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Sigma-Aldrich

CDI

≥97.0% (T), for peptide synthesis

Synonym(s):

1,1′-Carbonyldiimidazole

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About This Item

Empirical Formula (Hill Notation):
C7H6N4O
CAS Number:
530-62-1
Molecular Weight:
162.15
Beilstein:
6826
EC Number:
208-488-9
MDL number:
MFCD00005286
UNSPSC Code:
12352115
PubChem Substance ID:
57647944
NACRES:
NA.22

product name

CDI, ≥97.0% (T)

Quality Level

200

Assay

≥97.0% (T)

form

solid

reaction suitability

reaction type: Carbonylations

mp

115-122 °C
117-122 °C (lit.)

application(s)

peptide synthesis

storage temp.

2-8°C

SMILES string

O=C(n1ccnc1)n2ccnc2

InChI

1S/C7H6N4O/c12-7(10-3-1-8-5-10)11-4-2-9-6-11/h1-6H

InChI key

PFKFTWBEEFSNDU-UHFFFAOYSA-N

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General description

CDI serves as a powerful coupling reagent in peptide synthesis and organic chemistry.

Application

CDI (1,1′-Carbonyldiimidazole) can be used:
  • In the activation of malonic acid derivatives to prepare carbonyl imidazoles by mild decarboxylation.
  • In the activation of cellulose membranes for the development of immunosensors.
  • In the synthesis of substituted 1,3-oxazolo[4,5-d] pyridazinones.
  • As a reagent for the conversion of various hydroxamic acids to isocyanates by Lossen rearrangement.
  • In the synthesis of 1,3,4-oxadiazole derivatives , and peptide thioesters in water.
  • As an acylation agent for the synthesis of carbamates.

Other Notes

Reactive reagent for the activation of acids as imidazolides: synthesis of esters, amides, ketones etc. Reagent for immobilizing enzymes and affinity ligands; Carbonyl-transfer reagent for the synthesis of various heterocycles, some recent applications

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 2

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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J. Barluenga et al.
The Journal of Organic Chemistry, 56, 6751-6751 (1991)
Mechanochemical 1, 1′-Carbonyldiimidazole-Mediated Synthesis of Carbamates
Lanzillotto M, et al.
ACS sustainable chemistry & engineering, 11(3), 2882-2889 (2015)
An efficient synthesis of novel 1, 3-oxazolo [4, 5-d] pyridazinones
Frolov EB, et al.
Tetrahedron Letters, 45(24), 4693-4696 (2004)
Activation of cellulose membranes with 1, 1′-carbonyldiimidazole or 1-cyano-4-dimethylaminopyridinium tetrafluoroborate as a basis for the development of immunosensors
Stollner, D, et al.
Analytical Biochemistry, 2(304), 157-165 (2002)
Mild Decarboxylative Activation of Malonic Acid Derivatives by 1, 1′-Carbonyldiimidazole
Lafrance D, et al.
Organic Letters, 9(13), 2322-2325 (2011)
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