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38370

Sigma-Aldrich

DIC

purum, ≥98.0% (GC)

Sinónimos:
N,N′-Diisopropylcarbodiimide
Fórmula lineal:
(CH3)2CHN=C=NCH(CH3)2
Número de CAS:
Peso molecular:
126.20
Beilstein:
878281
Número de EC:
Número MDL:
ID de la sustancia en PubChem:
NACRES:
NA.22

Nivel de calidad

200

grado

purum

ensayo

≥98.0% (GC)

reaction suitability

reaction type: Coupling Reactions

índice de refracción

n20/D 1.433 (lit.)

bp

145-148 °C (lit.)

densidad

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

application(s)

peptide synthesis

SMILES string

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

InChI

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

InChI key

BDNKZNFMNDZQMI-UHFFFAOYSA-N

Gene Information

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

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Descripción general

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.

Aplicación

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.

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.

Alternative to dicyclohexylcarbodiimide in peptide synthesis.

Palabra de señalización

Danger

Clasificaciones de peligro

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

Código de clase de almacenamiento

3 - Flammable liquids

WGK

WGK 3

Punto de inflamabilidad F

91.4 °F

Punto de inflamabilidad C

33 °C

Equipo de protección personal

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

Certificado de Análisis

Certificado de origen

1, 3-Diisopropylcarbodiimide
Nora GP, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Amidation and esterification of carboxylic acids with amines and phenols by N, N?-diisopropylcarbodiimide: A new approach for amide and ester bond formation in water
Fattahi N, et al.
Tetrahedron, 74(32), 4351-4356 (2018)
Stefano Crosignani et al.
Chemical communications (Cambridge, England), (2), 260-261 (2003-02-15)
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.
Hubert A
Tetrahedron Letters, 17(16), 1317-1318 (1976)
Insertion of a carbodiimide into the Ln? N ?-bond of organolanthanide complexes. Isomerization and rearrangement of organolanthanides containing guanidinate ligands.
Zhang J
Organometallics, 23(13), 3303-3308 (2004)

Artículos

Coupling Reagents

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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