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38370

Sigma-Aldrich

DIC

≥98.0% (GC), for peptide synthesis

Synonyme(s) :

N,N′-Diisopropylcarbodiimide

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About This Item

Formule linéaire :
(CH3)2CHN=C=NCH(CH3)2
Numéro CAS:
Poids moléculaire :
126.20
Numéro Beilstein :
878281
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352001
ID de substance PubChem :
Nomenclature NACRES :
NA.22

product name

DIC, purum, ≥98.0% (GC)

Qualité

purum

Niveau de qualité

Pureté

≥98.0% (GC)

Forme

liquid

Capacité de réaction

reaction type: Coupling Reactions

Indice de réfraction

n20/D 1.433 (lit.)

Point d'ébullition

145-148 °C (lit.)

Densité

0.815 g/mL at 20 °C (lit.)
0.815 g/mL at 20 °C

Application(s)

peptide synthesis

Chaîne SMILES 

CC(C)N=C=NC(C)C

InChI

1S/C7H14N2/c1-6(2)8-5-9-7(3)4/h6-7H,1-4H3

Clé InChI

BDNKZNFMNDZQMI-UHFFFAOYSA-N

Informations sur le gène

human ... EPHX2(2053)
mouse ... Ephx2(13850)

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Description générale

N,N′-Diisopropylcarbodiimide (DIC) is a carbodiimide used as a coupling reagent in the synthesis of amides, peptides, ureas, heterocycles, and unsymmetrical carbodiimides. It is also used in the polymerization reactions as an activator.

Application

N,N′-Diisopropylcarbodiimide can be used:
  • To synthesize lanthanide (Ln) guanidinate complexes via insertion of carbodiimide into the Ln-N bond of lanthanocene secondary amido complexes.
  • To facilitate the cyclization of N-(β-Hydroxy)amides to form 2-oxazolines.
  • To synthesize 1-isopropyl-2-alkoxycarbonyl-3-isopropyliminio-aziridine by reacting with alkyl diazoacetates in the presence of transition metal salts.

DIC can be used as:
  • A coupling reagent for the synthesis of various esters and amides by treating carboxylic acids with phenols and amines respectively.
  • A reagent for the conversion of alcohols to aldehydes or ketones in the presence of DMSO via modified Moffatt-type oxidation reaction.
  • A reagent to facilitates the preparation of alkyl halides from corresponding alcohols via the formation of o-alkylisourea.

Alternative au dicyclohexylcarbodiimide en synthèse peptidique.

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Mention d'avertissement

Danger

Mentions de danger

Classification des risques

Acute Tox. 1 Inhalation - Eye Dam. 1 - Flam. Liq. 3 - Resp. Sens. 1 - Skin Sens. 1

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

91.4 °F

Point d'éclair (°C)

33 °C

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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1, 3-Diisopropylcarbodiimide
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Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
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Alcohols can be converted in high yields to the corresponding alkyl halides in a one-pot procedure via the corresponding O-alkylisourea; very short reaction times are possible when microwave irradiation is used.
Synthesis of iminoaziridines from carbodiimides and diazoesters: a new example of transition metal salt catalysed reactions of carbenes.
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Articles

In principle, the seemingly simple formation of a peptide bond can be accomplished using all the procedures available in organic chemistry for the synthesis of carboxylic acid amides. However, due to the presence of various functional groups in natural and unnatural amino acids and particularly the requirement for full retention of chiral integrity, the coupling of amino acids and peptides under mild conditions can be challenging. A plethora of coupling reagents has been developed superseding each other in efficiency and suitability for specific applications (e.g., solid-phase peptide synthesis or fragment condensation).

In principle, the seemingly simple formation of a peptide bond can be accomplished using all the procedures available in organic chemistry for the synthesis of carboxylic acid amides. However, due to the presence of various functional groups in natural and unnatural amino acids and particularly the requirement for full retention of chiral integrity, the coupling of amino acids and peptides under mild conditions can be challenging. A plethora of coupling reagents has been developed superseding each other in efficiency and suitability for specific applications (e.g., solid-phase peptide synthesis or fragment condensation).

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