Trichloroacetyl isocyanate (HCID 76400)

Namen und Bezeichner

Bevorzugter Name: Trichloroacetyl isocyanate
IUPAC: 2,2,2-trichloroacetyl isocyanate
Lokaler Name: Trichloracetylisocyanat
Englischer Name: Trichloroacetyl isocyanate
Summenformel: C3Cl3NO2
Molmasse: 188.4

Namen und Synonyme

Trichloroacetyl isocyanate3019-71-4Acetyl isocyanate, trichloro-QXV1P5J6JLAcetyl isocyanate, 2,2,2-trichloro-DTXSID7062790CCl3CONCORefChem:899215DTXCID2038150221-165-72,2,2-Trichloroacetyl isocyanatetrichloroethanecarbonyl isocyanate

Weitere Namen anzeigen

Trichloroacetyl isocyatetrichloro-acetylisocyanatTrichloroacetyl isocyanate ,97%Trichloroacetyl isocyanate, GC 97%

Isocyanic Acid Trichloroacetyl EsterTrichloroacetylisocyanate2,2,2-trichloroethanecarbonyl isocyanateMFCD00002033UNII-QXV1P5J6JLC3Cl3NO2PARAGOS 331057EINECS 221-165-7

Datenbank-Bezeichner

CAS: 3019-71-4
PubChem CID: 76400
DTXSID: DTXSID7062790
UNII: QXV1P5J6JL
EC Number: 221-165-7
Nikkaji: J205.322E

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,8
Polarare Oberfläche (TPSA): 46,5 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 2
Frei drehbare Bindungen: 0
Schwere Atome: 9
Formalladung: 0
Komplexität: 166

Experimentelle und physikochemische Eigenschaften

SpringerMaterials PropertiesChemical shift

Physikochemische Eigenschaften

Schmelzpunkt: 135 · 135-140 °C
Siedepunkt: 80 · 80-85 °C/20 mmHg (lit.)
Dichte: 1.581 g/mL · 1.581 g/mL at 25 °C (lit.)
Brechungsindex: 20 · n20/D 1.480(lit.)
Flammpunkt: 150 °F · 150 °F
storage temp.: 2 · 2-8°C
Löslichkeit: Miscible with dichloromethane, ether, terahydrofuran and protic solvents.
Aggregatzustand: Liquid
Farbe: Clear colorless to slightly yellow
Wasserlöslichkeit: Decomposition
BRN: 971201 · 971201
Stabilität: Hygroscopic, Moisture Sensitive
InChI: 1S/C3Cl3NO2/c4-3(5,6)2(9)7-1-8
InChIKey: GRNOZCCBOFGDCL-UHFFFAOYSA-N
SMILES: ClC(Cl)(Cl)C(=O)N=C=O
CAS Datenbank: 3019 · 3019-71-4(CAS DataBase Reference)
NIST chemische Informationen: Trichloroacetyl isocyanate(3019-71-4)
EPA chemische Informationen: Acetyl isocyanate, trichloro- (3019-71-4)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H311 (87%): Toxic in contact with skin [Danger Acute toxicity, dermal]

P233, P260, P261, P262, P264, P270, P271, P280, P284, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P342+P316, P361+P364, P363, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 46 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 2 Einträge

Status: No longer Valid Update: 20-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24187

Trichloroacetyl isocyanate: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesAcute Tox. 3 (87%)

Sicherheitsdaten

F: 10-19
wgk: 3
tsca: TSCA listed
ridadr: UN 2206 6.1/PG 3
hs_code: 29291090
risk_code: 14-23/24-34-42-23/24/25-36/37/38
hazard_code: T
safety_code: 23-26-36/37/39-45-8-7/9
hazard_class: 6.1
packing_group: II
Speicherklasse: 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications: Acute Tox. 3 DermalAcute Tox. 3 InhalationEye Dam. 1Resp. Sens. 1Skin Corr. 1BSkin Sens. 1

Chemie und Industrie

Verwendung und Herstellung

General Manufacturing InformationAcetyl isocyanate, 2,2,2-trichloro-: ACTIVE

Anwendungen

VerwendenTrichloroacetyl isocyanate was used in catalytic one-pot dehydrative glycosylation of 1-hydroxy carbohydrate. It was also used as a reagent for the conversion of alcohols to carbamates.

Darstellung · 1 Eintrag

synthetischeTrichloroacetyl isocyanate can be obtained by reacting 2,2,2-trichloroacetamide with oxalyl chloride. Procedure: A reaction mixture of 2,2,2-trichloroacetamide (100 g, 616 mmol, 1.0 eq) in (COCl)2 (725 g, 5.71 mol, 500 mL, 9.28 eq) was heated to 70°C for 24 hours. The reaction mixture was concentrated under vacuum. To the mixture was added 1,2,4-trichlorobenzene (500 mL) and (COCl)2 (116 g, 914 mmol, 80 mL, 1.48 eq). The reaction mixture was stirred at 100°C for 5 hours. Heat to 125°C for 15 hours. The mixture was then heated to 140°C for 5 hours. The reaction mixture was distilled under water pump (72°C-76°C fractions) to give trichloroacetyl isocyanate (60 g, 319 mmol, 52% yield) as a colorless oil.