Trichloracetylisocyanat
2,2,2-TRICHLOROACETYL ISOCYANATE · trichloroethanecarbonyl isocyanate · Trichloroacetyl isocyate · trichloro-acetylisocyanat · TRICHLOROACETYL ISOCYANATE · Acetyl isocyanate, trichloro- · Trichloroacetyl isocyanate ,97% · Trichloroacetyl isocyanate, GC 97%
Identifikatoren & physikalische Daten
| CAS No. | 3019-71-4 |
|---|---|
| Summenformel | C3Cl3NO2 |
| Durchschnittliche Molmasse | 188,39 g/mol |
| Monoisotopische Masse | 186,89946128 g/mol |
| SMILES | O=C=NC(=O)C(Cl)(Cl)Cl |
| InChIKey | GRNOZCCBOFGDCL-UHFFFAOYSA-N |
| PubChem CID | 76400 |
| EC No. | 221-165-7 |
| DTXSID | DTXSID7062790 |
| Lokaler Name | Trichloracetylisocyanat |
Chemische & physikalische Eigenschaften
| XLogP | 2,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 46,5 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 166 |
| SpringerMaterials Properties | Chemical shift |
| Schmelzpunkt | 135-140 °C |
| Siedepunkt | 80-85 °C/20 mmHg (lit.) |
| Dichte | 1.581 g/mL at 25 °C (lit.) |
| Brechungsindex | n20/D 1.480(lit.) |
| Flammpunkt | 150 °F |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Miscible with dichloromethane, ether, terahydrofuran and protic solvents.Decomposition |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless to slightly yellow |
| BRN | 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 | 3019-71-4(CAS DataBase Reference) |
| NIST chemische Informationen | Trichloroacetyl isocyanate(3019-71-4) |
| EPA chemische Informationen | Acetyl isocyanate, trichloro- (3019-71-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH311 (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. |
|---|---|
| Regulatorische Informationen | Status: No longer Valid Update: 20-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24187Trichloroacetyl isocyanate: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Acute Tox. 3 (87%) |
| F | 10-19 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2206 6.1/PG 3 |
| Zollcode | 29291090 |
| R-Sätze (R) | 14-23/24-34-42-23/24/25-36/37/38 |
| Gefahrensymbole | T |
| Sicherheitshinweise (S) | 23-26-36/37/39-45-8-7/9 |
| Gefahrenklasse | 6.1Acute Tox. 3 DermalAcute Tox. 3 InhalationEye Dam. 1Resp. Sens. 1Skin Corr. 1BSkin Sens. 1 |
| Verpackungsgruppe | II |
| Lagerklasse | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
Anwendungen & Verwendung
Verwenden
Trichloroacetyl 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.
Herstellung & Synthese
synthetische
Trichloroacetyl 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.