1122-28-7,MFCD00005194
Catalog No.:AA0033SJ

1122-28-7 | 4,5-Dicyanoimidazole

Pack Size
Purity
Availability
Price(USD)
Quantity
  
10g
98%
in stock  
$9.00   $6.00
- +
100g
98%
in stock  
$73.00   $51.00
- +
500g
98%
in stock  
$352.00   $246.00
- +
  • Technical Information
  • Properties
  • Literature
  • Application
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA0033SJ
Chemical Name:
4,5-Dicyanoimidazole
CAS Number:
1122-28-7
Molecular Formula:
C5H2N4
Molecular Weight:
118.0962
MDL Number:
MFCD00005194
SMILES:
N#Cc1[nH]cnc1C#N
NSC Number:
113954
Properties
Properties
 
BP:
569.3 °C at 760 mmHg  
Form:
Solid  
MP:
168-175 °C  
Solubility:
Soluble in Acetonitrile: 1.8g/10ml, DMSO, Methanol.  
Storage:
Inert atmosphere;Room Temperature;  

Computed Properties
 
Complexity:
192  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
9  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0  
Rotatable Bond Count:
0  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
0.2  

Literature

Title: Novel coumarin derivatives containing 1,2,4-triazole, 4,5-dicyanoimidazole and purine moieties: synthesis and evaluation of their cytostatic activity.

Journal: Molecules (Basel, Switzerland) 20120912

Title: Effects of the nature and length of the π-conjugated bridge on the second-order nonlinear optical responses of push-pull molecules including 4,5-dicyanoimidazole and their protonated forms.

Journal: Chemphyschem : a European journal of chemical physics and physical chemistry 20111209

Title: Push-pull fluorophores based on imidazole-4,5-dicarbonitrile: a comparison of spectral properties in solution and polymer matrices.

Journal: Journal of fluorescence 20110701

Title: Imidazole as a donor/acceptor unit in charge-transfer chromophores with extended π-linkers.

Journal: Chemistry, an Asian journal 20110606

Title: Michael-type addition of azoles of broad-scale acidity to methyl acrylate.

Journal: Beilstein journal of organic chemistry 20110101

Title: Efficiency, error and yield in light-directed maskless synthesis of DNA microarrays.

Journal: Journal of nanobiotechnology 20110101

Title: Optical operation by chromophores featuring 4,5-dicyanoimidazole embedded within poly(methyl methacrylate) matrices.

Journal: The journal of physical chemistry. A 20100909

Title: Acetal levulinyl ester (ALE) groups for 2'-hydroxyl protection of ribonucleosides in the synthesis of oligoribonucleotides on glass and microarrays.

Journal: Journal of the American Chemical Society 20090624

Title: 4,5-Bis(1H-tetra-zol-5-yl)-1H-imidazole monohydrate.

Journal: Acta crystallographica. Section E, Structure reports online 20090601

Title: Monolithic silica capillary columns having immobilized lectins and surface bound polar functionalities for lectin affinity and normal phase nano-LC and CEC of glycoconjugates, respectively.

Journal: Journal of separation science 20090501

Title: Capillary electrochromatography with monolithic silica columns. V. Study of the electrochromatographic behaviors of polar compounds on monolithic silica having surface bound cyano functionalities.

Journal: Journal of separation science 20060801

Title: Capillary electrochromatography with monolithic silica columns. IV. Electrochromatographic characterization of polar bonded monolithic stationary phases having surface-bound cyano functionalities.

Journal: Journal of separation science 20060801

Title: Antisense oligonucleotides: efficient synthesis of 2'-O-methoxyethyl phosphorothioate oligonucleotides using 4,5-dicyanoimidazole. Are these oligonucleotides comparable to those synthesized using 1H-tetrazole as coupling activator?

Journal: Bioorganic & medicinal chemistry 20060715

Title: Synthesis and biochemical evaluation of phosphonoformate oligodeoxyribonucleotides.

Journal: Journal of the American Chemical Society 20060419

Title: Nitrosative adenine deamination: facile pyrimidine ring-opening in the dediazoniation of adeninediazonium ion.

Journal: Organic letters 20031030

Title: A method to accurately determine the extent of solid-phase reactions by monitoring an intermediate in a nondestructive manner.

Journal: Analytical chemistry 20020315

Title: Chemical synthesis and biological investigation of a 77-mer oligoribonucleotide with a sequence corresponding to E. coli tRNA(Asp).

Journal: Bioorganic & medicinal chemistry 20010101

Title: Solid-phase synthesis of oligodeoxynucleotides containing 3'-S-phosphorothiolate linkages.

Journal: Nucleosides, nucleotides & nucleic acids 20010101

Application
4,5-Dicyanoimidazole (DCI) plays a crucial role as an activator in the synthesis of oligonucleotides, a fundamental process in nucleic acid chemistry. Its versatile nature extends to various synthetic applications, making it an essential reagent in molecular biology and organic synthesis.

In practical terms, 4,5-Dicyanoimidazole finds application in the synthesis of diverse compounds, showcasing its utility in the field of organic chemistry. Notable examples include its use in the synthesis of 5′-O-(4,4′-dimethoxytrityl)-2′-deoxythymidine 3′-O-(2-cyanoethyl N,N-diisopropylphosphoramidite), a crucial intermediate in nucleotide synthesis. Additionally, it participates in the synthesis of 4,5-di(amidoximyl)imidazole [4,5-(DAO)Im], 1-(4-methoxybenzyl)-4,5-dicyanoimidazole, and novel imidazo[4 5-e][1 3]diazepine analogs, showcasing its versatility in the creation of diverse molecular structures.

Moreover, 4,5-Dicyanoimidazole is employed in the synthesis of N-benzyl-4,5-dicyanoimidazole, further highlighting its role in the preparation of functionalized imidazole derivatives.
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Tags:1122-28-7 Molecular Formula|1122-28-7 MDL|1122-28-7 SMILES|1122-28-7 4,5-Dicyanoimidazole
Catalog No.: AA0033SJ
1122-28-7,MFCD00005194
1122-28-7 | 4,5-Dicyanoimidazole
Pack Size: 10g
Purity: 98%
in stock
$9.00 $6.00
Pack Size: 100g
Purity: 98%
in stock
$73.00 $51.00
Pack Size: 500g
Purity: 98%
in stock
$352.00 $246.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
Technical Information
Catalog Number: AA0033SJ
Chemical Name: 4,5-Dicyanoimidazole
CAS Number: 1122-28-7
Molecular Formula: C5H2N4
Molecular Weight: 118.0962
MDL Number: MFCD00005194
SMILES: N#Cc1[nH]cnc1C#N
NSC Number: 113954
Properties
BP: 569.3 °C at 760 mmHg  
Form: Solid  
MP: 168-175 °C  
Solubility: Soluble in Acetonitrile: 1.8g/10ml, DMSO, Methanol.  
Storage: Inert atmosphere;Room Temperature;  
Complexity: 192  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 0  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 9  
Hydrogen Bond Acceptor Count: 3  
Hydrogen Bond Donor Count: 1  
Isotope Atom Count: 0  
Rotatable Bond Count: 0  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 0.2  
Literature fold

Title: Novel coumarin derivatives containing 1,2,4-triazole, 4,5-dicyanoimidazole and purine moieties: synthesis and evaluation of their cytostatic activity.

Journal: Molecules (Basel, Switzerland)20120912

Title: Effects of the nature and length of the π-conjugated bridge on the second-order nonlinear optical responses of push-pull molecules including 4,5-dicyanoimidazole and their protonated forms.

Journal: Chemphyschem : a European journal of chemical physics and physical chemistry20111209

Title: Push-pull fluorophores based on imidazole-4,5-dicarbonitrile: a comparison of spectral properties in solution and polymer matrices.

Journal: Journal of fluorescence20110701

Title: Imidazole as a donor/acceptor unit in charge-transfer chromophores with extended π-linkers.

Journal: Chemistry, an Asian journal20110606

Title: Michael-type addition of azoles of broad-scale acidity to methyl acrylate.

Journal: Beilstein journal of organic chemistry20110101

Title: Efficiency, error and yield in light-directed maskless synthesis of DNA microarrays.

Journal: Journal of nanobiotechnology20110101

Title: Optical operation by chromophores featuring 4,5-dicyanoimidazole embedded within poly(methyl methacrylate) matrices.

Journal: The journal of physical chemistry. A20100909

Title: Acetal levulinyl ester (ALE) groups for 2'-hydroxyl protection of ribonucleosides in the synthesis of oligoribonucleotides on glass and microarrays.

Journal: Journal of the American Chemical Society20090624

Title: 4,5-Bis(1H-tetra-zol-5-yl)-1H-imidazole monohydrate.

Journal: Acta crystallographica. Section E, Structure reports online20090601

Title: Monolithic silica capillary columns having immobilized lectins and surface bound polar functionalities for lectin affinity and normal phase nano-LC and CEC of glycoconjugates, respectively.

Journal: Journal of separation science20090501

Title: Capillary electrochromatography with monolithic silica columns. V. Study of the electrochromatographic behaviors of polar compounds on monolithic silica having surface bound cyano functionalities.

Journal: Journal of separation science20060801

Title: Capillary electrochromatography with monolithic silica columns. IV. Electrochromatographic characterization of polar bonded monolithic stationary phases having surface-bound cyano functionalities.

Journal: Journal of separation science20060801

Title: Antisense oligonucleotides: efficient synthesis of 2'-O-methoxyethyl phosphorothioate oligonucleotides using 4,5-dicyanoimidazole. Are these oligonucleotides comparable to those synthesized using 1H-tetrazole as coupling activator?

Journal: Bioorganic & medicinal chemistry20060715

Title: Synthesis and biochemical evaluation of phosphonoformate oligodeoxyribonucleotides.

Journal: Journal of the American Chemical Society20060419

Title: Nitrosative adenine deamination: facile pyrimidine ring-opening in the dediazoniation of adeninediazonium ion.

Journal: Organic letters20031030

Title: A method to accurately determine the extent of solid-phase reactions by monitoring an intermediate in a nondestructive manner.

Journal: Analytical chemistry20020315

Title: Chemical synthesis and biological investigation of a 77-mer oligoribonucleotide with a sequence corresponding to E. coli tRNA(Asp).

Journal: Bioorganic & medicinal chemistry20010101

Title: Solid-phase synthesis of oligodeoxynucleotides containing 3'-S-phosphorothiolate linkages.

Journal: Nucleosides, nucleotides & nucleic acids20010101

Application fold
4,5-Dicyanoimidazole (DCI) plays a crucial role as an activator in the synthesis of oligonucleotides, a fundamental process in nucleic acid chemistry. Its versatile nature extends to various synthetic applications, making it an essential reagent in molecular biology and organic synthesis.

In practical terms, 4,5-Dicyanoimidazole finds application in the synthesis of diverse compounds, showcasing its utility in the field of organic chemistry. Notable examples include its use in the synthesis of 5′-O-(4,4′-dimethoxytrityl)-2′-deoxythymidine 3′-O-(2-cyanoethyl N,N-diisopropylphosphoramidite), a crucial intermediate in nucleotide synthesis. Additionally, it participates in the synthesis of 4,5-di(amidoximyl)imidazole [4,5-(DAO)Im], 1-(4-methoxybenzyl)-4,5-dicyanoimidazole, and novel imidazo[4 5-e][1 3]diazepine analogs, showcasing its versatility in the creation of diverse molecular structures.

Moreover, 4,5-Dicyanoimidazole is employed in the synthesis of N-benzyl-4,5-dicyanoimidazole, further highlighting its role in the preparation of functionalized imidazole derivatives.
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