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115533

Sigma-Aldrich

CDI

greener alternative

≥90.0% (proton, NMR), for peptide synthesis

Sinónimos:

1,1′-Carbonyldiimidazole

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About This Item

Fórmula empírica (notación de Hill):
C7H6N4O
Número de CAS:
530-62-1
Peso molecular:
162.15
Beilstein/REAXYS Number:
6826
EC Number:
208-488-9
MDL number:
MFCD00005286
UNSPSC Code:
12352115
PubChem Substance ID:
24847221
NACRES:
NA.22

Nombre del producto

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.

signalword

Danger

Hazard Classifications

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

Storage Class

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

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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Certificados de análisis (COA)

Lot/Batch Number
BGBB2488
BGBB2488
0000051296
0000051296
BCCF3194

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1,1′-Thiocarbonyldiimidazole technical grade, 90%

Sigma-Aldrich

156051

1,1′-Thiocarbonyldiimidazole

Tetrahedron Letters, 34, 725-725 (1993)
Inorganic Chemistry, 32, 3052-3052 (1993)
The Journal of Organic Chemistry, 54, 5620-5620 (1989)
Polym. Mater. Sci. Eng., 61, 936-936 (1989)
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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Artículos

Imidazolium Derived Reagents

N-Acylimidazoles were recognized in the early 1950s as reactive intermediates suitable for the acylation of amino compounds. The search for better coupling reagents than DCC led to the development of CDI (1,1’-carbonyldiimidazole) and related carbonylimidazoles.

Greener Chemistry: Methods and Products for Amide Bond Formation

Amide bonds are ubiquitous in both nature and industrial applications. They are vital to the structure and function of biological macromolecules and polymers. The importance of this functionality has resulted in numerous approaches to its formation, ranging from stoichiometric activation of carboxylic acids to more recent advances in catalytic amide bond formation.

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