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36650

DCC

Name: DCC
Brand: SIAL

≥99.0% (GC), for peptide synthesis

Synonym(s):

N,N′-Dicyclohexylcarbodiimide

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About This Item

Linear Formula:

C₆H₁₁N=C=NC₆H₁₁

CAS Number:

538-75-0

Molecular Weight:

206.33

NACRES:

NA.22

PubChem Substance ID:

329755430

UNSPSC Code:

12352000

EC Number:

208-704-1

MDL number:

MFCD00011659

Beilstein/REAXYS Number:

610662

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Product Name

DCC, puriss., ≥99.0% (GC)

grade

puriss.

Quality Level

200

assay

≥99.0% (GC)

form

solid

reaction suitability

reaction type: Coupling Reactions

bp

122-124 °C/6 mmHg (lit.)

mp

32.0-37.0 °C, 34-35 °C (lit.)

solubility

methylene chloride: 0.1 g/mL, clear, colorless

application(s)

peptide synthesis

SMILES string

C1CCC(CC1)N=C=NC2CCCCC2

InChI

1S/C13H22N2/c1-3-7-12(8-4-1)14-11-15-13-9-5-2-6-10-13/h12-13H,1-10H2

InChI key

QOSSAOTZNIDXMA-UHFFFAOYSA-N

Gene Information

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

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Related Categories

Amino Acids, Resins & Reagents for Peptide Synthesis

Building Blocks, Resins, and Coupling Reagents for GLP-1 Synthesis

General description

DCC is an organic compound widely used as a coupling reagent in peptide synthesis. It is also employed as an efficient dehydrating agent for the preparation of amides, esters, nitriles, and anhydrides. Alcohols can be converted into aldehydes and ketone by Moffatt oxidation reaction in the presence of DCC and dimethyl sulfoxide (DMSO).

Application

DCC may be used to promote the esterification of 7-((tert-butyldimethylsilyl)oxy)hepta-2,4-diyn-1-ol with propiolic acid to form 7-((tert-butyldimethylsilyl)oxy)hepta-2,4-diyn-1-yl propynoate.
It may be also used to synthesize:

1,3-Thiazetedine derivatives via [2+2] cycloaddition with 2-phenylethenyl- and 2-(4-nitrophenyl)ethenyl isothiocyanates.
1,3,5-Oxadiazine-4-thiones via [4+2] cycloaddition with benzoyl isothiocyanates.
Sterically hindered 1,3,4-oxadiazole derivatives by reacting with (N-isocyanimino)triphenylphosphorane the presence of aromatic (or heteroaromatic) carboxylic acids.

Other Notes

Coupling reagent, reagent for dehydrations etc. Modifies bovine heart mitochondrial transhydrogenase; Inhibition of F₁F₀-ATPase and other proton-translocating enzymes

pictograms

GHS06,GHS05

signalword

Danger

hcodes

H302,H311,H317,H318

pcodes

P261 - P264 - P280 - P301 + P312 - P302 + P352 + P312 - P305 + P351 + P338

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Sens. 1

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Storage Class

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

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Dicyclohexylcarbodiimide (DCC)

Kvasnica M

Synlett, 2007(14), 2306-2307 (2007)

1, 3-Dicyclohexylcarbodiimide

Albert JS, et al.

Encyclopedia of Reagents for Organic Synthesis, Second Edition, 1-9 (2001)

Light-dependent chemical modification of thylakoid membrane protein with carboxyl-directed reagents.

J A Laszlo et al.

Archives of biochemistry and biophysics, 215(2), 571-581 (1982-05-01)

Formation of optically pure N-acyl-N,N'-dicyclohexylurea in N,N'-dicyclohexylcarbodiimide-mediated peptide synthesis.

M Slebioda et al.

International journal of peptide and protein research, 35(6), 539-541 (1990-06-01)

N-acylurea, a side product in peptide synthesis from DCC, preserves its chiral integrity although peptides formed simultaneously in the same reaction are racemized to a large extent. This observation is inconsistent with the generally accepted opinion that racemization-prone O-acylisourea is

Review of synthesis of 1, 3, 4-oxadiazole derivatives.

Patel K D, et al.

Synthetic Communications, 44(13), 1859-1875 (2014)

View All Related Papers

Global Trade Item Number

SKU	GTIN
W383902-100G-K	04061838258144
W383902-1KG-K	04061837537530
W383902-SAMPLE-K	04061837537547
W383902-4KG-K	04061834406419
36650-2.5KG	04061831826197
36650-500G	04061831826234
36650-100G	04061831826173

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