Dichloroacetyl chloride
-
Dichloroacetyl chloride
structure -
-
CAS No:
79-36-7
-
Formula:
C2HCl3O
-
Chemical Name:
Dichloroacetyl chloride
-
Synonyms:
Acetyl chloride,2,2-dichloro-;Acetyl chloride,dichloro-;2,2-Dichloroacetyl chloride;Dichloracetyl chloride;Dichloroethanoyl chloride;Dichloroacetyl chloride;α,α-Dichloroacetyl chloride;Dichloroacetic acid chloride
- Categories:
-
CAS No:
Description
colourless to light yellow fuming liquid
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|COLOURLESS-TO-YELLOW FUMING LIQUID WITH PUNGENT ODOUR.
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.|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.
Dichloroacetyl chloride Basic Attributes
147.39
147.39
201-199-9
52O60099FY
0869
1765
DTXSID6024965
LIQUID
29159000
Characteristics
17.07000
1.27
Clear colorless to light yellow Liquid
1.5315 g/cm3 @ Temp: 16 °C
<25 °C
107-108 °C @ Press: 760 Torr
66 °C
1.467
H2O: MAY DECOMPOSE
2-8°C
154 mm Hg at 77° F (NTP, 1992)
Relative vapour density (air = 1): 5.1
Oral-Rat LD50: 2460 mg/kg
Combustible in case of open flame, high heat, oxidant; decomposing toxic chloride gas when heated or in contact with water, acid
Explosive limits , vol% in air: 11.9-?
PENETRATING ODOR
DECOMPOSES UPON CONTACT WITH WATER & ALCOHOL
Fumes in air. Decomposed by water to dichloroacetic acid and hydrochloric acid, both corrosive, with release of heat. (NIP). Based on a scenario where the chemical is spilled into an excess of water (at least 5 fold excess of water), half of the maximum theoretical yield of Hydrogen Chloride gas will be created in 0.94 minutes. After mixing particular chemicals into water, there may be a delay of <1-10 minutes before gas generation may be observed. For this chemical, a 4 second induction time was observed. Experimental details are in the following: "Development of the Table of Initial Isolation and Protective Distances for the 2008 Emergency Response Guidebook", ANL/DIS-09-2, D.F. Brown, H.M. Hartmann, W.A. Freeman, and W.D. Haney, Argonne National Laboratory, Argonne, Illinois, June 2009.
Halogenated Organic Compounds
Water-Reactive
Solutions 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].
585 °C
Safety Information
II
8
UN 1765 8/PG 2
2
35-50
9-26-45-61
AO6650000
C,N
The warehouse is ventilated, low temperature and dry; stored separately from oxidants and acids
Corrosive/Moisture Sensitive
Stable. Combustible. Incompatible with water, alcohols and oxidizing agents. Fumes in air.
P273-P280-P305 + P351 + P338-P310
H314-H400
Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]: Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water. (ERG, 2016)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 66 °C explosive vapour/air mixtures may be formed.|Corrosives, Flammable - 2nd degree, Reactive - 2nd degree
|Danger|H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P273, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P391, P405, and P501|H226 (61.18%): Flammable liquid and vapor [Warning Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P260, P264, P273, P280, P281, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P321, P363, P370+P378, P391, P403+P235, P405, and P501|Aggregated GHS information provided by 256 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H227: Combustible liquid [Warning Flammable liquids]|P210, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P403+P235, P405, and P501
Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: See ERG Table 1 - Initial Isolation and Protective Action Distances on the UN/NA 1765 datasheet. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. A vapor-suppressing foam may be used to reduce vapors. FOR CHLOROSILANES, use AFFF alcohol-resistant medium-expansion foam to reduce vapors. DO NOT GET WATER on spilled substance or inside containers. Use water spray to reduce vapors or divert vapor cloud drift. Avoid allowing water runoff to contact spilled material. Prevent entry into waterways, sewers, basements or confined areas. SMALL SPILL: Cover with DRY earth, DRY sand or other non-combustible material followed with plastic sheet to minimize spreading or contact with rain. Use clean, non-sparking tools to collect material and place it into loosely covered plastic containers for later disposal. (ERG, 2016)
Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)
Explosive limits , vol% in air: 11.9-?
ALCOHOL FOAM
If ... THERE IS NO FIRE, go directly to the Table of Initial Isolation and Protective Action Distances /(see table below)/ ... to obtain initial isolation and protective action distances. IF THERE IS A FIRE, or IF A FIRE IS INVOLVED, go directly to the appropriate guide /(see guide(s) below)/ and use the evacuation information shown under PUBLIC SAFETY.|Table of Water-Reactive Materials Which Produce Toxic Gases. Dichloroacetyl chloride|/GUIDE 156: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible/Water-Sensitive)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.|/GUIDE 156: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible/Water-Sensitive)/ Health: TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.|For more DOT Emergency Guidelines (Complete) data for DICHLOROACETYL CHLORIDE (10 total), please visit the HSDB record page.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
IRRITATING TO EYES, MUCOUS MEMBRANES
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.
Separated from strong oxidants, strong bases, food and feedstuffs, alcohols and water. Dry. Well closed. Keep in a well-ventilated room.
No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
Lachrymation. The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Inhalation may cause lung oedema. Exposure could cause death.
NO open flames. NO contact with water. Above 66 °C use a closed system and ventilation.
PREVENT GENERATION OF MISTS! AVOID ALL CONTACT! IN ALL CASES CONSULT A DOCTOR!
Use ventilation, local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear face shield or eye protection in combination with breathing protection.
| 3 - Materials that, under emergency conditions, can cause serious or permanent injury.| 2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.| 1 - Materials that in themselves are normally stable but that can become unstable at elevated temperatures and pressures.
Toxicity
moderately
Dichloroacetyl chloride is not known to occur naturally. (SRC)
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).
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)
Dichloroacetyl chloride decomposes upon contact with water or alcohol(1). The rate of hydrolysis in a solution of 89.1% acetone and 10.9% water at -20 degC was experimentally determined to be 3.1 1/sec(2), which corresponds to a half-life of 0.22 sec(SRC). Hydrolysis products are expected to include HCl and dichloroacetic acid(SRC). Based upon data obtained from static reactor experiments at 476 to 546 degK, the gas-phase hydrolysis half-life between water and dichloroacetyl chloride in the troposphere has been determined to be in excess of 100 years(3). The rate constant for the gas-phase reaction of dichloroacetyl chloride with photochemically produced hydroxyl radicals has been estimated to be 4.4X10-13 cu cm/molecule-sec at 25 degC which corresponds to a half-life of 22.8 days in an average atmosphere containing 8X10+5 hydroxyl radicals/cu cm(4).
Dichloroacetyl chloride hydrolyzes on contact with water(1), therefore, bioconcentration in aquatic organisms is not possible. (SRC)
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)
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).
Occupational exposure by inhalation and dermal routes related to the commercial production and use of dichloroacetyl chloride may occur. (SRC)|WELDING IN AIR CONTAINING TRICHLORETHYLENE PRODUCES PHOSGENE BY PHOTOCHEMICAL OXIDATION OF VAPOR. IT IS NOW ESTABLISHED THAT PHOSGENE IS NOT THE MAIN PRODUCT IN THIS REACTION. DICHLOROACETYL CHLORIDE (DCAC) IS FORMED IN A YIELD 5 TIMES THAT OF PHOSGENE.
Drug Information
Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]: TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)
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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and volatile chemicals have a high risk of being aspirated into the victim's lungs during vomiting. Thus, the risk of increasing the medical problems by inducing vomiting of a volatile corrosive chemical is very high. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
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.
...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/
2,2-dichloroacetyl chloride
The substance can be absorbed into the body by inhalation, through the skin and by ingestion.
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.
Dichloroacetyl chloride Use and Manufacturing
Various process routes can be used in the preparation method. The reaction of dichloroacetic acid and chlorosulfonic acid, the reaction of chloroform and carbon monoxide under the catalysis of anhydrous aluminum trichloride, the reaction of dichloroacetic acid and phosgene in dimethylformamide, and the oxidation of trichloroethylene can be obtained. The product. Trichloroethylene and azobisisobutyronitrile (catalyst) are heated to 100°C, oxygen is introduced, and the reaction is carried out at 0.6 MPa pressure, maintaining the oil bath temperature at 110°C, reacting for 10 hours, and steaming the product dichloroethane under normal pressure Acid chloride. The byproduct of this reaction, trichloroethylene oxide, reacts with methylamine, triethylamine, pyridine and other amine compounds, and can also be converted into dichloroacetyl chloride.
Used in the synthesis of vinyl insecticides, also used in wool felting, finishing, bleaching, decolorizing, keeping fresh, sterilizing, disinfecting, etc.
Intermediates
Non-TSCA use
1,000,000 - 10,000,000 lb|(1977) AT LEAST 9.08X10+8 G|(1982) PROBABLY GREATER THAN 2.27X10+6 G
Pesticide, fertilizer, and other agricultural chemical manufacturing|Acetyl chloride, 2,2-dichloro-: ACTIVE
SENSITIVITY OF DETECTION FOR DICHLOROACETYL CHLORIDE IN AIR WAS 0.8 MG/CU M BY GC.
Fire Hazards -> Corrosives, Flammable - 2nd degree, Reactive - 2nd degree
Computed Properties
Molecular Weight:147.38
XLogP3:2.1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:145.909298
Monoisotopic Mass:145.909298
Topological Polar Surface Area:17.1
Heavy Atom Count:6
Complexity:59.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Recommended Suppliers of Dichloroacetyl chloride
-
CN
5 YRS
Business licensedTrader Supplier of Ethyl chloroacetate,Methyl chloroacetate,2-ThiophenecarboxaldehydeInquiryCAS No.: 79-36-7Grade: Industrial GradeContent: 98.5%
Learn More Other Chemicals
-
1,3,5-Cycloheptatriene-1-carbonyl chloride (9CI)
103533-75-1
-
3'-De(diMethylaMino)-3'-[[(2-Methoxyethoxy)Methyl]diMethylaMMonio]erythroMycin 9-OxiMe Chloride
151750-47-9
-
decoxymethyl-dimethyl-octyl-azanium chloride
366491-03-4
-
4-[3-(3,5-DICHLORO-PHENYL)-UREIDO]-BENZENESULFONYL CHLORIDE Formula
677326-84-0
-
2,5-DICHLOROBENZYLZINC CHLORIDE Formula
737797-20-5
-
2,5-DIBROMO-3,6-DIFLUOROBENZENESULFONYL CHLORIDE Formula
207853-66-5
-
Dibenzofuran-3-sulfonyl chloride Structure
42138-14-7
-
2,4-Dibromo-5-fluorobenzenesulfonyl chloride Structure
1000578-09-5
-
What is Selenium(I) chloride (99%-Se)
21317-32-8
-
What is 2,6-dibromo-4-methylbenzene-1-sulfonyl chloride
73732-31-7