1H-Imidazole-4,5-dicarbonitrile

Base Information

• Chemical Name: 1H-Imidazole-4,5-dicarbonitrile
• CAS No.: 1122-28-7
• Molecular Formula: C5H2N4
• Molecular Weight: 118.098
• Hs Code.: 29332900
• European Community (EC) Number: 214-344-6
• NSC Number: 113954
• UNII: AZ5X73C3CC
• DSSTox Substance ID: DTXSID00149943
• Nikkaji Number: J203.354B
• Wikidata: Q72468583
• Mol file: 1122-28-7.mol

Synonyms:4,5-dicyanoimidazole

Chemical Property of 1H-Imidazole-4,5-dicarbonitrile

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 5.65E-13mmHg at 25°C
• Melting Point: 174- 178 °C
• Refractive Index: 1.584
• Boiling Point: 569.3 °C at 760 mmHg
• PKA: 5.01±0.10(Predicted)
• Flash Point: 170.2 °C
• PSA: 76.26000
• Density: 1.43 g/cm³
• LogP: 0.15306
• Storage Temp.: Store below +30°C.
• Solubility.: Soluble in Acetonitrile: 1.8g/10ml, DMSO, Methanol.
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 118.027946081
• Heavy Atom Count: 9
• Complexity: 192

Purity/Quality:

99% ^*data from raw suppliers

4,5-Dicyanoimidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn,F
• Hazard Codes: Xi,Xn,F
• Statements: 37/38-41-36/37/38-20/22-36-20/21/22-11
• Safety Statements: 26-39-36/37/39-36/37-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=NC(=C(N1)C#N)C#N
• Uses: 4,5-Dicyanoimidazole is used in activation of nucleoside phosphoramidites during solid-phase oligonucleotide synthesis, and synthesis of nucleoside phosphoramidites, synthesis of novel nucleosides. It is often used as an alternative to tetrazole.

Technology Process of 1H-Imidazole-4,5-dicarbonitrile

There total 11 articles about 1H-Imidazole-4,5-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: 83.0%

diaminomaleonitrile (1187-42-4) + trimethyl orthoformate (149-73-5) → 4,5-dicyano-1H-imidazole (1122-28-7)

Guidance literature:

In xylene; at 130 ℃;

DOI:10.1021/ol053118z

Reference yield: 83.0%

orthoformic acid triethyl ester (122-51-0) + diaminomaleonitrile (1187-42-4) → 4,5-dicyano-1H-imidazole (1122-28-7)

Guidance literature:

With sodium methylate; 1.) anisole, 135 deg C, 2 h, 2.) 135 deg C;

DOI:10.1055/s-1988-27702

Reference yield: 80.0%

2,3-diaminomaleonitrile (18514-52-8) + trimethyl orthoformate (149-73-5) → 4,5-dicyano-1H-imidazole (1122-28-7)

Guidance literature:

With sodium methylate; methoxybenzene;

DOI:10.1016/j.tetlet.2010.02.067

upstream raw materials:

orthoformic acid triethyl ester

diaminomaleonitrile

(Z)-3-((Z)-2-Amino-1,2-dicyano-vinylamino)-2-benzoylamino-acrylic acid ethyl ester

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

Downstream raw materials:

5-cyano-1(3)H-imidazole-4-carbonimidic acid ethyl ester; hydrochloride

1H-imidazole-4,5-dicarboxamide

1-(α-Phenylbenzyl)imidazole-4,5-dicarbonitrile

(R,S)-1-(1-Phenyl-1-propyl)imidazole-4,5-dicarbonitrile

Refernces

• 1、 Yamada et al.. "-". . p. 642. Retrieved 1968.
• 2、 Wakamatsu et al.. "-". . p. 2035. Retrieved 1966.
• 3、 Kobayashi,Honjo. "Synthesis of purine derivatives from single-carbon compounds.". . p. 703 - 708. Retrieved 1969.
• 4、 Bure?, Filip,Kulhánek, Ji?í,Mikysek, Tomá?,Ludvík, Ji?í,Lokaj, Ján. "Branched charge-transfer chromophores featuring a 4,5-dicyanoimidazole unit". scheme or table. p. 2055 - 2058. Retrieved 2010/06/19.