Dicyclohexylcarbodiimid

DCC · N,N'-Dicyclohexylcarbodiimide · DCCI · 1,3-DICYCLOHEXYLCARBODIIMIDE · DCCD · N,N'-Dicyclohexylmethanediimine · N,N-DICYCLOHEXYL CARBODIIMIDE · dicyclohexyl-carbodiimid

https://huagongshe.com/de/chemical/10868

Molekülstruktur von Dicyclohexylcarbodiimid

Identifikatoren & physikalische Daten

CAS No.	538-75-0
Summenformel	C13H22N2
Durchschnittliche Molmasse	206,33 g/mol
Monoisotopische Masse	206,17829871 g/mol
SMILES	C(=NC1CCCCC1)=NC1CCCCC1
InChIKey	QOSSAOTZNIDXMA-UHFFFAOYSA-N
PubChem CID	10868
ChEMBL	CHEMBL162598
ChEBI	CHEBI:53090
EC No.	208-704-1
DTXSID	DTXSID1023817
Lokaler Name	Dicyclohexylcarbodiimid

Chemische & physikalische Eigenschaften

XLogP	4,7
Polarare Oberfläche (TPSA)	24,7
H-Brücken-Donoren	0
H-Brücken-Akzeptoren	2
Frei drehbare Bindungen	2
Schwere Atome	15
Formalladung	0
Komplexität	201
LogP (Verteilungskoeffizient)	log Kow = 6.83 (estvalue theoretical as compound reacts with water)
Geruch	Heavy sweet odor
Color/Form	Crystalline massWhite crystalsColorless crystalline solid
Löslichkeit	Reaction (NTP, 1992)Moisture sensitive, reacts with waterSoluble in organic solventsmethylene chloride: 0.1 g/mL, clear, colorless
Corrosivity	Corrosive to tissue
Flammpunkt	greater than 235 °F (NTP, 1992)Flash Point > 235 °F190 °F
Siedepunkt	252 to 255 °F at 6 mmHg (NTP, 1992)BP: 154-156 °C at 11 mm Hg122-124 °C6 mm Hg(lit.)
Decomposition	When heated to decomposition it emits toxic vapors of /oxides of nitrogen/.
Schmelzpunkt	93 to 95 °F (NTP, 1992)34.5 °C34-35 °C(lit.)
Dampfdruck	VP: 0.5 mm Hg at 98-100 °C, 2 mm Hg at 138-140 °C, 11 mm Hg at 154-156 °C1.044-1.15Pa at 20-25℃
Physical Description	N,n'-dicyclohexylcarbodiimide is a white crystalline solid with a heavy sweet odor. (NTP, 1992)Dry PowderWhite solid with a sweet odor[Hawley] White meltmp = 33-36 deg C[MSDSonline]
Other Experimental Properties	Set point = 29-30 °CIncompatible with acids and oxidizersemits toxic fumes when combusted
Dichte	1.247 g/mL at 25 °C
Brechungsindex	n20/D 1.48
Lagerbedingungen	Store below +30°C.
Aggregatzustand	Waxy Solid or Crystalline Mass
Wichte	1.247
Farbe	White to pale yellow
Merck	14,3096
BRN	610662
Stabilität	Stable, but moisture sensitive. Combustible. Incompatible with strong oxidizing agents. Avoid exposure to air or moisture.
Hauptanwendungen	peptide synthesis
InChI	1S/C13H22N2/c1-3-7-12(8-4-1)14-11-15-13-9-5-2-6-10-13/h12-13H,1-10H2
InChIKey	QOSSAOTZNIDXMA-UHFFFAOYSA-N
SMILES	C1CCC(CC1)N=C=NC2CCCCC2
LogP (Verteilungskoeffizient)	5.567-6.83 at 25℃
CAS Datenbank	538-75-0(CAS DataBase Reference)
NIST chemische Informationen	Methanediimine, n,n'-dicyclohexyl-(538-75-0)
EPA chemische Informationen	Dicyclohexylcarbodiimide (538-75-0)

Sicherheit & Vorschriften

GHS-Einstufung	DangerH302: Harmful if swallowed [Warning Acute toxicity, oral]H311: Toxic in contact with skin [Danger Acute toxicity, dermal]H317: May cause an allergic skin reaction [Warning Sensitization, Skin]H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]P261, P262, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P354+P338, P316, P317, P321, P330, P333+P317, P361+P364, P362+P364, P405, and P501 (click each P-code to see the statement)
Regulatorische Informationen	Chemical: Cyclohexanamine, N,N'-methanetetraylbis-Cyclohexanamine, N,N'-methanetetraylbis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclohexanamine, N,N'-methanetetraylbis- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 17-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/12761Dicyclohexylcarbodiimide: HSNO Approval: HSR004069 Approved with controls
DOT-Kennzeichnung	Poison
Brandgefahren	This chemical is probably combustible. (NTP, 1992)
Gesundheitsgefahren	SYMPTOMS: Symptoms of exposure to this compound may include skin irritation and sensitization, severe eye irritation, irritation of the mucous membranes and upper respiratory tract, and subsequent allergic reactions. It can cause severe destruction of tissue, depending on the intensity and duration of exposure.ACUTE/CHRONIC HAZARDS: This compound is highly toxic by inhalation. It is an irritant of the skin, mucous membranes and upper respiratory tract, and is a severe irritant of the eyes. It can be corrosive to tissues if exposure is in high concentrations or over extended periods of time. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide, and NOx. (NTP, 1992)
Gefahrenübersicht	A skin, eye, and respiratory tract irritantHigh concentrations can be corrosive and very damaging to tissue[CAMEO] Contact allergen[Merck Index] An irritant

Anwendungen & Verwendung

Beschreibung

Dicydohexyl carbodiimide is used in peptide chemistry as a coupling reagent. It is both an irritant and a sensitizer, and caused contact dermatitis in pharmacists and chemists.

Verwenden

N,N'-Dicyclohexylcarbodiimide is a carbodiimide used to couple amino acids during peptide synthesis. N,N'-Dicyclohexylcarbodiimide is used as a dehydrating agent for the preparation of amides, ketones , nitriles as well as in the inversion and esterification of secondary alcohols.

Herstellung & Synthese

synthetische

A stirred mixture of N,N′-dicyclohexylurea (19.7 g), phosphorus pentoxide (100 g), sand (175 g), and pyridine (700 mL) was refluxed for 2.25 h. Stirring was no longer possible after about 30 min. The mixture was filtered and the residue was extracted with pyridine (100 mL). Pyridine was removed from the combined solutions on a flash evaporator, and the residual oil was extracted with boiling petroleum ether (bp 60–80 C°) (2 × 100 mL), and then with diethyl ether (100 mL). The combined extracts were washed with iced water (3×80 mL), dried over calcium chloride, and filtered. The solvents were removed from the filtrate under reduced pressure to give 17.4 g of an oil, which on distillation yielded 13.7 g (76%) of a clear liquid; bp 143 C° (3.5 mmHg), which solidified in the receiver; mp 34–35 C°. Another method for producing DCC from dicyclohexylurea is a two-step process using phosphoryl chloride in dichloromethane at 40 C° for 4 h under non-basic conditions followed by removal of acidic components with aq. sodium hydroxide. This method, which gives an 89% yield of DCC, has been presented in a patent application.