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Dichloracetylchlorid
2,2-DICHLOROACETYL CHLORIDE · CHCl2COCl · 2,2-dichloroac · 2,2-dichloroacetyl · Dichloroacetyl chlor · Dichloracetylchlorid · DichloroacetylChoride · DICHLORACETYL CHLORIDE
Identifikatoren & physikalische Daten
| CAS No. | 79-36-7 |
|---|---|
| Summenformel | C2HCl3O |
| Durchschnittliche Molmasse | 147,38 g/mol |
| Monoisotopische Masse | 145,90929769 g/mol |
| SMILES | O=C(Cl)C(Cl)Cl |
| InChIKey | FBCCMZVIWNDFMO-UHFFFAOYSA-N |
| PubChem CID | 6593 |
| ChEMBL | CHEMBL449486 |
| ChEBI | CHEBI:34688 |
| EC No. | 201-199-9 |
| DTXSID | DTXSID6024965 |
| Lokaler Name | Dichloracetylchlorid |
Chemische & physikalische Eigenschaften
| XLogP | 2,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 17,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 6 |
| Formalladung | 0 |
| Komplexität | 59,8 |
| Stoffklassen | Toxic Gases & Vapors -> Acid HalidesCorrosives |
| SpringerMaterials Properties | Schoenflies notation |
| Geruch | PENETRATING ODORACRID |
| Dichte | 1.5315 at 61 °F (NTP, 1992) - Denser than waterwill sink1.5315 @ 16 °C/4 °CRelative density (water = 1): 1.515315 @ 16°C1.532 g/mL at 25 °C (lit.) |
| Color/Form | LIQUID |
| Löslichkeit | Decomposes (NTP, 1992)SOL IN ETHERSolubility in water: decomposesChloroform, HexanesMAY DECOMPOSE |
| Flammpunkt | 151 °F (NTP, 1992)66 °C, 151 °F |
| Siedepunkt | 225 to 226 °F at 760 mmHg (NTP, 1992)107-108 °C @ 760 MM HG108 °C @760 [mm Hg]107-108 °C (lit.) |
| Dampfdichte | 5.1 (NTP, 1992) - Heavier than airwill sink (Relative to Air)5.1 (AIR= 1)Relative vapor density (air = 1): 5.1 |
| Dampfdruck | 154 mmHg at 77 °F (NTP, 1992)23.0 [mmHg]Vapor pressure, kPa at 20 °C: 3.1 |
| Brechungsindex | INDEX OF REFRACTION: 1.4638 @ 16 °C/Dn20/D 1.46(lit.) |
| Physical Description | Dichloroacetyl chloride is a colorless liquid with a pungent odor. Flash point 151 °F Boiling point 107-108 °F. Vapors are irritating to the eyes and mucous membranes. Corrosive to metals and tissue.Liquid with a penetrating odor[HSDB]COLOURLESS-TO-YELLOW FUMING LIQUID WITH PUNGENT ODOUR. |
| Schmelzpunkt | <25 °C |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless to light yellow |
| Wichte | 1.537 (20/4℃) |
| Merck | 14,3053 |
| BRN | 1209426 |
| Stabilität | Stable. Combustible. Incompatible with water, alcohols and oxidizing agents. Fumes in air. |
| InChI | 1S/C2HCl3O/c3-1(4)2(5)6/h1H |
| InChIKey | FBCCMZVIWNDFMO-UHFFFAOYSA-N |
| SMILES | ClC(Cl)C(Cl)=O |
| CAS Datenbank | 79-36-7(CAS DataBase Reference) |
| NIST chemische Informationen | Acetyl chloride, dichloro-(79-36-7) |
| EPA chemische Informationen | Dichloroacetyl chloride (79-36-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]P260, P264, P273, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P391, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.4% (1 of 243) of reports.H314 (99.6%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation] |
|---|---|
| Hazards Identification | Water-reactive material (WR) |
| Regulatorische Informationen | Chemical: Acetyl chloride, dichloro-Acetyl chloride, 2,2-dichloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetyl chloride, 2,2-dichloro- 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: 04-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/33168Dichloroacetyl 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 |
| Brandgefahren | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:· Combustible material: may burn but does not ignite readily.Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 66 °C explosive vapour/air mixtures may be formed. |
| Gesundheitsgefahren | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:· TOXIC and/or CORROSIVEinhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. |
| Gefahrenübersicht | Highly corrosive to skin[Quick CPC] Tear drawing. High inhalation exposure can cause pulmonary edema[ICSC] |
| DOT-Nummer und Handbuch | 1765 156 |
| Reaktive Gruppe | Halogenated Organic Compounds |
| EG-Einstufung | Symbol: C, NR: 35-50S: (1/2)-9-26-45-61 |
| UN-Einstufung | UN Hazard Class: 8UN Pack Group: II |
| Reactivity Alerts | Water-Reactive |
| Reactivity Profile | Solutions of DICHLOROACETYL CHLORIDE in acetone are stable for less than two hours and fresh solution should be prepared before each use (NIP). May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291]. |
| Brandbekämpfung | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:Use powder, carbon dioxide. NO water. In case of fire: keep drums, etc., cool by spraying with water. NO direct contact with water. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Do NOT induce vomiting. Give nothing to drink. Refer for medical attention . |
| Freisetungsmaßnahmen | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.General First Aid: |
| Sichere Lagerung | Separated from strong oxidants, strong bases, food and feedstuffs, alcohols and water. Dry. Well closed. Keep in a well-ventilated room. |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| Brandbekämpfungsverfahren | ALCOHOL FOAM |
| Freisetung ohne Brand | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]: |
| Verschüttetes entsorgen | Evacuate danger area! Consult an expert! Personal protection: complete protective clothing including self-contained breathing apparatus. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Isolation and Evacuation | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:Immediate precautionary measureWhen spilled in water |
| Eye Prevention | Wear face shield or eye protection in combination with breathing protection. |
| Fire Prevention | NO open flames. NO contact with water. Above 66 °C use a closed system and ventilation. |
| Umweltverhalten | TERRESTRIAL FATE: Dichloroacetyl chloride hydrolyzes on contact with water(1)therefore, hydrolysis is expected to be the only important environmental fate process in moist soils. Based on a vapor pressure of 25.3 mm Hg at 25 degC(2), dichloroacetyl chloride is expected to evaporate relatively rapidly from dry surfaces. (SRC)AQUATIC FATE: Dichloroacetyl chloride hydrolyzes on contact with water(1)therefore, hydrolyses is expected to be the only important environmental fate process in water. The hydrolysis products are expected to be HCl and dichloroacetic acid. (SRC)ATMOSPHERIC FATE: When released to the atmosphere, vapor phase dichloroacetyl chloride is expected to react with photochemically produced hydroxyl radicals at a theoretically estimated half-life rate of 22.8 days(1). The tropospheric gas-phase hydrolysis reaction between dichloroacetyl chloride and water has a half-life in excess of 100 years(2). Atmospheric wash-out and transformation via rain may be possible. (SRC) |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns. |
| Expositionspfade | The substance can be absorbed into the body by inhalation, through the skin and by ingestion. |
| Signs and Symptoms | Sore throat. Cough. Burning sensation. Shortness of breath. Laboured breathing. Symptoms may be delayed.Pain. Redness. Blisters. Skin burns.Pain. Redness. Severe deep burns. Loss of vision.Burning sensation. Abdominal cramps. Shock or collapse. |
| ICSC Environmental Data | This substance may be hazardous to the environment. Special attention should be given to water quality. |
| Soil Adsorption/Mobility | Dichloroacetyl chloride hydrolyzes on contact with water(1), therefore, leaching in moist soils will not occur as the compound will be chemically transformed. The hydrolysis product, dichloroacetic acid, should be susceptible to leaching. (SRC) |
| Natural Pollution Sources | Dichloroacetyl chloride is not known to occur naturally. (SRC) |
| Human Toxicity Excerpts | ...STRONG IRRITANT TO SKIN & EYES.SYMPTOMATOLOGY (...INGESTION OR SKIN CONTACT): 1. CORROSION OF MUCOUS MEMBRANES OF MOUTH, THROAT AND ESOPHAGUS, WITH IMMEDIATE PAIN AND DYSPHAGIA. NECROTIC AREAS...GRAYISH WHITE BUT SOON ACQUIRE A BLACKISH DISCOLORATION (YELLOW IN CASE OF NITRIC ACID) & SOMETIMES SHRUNKEN OR WRINKLED TEXTURE... 2. EPIGASTRIC PAIN...MAY BE ASSOC WITH NAUSEA & VOMITING... AT TIMES, GASTRIC HEMORRHAGE MAY BE INTENSE, AND VOMITUS THEN CONTAINS FRESH BLOOD. PROFOUND THIRST. 3. ULCERATION OF ALL MEMBRANES AND TISSUES WITH WHICH THE ACID COMES IN CONTACT. AFTER THE INGESTION OF CONCN MINERAL ACID, THIS CORROSION MAY LEAD WITHIN A FEW HR OR A FEW DAYS TO GASTRIC PERFORATION AND PERITONITIS. 4. CIRCULATORY COLLAPSE WITH CLAMMY SKIN, WEAK & RAPID PULSE, SHALLOW RESP, AND SCANTY URINE. CIRCULATORY SHOCK IS OFTEN IMMEDIATE CAUSE OF DEATH. /ACIDS/ |
| Artificial Pollution Sources | Fugitive atmospheric emissions resulting from industrial production and use operations are a potential source of dichloroacteyl chloride release to the environment(SRC). Dichloroacetyl chloride can be formed in the atmosphere by the atmospheric oxidation of trichloroethylene(1). |
| Environmental Bioconcentration | Dichloroacetyl chloride hydrolyzes on contact with water(1), therefore, bioconcentration in aquatic organisms is not possible. (SRC) |
| Volatilization from Water/Soil | Dichloroacetyl chloride hydrolyzes on contact with water(1)therefore, volatilization from water or wet soils will not occur(SRC). With a vapor pressure of 25.3 mm Hg at 25 degC(2), dichloroacetyl chloride is expected to evaporate relatively rapidly from dry surfaces(SRC). |
| Non-Human Toxicity Excerpts | RATED 10 ON RABBIT EYES. ...TESTED EXTERNALLY ON EYES OF RABBITS &...RATED NUMERICALLY ON SCALE OF 1-10 ACCORDING TO DEGREE OF INJURY...AFTER 24 HR /OBSERVATION/, PAYING PARTICULAR ATTENTION TO CONDITION OF CORNEA. MOST SEVERE INJURIES HAVE BEEN RATED 10.Dichloroacetyl chloride (1 and 5% LD50 for 4 wk) is not toxic to liver of rats of both sexes, as shown by histochem studies. |
| F | 19-21 |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1765 |
| Zollcode | 29159000 |
| RTECS-Nr. | AO6650000 |
| R-Sätze (R) | 35-50 |
| Gefahrensymbole | C,N |
| hazard_note | Corrosive/Moisture Sensitive |
| Sicherheitshinweise (S) | 9-26-45-61 |
| Gefahrenklasse | 8Aquatic Acute 1Carc. 1BEye Dam. 1Skin Corr. 1A |
| Verpackungsgruppe | II |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 79-36-7(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
Dichloroacetyl Chloride is a reagent used in the synthesis of substituted benzothiazoles exhibiting antitumor and anticancer activity.
Herstellung & Synthese
synthetische
Dichloroacetyl chloride can be synthesized by the reaction of dichloroacetic acid and chlorosulfonic acid. Or from the oxidation of trichloroethylene. Trichloroethylene and azobisisobutyronitrile (catalyst) were heated to 100°C, and oxygen was introduced to react under 0.6MPa pressure, maintaining the oil bath temperature at 110°C, and reacted for 10h, The product dichloroacetyl chloride is distilled off under normal pressure.