36650

DCC

puriss., ≥99.0% (GC)

• Synonym(s): N,N′-Dicyclohexylcarbodiimide
• Linear Formula: C₆H₁₁N=C=NC₆H₁₁
• CAS Number: 538-75-0
• Molecular Weight: 206.33
• Beilstein: 610662
• EC Number: 208-704-1
• MDL number: MFCD00011659
• UNSPSC Code: 12352000
• PubChem Substance ID: 329755430
• NACRES: NA.22

Properties

• 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)

Description

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

Safety Information

• Pictograms: GHS05,GHS06
• Signal Word: Danger
• Hazard Statements: H302 - H311 - H317 - H318
• Precautionary Statements: 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
• Storage Class Code: 6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
• WGK: WGK 3
• Flash Point(F): 235.4 °F - closed cup
• Flash Point(C): 113 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves