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Sigma-Aldrich

4,5-Dicyanoimidazole

99.0%

Synonym(s):

4,5-Imidazoledicarbonitrile

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About This Item

Empirical Formula (Hill Notation):
C5H2N4
CAS Number:
1122-28-7
Molecular Weight:
118.10
Beilstein:
118208
EC Number:
214-344-6
MDL number:
MFCD00005194
UNSPSC Code:
12352005
PubChem Substance ID:
24879368
NACRES:
NA.22

Assay

99.0%

mp

168-175 °C (lit.)

SMILES string

N#Cc1nc[nH]c1C#N

InChI

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

InChI key

XGDRLCRGKUCBQL-UHFFFAOYSA-N

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General description

4,5-Dicyanoimidazole (DCI) participates as an activator in the synthesis of oligonucleotides.

Application

4,5-Dicyanoimidazole may be used to synthesize:
  • 5′-O-(4,4′-dimethoxytrityl)-2′-deoxythymidine 3′-O-(2-cyanoethyl N,N-diisopropylphosphoramidite)
  • 4,5-di(amidoximyl)imidazole [4,5-(DAO)Im]
  • 1-(4-methoxybenzyl)-4,5-dicyanoimidazole
  • novel imidazo[4 5-e][1 3]diazepine analog
  • N-benzyl-4,5-dicyanoimidazole]

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H315,H318,H335

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Synthesis of 1-benzyl-8, 9-dihydroimidazo [4, 5-c] pyrrolo [3, 2-g] quinolin-4 (5H)-one via palladium-catalyzed intramolecular arylation.
Delest B, et al.
Tetrahedron, 60(29), 6079- 6083 (2004)
4, 5-Dicyanoimidazole.
Sebesta DP and Vagle K.
e-EROS Encyclopedia of Reagents for Organic Synthesis. null
Steven P Kelley et al.
Chemical communications (Cambridge, England), 50(83), 12504-12507 (2014-09-06)
Here we present the first structural comparison of amidoxime complexes of UO2(2+) and VO2(+) (the main competitor in the extraction of uranium from seawater using amidoxime-based sorbents) using a 4,5-di(amidoxime)-functionalized imidazole ligand. The amidoxime groups resist tautomerization in both cases
C Vargeese et al.
Nucleic acids research, 26(4), 1046-1050 (1998-03-21)
A new activator for the coupling of phosphoramidites to the 5'-hydroxyl group during oligonucleotide synthesis is introduced. The observed time to complete coupling is twice as fast with 4, 5-dicyanoimidazole (DCI) as the activator, compared with 1 H -tetrazole. The
Matthew T Holden et al.
Analytical chemistry, 87(22), 11420-11428 (2015-10-24)
The photolithographic fabrication of high-density DNA and RNA arrays on flexible and transparent plastic substrates is reported. The substrates are thin sheets of poly(ethylene terephthalate) (PET) coated with cross-linked polymer multilayers that present hydroxyl groups suitable for conventional phosphoramidite-based nucleic

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