36650

DCC

≥99.0% (GC), for peptide synthesis

• Synonim(y): N,N′-Dicyclohexylcarbodiimide
• Wzór liniowy: C₆H₁₁N=C=NC₆H₁₁
• Numer CAS: 538-75-0
• Masa cząsteczkowa: 206.33
• NACRES: NA.22
• PubChem Substance ID: 329755430
• UNSPSC Code: 12352000
• EC Number: 208-704-1
• MDL number: MFCD00011659
• Beilstein/REAXYS Number: 610662

Właściwości

• Nazwa produktu: DCC, puriss., ≥99.0% (GC)
• grade: puriss.
• Quality Segment: 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)

Opis

General description

DCC is an organic compound widely used as a coupling reagent in peptide synthesis.[1] 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;[2][3] Inhibition of F₁F₀-ATPase and other proton-translocating enzymes

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Informacja o środkach bezpieczeństwa

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