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Sigma-Aldrich

DIC

≥98.0% (GC), for peptide synthesis

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Synonym(s):
N,N′-Diisopropylcarbodiimide
Linear Formula:
(CH3)2CHN=C=NCH(CH3)2
CAS Number:
693-13-0
Molecular Weight:
126.20
Beilstein:
878281
EC Number:
211-743-7
MDL number:
MFCD00065689
UNSPSC Code:
12352001
PubChem Substance ID:
329755678
NACRES:
NA.22

grade

purum

Quality Level

200

Assay

≥98.0% (GC)

form

liquid

reaction suitability

reaction type: Coupling Reactions

refractive index

n20/D 1.433 (lit.)

bp

145-148 °C (lit.)

density

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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General description

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 to dicyclohexylcarbodiimide in peptide synthesis.

related product

Product No.
Description
Pricing

Signal Word

Danger

Hazard Statements

H226,H317,H318,H330,H334

Hazard Classifications

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

WGK

WGK 3

Flash Point(F)

91.4 °F

Flash Point(C)

33 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

非剧毒-急性毒性1
危险化学品

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1, 3-Diisopropylcarbodiimide
Nora GP, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
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)
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)
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)
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