2-Cyanopyridine

Base Information

• Chemical Name: 2-Cyanopyridine
• CAS No.: 100-70-9
• Molecular Formula: C6H4N2
• Molecular Weight: 104.111
• Hs Code.: 29333999
• European Community (EC) Number: 202-880-3
• NSC Number: 59697
• UNII: WHR1DPG7YS
• DSSTox Substance ID: DTXSID9021843
• Nikkaji Number: J58.011B
• Wikidata: Q27103368
• Metabolomics Workbench ID: 51475
• ChEMBL ID: CHEMBL3185861
• Mol file: 100-70-9.mol

Synonyms:pyridine-2-carbonitrile

Chemical Property of 2-Cyanopyridine

Chemical Property:

• Appearance/Colour: white to brown low melting crystalline solid
• Vapor Pressure: 0.0861mmHg at 25°C
• Melting Point: 26-28 °C
• Refractive Index: n20/D 1.529(lit.)
• Boiling Point: 225.5 °C at 760 mmHg
• PKA: pK1:-0.26(+1) (25°C)
• Flash Point: 89.4 °C
• PSA: 36.68000
• Density: 1.12 g/cm³
• LogP: 0.95328
• Storage Temp.: 2-8°C
• Solubility.: 67g/l
• Water Solubility.: immiscible
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 104.037448136
• Heavy Atom Count: 8
• Complexity: 111

Purity/Quality:

99% ^*data from raw suppliers

2-Cyanopyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C1=CC=NC(=C1)C#N
• Uses: 2-Cyanopyridine is a cyano substituted pyridine. 2-Cyanopyridine is a related compound of nicotine and is a component of tobacco smoke condensate. It is employed as an important chemical intermediate for rimiterol hydrobromide and used as a bronchodilator. It is also used as intermediates of pharmaceutical and dye and pigment. It acts as a precursor of the respective amidate for protein modification via amidation.

Technology Process of 2-Cyanopyridine

There total 149 articles about 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: 17.0%

(E/Z)-N-(3-Cyanopropyliden)asparaginsaeuredinitril → 2-Cyanopyridine (100-70-9,1232006-36-8) + pyridine-3-carbonitrile (100-54-9,121697-66-3,1232169-17-3,68271-95-4) + 2-methyl-(1H)-pyrrole-3-carbonitrile (26187-27-9) + 1,4-dihydronicotinamide (23974-91-6)

Guidance literature:

With 4 A molecular sieve; at 550 ℃; under 0.1 Torr; Further byproducts given. Title compound not separated from byproducts;

DOI:10.1002/hlca.19940770814

Reference yield: 1.3%

(E/Z)-N-(3-Cyanopropyliden)asparaginsaeuredinitril → 2-Cyanopyridine (100-70-9,1232006-36-8) + pyridine-3-carbonitrile (100-54-9,121697-66-3,1232169-17-3,68271-95-4) + 2-methyl-(1H)-pyrrole-3-carbonitrile (26187-27-9) + pyrrole-3-carbonitrile (7126-38-7)

Guidance literature:

With 4 A molecular sieve; at 550 ℃; under 0.1 Torr;

DOI:10.1002/hlca.19940770814

Reference yield:

Anabasine (494-52-0) → pyridine (110-86-1) + 2-Cyanopyridine (100-70-9,1232006-36-8) + pyridine-3-carbonitrile (100-54-9,121697-66-3,1232169-17-3,68271-95-4)

Guidance literature:

With ammonia; water; oxygen; vanadia; titanium(IV) oxide; at 360 - 440 ℃; Further Variations:; contact time; Product distribution;

DOI:10.1007/BF02236296

upstream raw materials:

1,4-dioxane

potassium cyanide

1-Methoxypyridinium iodide

α-picoline

Downstream raw materials:

pyridin-2-yl(pyridin-4-yl)methanone

2,2'-dipyridyl ketone

N-(2-pyridyl)-2-pyridinecarboxamidine

2-cyano-isonicotinic acid ethyl ester

Refernces

• 1、 Kim, Ha Young,Lantrip, Douglas A.,Fuchs, Philip L.. "Relative reactivity of anti- and syn-oximino carbonates and carbamates of 2-pyridylacetic acid esters". . p. 2137 - 2140. Retrieved 2001.
• 2、 Zhang, Xingjie,Xia, Aiyou,Chen, Haoyi,Liu, Yuanhong. "General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN)2: Key Roles of DMAP". . p. 2118 - 2121. Retrieved 2017.
• 3、 Li, Yamei,Zhao, Yujun,Wang, Shengping,Ma, Xinbin. "Silica supported potassium oxide catalyst for dehydration of 2-picolinamide to form 2-cyanopyridine". . p. 494 - 498. Retrieved 2019.
• 4、 Fukazawa, Yasuaki,Rubtsov, Aleksandr E.,Malkov, Andrei V.. "A Mild Method for Electrochemical Reduction of Heterocyclic N-Oxides". . p. 3317 - 3319. Retrieved 2020.
• 5、 Syvorov et al.. "-". . . Retrieved 1973.
• 6、 Hawkins,Janz. "-". . p. 1790. Retrieved 1952.
• 7、 McAllister, Graeme D.,Wilfred, Cecilia D.,Taylor, Richard J. K.. "Tandem oxidation processes: The direct conversion of activated alcohols into nitriles". . p. 1291 - 1292. Retrieved 2002.
• 8、 Chelucci, Giorgio. "Hydrodehalogenation of halogenated pyridines and quinolines by sodium borohydride/N,N,N′,N′-tetramethylethylenediamine under palladium catalysis". . p. 1562 - 1565. Retrieved 2010.
• 9、 Mosalkova, Anastasiya P.,Voitekhovich, Sergei V.,Lyakhov, Alexander S.,Ivashkevich, Ludmila S.,Lach, Jochen,Kersting, Berthold,Gaponik, Pavel N.,Ivashkevich, Oleg A.. "2-tert-Butyl-5-(2-pyridyl)-2H-tetrazole as a chelating ligand in the direct synthesis of novel Cu(ii) and heterobimetallic Cu(ii)/Mn(ii) complexes". . p. 2985 - 2997. Retrieved 2013.
• 10、 Fife, Wilmer K.. "Regioselective Cyanation of Pyridine 1-Oxides with Trimethylsilanecarbonitrile: A Modified Reissert-Henze Reaction". . p. 1375 - 1377. Retrieved 1983.