Pyridine-2,4-dicarbonitrile

Base Information

• Chemical Name: Pyridine-2,4-dicarbonitrile
• CAS No.: 29181-50-8
• Molecular Formula: C7H3N3
• Molecular Weight: 129.121
• Hs Code.: 29333990
• European Community (EC) Number: 249-492-0
• UNII: HJ2X384UBJ
• DSSTox Substance ID: DTXSID8067448
• Nikkaji Number: J250.789G
• Wikidata: Q72468607
• Mol file: 29181-50-8.mol

Synonyms:Pyridine-2,4-dicarbonitrile;29181-50-8;2,4-Pyridinedicarbonitrile;2,4-Dicyanopyridine;HJ2X384UBJ;EINECS 249-492-0;UNII-HJ2X384UBJ;methyl?4-cyclopropylbenzoate;YSWG444;SCHEMBL995799;DTXSID8067448;2,4-Pyridinedicarbonitrile, 97%;2 pound not4-pyridinedicarbonitrile;MFCD00014627;AKOS015892293;AS-58697;CS-0110789;FT-0638837;J-017425;J-524112

Chemical Property of Pyridine-2,4-dicarbonitrile

Chemical Property:

• Vapor Pressure: 0.0113mmHg at 25°C
• Melting Point: 89-93 °C(lit.)
• Refractive Index: 1.567
• Boiling Point: 261.8 °C at 760 mmHg
• PKA: -3.67±0.10(Predicted)
• Flash Point: 100.1 °C
• PSA: 60.47000
• Density: 1.25g/cm³
• LogP: 0.82496
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 129.032697108
• Heavy Atom Count: 10
• Complexity: 203

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,4-Pyridinedicarbonitrile 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-37/38-41-43
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN=C(C=C1C#N)C#N

Technology Process of Pyridine-2,4-dicarbonitrile

There total 8 articles about Pyridine-2,4-dicarbonitrile 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: 93.0%

pyridine-4-carbonitrile (100-48-1) + trimethylsilyl cyanide (7677-24-9) → 2,4-Dicyanopyridine (29181-50-8)

Guidance literature:

pyridine-4-carbonitrile; 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; Inert atmosphere; Sealed tube;

DOI:10.1002/chem.201703931

Reference yield: 75.0%

potassium cyanide (151-50-8) + N-methoxy-4-cyanopyridinium methylsulfate (51342-23-5) → 2,4-Dicyanopyridine (29181-50-8)

Guidance literature:

In ethanol; water; at -18 - -12 ℃; for 3h;

Reference yield: 68.3%

2,4-dichloropyridine (26452-80-2) + dicyanozinc (557-21-1) → 2,4-Dicyanopyridine (29181-50-8)

Guidance literature:

With racemic 2-di-tert-butylphosphino-1,1'-binaphthyl; palladium(II) trifluoroacetate; zinc; In N,N-dimethyl acetamide; at 80 ℃; for 17h;

DOI:10.1021/ol070372d

upstream raw materials:

4-cyanopyridine N-oxide

dimethyl sulfate

trimethylsilyl cyanide

potassium cyanide

Downstream raw materials:

2-Cyanopyridine

2-(propylamino)isonicotinonitrile

4-Propylamino-pyridine-2-carbonitrile

2-(α-Hydroxydiphenylmethyl)pyridine-4-carbonitrile

Refernces

• 1、 Huo, Zhibao,Kosugi, Teruo,Yamamoto, Yoshinori. "Zinc cyanide mediated direct α-cyanation of isonicotinic acid N-oxide. Application to the synthesis of FYX-051, a xanthine oxidoreductase inhibitor". . p. 4369 - 4371. Retrieved 2008/12/21.
• 2、 Sakamoto, Takao,Kaneda, Soh-ichi,Nishimura, Sumiko,Yamanaka, Hiroshi. "Site-Selectivity in the Cyanation of 3-Substituted Pyridine 1-Oxides with Trimethylsilanecarbonitrile". . p. 565 - 571. Retrieved 2007/10/02.