4-Cyanopyridine

Base Information

• Chemical Name: 4-Cyanopyridine
• CAS No.: 100-48-1
• Molecular Formula: C6H4N2
• Molecular Weight: 104.111
• Hs Code.: 2933.33
• European Community (EC) Number: 202-856-2
• NSC Number: 60681
• UNII: BY3226D010
• DSSTox Substance ID: DTXSID9041528
• Nikkaji Number: J39.102F
• Wikidata: Q27274960
• Metabolomics Workbench ID: 67546
• ChEMBL ID: CHEMBL504918
• Mol file: 100-48-1.mol

Synonyms:4-cyanopyridine

Chemical Property of 4-Cyanopyridine

Chemical Property:

• Appearance/Colour: beige solid
• Vapor Pressure: 0.401mmHg at 25°C
• Melting Point: 76-79 °C(lit.)
• Refractive Index: 1.539
• Boiling Point: 196.3 °C at 760 mmHg
• PKA: pK1:1.90(+1) (25°C)
• Flash Point: 82.7 °C
• PSA: 36.68000
• Density: 1.12 g/cm³
• LogP: 0.95328
• Storage Temp.: Store below +30°C.
• Solubility.: 40g/l
• Water Solubility.: 3.2 g/100ml (16.4 ºC)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 104.037448136
• Heavy Atom Count: 8
• Complexity: 105

Purity/Quality:

99% ^*data from raw suppliers

4-Cyanopyridine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C1=CN=CC=C1C#N
• Uses: 4-Cyanopyridine is used as an intermediate in organic synthesis and pharmaceutical substances like isonicotinylhydrazide, which is used in the treatment of tuberculosis. It is used as a precursor for the preparation of isonicotinic acid and 4-diemthylaminopyridine (DMAP). It is involved in the synthesis of 6-methyl-2-pyridin-4-yl-pyrimidin-4-ylamine by reacting with acetonitrile.

Technology Process of 4-Cyanopyridine

There total 136 articles about 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: 49.0%

4-cyanopyridine N-oxide (14906-59-3) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → pyridine-4-carbonitrile (100-48-1) + C9H9N3OS

Guidance literature:

In acetonitrile; at 81 ℃; for 4h;

DOI:10.1002/jhet.5570440236

Reference yield:

4-cyano-1-(4-nitro-phenoxythiocarbonyl)-pyridinium; chloride → pyridine-4-carbonitrile (100-48-1) + 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + carbon oxide sulfide (463-58-1)

Guidance literature:

With phosphate buffer; potassium chloride; In water; at 25 ℃; pH=6.5; Further Variations:; pH-values; Kinetics;

DOI:10.1021/jo049559y

Reference yield:

(E)-4-pyridinecarboxaldehyde O-methyloxime (126527-31-9) → pyridine-4-carbonitrile (100-48-1)

Guidance literature:

With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Ru(CO)(PPh₃)3H₂; In toluene; for 24h; Heating;

DOI:10.1016/j.tetlet.2007.09.028

upstream raw materials:

1,4-dioxane

potassium cyanide

1-Methoxypyridinium iodide

picoline

Downstream raw materials:

5-(4’-pyridyl)-3-phenyl-1,2,4-oxadiazole

methyl (4-pyridyl) ketone

pyridine-4-methylimine acid ethyl ester

1-(4-pyridyl)-1-propanone

Refernces

• 1、 Pokhodylo,Shiika,Matiichuk,Obushak. "Synthesis of [5-(1H-1,2,3-triazol-4-yl)-1,3,4-oxadiazol-2-yl]pyridines". . p. 417 - 421. Retrieved 2010.
• 2、 Yamazaki, Shigekazu. "A simple and convenient method for the synthesis of nitriles by oxidation of primary amines with NaOCl in ethanol". . p. 3559 - 3564. Retrieved 1997.
• 3、 Ponaras, Anthony A.,Zaim, Oemer. "Deoxygenation of pyridine N-oxides with dimethylthiocarbamoyl chloride". . p. 487 - 489. Retrieved 2007.
• 4、 Burgess, John,Patei, Marttand S.. "Pentacyanoferrates(II): Solvatochromism and Reactivity in Micelles and in Reversed Micelles". . p. 783 - 788. Retrieved 1993.
• 5、 Arnett, Edward M.,Reich, Ronald. "Electronic Effects on the Menschutkin Reaction. A Complete Kinetic and Thermodynamic Dissection of Alkyl Transfer to 3- and 4-Substituted Pyridines". . p. 5892 - 5902. Retrieved 1980.
• 6、 Morita, Tsuyoshi,Kuroda, Koji,Okamoto, Yoshiki,Sakurai, Hiroshi. "A NEW METHOD FOR DEOXYGENATION OF HETEROAROMATIC N-OXIDES WITH CHLOROTRIMETHYLSILANE/SODIUM IODIDE/ZINC". . p. 921 - 924. Retrieved 1981.
• 7、 Andrieux,Gelis,Saveant. "Outer-sphere and inner-sphere processes in organic chemistry. Reaction of trifluoromethyl bromide with electrochemically generated aromatic anion radicals and sulfur dioxide anion radicals". . p. 786 - 791. Retrieved 1990.
• 8、 Lee, Kieseung,Han, Sang-Bae,Yoo, Eun-Mi,Chung, Soon-Ryang,Oh, Haibum,Hong, Sungwan. "Efficient transformation of aldoximes to nitriles using 2-chloro-1-methylpyridinium iodide under mild conditions". . p. 1775 - 1782. Retrieved 2004.
• 9、 Toganoh, Motoki,Fujino, Keitaro,Ikeda, Shinya,Furuta, Hiroyuki. "Catalytic deoxygenation of pyridine N-oxides with N-fused porphyrin rhenium complexes". . p. 1488 - 1491. Retrieved 2008.
• 10、 Barlin,Brown. "-". . p. 2473. Retrieved 1967.