Basic information
- Standard SMILES
O=C(Cl)C(Cl)Cl- InChIKey
FBCCMZVIWNDFMO-UHFFFAOYSA-N- Molecular formula
- C2HCl3O
- Average molar mass
- 147.38 g/mol
- Monoisotopic mass
- 145.90929769
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 dichloracetyleDTXSID6024965alpha,alpha-Dichloroacetyl chlorideUN1765CHEBI:34688
Show more names
2,2-dichloroac2,2-dichloroacetylDichloroacetyl chlorDichloracetylchloridDichloroacetylChoridedichloro-acetylchlorid
52O60099FYDTXCID004965UN-1765RefChem:586729201-199-9MFCD00000840Chlorid kyseliny dichloroctoveCHCl2COCl
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
Toxic Gases & Vapors -> Acid Halides
Corrosives
SpringerMaterials PropertiesSchoenflies notation
Odor
PENETRATING ODOR
ACRID
Density
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
Decomposes (NTP, 1992)
SOL IN ETHER
Solubility in water: decomposes
Flash Point
151 °F (NTP, 1992)
66 °C, 151 °F
66 °C
Boiling Point
225 to 226 °F at 760 mmHg (NTP, 1992)
107-108 °C @ 760 MM HG
107-108 °C
108 °C @760 [mm Hg]
Vapor Density
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
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
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 · 107-108 °C (lit.)
- Density
- 1.532 g/mL · 1.532 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.46(lit.)
- Flash point
- 66 °C · 66 °C
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform, Hexanes
- form
- Liquid
- color
- Clear colorless to light yellow
- 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
- 29159000 · 29159000
- 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)
Safety & regulation
GHS classification
GHS Classification
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
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
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
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
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
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
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
· 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
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
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 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
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
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
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
...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 BioconcentrationDichloroacetyl 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.
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
- 29159000
- 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)
Chemistry & industry
Uses & manufacturing
Uses
Used as a chemical intermediate; [HSDB]
Toxic Gas from Spilling Chemical in Water [Category: Other]
INTERMEDIATE
CHEM INT
U.S. Exports
(1978) No Data
(1982) No Data
U.S. Imports
(1977) AT LEAST 4.54X10+5 G
(1982) No Data
U.S. Production
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
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
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
Downstream products
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.
Related reactions
307 records
Linked notes
Loading…