3-Chloro-4-cyanopyridine

Base Information

• Chemical Name: 3-Chloro-4-cyanopyridine
• CAS No.: 68325-15-5
• Molecular Formula: C6H3ClN2
• Molecular Weight: 138.556
• Hs Code.: 29333990
• European Community (EC) Number: 640-747-5
• DSSTox Substance ID: DTXSID40443311
• Nikkaji Number: J2.121.240G
• Wikidata: Q72518007
• Mol file: 68325-15-5.mol

Synonyms:3-Chloro-4-cyanopyridine;68325-15-5;3-chloroisonicotinonitrile;3-chloropyridine-4-carbonitrile;MFCD05663706;3-Chloro-isonicotinonitrile;4-PYRIDINECARBONITRILE, 3-CHLORO-;3-CHLORO-4-PYRIDINECARBONITRILE;SCHEMBL190868;3-chloro-4-pyridine carbonitrile;4-Pyridinecarbonitrile,3-chloro-;DTXSID40443311;JLLJPPBGJVCFGG-UHFFFAOYSA-N;BCP34252;BBL101845;GEO-03482;STL555642;AKOS005199115;AB21895;AC-1913;CS-W003228;PS-4536;AM804228;SY007546;A9107;C2998;FT-0647768;EN300-100844;2,3-Butanediol,1,4-dimercapto-, (2R,3S)-rel-;J-512222;Z1201623149

Chemical Property of 3-Chloro-4-cyanopyridine

Chemical Property:

• Appearance/Colour: Pale yellow solid
• Vapor Pressure: 0.056mmHg at 25°C
• Melting Point: 71-73°C
• Refractive Index: 1.566
• Boiling Point: 233.304 °C at 760 mmHg
• PKA: -0.41±0.18(Predicted)
• Flash Point: 94.899 °C
• PSA: 36.68000
• Density: 1.331 g/cm³
• LogP: 1.60668
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 137.9984758
• Heavy Atom Count: 9
• Complexity: 137

Purity/Quality:

98.0% Min., ^*data from raw suppliers

3-Chloro-4-cyanopyridine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN=CC(=C1C#N)Cl
• Uses: 3-Chloro-4-cyanopyridine (cas# 68325-15-5) is a compound useful in organic synthesis.

Technology Process of 3-Chloro-4-cyanopyridine

There total 2 articles about 3-Chloro-4-cyanopyridine 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:

3-Chloropyridine (626-60-8) + trimethylsilyl cyanide (7677-24-9) → 2-cyano-5-chloropyridine (89809-64-3) + 3-chloro-2-cyanopyridine (38180-46-0) + 3-chloro-isonicotinonitrile (68325-15-5)

Guidance literature:

3-Chloropyridine; With trifluoromethylsulfonic anhydride; In chloroform; at 20 ℃; for 1h; Inert atmosphere; Sealed tube;

trimethylsilyl cyanide; In chloroform; at 60 ℃; for 3h; Inert atmosphere; Sealed tube;

With 4-methyl-morpholine; In chloroform; at 60 ℃; for 17h; Overall yield = 63 %; Inert atmosphere; Sealed tube;

DOI:10.1002/chem.201703931

Reference yield:

1-methyl-1H-imidazole (616-47-7) + chloroform (67-66-3,8013-54-5) → 2-chloropyrazin (14508-49-7) + 5-chloropyrimidine (17180-94-8) + 5-chloronicotinonitrile (51269-82-0) + 3-chloro-isonicotinonitrile (68325-15-5)

Guidance literature:

at 550 ℃; Yield given. Further byproducts given. Yields of byproduct given;

DOI:10.1039/P19800001431

Reference yield: 97.0%

N,N'-dimethylbenzylamine (103-83-3) + 3-chloro-isonicotinonitrile (68325-15-5) → C14H15ClN2

Guidance literature:

With thiobenzoic acid; dipotassium hydrogenphosphate; fac-tris(2-phenylpyridinato-N,C₂')iridium(III); In N,N-dimethyl acetamide; at 20 ℃; for 2h; regioselective reaction; Irradiation;

DOI:10.1039/c8sc02965b

upstream raw materials:

1-methyl-1H-imidazole

chloroform

3-Chloropyridine

trimethylsilyl cyanide

Downstream raw materials:

4-acetyl-3-chloropyridine

3-methoxypyridine-4-carbonitrile

3-amino-2-carbomethoxythieno[2,3-c]pyridine

4-cyano-3-(phenylethynyl)pyridine

Refernces

• 1、 Busby, Reginald E.,Khan, Mohammad A.,Khan, Mohammad R.,Parrick, John,Shaw, C. J. Granville. "Reactions of Halogenomethanes in the Vapour Phase. Part 5. The Reactions of Imidazolines, Anils, and 1-Methylimidazole with Chloroform at 550 deg C, and a Comparison with their Liquid-Phase Reactions with Trichloroacetate Ion or Hexachloroacetone and Base". . p. 1431 - 1435. Retrieved 2007/10/02.