3-Cyanopyridine

Base Information

• Chemical Name: 3-Cyanopyridine
• CAS No.: 100-54-9
• Molecular Formula: C6H4N2
• Molecular Weight: 104.111
• Hs Code.: 2933.33
• European Community (EC) Number: 202-863-0
• NSC Number: 17558
• UNII: X64V0K6260
• DSSTox Substance ID: DTXSID1026665
• Nikkaji Number: J149.678F
• Wikipedia: Nicotinonitrile
• Wikidata: Q18730591
• Metabolomics Workbench ID: 67388
• ChEMBL ID: CHEMBL3181972
• Mol file: 100-54-9.mol

Synonyms:3-cyanopyridine;nicotinic acid nitrile

Chemical Property of 3-Cyanopyridine

Chemical Property:

• Appearance/Colour: white to beige solid
• Vapor Pressure: 1.94mmHg at 25°C
• Melting Point: 48-52 °C(lit.)
• Refractive Index: 1.542
• Boiling Point: 202.985 °C at 760 mmHg
• PKA: pK1:1.45(+1) (25°C)
• Flash Point: 84.444 °C
• PSA: 36.68000
• Density: 1.159 g/cm³
• LogP: 0.95328
• Storage Temp.: Store below +30°C.
• Solubility.: 140g/l
• Water Solubility.: 140 g/L (20 ºC)
• XLogP3: 0.2
• 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:

99.9% ^*data from raw suppliers

3-Pyridinecarbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 22-24/25-36/37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C1=CC(=CN=C1)C#N
• Uses: 3-Cyanopyridine is used in the preparation of arylthiazolines and arylimidazolines via dibromodimethylhydantoin-catalyzed condensation of aryl nitriles with ethylene diamine or aminoethanethiol.

Technology Process of 3-Cyanopyridine

There total 165 articles about 3-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: 99.0%

3-pyridinecarboxaldehyde (500-22-1) → pyridine-3-carbonitrile (100-54-9,121697-66-3,1232169-17-3,68271-95-4)

Guidance literature:

With ammonium sulfate; sodium carbonate; sulfur; In dimethyl sulfoxide; at 120 ℃; for 10h; Sealed tube;

Reference yield: 99.0%

3-hydroxymethylpyridin (100-55-0) → pyridine-3-carbonitrile (100-54-9,121697-66-3,1232169-17-3,68271-95-4)

Guidance literature:

3-hydroxymethylpyridin; With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tert-butylhypochlorite; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

With ammonia; iodine; In dichloromethane; water; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1055/s-0033-1338489

Reference yield: 99.0%

nicotinamide (98-92-0,1255150-40-3) → pyridine-3-carbonitrile (100-54-9,121697-66-3,1232169-17-3,68271-95-4)

Guidance literature:

With N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; copper(l) chloride; In toluene; at 100 ℃; for 24h;

DOI:10.1007/s10562-011-0660-9

upstream raw materials:

pyridin-3-ylamine

3-Bromopyridine

nicotinic acid

toluene-4-sulfonamide

Downstream raw materials:

N-Phenacyl-3-cyanopyridiniumbromid

6-hydroxy-3-pyridinecarbonitrile

3-cyano-1-(4-nitro-benzyl)-pyridinium

1-benzyl-3-cyano-pyridinium

Refernces

• 1、 Yang, Fa-Liu,Zhu, Xinju,Rao, Dun-Kang,Cao, Xiao-Niu,Li, Ke,Xu, Yan,Hao, Xin-Qi,Song, Mao-Ping. "Highly efficient synthesis of primary amides: Via aldoximes rearrangement in water under air atmosphere catalyzed by an ionic ruthenium pincer complex". . p. 37093 - 37098. Retrieved 2016.
• 2、 Ilias, Md,Barman, Dhiren C,Prajapati, Dipak,Sandhu, Jagir S. "An indium mediated efficient chemoselective deoxygenation of N-oxides and nitrones". . p. 1877 - 1879. Retrieved 2002.
• 3、 Kagarlitskii,Iskakova,Turmukhambetov. "Catalytic conversion of nicotine into nicotinonitrile - A pharmaceutical intermediate product". . p. 26 - 27. Retrieved 2002.
• 4、 Janke, Christiane,Radnik, J?rg,Bentrup, Ursula,Martin, Andreas,Brückner, Angelika. "Ternary VZrALON oxynitrides - Efficient catalysts for the ammoxidation of 3-picoline". . p. 2687 - 2695. Retrieved 2014.
• 5、 Stazi, Federica,Palmisano, Giovanni,Turconi, Marco,Santagostino, Marco. "Statistical experimental design-driven discovery of room-temperature conditions for palladium-catalyzed cyanation of aryl bromides". . p. 1815 - 1818. Retrieved 2005.
• 6、 Furuya, Yoshiro,Ishihara, Kazuaki,Yamamoto, Hisashi. "Perrhenic acid-catalyzed dehydration from primary amides, aldoximes, N-monoacylureas, and α-substituted ketoximes to nitrile compounds". . p. 400 - 406. Retrieved 2007.
• 7、 Gagnon et al.. "-". . p. 1662,1666. Retrieved 1956.
• 8、 Kinarivala, Nihar,Trippier, Paul C.. "Exploration of relative chemoselectivity in the hydrodechlorination of 2-chloropyridines". . p. 5386 - 5389. Retrieved 2014.
• 9、 Bose, D. Subhas,Goud, P. Ravinder. "bis(trichloromethyl)carbonate, an efficient activator for the one-pot conversion of aldehydes into nitriles under mild conditions". . p. 3621 - 3624. Retrieved 2002.
• 10、 Chary, Komandur V.R.,Bhaskar, Thallada,Kishan, Gurram,Reddy, Kondakindi Rajender. "Characterization and reactivity of molybdenum oxide catalysts supported on niobia". . p. 4392 - 4399. Retrieved 2001.