Trichloracetylchlorid
2,2,2-trichloroAcetyl chloride · CCl3COCl · Trichloroacetic chloride · Superpalite · TRICHLOROACETIC ACID CHLORIDE · Green cross gas · trichloroacetyl · Trichloroacetyl chlo
Identifikatoren & physikalische Daten
| CAS No. | 76-02-8 |
|---|---|
| Summenformel | C2Cl4O |
| Durchschnittliche Molmasse | 181,8 g/mol |
| Monoisotopische Masse | 179,87032534 g/mol |
| SMILES | O=C(Cl)C(Cl)(Cl)Cl |
| InChIKey | PVFOMCVHYWHZJE-UHFFFAOYSA-N |
| PubChem CID | 6420 |
| ChEMBL | CHEMBL3186657 |
| EC No. | 200-926-7 |
| DTXSID | DTXSID9034070 |
| Lokaler Name | Trichloracetylchlorid |
Chemische & physikalische Eigenschaften
| XLogP | 2,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 17,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 7 |
| Formalladung | 0 |
| Komplexität | 82,2 |
| Stoffklassen | Toxic Gases & Vapors -> Acid HalidesCorrosives |
| SpringerMaterials Properties | Schoenflies notation |
| Dichte | 1.654 at 32 °F (EPA, 1998) - Denser than waterwill sink1.6202 at 20 °C/4 °C1.629 @25 °C1.629 g/mL at 25 °C(lit.) |
| Color/Form | Liquid |
| Löslichkeit | Sol in etherSol in alcoholChloroform (Soluble), Ethyl Acetate (Soluble)reacts violently |
| Siedepunkt | 244 °F at 760 mmHg (EPA, 1998)117.9 °C114-116 °C(lit.) |
| Schmelzpunkt | -31.8 °C-146 °C-57 °C |
| Dampfdruck | 21.3 [mmHg]21.32 mm Hg @ 25 °C, determined from experimentally derived coefficients21.32 [mm Hg] @25 °C16 mm Hg ( 20 °C) |
| Brechungsindex | Index of refraction: 1.4695 at 20 °Cn20/D 1.470(lit.) |
| Physical Description | Trichloroacetyl chloride appears as a colorless volatile liquid with a strong odor. Denser than water. Contact severely irritates skin, eyes and mucous membranes. May be very toxic by ingestion and inhalation. May be combustible.Liquid that decomposes in water[Hawley] |
| Other Experimental Properties | Decomposes in waterLiquid molar volume = 0.112702 cu m/Kmol |
| Flammpunkt | 100 °C |
| Lagerbedingungen | Refrigerator, Under inert atmosphere |
| Aggregatzustand | Oil |
| Farbe | Colourless |
| pH | 1.11 (25°C, 16.2g/L in H2O) |
| BRN | 774120 |
| Henry-Konstante | 2.0×10-2 mol/(m3Pa) at 25℃, Mirabel et al. (1996) |
| Stabilität | Stable. Reacts violently with water. Incompatible with alcohols, oxidizing agents, strong bases. |
| InChI | 1S/C2Cl4O/c3-1(7)2(4,5)6 |
| InChIKey | PVFOMCVHYWHZJE-UHFFFAOYSA-N |
| SMILES | ClC(Cl)(Cl)C(=O)Cl |
| CAS Datenbank | 76-02-8(CAS DataBase Reference) |
| NIST chemische Informationen | Trichloroacetyl chloride(76-02-8) |
| EPA chemische Informationen | Trichloroacetyl chloride (76-02-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH290 (67.5%): May be corrosive to metals [Warning Corrosive to Metals]P234, P260, P261, P264, P264+P265, P270, P271, P273, P280, P284, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P320, P321, P330, P363, P390, P391, P403+P233, P405, P406, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 160 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazards Identification | Toxic/poison by inhalation (TIH/PIH) |
| Regulatorische Informationen | Chemical: Acetyl chloride, trichloro-Status: Cease Manufacture Update: 28-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/11166Trichloroacetyl chloride: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| DOT-Kennzeichnung | Corrosive Poison Inhalation Hazard |
| Brandgefahren | Material may burn but does not ignite readily. Poisonous if inhaled or swallowedskin contact poisonous. Contact may cause burns to skin and eyes. (EPA, 1998)· Combustible material: may burn but does not ignite readily. |
| Gesundheitsgefahren | Highly toxic by ingestion and inhalationstrong irritant to skin and tissues. (EPA, 1998)· TOXIC and/or CORROSIVEinhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. |
| Gefahrenübersicht | Experiments conducted at Argonne showed that no gas is generated upon mixing with water. No apparent evolution of hydrochloric acid after mixing with waterA strong skin irritant[CAMEO] |
| DOT-Nummer und Handbuch | 2442 156 |
Anwendungen & Verwendung
Verwenden
Trichloroacetyl chloride can be used for the manufacture of the esters and the anhydrides of trichloroacetic acid.It was used in the preparation of dihydro-1H-benzindoles. It was also used in the synthesis of 3-alkylbenzoxazolones.
Herstellung & Synthese
synthetische
The acetyl chloride is prepared from trichloroacetic acid and various inorganic acid chlorides (e.g., SOCl2, PCl3) or with P2O5 and HCl. More useful methods are the oxidation of tetrachloroethylene with fuming sulfuric acid, oxygen, or fuming nitric acid and sulfuric acid at 18-20°C, or from the reaction of pentachloroethane and dry oxygen under UV light. It has been obtained in 37 % yield from carbon tetrachloride and carbon monoxide in the presence of aluminum chloride at 200°C and high pressure.The most common production method is the gas-phase, photochemical oxidation of tetrachloroethylene with oxygen. The reaction is initiated with UV light, with radioactive irradiation, or it is sensitized with chlorine or iodine.