Dichloracetylchlorid

Dichloroacetyl chloride

HCID 6593CAS 79-36-7

Grundinformationen

Standard-SMILES
O=C(Cl)C(Cl)Cl
InChIKey
FBCCMZVIWNDFMO-UHFFFAOYSA-N
Summenformel
C2HCl3O
Durchschnittliche Molmasse
147,38 g/mol
Monoisotopische Masse
145,90929769

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Dichloroacetyl chloride
IUPAC
2,2-dichloroacetyl chloride
Lokaler Name
Dichloracetylchlorid
Englischer Name
Dichloroacetyl chloride
Summenformel
C2HCl3O
Molmasse
147.39

Namen und Synonyme

DICHLOROACETYL CHLORIDE79-36-72,2-Dichloroacetyl chlorideDichloracetyl chlorideAcetyl chloride, dichloro-Dichloroethanoyl chlorideDichloroacetic acid chlorideChlorure de dichloracetyleDTXSID6024965alpha,alpha-Dichloroacetyl chlorideUN1765CHEBI:34688
Weitere Namen anzeigen
2,2-dichloroac2,2-dichloroacetylDichloroacetyl chlorDichloracetylchloridDichloroacetylChoridedichloro-acetylchlorid
52O60099FYDTXCID004965UN-1765RefChem:586729201-199-9MFCD00000840Chlorid kyseliny dichloroctoveCHCl2COCl

Datenbank-Bezeichner

CAS
79-36-7
PubChem CID
6593
DTXSID
DTXSID6024965
ChEMBL
CHEMBL449486
ChEBI
CHEBI:34688
UNII
52O60099FY
EC Number
201-199-9
Nikkaji
J3.841E

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,1
Polarare Oberfläche (TPSA)
17,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
1
Schwere Atome
6

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Toxic Gases & Vapors -> Acid Halides

Corrosives

SpringerMaterials PropertiesSchoenflies notation
Odor · 2 Einträge

PENETRATING ODOR

ACRID

Density · 4 Einträge

1.5315 at 61 °F (NTP, 1992) - Denser than water; will sink

1.5315 @ 16 °C/4 °C

Relative density (water = 1): 1.5

15315 @ 16°C

Color/FormLIQUID
Solubility · 3 Einträge

Decomposes (NTP, 1992)

SOL IN ETHER

Solubility in water: decomposes

Physikochemische Eigenschaften

Schmelzpunkt
25 °C · <25 °C
Siedepunkt
107 · 107-108 °C (lit.)
Dichte
1.532 g/mL · 1.532 g/mL at 25 °C (lit.)
Brechungsindex
20 · n20/D 1.46(lit.)
Flammpunkt
66 °C · 66 °C
storage temp.
2 · 2-8°C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H314: 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.

Danger

H314 (99.6%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

Gefahrenhinweise

Hazards IdentificationWater-reactive material (WR)
Regulatory Information · 5 Einträge

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/33168

Dichloroacetyl chloride: Does not have an individual approval but may be used under an appropriate group standard

The 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 LabelCorrosive
Fire Hazards · 3 Einträge

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.

Health Hazards · 2 Einträge

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

Hazards SummaryHighly corrosive to skin; [Quick CPC] Tear drawing. High inhalation exposure can cause pulmonary edema; [ICSC]

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

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.

First Aid Measures · 4 Einträge

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 .

Accidental Release Measures · 2 Einträge

· 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.

First Aid · 2 Einträge

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:

Safe StorageSeparated from strong oxidants, strong bases, food and feedstuffs, alcohols and water. Dry. Well closed. Keep in a well-ventilated room.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).

Toxikologische Informationen

Environmental Fate · 3 Einträge

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)

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesThe substance can be absorbed into the body by inhalation, through the skin and by ingestion.
Signs and Symptoms · 4 Einträge

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 DataThis substance may be hazardous to the environment. Special attention should be given to water quality.
Soil Adsorption/Mobility · 1 Eintrag

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)

Sicherheitsdaten

F
19-21
wgk
2
tsca
TSCA listed
ridadr
UN 1765
hs_code
29159000
RTECS-Nr.
AO6650000

Chemie und Industrie

Verwendung und Herstellung

Uses · 4 Einträge

Used as a chemical intermediate; [HSDB]

Toxic Gas from Spilling Chemical in Water [Category: Other]

INTERMEDIATE

CHEM INT

U.S. Exports · 2 Einträge

(1978) No Data

(1982) No Data

U.S. Imports · 2 Einträge

(1977) AT LEAST 4.54X10+5 G

(1982) No Data

U.S. Production · 3 Einträge

2023: 1,000,000 - <8,500,000 lb

(1977) AT LEAST 9.08X10+8 G

(1982) PROBABLY GREATER THAN 2.27X10+6 G

Industry UsesIntermediate
Methods of ManufacturingPREPD FROM PENTACHLOROETHANE: OTT, GERMAN PATENT 362,748 (1922 TO WEILER TER MEER); FROM CHLOROFORM & CARBON MONOXIDE IN PRESENCE OF ALUMINUM CHLORIDE @ HIGH PRESSURE (21% YIELD): FRANK ET AL, IND ENG CHEM 41, 2061 (1949).

Anwendungen

VerwendenDichloroacetyl Chloride is a reagent used in the synthesis of substituted benzothiazoles exhibiting antitumor and anticancer activity.

Darstellung · 1 Eintrag

synthetischeDichloroacetyl 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.

Ergänzende Hinweise

DefinitionChEBI: Dichloroacetyl chloride is the acyl chloride obtained by displacement of the hydroxy group of dichloroacetic acid by chloride. It has a role as a hapten. It derives from a dichloroacetic acid.

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