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21860

Sigma-Aldrich

CDI

≥97.0% (T)

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Synonym(s):
1,1′-Carbonyldiimidazole
Empirical Formula (Hill Notation):
C7H6N4O
CAS Number:
Molecular Weight:
162.15
Beilstein/REAXYS Number:
6826
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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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This Item
115533T4069700746
CDI ≥97.0% (T)

21860

CDI

CDI reagent grade

115533

CDI

JC-1 solid

T4069

JC-1

(S)-SDP ≥95%

700746

(S)-SDP

assay

≥97.0% (T)

assay

≥90.0% (proton, NMR)

assay

≥97%

assay

≥95%

storage temp.

2-8°C

storage temp.

-

storage temp.

room temp

storage temp.

−20°C

Quality Level

200

Quality Level

200

Quality Level

-

Quality Level

-

mp

115-122 °C, 117-122 °C (lit.)

mp

117-122 °C (lit.)

mp

-

mp

199-204 °C

reaction suitability

reaction type: Carbonylations

reaction suitability

reaction type: Carbonylations

reaction suitability

-

reaction suitability

-

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

signalword

Danger

Hazard Classifications

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

Storage Class

8A - Combustible, corrosive hazardous materials

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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Carbonyldiimidazole-mediated Lossen rearrangement
Dube P, et al.
Organic Letters, 11(24), 5622-5625 (2009)
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)
Sequential One-Pot Synthesis of Dipeptides through the Transient Formation of CDI-N-Protected \alpha-Aminoesters
Renata Marcia D et al.
advanced synthesis and catalysis, 359, 1963-1968 (2017)
Mild Decarboxylative Activation of Malonic Acid Derivatives by 1, 1′-Carbonyldiimidazole
Lafrance D, et al.
Organic Letters, 9(13), 2322-2325 (2011)
Synthesis and antimicrobial activity of some 1, 3, 4-oxadiazole derivatives
Dube P, et al.
Il Farmaco (Societa Chimica Italiana : 1989), 57(7), 539-542 (2002)

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