5-Chloro-2-cyanopyridine

Base Information

• Chemical Name: 5-Chloro-2-cyanopyridine
• CAS No.: 89809-64-3
• Molecular Formula: C6H3ClN2
• Molecular Weight: 138.556
• Hs Code.: 29333990
• European Community (EC) Number: 640-750-1
• DSSTox Substance ID: DTXSID90397072
• Wikidata: Q72518005
• Mol file: 89809-64-3.mol

Synonyms:5-Chloro-2-cyanopyridine;89809-64-3;5-chloropicolinonitrile;5-chloropyridine-2-carbonitrile;6-Cyano-3-chloropyridine;2-Cyano-5-chloro pyridine;2-Pyridinecarbonitrile, 5-chloro-;5-chloro-2-cyano pyridine;5-chloro-2-pyridinecarbonitrile;MFCD03788835;3-Chloro-6-cyanopyridine;2-cyano-5-chloropyridine;5-chloropicolinenitrile;SCHEMBL69932;5-chloro-pyridine-2-carbonitrile;DTXSID90397072;WTHODOKFSYPTKA-UHFFFAOYSA-N;5-chloranylpyridine-2-carbonitrile;BCP22240;BBL100618;RB1002;STL554412;AKOS005255050;AC-5432;CS-W019579;PS-3446;SY007565;AM20070055;C3023;FT-0601009;EN300-100627;A843328;Q-101262

Chemical Property of 5-Chloro-2-cyanopyridine

Chemical Property:

• Appearance/Colour: Light yellow cryst.
• Vapor Pressure: 0.0403mmHg at 25°C
• Melting Point: 106-108℃
• Refractive Index: 1.565
• Boiling Point: 239.3 °C at 760 mmHg
• PKA: -2.60±0.10(Predicted)
• Flash Point: 98.5 °C
• Density: 1.33 g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Methanol
• XLogP3: 1.5
• 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:

99% ^*data from raw suppliers

6-Cyano-3-chloropyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T， Xi
• Hazard Codes: T,Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=NC=C1Cl)C#N
• Uses: 6-Cyano-3-chloropyridine (cas# 89809-64-3) is a compound useful in organic synthesis.

Technology Process of 5-Chloro-2-cyanopyridine

There total 14 articles about 5-Chloro-2-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: 85.0%

3-chloropyridine-N-oxide (1851-22-5) + trimethylsilyl cyanide (7677-24-9) → 2-cyano-5-chloropyridine (89809-64-3) + 3-chloro-2-cyanopyridine (38180-46-0)

Guidance literature:

With triethylamine; In acetonitrile; for 6h; Heating;

Reference yield: 70.0%

copper(I) cyanide (544-92-3) + 5-chloro-2-iodo-pyridine (244221-57-6) → 2-cyano-5-chloropyridine (89809-64-3)

Guidance literature:

With pyridine; at 130 ℃; for 1.5h;

DOI:10.1021/jm050292k

Reference yield: 59.0%

2,5 dichloropyridine (16110-09-1) + dicyanozinc (557-21-1) → 2-cyano-5-chloropyridine (89809-64-3)

Guidance literature:

With zinc; bis(diphenylphosphino)dipalladium (II) CH₂Cl₂ complex; at 160 - 185 ℃;

upstream raw materials:

ethanedinitrile

chloroprene

1-methyl-1H-imidazole

chloroform

Downstream raw materials:

5-chloro-N'-hydroxypyridine-2-carboximidamide

6-cyano-N-(piperidine-1-carbonyl)nicotinamide

1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethanamine

(5-chloropyridin-2-yl)(3-fluoro-5-(trifluoromethyl)phenyl)methanimine

Refernces

• 1、 Elbert, Bryony L.,Farley, Alistair J. M.,Gorman, Timothy W.,Johnson, Tarn C.,Genicot, Christophe,Lallemand, Bénédicte,Pasau, Patrick,Flasz, Jakub,Castro, José L.,MacCoss, Malcolm,Paton, Robert S.,Schofield, Christopher J.,Smith, Martin D.,Willis, Michael C.,Dixon, Darren J.. "C?H Cyanation of 6-Ring N-Containing Heteroaromatics". supporting information. p. 14733 - 14737. Retrieved 2017/10/07.
• 2、 Zhang, Han-Zhong,Kasibhatla, Shailaja,Kuemmerle, Jared,Kemnitzer, William,Ollis-Mason, Kristin,Qiu, Ling,Crogan-Grundy, Candace,Tseng, Ben,Drewe, John,Cai, Sui Xiong. "Discovery and structure-activity relationship of 3-aryl-5-aryl-1,2,4- oxadiazoles as a new series of apoptosis inducers and potential anticancer agents". . p. 5215 - 5223. Retrieved 2007/10/03.