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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

Quality Level

200

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
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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