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Dichloracetylchlorid

Dichloroacetyl chloride

HCID 6593
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Grundinformationen

CAS
79-36-7
Standard-SMILES
O=C(Cl)C(Cl)Cl
InChIKey
FBCCMZVIWNDFMO-UHFFFAOYSA-N
Summenformel
C2HCl3O
Durchschnittliche Molmasse
147,38 g/mol
Monoisotopische Masse
145,909298

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 dichloracetylealpha,alpha-Dichloroacetyl chlorideDTXSID6024965UN1765CHEBI:34688
Weitere Namen anzeigen
2,2-dichloroac2,2-dichloroacetylDichloroacetyl chlorDichloracetylchloridDichloroacetylChoridedichloro-acetylchlorid
52O60099FYDTXCID004965UN-1765RefChem:586729201-199-9CHCl2COClChlorid kyseliny dichloroctoveMFCD00000840

Datenbank-Bezeichner

CAS
79-36-7
PubChem CID
6593
DTXSID
DTXSID6024965
ChEMBL
CHEMBL449486
ChEBI
CHEBI:34688

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
Formalladung
0
Komplexität
59,8

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

Flash Point · 3 Einträge

151 °F (NTP, 1992)

66 °C, 151 °F

66 °C

Boiling Point · 4 Einträge

225 to 226 °F at 760 mmHg (NTP, 1992)

107-108 °C @ 760 MM HG

107-108 °C

108 °C @760 [mm Hg]

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

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)

REACH registered substance: Dichloroacetyl chloride (EC: 201-199-9)

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.

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).
General Manufacturing Information · 2 Einträge

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

Acetyl chloride, 2,2-dichloro-: ACTIVE

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.

Zugehörige Reaktionen

307
Reaktionsaufzeichnung erstellen
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HRID 13043als Eduktuspto-grants-2010_06
Reaktionsgleichung von HRID 34859
HRID 34859als Eduktuspto-grants-1988_08
Reaktionsgleichung von HRID 65387
HRID 65387als Eduktuspto-grants-1986_09
Reaktionsgleichung von HRID 90118
HRID 90118als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 95507
HRID 95507als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 101611
HRID 101611als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 102868
HRID 102868als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 104380
HRID 104380als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
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UNII
52O60099FY
EC Number
201-199-9
Nikkaji
J3.841E
Vapor Density · 3 Einträge

5.1 (NTP, 1992) - Heavier than air; will sink (Relative to Air)

5.1 (AIR= 1)

Relative vapor density (air = 1): 5.1

Vapor Pressure · 3 Einträge

154 mmHg at 77 °F (NTP, 1992)

23.0 [mmHg]

Vapor pressure, kPa at 20 °C: 3.1

Refractive IndexINDEX OF REFRACTION: 1.4638 @ 16 °C/D
Physical Description · 4 Einträge

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

Liquid with a penetrating odor; [HSDB]

COLOURLESS-TO-YELLOW FUMING LIQUID WITH PUNGENT ODOUR.

Physikochemische Eigenschaften

Schmelzpunkt
25 °C · <25 °C
Siedepunkt
107 °C · 107 °C (225 °F; 380 K)
Dichte
1.5315 g/cm3 · 1.5315 g/cm3
Brechungsindex
1.46 · 1.46
Flammpunkt
66 °C · 66 °C
storage temp.
2 · 2-8°C
Löslichkeit
Chloroform, Hexanes
Aggregatzustand
fuming liquid
Farbe
colorless
Wichte
1.537 · 1.537 (20/4℃)
Wasserlöslichkeit
MAY DECOMPOSE
Merck
14 · 14,3053
BRN
1209426 · 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 · 79-36-7(CAS DataBase Reference)
NIST chemische Informationen
Acetyl chloride, dichloro-(79-36-7)
EPA chemische Informationen
Dichloroacetyl chloride (79-36-7)
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]
DOT ID and Guide1765 156
Reactive GroupHalogenated Organic Compounds
EC ClassificationSymbol: C, N; R: 35-50; S: (1/2)-9-26-45-61
UN ClassificationUN Hazard Class: 8; UN Pack Group: II
Reactivity AlertsWater-Reactive
Reactivity Profile · 1 Eintrag

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].

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).
Fire Fighting ProceduresALCOHOL FOAM
Nonfire Spill ResponseExcerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
Spillage Disposal · 1 Eintrag

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 · 4 Einträge

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

Immediate precautionary measure

When spilled in water

When spilled in water

Eye PreventionWear face shield or eye protection in combination with breathing protection.
Fire PreventionNO open flames. NO contact with water. Above 66 °C use a closed system and ventilation.

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)

Natural Pollution SourcesDichloroacetyl chloride is not known to occur naturally. (SRC)
Human Toxicity Excerpts · 2 Einträge

...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 · 1 Eintrag

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 BioconcentrationDichloroacetyl chloride hydrolyzes on contact with water(1), therefore, bioconcentration in aquatic organisms is not possible. (SRC)
Volatilization from Water/Soil · 1 Eintrag

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 · 2 Einträge

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.

Sicherheitsdaten

F
19-21
wgk
2
tsca
TSCA listed
ridadr
UN 1765
hs_code
2915900090
RTECS-Nr.
AO6650000
risk_code
35-50
hazard_code
C,N
hazard_note
Corrosive/Moisture Sensitive
safety_code
9-26-45-61
hazard_class
8
packing_group
II
Speicherklasse
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Giftige Stoffe Daten
79-36-7(Hazardous Substances Data)
Hazard Classifications
Aquatic Acute 1Carc. 1BEye Dam. 1Skin Corr. 1A

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

2,2'-Dimethyl-2,2'-azodipropiono-nitrilSauerstoffTrichlorethylenDichloressigsureAluminiumchloridChloroschwefelsureOxirane, 2,3-dichloro-, (2R,3R)-rel-trichloroepoxyethanetrans-Dichlorethylen

Nachgelagerte Produkte

TetrachlorvinphosHeptenophos (ISO)3-Chlor-4-(chlormethyl)-1-[3-(trifluormethyl)phenyl]pyrrolidin-2-onTrichloracetylchlorid4-Hydroxy-3-methylacetophenon7,7-Dichlorbicyclo[3.2.0]hept-2-en-6-onFurilazole(1-Cyclopenten-1-yloxy)trimethylsilan4-Methyltropolone

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.