1122-28-7

Basic information

• Product Name: 4,5-Dicyanoimidazole
• Synonyms: AURORA 15196;IMIDAZOLE-4,5-DICARBONITRILE;DCI;1h-imidazole-4,5-dicarbonitrile;4,5-DICYANOIMIDAZOLE;4,5-IMIDAZOLEDICARBONITRILE;ACTIVATOR;4,5-DICYANOIMIDAZOL
• CAS NO: 1122-28-7
• Molecular Formula: C₅H₂N₄
• Molecular Weight: 118.1
• EINECS: 214-344-6
• Product Categories: blocks;Carboxes;Imidazoles;Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines;Imidazol&Benzimidazole;Coupling Reagent;Imidaxoles;Dicyanopyrazines, etc. (Building Blocks for Phthalonitriles & Naphthalonitriles);Functional Materials;Phthalonitriles & Naphthalonitriles;Naphthyridine,Quinoline;Pyridines ,Halogenated Heterocycles
• Mol File: 1122-28-7.mol

Chemical Properties

• Melting Point: 168-175 °C(lit.)
• Boiling Point: 569.3 °C at 760 mmHg
• Flash Point: 50 °F
• Appearance: solid white/Crystalline Powder
• Density: 0.791 g/mL at 25 °C
• Vapor Pressure: 5.65E-13mmHg at 25°C
• Refractive Index: 1.584
• Storage Temp.: Store below +30°C.
• Solubility: Soluble in Acetonitrile: 1.8g/10ml, DMSO, Methanol.
• PKA: 5.01±0.10(Predicted)
• BRN: 118208
• CAS DataBase Reference: 4,5-Dicyanoimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-Dicyanoimidazole(1122-28-7)
• EPA Substance Registry System: 4,5-Dicyanoimidazole(1122-28-7)

Safety Data

• 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
• RIDADR: UN 1648 3/PG 2
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1122-28-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Biochemical Research:
4,5-Dicyanoimidazole is used as an activator for nucleoside phosphoramidites in the synthesis of oligonucleotides. It plays a crucial role in the development of novel nucleosides and the advancement of pharmaceutical and biochemical research.
Used in Synthesis of Nucleoside Phosphoramidites:
4,5-Dicyanoimidazole is used as a catalyst in the synthesis of nucleoside phosphoramidites, which are essential building blocks for the creation of various types of nucleic acids.
Used in Synthesis of Novel Nucleosides:
4,5-Dicyanoimidazole is utilized as a key component in the synthesis of novel nucleosides, contributing to the discovery of new compounds with potential applications in medicine and biotechnology.
Used as an Alternative to Tetrazole:
4,5-Dicyanoimidazole is used as a substitute for tetrazole in certain chemical reactions, offering an effective alternative for activating nucleoside phosphoramidites during the synthesis process.

Synthesis Reference(s)

Synthesis, p. 767, 1988 DOI: 10.1055/s-1988-27702

InChI:InChI=1/C5H2N4/c6-1-4-5(2-7)9-3-8-4/h3H,(H,8,9)

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 1187-42-4 diaminomaleonitrile 
• 876173-91-0 (Z)-3-((Z)-2-Amino-1,2-dicyano-vinylamino)-2-benzoylamino-acrylic acid ethyl ester 
• 53144-01-7 N-((Z)-2-amino-1,2-dicyanoethenyl)formamide 
• 149-73-5 trimethyl orthoformate 
• 74-90-8 hydrogen cyanide 
• 71749-37-6 N-(2-amino-1,2-dicyanovinyl)formamidine 
• 18514-52-8 2,3-diaminomaleonitrile 
• 16712-16-6 ammonium formate 

Downstream Products

• 113187-02-3 5-cyano-1(3)H-imidazole-4-carbonimidic acid ethyl ester; hydrochloride 
• 83-39-6 1H-imidazole-4,5-dicarboxamide 
• 19485-35-9 1-methyl-4,5-dicyanoimidazole 
• 133123-69-0 1-Isopropyl-1H-imidazole-4,5-dicarbonitrile 
• 59253-74-6 5-cyano-1H-imidazole-4-carboxylic acid ethyl ester 
• 133123-67-8 4,5-Dicyano-1-ethylimidazole 
• 155446-32-5 (R,S)-1-(1-Phenyl-2-propyl)imidazole-4,5-dicarbonitrile 
• 162824-35-3 (R,S)-1-(1-Phenyl-1-propyl)imidazole-4,5-dicarbonitrile 
• 162989-77-7 (S)-(+)-1-(1-Phenyl-2-propyl)imidazole-4,5-dicarbonitrile 
• 70042-26-1 4,5-dicyano-1-(2',3',4'-tri-O-acetyl-D-ribopyranosyl)imidazole 
• 70042-27-2 4,5-dicyano-1-(2',3',4'-tri-O-acetyl-D-ribopyranosyl)imidazole 
• 570-22-9 4,5-imidazoledicarboxylic acid 
• 123124-90-3 4,5-dicyano-1-(phenylmethyl)-1H-imidazole 
• 162009-79-2 4,6,8-triaminoimidazo<4,5-e><1,3>diazepine 

Related news

Fluorescence and photophysical properties of D-π-A push-pull systems featuring a 4,5-Dicyanoimidazole (cas 1122-28-7) unit09/30/2019

Absorption and fluorescence spectra and fluorescence quantum yields of 18 D-;π-A push-pull compounds were measured. The investigated chromophores consist of 4,5-dicyanoimidazole — bearing donor — substituted and systematically extended π-conjugated spacers. The influence of temperature and s...detailed

Branched charge-transfer chromophores featuring a 4,5-Dicyanoimidazole (cas 1122-28-7) unit10/01/2019

Six branched and stable push–pull chromophores featuring 4,5-dicyanoimidazole as an acceptor moiety, an N,N-dimethylamino group as a donor and various π-conjugated linkers are reported. Systematic extension of the π-linker revealed that the optical and electrochemical properties of A–π–D c...detailed

Theoretical investigation of the static (hyper)polarizabilities and reorganization energy of 4,5-Dicyanoimidazole (cas 1122-28-7) chromophore and derivatives containing benzene rings and a saturated bridge09/25/2019

Calculations at HF, DFT (CAM-B3LYP) and MP2 level were carried out with a 6-31+G(d,p) basis set to estimate the polarizability α, the first β and second hyperpolarizability γ and reorganization energy λ of 4,5-dicyanoimidazole chromophore 1 and derivatives formed by adding a benzene ring 2, ...detailed

Relevant articles and documents

Harnessing chemical energy for the activation and joining of prebiotic building blocks

Life is an out-of-equilibrium system sustained by a continuous supply of energy. In extant biology, the generation of the primary energy currency, adenosine 5′-triphosphate and its use in the synthesis of biomolecules require enzymes. Before their emergence, alternative energy sources, perhaps assisted by simple catalysts, must have mediated the activation of carboxylates and phosphates for condensation reactions. Here, we show that the chemical energy inherent to isonitriles can be harnessed to activate nucleoside phosphates and carboxylic acids through catalysis by acid and 4,5-dicyanoimidazole under mild aqueous conditions. Simultaneous activation of carboxylates and phosphates provides multiple pathways for the generation of reactive intermediates, including mixed carboxylic acid–phosphoric acid anhydrides, for the synthesis of peptidyl–RNAs, peptides, RNA oligomers and primordial phospholipids. Our results indicate that unified prebiotic activation chemistry could have enabled the joining of building blocks in aqueous solution from a common pool and enabled the progression of a system towards higher complexity, foreshadowing today’s encapsulated peptide–nucleic acid system. [Figure not available: see fulltext.].

A tropylium annulated N-heterocyclic carbene

Derivatives of the cationic tropylium annulated imidazolylidene ITrop+ are obtained by hydride abstraction from related cycloheptatriene compounds. Spectroscopic, structural and theoretical data indicate that, as a cationic relative of benzimidazolylidenes, ITrop+ has highly reduced σ-donor and strong π-acceptor character.

Branched charge-transfer chromophores featuring a 4,5-dicyanoimidazole unit

Six branched and stable push-pull chromophores featuring 4,5-dicyanoimidazole as an acceptor moiety, an N,N-dimethylamino group as a donor and various π-conjugated linkers are reported. Systematic extension of the π-linker revealed that the optical and electrochemical properties of A-π-D chromophores are mainly affected by the nature of the π-conjugated backbone (length and planarity) as well as by the number of appended donors.

Push-pull molecules with a systematically extended π-conjugated system featuring 4,5-dicyanoimidazole

Eighteen chromophores featuring 4,5-dicyanoimidazole as an acceptor moiety, a systematically enlarged π-conjugated spacer and methoxy and N,N-dimethylamino groups as donors were synthesised and characterised by X-ray analysis, electrochemistry, UV-Vis and fluorescence spectroscopy whilst NLO properties were calculated. Quantitative relationships between measured properties and structural features of the chromophores were also evaluated.

METHOD FOR PRODUCTION OF N-(2-AMINO-1,2-DICYANOVINYL)IMIDATE, METHOD FOR PRODUCTION OF N-(2-AMINO-1,2-DICYANOVINYL)FORMAMIDINE, AND METHOD FOR PRODUCTION OF AMINOIMIDAZOLE DERIVATIVE

A method for producing N-(2-amino-1,2-dicyanovinyl)imidates represented by the following formula (1-III) under low temperature conditions within a short period of time in high yield is provided. In addition, a method for producing N-(2-amino-1,2-dicyanovinyl)formamidine represented by the following formula (2-II) which is suitably applicable to a cyclization reaction for producing AICN, AICA or the like and which enhances yield of the cyclization reaction is provided. In addition, a method for producing aminoimidazole derivatives represented by the following formula (3-V) in high yield by using diaminomaleonitrile as a starting material is provided.

Efficient synthesis of trisimidazole and glutaric acid bearing porphyrins: Ligands for active-site models of bacterial nitric oxide reductase

Ligands (1) for active-site models of bacterial nitric oxide reductase (NOR) have been efficiently synthesized. These compounds (1) feature three imidazolyl moieties and one carboxylic acid residue at the FeB site, which represent the closest available synthetic model ligands of NOR active center. The stereo conformations of these ligands are established on the basis of steric effects and 1H NMR chemical shifts under the ring current effect of the porphyrin.

Synthesis of 4,5-dicyanoimidazoles

The effective procedure of preparation of 2-trifluoromethyl-4,5- dicyanoimidazole (3a) from diaminomaleonitrile (1) and trifluoroacetic anhydride has been elaborated. The syntheses of five other 2-substituted imidazoles from appropriate acyl derivatives of 1 have been attempted. Out of them only 4,5-dicyanoimidazole (3b) could be obtained in good yield.

A novel approach to imidazo[1,5-a]pyrazines

A novel one-pot approach to the imidazo[1,5-a]pyrazine system has been elaborated based on the cyclization of 3-[(2-amino-1,2-dicyanoethen-1-yl)amino]-2-(benzoylamino)propenoates with orthoesters.

Convenient Synthesis of Methyl 1-Methyl-2,4-dibromo-5-imidazolecarboxylate

Three syntheses of methyl 1-methyl-2,4-dibromo-5-imidazolecarboxylate (8) are presented.One proceeds from sarcosine via ring closure, bromination, and desulfurization.The second uses N-methylimidazole, polybromination, and selective halogen-metal interchange.The third and most efficient and preparatively useful route begins with diaminomaleonitrile (13).Ring closure with triethyl orthoformate followed by methylation and hydrolysis affords 1-methyl-4,5-imidazoledicarboxylic acid (16).Regioselective decarboxylation followed by esterification yields methyl 1-methyl-5-imidazolecarboxylate (18).Subsequent dibromination gives the completely substituted imidazole 8.The primary purification in this sequence is fractional sublimation of 18 after the esterification step.An overall yield of 26percent is achieved from diaminomaleonitrile (13) to methyl 1-methyl-2,4-dibromo-5-imidazolecarboxylate (8), which is a key intermediate for the synthesis of tricyclic imidazo cooked food mutagens.