synthesis of ethyl isoquinoline-3-carboxylate by domino reactions: A potential entry to constrained nonproteogenic amino acid derivatives". . p. 1017 - 1020. Retrieved 2007/10/03.