2,3-Diaminomaleonitrile

Base Information

• Chemical Name: 2,3-Diaminomaleonitrile
• CAS No.: 1187-42-4
• Deprecated CAS: 54414-88-9
• Molecular Formula: C4H4N4
• Molecular Weight: 108.103
• Hs Code.: 2926909090
• European Community (EC) Number: 214-697-6
• NSC Number: 266758
• UN Number: 2811
• UNII: E8C63N8TWR
• DSSTox Substance ID: DTXSID0024923
• Nikkaji Number: J38.151I
• Wikipedia: Diaminomaleonitrile
• Wikidata: Q21099121
• ChEMBL ID: CHEMBL1701646
• Mol file: 1187-42-4.mol

Synonyms:2-Butenedinitrile,2,3-diamino-, (Z)-;Maleonitrile, diamino- (6CI,7CI,8CI);(2Z)-2,3-Diamino-2-butenedinitrile;2,3-Diaminomaleonitrile;DAMN;2-Butenedinitrile,2,3-diamino-, (2Z)-;Hydrogen cyanide tetramer;

Chemical Property of 2,3-Diaminomaleonitrile

Chemical Property:

• Appearance/Colour: brown crystalline powder
• Vapor Pressure: 0.159mmHg at 25°C
• Melting Point: 178-179 °C
• Refractive Index: 1.6
• Boiling Point: 444.7 °C at 760 mmHg
• PKA: -2.77±0.70(Predicted)
• Flash Point: 222.7 °C
• PSA: 99.62000
• Density: 1.319 g/cm³
• LogP: 0.56316
• Water Solubility.: 5 g/L (25℃)
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 108.043596145
• Heavy Atom Count: 8
• Complexity: 183
• Transport DOT Label: Poison

Purity/Quality:

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

Safty Information:

• Pictogram(s): Xn,T
• Hazard Codes: T:Toxic
• Statements: R25:
• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(#N)C(=C(C#N)N)N
• Isomeric SMILES: C(#N)/C(=C(\C#N)/N)/N

Technology Process of 2,3-Diaminomaleonitrile

There total 10 articles about 2,3-Diaminomaleonitrile 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: 99.2%

→ diaminomaleonitrile (1187-42-4)

Guidance literature:

Reference yield: 88.0%

2-hydroxy-2-methylpropanenitrile (75-86-5) → diaminomaleonitrile (1187-42-4)

Guidance literature:

With sodium cyanide; methylthiol; at 60 ℃; for 2h; Temperature; Time; Reagent/catalyst; Autoclave;

Reference yield: 68.0%

ethyl (Z)-N-(2-amino-1,2-dicyanovinyl)formamidate (129694-52-6) + 4-methoxycarbonyl aniline (619-45-4) → methyl 4-{[(Z)-2-amino-1,2-dicyanovinyl]amino}methyleneaminobenzoate (931424-12-3) + diaminomaleonitrile (1187-42-4)

Guidance literature:

aniline hydrochloride; In methanol; at 23 ℃; for 20h;

DOI:10.1002/jhet.5570440103

upstream raw materials:

hydrogen cyanide

potassium cyanide

ethanedinitrile

(E/Z)-α-iminoacetonitrile

Downstream raw materials:

N-((Z)-2-amino-1,2-dicyanoethenyl)acetamide

(2Z)-2-Amino-3-{[(1E)-(4-hydroxyphenyl)methylidene]-amino}but-2-enedinitrile

N-salicylidene-2,3-diamino-cis-2-butenedinitrile

amino-benzoylamino-maleonitrile

Refernces

• 1、 Yamada,Nagashima,Iwashita,Nakamura,Kumashiro. "The synthesis and the molecular structure of diaminofumaronitrile". . p. 4529 - 4532. Retrieved 1968.
• 2、 Matthews,Moser. "Peptide synthesis from hydrogen cyanide and water.". . p. 1230 - 1234. Retrieved 1967.
• 3、 Becker et al.. "-". . p. 1269. Retrieved 1973.
• 4、 -. "METHOD FOR PREPARING DIAMINOMALEONITRILE". Paragraph 0029. . Retrieved 2015/07/22.
• 5、 Xiang, Yi-Bin,Drenkard, Susanne,Baumann, Karl,Hickey, Deirdre,Eschenmoser, Albert. "Chemistry of α-Amino Nitriles. Exploratory Experiments on Thermal Reactions of α-Amino Nitriles". . p. 2209 - 2250. Retrieved 2007/10/02.