Ethyl chloroacetate
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Ethyl chloroacetate
structure -
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CAS No:
105-39-5
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Formula:
C4H7ClO2
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Chemical Name:
Ethyl chloroacetate
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Synonyms:
Acetic acid,2-chloro-,ethyl ester;Acetic acid,chloro-,ethyl ester;Ethyl chloroacetate;Ethyl chloroethanoate;Ethyl α-chloroacetate;Ethyl monochloracetate;Chloroacetic acid ethyl ester;Ethyl chloracetate;Ethyl monochloroacetate;Ethyl 2-chloroacetate;(Ethoxycarbonyl)methyl chloride;2-Chloroacetic acid ethyl ester;NSC 8833;Ethyl 2-monochloroacetate
- Categories:
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CAS No:
Description
COLOURLESS LIQUID WITH PUNGENT ODOUR.
Ethyl chloroacetate appears as a clear colorless liquid with a pungent odor. Flash point 100°F. Denser than water and insoluble in water. Vapors heavier than air.|Liquid|COLOURLESS LIQUID WITH PUNGENT ODOUR.
Ethyl chloroacetate appears as a clear colorless liquid with a pungent odor. Flash point 100°F. Denser than water and insoluble in water. Vapors heavier than air.
Ethyl chloroacetate Basic Attributes
122.55
122.55
506455
203-294-0
6H07TEH4TF
1081
8833
1181
DTXSID4026715
Water-white mobile liq|Liquid
2905199090
Characteristics
26.30000
0.78830
Clear colorless Liquid
1.1498 g/cm3 @ Temp: 20 °C
-26 °C
144-146 °C
150 °F
n20/D 1.421(lit.)
H2O: 20 g/L (20 ºC)
Flammables area
10 mm Hg ( 38 °C)
Relative vapour density (air = 1): 4.2
Subcutaneous-Mouse LD50: 250 mg/kg
Combustible in case of fire, high temperature and strong oxidant; burning produces irritating smoke
2.6%(V)
Fruity pungent odor
Decomp by hot water and alkalies|SOLIDIFIES @ -26 °C|LIQ-WATER INTERFACIAL TENSION: (EST) 24 DYNES/CM= 0.024 N/M @ 20 °C
Highly flammable. Slow hydrolysis to acidic products will cause slow corrosion of common metals. No hazard involved. (USCG, 1999).
Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Highly Flammable
ETHYL CHLOROACETATE is a chlorinated ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.
452 °C
-7,250 BTU/LB= -2,028 CAL/G= -168X10+5 JOULES/KG
The vapour is heavier than air.
4.94X10+7 J/kmol @ 247.15 K
Critical temperature: 618 K; Critical pressure: 3.79X10+6 Pa
Safety Information
II
6.1
UN 1181 6.1/PG 2
2
23/24/25-50-10
45-61-7/9-16
AF9110000
T,N
Complete packaging, light loading and unloading; warehouse ventilated, away from open flame, high temperature, and stored separately from oxidant
Stable. Incompatible with acids, bases, oxidizing agents, reducing agents. Flammable.
P261-P273-P280-P301 + P310-P305 + P351 + P338-P311
H226-H301-H311-H318-H331-H400
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
... CAN REACT VIGOROUSLY WITH OXIDIZING MATERIALS. WILL REACT WITH WATER OR STEAM TO PRODUCE TOXIC & CORROSIVE FUMES. VIGOROUS REACTION WITH SODIUM CYANIDE.
Special Hazards of Combustion Products: Irritating, toxic hydrogen chloride and phosgene may be generated in fires. (USCG, 1999)|Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 53 °C explosive vapour/air mixtures may be formed.|Flammable - 2nd degree
|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P311, P312, P321, P322, P330, P361, P363, P391, P403+P233, P405, and P501|H226 (62.14%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P262, P264, P270, P271, P272, P273, P280, P301+P310, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P330, P332+P313, P333+P313, P361, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 140 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P270, P272, P280, P301+P310, P302+P350, P302+P352, P303+P361+P353, P305+P351+P338, P309+P311, P310, P321, P322, P330, P332+P313, P333+P313, P337+P313, P361, P362, P363, P370+P378, P403+P235, P405, and P501|P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P270, P271, P272, P280, P301+P310, P301+P330+P331, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P310, P311, P312, P321, P322, P330, P333+P313, P361, P363, P370+P378, P403+P233, P403+P235, P405, and P501
Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / 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: Increase, in the downwind direction, as necessary, the isolation distance shown above. 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 155 [Substances - Toxic and/or Corrosive (Flammable / 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)
Organic canister mask; rubber gloves; chemical goggles. (USCG, 1999)|ORGANIC CANISTER MASK; RUBBER GLOVES; CHEMICAL GOGGLES.
FLAMMABLE LIQUID; A DANGEROUS FIRE HAZARD WHEN EXPOSED TO HEAT OR FLAME ...
To fight fire, use water, foam, carbon dioxide, dry chemical.|If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water form as far a distance as possible. Use foam, dry chemical, or carbon dioxide.
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors.|Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. ...|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
/GUIDE 155: SUBSTANCES - TOXIC and/or CORROSIVE (Flammable/Water-Sensitive)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors 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. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.|/GUIDE 155: SUBSTANCES - TOXIC and/or CORROSIVE (Flammable/Water-Sensitive)/ Health: TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Bromoacetates and chloroacetates are extremely irritating/lachrymators. 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.|/GUIDE 155: SUBSTANCES - TOXIC and/or CORROSIVE (Flammable/Water-Sensitive)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. 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. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.|/GUIDE 155: SUBSTANCES - TOXIC and/or CORROSIVE (Flammable/Water-Sensitive)/ Protective Clothing: 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.|For more DOT Emergency Guidelines (Complete) data for ETHYL CHLOROACETATE (8 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.
A severe eye irritant.
Remove all ignition sources. Personal protection: chemical protection suit including self-contained breathing apparatus. Collect leaking and spilled liquid in covered plastic containers as far as possible. Absorb remaining liquid in dry sand or inert absorbent. Then store and dispose of according to local regulations.
Fireproof. Separated from incompatible materials and food and feedstuffs. See Chemical Dangers. Dry.
A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
The substance is severely irritating to the eyes. The substance is moderately irritating to the skin and respiratory tract.
Repeated or prolonged contact may cause skin sensitization.
NO open flames, NO sparks and NO smoking. Above 53 °C use a closed system, ventilation and explosion-proof electrical equipment.
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.
This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Ethyl chloroacetate is produced, as an intermediate or a final product, by process units covered under this subpart.
| 0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.| 3 - Liquids and solids that can be ignited under almost all ambient temperature conditions. Materials produce hazardous atmospheres with air under almost all ambient temperatures or, though unaffected by ambient temperatures, are readily ignited under almost all conditions.| 0 - Materials that in themselves are normally stable, even under fire conditions.
Toxicity
highly toxic
LD50 Mouse sc 250 mg/kg|LD50 Rabbit skin 230 mg/kg
Ethyl chloroacetate's production and use in organic synthesis, vat dyestuff, and military poison(1) may result in its release to the environment through various waste streams.
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a log Kow of 0.94(2) and a regression-derived equation(3), indicates that ethyl chloroacetate is expected to have very high mobility in soil(SRC). Volatilization of ethyl chloroacetate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.20X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(4). The potential for volatilization of ethyl chloroacetate from dry soil surfaces may exist(SRC) based upon a vapor pressure of 4.87 mm Hg(5). Ethyl chloroacetate is subject to hydrolysis under acidic and alkaline conditions. Acid hydrolysis products could include ethyl alcohol and chloroacetic acid, both very soluble in water. Alkaline hydrolysis of the ester would yield products similar to acid hydrolysates except the chloroacetic acid would be in salt form. In addition, alkaline hydrolysis could result in the substitution of an OH group for the chlorine atom resulting in the production of glycolic acid in its salt form. Glycolic acid is water soluble as well as being susceptible to biodegradation(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a log Kow of 0.94(2) and a regression-derived equation(3), indicates that ethyl chloroacetate is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 8.20X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 15 hr and 11 days, respectively(SRC). Ethyl chloroacetate is subject to hydrolysis under acidic and alkaline conditions. Acid hydrolysis products could include ethyl alcohol and chloroacetic acid, both very soluble in water. Alkaline hydrolysis of the ester would yield products similar to acid hydrolysates except the chloroacetic acid would be in salt form. In addition, alkaline hydrolysis could result in the substitution of an OH group for the chlorine atom resulting in the production of glycolic acid in its salt form. Glycolic acid is water soluble as well as being susceptible to biodegradation(7). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethyl chloroacetate, which has a vapor pressure of 4.87 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethyl chloroacetate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 13 days(SRC), calculated from its rate constant of 1.2X10-12 cu cm/molecule-sec at 25 °C(SRC), determined using a structure estimation method(3).
The rate constant for the vapor-phase reaction of ethyl chloroacetate with photochemically-produced hydroxyl radicals has been estimated as 1.2X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 12 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 9 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 9 days and 22 hr at pH values of 7 and 8, respectively(2). Ethyl chloroacetate will hydrolyze in water with an ionic strength of 1.0 at pH 7 and 25 °C with a half-life of 74 days(4). Ethyl chloroacetate is subject to hydrolysis under acidic and alkaline conditions. Acid hydrolysis products could include ethyl alcohol and chloroacetic acid, both very soluble in water. Alkaline hydrolysis of the ester would yield products similar to acid hydrolysates except the chloroacetic acid would be in salt form. In addition, alkaline hydrolysis could result in the substitution of an OH group for the chlorine atom resulting in the production of glycolic acid in its salt form. Glycolic acid is water soluble as well as being susceptible to biodegradation(5).
An estimated BCF of 3 was calculated for ethyl chloroacetate(SRC), using a log Kow of 0.94(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.
The Koc of ethyl chloroacetate is estimated as 12(SRC), using a log Kow of 0.94(1). According to a classification scheme(3), this estimated Koc value suggests that ethyl chloroacetate is expected to have very high mobility in soil.
The Henry's Law constant for ethyl chloroacetate is estimated as 8.20X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that ethyl chloroacetate is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 15 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 11 days(SRC). Ethyl chloroacetate's estimated Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of ethyl chloroacetate from dry soil surfaces may exist(SRC) based upon a vapor pressure of 4.87 mm Hg(3).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 919 workers (306 of these are female) are potentially exposed to ethyl chloroacetate in the US(1). Occupational exposure to ethyl chloroacetate may occur through inhalation and dermal contact with this compound at workplaces where ethyl chloroacetate is produced or used(SRC).
Drug Information
...MAY BE ABSORBED PERCUTANEOUSLY...
Inhalation causes irritation of mucous membrane, headache, and nausea. Contact with liquid causes extreme eye irritation and conjunctivitis; irritates skin if not removed at once. Ingestion causes irritation of mouth and stomach. (USCG, 1999)
INHALATION: remove patient to fresh air; get medical attention. EYES: flush with copious quantities of water for at least 15 min.; get medical attention if irritation persists. SKIN: wash with soap and water. INGESTION: give large amount of water and induce vomiting; get medical attention. (USCG, 1999)
Fresh air, rest. Refer for medical attention.
Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
.../ETHYL CHLOROACETATE IS AMONG HALOGENATED ACID ESTERS WHICH HAVE/ POTENTIAL FOR PRODUCING PULMONARY EDEMA.|...POTENT LACRIMATOR.|SUMMARY TOXICITY STATEMENT /ACUTE/ MODERATE IRRITATION VIA ORAL & INHALATION ROUTES. MODERATE= MAY CAUSE REVERSIBLE OR IRREVERSIBLE CHANGES TO EXPOSED TISSUE, NOT PERMANENT INJURY OR DEATH; CAN CAUSE CONSIDERABLE DISCOMFORT.
EMCA
The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.
Cough. Sore throat.
MAY BE ABSORBED! Redness. Pain.
Watering of the eyes. Redness. Pain.
Ethyl chloroacetate Use and Manufacturing
Ethyl chloroacetate is obtained by esterification of chloroacetic acid and ethanol under the catalysis of sulfuric acid. The reaction equation is as follows: ClCH2COOH+C2H5OH[H2SO4]→ClCH2COOC2H5+H2O Add chloroacetic acid, ethanol and benzene to the esterification pot, turn on the stirrer, slowly add sulfuric acid, heat to reflux, and continuously distill out the benzene-water azeotrope, After decondensing, the separator separates the water generated by esterification, and returns the benzene to the esterification pot. When no more water is distilled off, it is cooled and discharged. The crude ester is washed with saturated sodium bicarbonate solution and water to medium It is distilled after drying with anhydrous calcium chloride. The fraction of 144-146°C is the finished product of ethyl chloroacetate, the content is ≥99.0%, and the yield is 85%.
Reagent used in the preparation of 5 member heterocycles.
Intermediates
(1977) AT LEAST 4.99X10+7 G|(1982) PROBABLY GREATER THAN 2.27X10+6 G
ESSENTIALLY 100% AS A CHEM INT
Pesticide, fertilizer, and other agricultural chemical manufacturing|Acetic acid, 2-chloro-, ethyl ester: ACTIVE
Fire Hazards -> Flammable - 2nd degree
Computed Properties
Molecular Weight:122.55
XLogP3:0.9
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:122.0134572
Monoisotopic Mass:122.0134572
Topological Polar Surface Area:26.3
Heavy Atom Count:7
Complexity:62.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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