Diaminomaleonitrile

Base Information

• Chemical Name: Diaminomaleonitrile
• CAS No.: 18514-52-8
• Deprecated CAS: 54414-88-9
• Molecular Formula: C4H4N4
• Molecular Weight: 108.103
• Hs Code.: 2926907090
• 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: 18514-52-8.mol

Synonyms:diaminomaleonitrile;diaminomaleonitrile, (Z)-isomer

Chemical Property of Diaminomaleonitrile

Chemical Property:

• Vapor Pressure: 4.2E-08mmHg at 25°C
• Melting Point: 178 °C
• Refractive Index: 1.579
• 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
• 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%Min ^*data from raw suppliers

2,3-diaminobut-2-enedinitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,F
• Hazard Codes: T,F

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 Diaminomaleonitrile

There total 14 articles about 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: 88.0%

2-hydroxy-2-methylpropanenitrile (75-86-5) → 2,3-diaminomaleonitrile (18514-52-8)

Guidance literature:

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

Reference yield: 69.0%

hydrogen cyanide (74-90-8) + acetonitrile (75-05-8,26809-02-9) → 2,3-diaminomaleonitrile (18514-52-8)

Guidance literature:

With triethylamine; diphenyldisulfane; for 24h;

DOI:10.1021/acs.orglett.9b01941

Reference yield: 2.5%

hydrogen cyanide (74-90-8) + (E/Z)-α-iminoacetonitrile (1726-32-5,34892-76-7,34892-77-8) → 1,1-diamino-2,2-ethenedicarbonitrile (1187-42-4,18514-52-8,20344-79-0) + diaminomaleonitrile (1187-42-4)

Guidance literature:

With triethylamine; In dichloromethane; acetonitrile; 1.) -78 up to -20 deg C within 1 h; 2.) -20 deg C, 16 h;

DOI:10.1002/hlca.19940770814

upstream raw materials:

hydrogen cyanide

(E/Z)-α-iminoacetonitrile

cyanide^(1-)

formamide

Downstream raw materials:

2,3-dicyanodipyrido<3,2-f:2',3'-h>quinoxaline

2,3-dicyanopyrazino phenanthrene

glycine

pyrazine-2,3,5,6-tetracarbonitrile

Refernces

• 1、 Grundke, Caroline,Kong, Caleb,Kampf, Christopher J.,Gupton, B. Frank,McQuade, D. Tyler,Opatz, Till. "Programmed Formation of HCN Oligomers through Organosulfur Catalysis". . p. 10320 - 10329. Retrieved 2021/07/31.
• 2、 Mattia Bizzarri, Bruno,Botta, Lorenzo,Pérez-Valverde, Maritza Iveth,Saladino, Raffaele,Di Mauro, Ernesto,García-Ruiz, Juan Manuel. "Silica Metal Oxide Vesicles Catalyze Comprehensive Prebiotic Chemistry". . p. 8126 - 8132. Retrieved 2018/05/29.