Pyrazine-2,3-dicarbonitrile

Base Information

• Chemical Name: Pyrazine-2,3-dicarbonitrile
• CAS No.: 13481-25-9
• Molecular Formula: C6H2N4
• Molecular Weight: 130.109
• Hs Code.: 2933990090
• European Community (EC) Number: 626-631-7
• NSC Number: 175270
• DSSTox Substance ID: DTXSID50306302
• Nikkaji Number: J27.887D
• Wikidata: Q82053335
• Mol file: 13481-25-9.mol

Synonyms:Pyrazine-2,3-dicarbonitrile;13481-25-9;2,3-Dicyanopyrazine;2,3-Pyrazinedicarbonitrile;NSC175270;2,3-dicyano-pyrazine;2, 3-dicyano-pyrazine;SCHEMBL217939;AMY4368;DTXSID50306302;2,3-Pyrazinedicarbonitrile, 98%;MFCD00059771;AKOS000268642;NSC-175270;AS-42886;CS-0181816;D1751;FT-0730956;AE-017/30096020;J-006606;ETHYL3-(4-METHOXY-PHENYL)-2-METHYLAMINOMETHYL-PROPIONATE

Chemical Property of Pyrazine-2,3-dicarbonitrile

Chemical Property:

• Vapor Pressure: 1.97E-05mmHg at 25°C
• Melting Point: 131-133 °C(lit.)
• Refractive Index: 1.57
• Boiling Point: 362.2 °C at 760 mmHg
• PKA: -7.49±0.10(Predicted)
• Flash Point: 124.8 °C
• PSA: 73.36000
• Density: 1.35 g/cm³
• LogP: 0.21996
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 130.027946081
• Heavy Atom Count: 10
• Complexity: 180

Purity/Quality:

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

Pyrazine-2,3-dicarbonitrile ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CN=C(C(=N1)C#N)C#N
• Uses: 2,3-Pyrazinedicarbonitrile may be used in the synthesis of pyrazino derivatives.

Technology Process of Pyrazine-2,3-dicarbonitrile

There total 10 articles about Pyrazine-2,3-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: 91.0%

Glyoxal (131543-46-9,107-22-2) + 2,3-diaminomaleonitrile (18514-52-8) → pyrazine-2,3-dicarbonitrile (13481-25-9)

Guidance literature:

With hydrogenchloride; In ethanol; water; for 0.5h; Reflux;

DOI:10.1055/s-0033-1340042

Reference yield: 90.0%

pyrazine-2,3-dicarboxamide (6164-78-9) → pyrazine-2,3-dicarbonitrile (13481-25-9)

Guidance literature:

With Burgess Reagent; In tetrahydrofuran; for 3h;

DOI:10.1021/jo00087a032

Reference yield: 40.0%

diiminosuccinonitrile (28321-79-1) + bicyclo[2.2.1]hepta-2,5-diene (121-46-0) → pyrazine-2,3-dicarbonitrile (13481-25-9) + 1,4-diamino-1,2,5-tricyano-3,6-diazahexatriene (88548-97-4) + 3-aza-3-(2-amino-1,2-dicyanovinyl)tricyclo<3.2.1.02,4>oct-6-ene (88549-07-9) + 2,5-diazatricyclo<6.2.1.02,6>undeca-3,5,9-triene-3,4-dicarbonitrile (88549-06-8) + 1,4,4a,5,8,8a-hexahydro-5,8-methanoquinoxaline-2,3-dicarbonitrile (88549-05-7)

Guidance literature:

In acetonitrile; at 25 ℃; for 168h; Product distribution; Mechanism; analogous reacztion with norbornene;

DOI:10.1021/jo00179a013

upstream raw materials:

Glyoxal

diaminomaleonitrile

pyrazine-2,3-dicarboxamide

cis-2,3-dimethoxy-5,6-dicyano-1,2,3,4-tetrahydropyrazine

Downstream raw materials:

2-pyrazylcarboxylic acid

2,3-dicarboxypyrazine

tetrapyrazinoporphyrazine

3-methoxypyrazinecarbonitrile

Refernces

• 1、 Danzig et al.. "-". . p. 668. Retrieved 1963.
• 2、 Stuzhin, Pavel A.,Skvortsov, Ivan A.,Zhabanov, Yuriy A.,Somov, Nikolai V.,Razgonyaev, Oleg V.,Nikitin, Ivan A.,Koifman, Oskar I.. "Subphthalocyanine azaanalogues – Boron(III) subporphyrazines with fused pyrazine fragments". . p. 888 - 897. Retrieved 2018/11/25.
• 3、 Ghosh, Pranab,Chakraborty, Rakesh Ranjan. "Clean and green approach for one-pot synthesis of pyrazines from Eth-ylenediamine and 1,2-diketone or its analogues under neat reaction condition". . p. 566 - 570. Retrieved 2017/09/29.