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21860

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:
Molecular Weight:
162.15
Beilstein/REAXYS Number:
6826
EC Number:
MDL number:
UNSPSC Code:
12352115
PubChem Substance ID:
NACRES:
NA.22

product name

CDI, ≥97.0% (T)

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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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

hcodes

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


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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1,1'-Carbonyldiimidazole-mediated immobilization of enzymes and affinity ligands.
M T Hearn
Methods in enzymology, 135, 102-117 (1987-01-01)
S.K. Kang et al.
Synthetic Communications, 23, 2219-2219 (1993)
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)
Carbonyldiimidazole-mediated Lossen rearrangement
Dube P, et al.
Organic Letters, 11(24), 5622-5625 (2009)
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)

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