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38370

Sigma-Aldrich

DIC

purum, ≥98.0% (GC)

Synonym(s):

N,N′-Diisopropylcarbodiimide

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About This Item

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.

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Description
Pricing

Signal Word

Danger

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

91.4 °F

Flash Point(C)

33 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH2478
BCCF5927
BCCC8108
BCBZ4926
BCBV5765

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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)
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)
Yu Shao et al.
Molecules (Basel, Switzerland), 24(11) (2019-06-07)
In this article, we report the facile synthesis, self-assembly, and characterization of shape amphiphiles (BPOSS-PDI-X) based on isobutyl-functionalized polyhedral oligomeric silsesquioxane (BPOSS), perylene tetracarboxylic diimide (PDI), and (60)fullerene (C60) moieties. Firstly, an asymmetrically functionalized diblock shape amphiphile precursor (BPOSS-PDI-OH) was
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Articles

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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