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115533

Sigma-Aldrich

CDI

greener alternative

≥90.0% (proton, NMR), 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:
24847221
NACRES:
NA.22

product name

CDI, reagent grade

grade

reagent grade

Quality Level

200

Assay

≥90.0% (proton, NMR)

form

solid

reaction suitability

reaction type: Carbonylations

greener alternative product characteristics

Designing Safer Chemicals
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

117-122 °C (lit.)

application(s)

peptide synthesis

greener alternative category

Aligned,

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

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. 1,1′-carbonyldiimidazole (CDI) is an alternative to highly toxic insidious poison phosgene and thus aligns with the principle "Designing Safer Chemicals". For more information see the article Controlled Synthesis of Asymmetric Dialkyl and Cyclic Carbonates Using the Highly Selective Reactions of Imidazole Carboxylic Esters.

Application

Coupling agent in the synthesis of dipolar polyamides for nonlinear optical applications and polypeptides. Also used to make β-keto sulfones and sulfoxides, lead sequestering agents, and β-enamino acid derivatives.

Signal Word

Danger

Hazard Statements

H302,H314,H360D

Hazard Classifications

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

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

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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1,1′-Thiocarbonyldiimidazole technical grade, 90%

Sigma-Aldrich

156051

1,1′-Thiocarbonyldiimidazole

Polym. Mater. Sci. Eng., 61, 936-936 (1989)
Tetrahedron Letters, 34, 725-725 (1993)
The Journal of Organic Chemistry, 54, 5620-5620 (1989)
Inorganic Chemistry, 32, 3052-3052 (1993)
A B Cheikh et al.
Journal of molecular evolution, 30(4), 315-321 (1990-04-01)
We have prepared the nucleoamino acids 1-(3'-amino,3'-carboxypropyl)uracil (3) and 9-(3'-amino,3'-carboxypropyl)adenine (4) as (L)-enantiomers and as racemic mixtures. When 3 or 4 is suspended in water and treated with N,N'-carbonyldiimidazole, peptides are formed in good yield. The products formed from the
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Articles

Imidazolium-Derived Reagents

N-Acylimidazoles and carbonylimidazoles are reactive intermediates used for amino compound acylation, surpassing DCC as coupling reagents.

Imidazolium-Derived Reagents

N-Acylimidazoles and carbonylimidazoles are reactive intermediates used for amino compound acylation, surpassing DCC as coupling reagents.

Imidazolium-Derived Reagents

N-Acylimidazoles and carbonylimidazoles are reactive intermediates used for amino compound acylation, surpassing DCC as coupling reagents.

Imidazolium-Derived Reagents

N-Acylimidazoles and carbonylimidazoles are reactive intermediates used for amino compound acylation, surpassing DCC as coupling reagents.

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