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Dichloroacetyl chloride

HCID 6593
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Basic information

CAS
79-36-7
Standard SMILES
O=C(Cl)C(Cl)Cl
InChIKey
FBCCMZVIWNDFMO-UHFFFAOYSA-N
Molecular formula
C2HCl3O
Average molar mass
147.38 g/mol
Monoisotopic mass
145.909298

Overview

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.

Names & identifiers

Preferred name
Dichloroacetyl chloride
IUPAC
2,2-dichloroacetyl chloride
English name
Dichloroacetyl chloride
Molecular formula
C2HCl3O
Molecular weight
147.39

Names & synonyms

DICHLOROACETYL CHLORIDE79-36-72,2-Dichloroacetyl chlorideDichloracetyl chlorideAcetyl chloride, dichloro-Dichloroethanoyl chlorideDichloroacetic acid chlorideChlorure de dichloracetylealpha,alpha-Dichloroacetyl chlorideDTXSID6024965UN1765CHEBI:34688
Show more names
2,2-dichloroac2,2-dichloroacetylDichloroacetyl chlorDichloracetylchloridDichloroacetylChoridedichloro-acetylchlorid
52O60099FYDTXCID004965UN-1765RefChem:586729201-199-9CHCl2COClChlorid kyseliny dichloroctoveMFCD00000840

Database identifiers

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

Properties

Computed structural properties

XLogP
2.1
Topological polar surface area
17.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
6
Formal charge
0
Complexity
59.8

Experimental & physicochemical properties

Chemical Classes · 2 items

Toxic Gases & Vapors -> Acid Halides

Corrosives

SpringerMaterials PropertiesSchoenflies notation
Odor · 2 items

PENETRATING ODOR

ACRID

Density · 4 items

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 items

Decomposes (NTP, 1992)

SOL IN ETHER

Solubility in water: decomposes

Flash Point · 3 items

151 °F (NTP, 1992)

66 °C, 151 °F

66 °C

Boiling Point · 4 items

225 to 226 °F at 760 mmHg (NTP, 1992)

107-108 °C @ 760 MM HG

107-108 °C

108 °C @760 [mm Hg]

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

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]

Hazard information

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

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 items

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.

Chemistry & industry

Uses & manufacturing

Uses · 4 items

Used as a chemical intermediate; [HSDB]

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

INTERMEDIATE

CHEM INT

U.S. Exports · 2 items

(1978) No Data

(1982) No Data

U.S. Imports · 2 items

(1977) AT LEAST 4.54X10+5 G

(1982) No Data

U.S. Production · 3 items

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 items

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

Acetyl chloride, 2,2-dichloro-: ACTIVE

Applications

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

General DescriptionDichloroacetyl 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.

Preparation methods · 1 item

Related reactions

307 records
New reaction record
HRID 13043 reaction equation
HRID 13043As reactantuspto-grants-2010_06
HRID 34859 reaction equation
HRID 34859As reactantuspto-grants-1988_08
HRID 65387 reaction equation
HRID 65387As reactantuspto-grants-1986_09
HRID 90118 reaction equation
HRID 90118As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 95507 reaction equation
HRID 95507As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 101611 reaction equation
HRID 101611As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 102868 reaction equation
HRID 102868As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 104380 reaction equation
HRID 104380As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Vapor Density · 3 items

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 items

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 items

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.

Physicochemical properties

Melting point
25 °C · <25 °C
Boiling point
107 °C · 107 °C (225 °F; 380 K)
Density
1.5315 g/cm3 · 1.5315 g/cm3
refractive index
1.46 · 1.46
Flash point
66 °C · 66 °C
storage temp.
2 · 2-8°C
solubility
Chloroform, Hexanes
form
fuming liquid
color
colorless
Specific Gravity
1.537 · 1.537 (20/4℃)
Water Solubility
MAY DECOMPOSE
Sensitive
Moisture Sensitive
Merck
14 · 14,3053
BRN
1209426 · 1209426
Stability
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 DataBase Reference
79 · 79-36-7(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
52 O60099FY · 52O60099FY
NIST Chemistry Reference
Acetyl chloride, dichloro-(79-36-7)
EPA Substance Registry System
Dichloroacetyl chloride (79-36-7)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
Symbol(GHS)
5 · GHS05,GHS06,GHS09
Signal word
Danger
Hazard statements
311 · H311-H303-H314-H400-H290
Precautionary statements
501 · P501-P273-P234-P264-P280-P390-P312-P391-P361+P364-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310-P406-P405
PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Hazard Codes
C,N
Risk Statements
35 · 35-50
Safety Statements
9 · 9-26-45-61
RIDADR
1765 · UN 1765
WGK Germany
2 · 2
RTECS
6650000 · AO6650000
F
19 · 19-21
Hazard Note
Corrosive/Moisture Sensitive
TSCA
TSCA listed
HazardClass
8 · 8
PackingGroup
II
HS Code
2915900090 · 2915900090
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
1 Carc · Aquatic Acute 1Carc. 1BEye Dam. 1Skin Corr. 1A
Hazardous Substances Data
79 · 79-36-7(Hazardous Substances Data)
REACH Registrations
Active
Limited Quantities
1 L · 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Health Hazards · 2 items

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 item

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].

Safety & protection

Fire Fighting · 2 items

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 items

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 items

· 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 items

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 item

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 items

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.

Toxicology

Environmental Fate · 3 items

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 items

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 item

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 items

...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 item

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 item

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 items

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.

Safety data

F
19-21
PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
2
tsca
TSCA listed
rtecs
AO6650000
ridadr
UN 1765
hs_code
2915900090
risk_code
35-50
Signal word
Danger
Symbol(GHS)
GHS05,GHS06,GHS09
hazard_code
C,N
hazard_note
Corrosive/Moisture Sensitive
safety_code
9-26-45-61
hazard_class
8
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
packing_group
II
Hazard statements
H311-H303-H314-H400-H290
Limited Quantities
1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
REACH Registrations
Active
Hazard Classifications
Aquatic Acute 1Carc. 1BEye Dam. 1Skin Corr. 1A
Precautionary statements
P501-P273-P234-P264-P280-P390-P312-P391-P361+P364-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310-P406-P405
Hazardous Substances Data
79-36-7(Hazardous Substances Data)

PreparationDichloroacetyl 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.

Upstream & downstream products

Upstream raw materials

AIBNOxygenTrichloroethyleneDichloroacetic acidAluminum chlorideChlorosulfonic acidOxirane, 2,3-dichloro-, (2R,3R)-rel-trichloroepoxyethanetrans-1,2-Dichloroethylene

Downstream products

TetrachlorvinphosHEPTENOPHOSFluorochloridoneTrichloroacetyl chloride4'-Hydroxy-3'-methylacetophenone7,7-Dichlorobicyclo[3.2.0]hept-2-en-6-oneFurilazole1-(Trimethylsiloxy)cyclopentene4-Methyltropolone

Additional notes

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.