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554030

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
Pricing and availability is not currently available.

Quality Level

200

Assay

99.0%

mp

168-175 °C (lit.)

functional group

nitrile

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.[1]

Application

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
HMBK5065
HMBK1952
HMBK3533
HMBK2108
HMBK2107

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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

Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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