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Chloroacetic acid

Chloroacetic acid Basic information
Product Name:Chloroacetic acid
Synonyms:acidechloroacetique;acidechloroacetique(french);acidemonochloracetique;acidemonochloracetique(french);acidemonochloracetique(solide);acidemonochloracetique(solutions);Acidomonocloroacetico;alpha-Chloroacetic acid
CAS:79-11-8
MF:C2H3ClO2
MW:94.5
EINECS:201-178-4
Product Categories:Aliphatics, Miscellaneous Reagents;API Intermediate;500 Series Drinking Water Methods;EPA;Aliphatics;Miscellaneous Reagents;Pharmaceutical Intermediates;Other Reagents;omega-Chlorocarboxylic Acids;omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;Method 552
Mol File:79-11-8.mol
Chloroacetic acid Structure
Chloroacetic acid Chemical Properties
Melting point 60-63 °C (lit.)
Boiling point 189 °C (lit.)
density 1.58
vapor density 3.26 (vs air)
vapor pressure 0.75 mm Hg ( 20 °C)
refractive index 1.4330
Fp 126°C
storage temp. Store below +30°C.
solubility Soluble in methanol, acetone, diethyl ether, benzene, chloroform and ethanol.
pka2.85(at 25℃)
form Liquid
color White
OdorPenetrating, burning odor
PH Range< 1 at 800 g/l at 20 °C
explosive limit8%
Water Solubility SOLUBLE
Sensitive Hygroscopic
Merck 14,2112
BRN 605438
Specific Activity5-10 Ci/mmol
SolventSterile water in sealed ampoule
Concentration1 mCi/ml
Stability:Stable. Deliquescent. Incompatible with strong bases, alkalies, most common metals, strong oxidizing agents.
CAS DataBase Reference79-11-8(CAS DataBase Reference)
NIST Chemistry ReferenceAcetic acid, chloro-(79-11-8)
EPA Substance Registry SystemChloroacetic acid (79-11-8)
Safety Information
Hazard Codes T,N,Xi,F
Risk Statements 25-34-50-40-36/37/38-23/24/25-38
Safety Statements 23-37-45-61-36-26-16-63-36/37/39
RIDADR UN 1751 6.1/PG 2
WGK Germany 2
RTECS AF8575000
3
TSCA Yes
HazardClass 6.1
PackingGroup II
HS Code 29154000
Hazardous Substances Data79-11-8(Hazardous Substances Data)
MSDS Information
ProviderLanguage
MCA English
SigmaAldrich English
ALFA English
Chloroacetic acid Usage And Synthesis
DescriptionChloroacetic acid (CAA) is a monohalogenated acetic acid (m-HAA) that is used as a photosensitizing agent and in industrial synthesis of certain organic chemicals such as indigoid dyes. The m-HAAs are a major class of drinking water disinfection by-products during chlorination of drinking water.
Chemical Propertiescolourless or white crystals
Chemical PropertiesChloroacetic acid is a colorless to white crystalline solid. It has a strong vinegar-like odor and an Odor Threshold of 0.15 milligram per cubic meter.
UsesHerbicide, preservative, bacteriostat, intermediate in production of carboxymethylcellulose; ethyl chloroacetate, glycine, synthetic caffeine, sarcosine, thioglycolic acid, EDTA, 2,4-D, 2,4,5-T.
UsesChloroacetic acid behaves as a very strong monobasic acid and is used as a strong acid catalyst for diverse reactions. The Cl function can be displaced in base-catalyzed reactions.
UsesCAA is one of these agents used in the topical treatment of warts in most European countries and also as an herbicidal agent and a bleaching agent for silkworm cocoons. It can be found in wines and beers using static headspace extraction coupled with gas chromatography–mass spectrometry. CCA is the main toxic metabolite of vinyl chloride. CAA and volatile organochlorines are suspected to contribute to forest dieback and stratospheric ozone destruction.
DefinitionA colorless crystalline solid made by substituting one of the hydrogen atoms of the methyl group of ethanoic acid with chlorine, using red phosphorus. It is a stronger acid than ethanoic acid because of the electron-withdrawing effect of the chlorine atom. Dichloroethanoic acid (dichloroacetic acid, CHCl2COOH) and trichloroethanoic acid (trichloroacetic acid,CCl3COOH) are made in the same way. The acid strength increases with the number of chlorine atoms present.
Production MethodsChloroacetic acid can be synthesized by the radical chlorination of acetic acid, treatment of trichloroethylene with concentrated H2SO4, oxidation of 1,2-dichloroethane or chloroacetaldehyde, amine displacement from glycine, or chlorination of ketene.
DefinitionChEBI: A chlorocarboxylic acid that is acetic acid carrying a 2-chloro substituent.
General DescriptionChloroacetic acid, solution is a colorless solution of the white crystalline solid. The acid concentration can be up to 80%.It is used in manufacturing dyes and in medicine. Chloroacetic acid is toxic by inhalation, ingestion and skin contact. Chloroacetic acid is corrosive to metals and tissue. Chloroacetic acid is used as an herbicide, preservative and bacteriostat.
Air & Water ReactionsWater soluble.
Reactivity ProfileThese organic compounds donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Chloroacetic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.
HazardUse in foods prohibited by FDA. Irritating and corrosive to skin. Upper respiratory tract irritant. Questionable carcinogen.
Health HazardInhalation causes mucous membrane irritation. Contact with liquid causes severe irritation and burns of the eyes and irritation and burns of skin. Ingestion causes burns of mouth and stomach.
Fire HazardSpecial Hazards of Combustion Products: Toxic gases, such as hydrogen chloride, phosgene and carbon monoxide, may be generated.
Safety ProfilePoison by ingestion, inhalation, subcutaneous, and intravenous routes. A corrosive skin, eye, and mucous membrane irritant. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. Combustible liquid when exposed to heat or flame. To fight fire, use water spray, fog, mist, dry chemical, foam. When heated to decomposition it emits toxic fumes of Cl-. See also CHLORIDES.
Potential ExposureThis haloacetic acid can be a byproduct of drinking water disinfection and may increase the risk of cancer. Monochloracetic acid is used primarily as a chemical intermediate in the synthesis of sodium carboxymethyl cellulose; and such other diverse substances as ethyl chloroacetate, glycine, synthetic caffeine, sarcosine, thioglycolic acid, and various dyes. Hence, workers in these areas are affected. It is also used as an herbicide. Therefore, formulators and applicators of such herbicides are affected.
Environmental FateCCA by inhibition of the pyruvate-dehydrogenase, aconitase, and a-ketoglutarate dehydrogenase that contribute in tricarboxylic acid cycle and also inhibition of glyceraldehyde- 3-phosphate dehydrogenase can impair production of cellular energy and conversion to anaerobic glycolysis, resulting in increasing acidosis with accumulation of glycolic acid, oxalate, and lactate production. CCA can also affect cellular components via sulfhydryl groups. Both of these effects may contribute to central nervous system (CNS), cardiovascular, renal, and hepatic effects. The metabolites glycolic acid and oxalate may contribute to CNS and renal toxicity (myoglobin and oxalate precipitation in the tubuli). Binding of calcium to oxalates probably causes the hypocalcemia, but hypocalcemia can be secondary to rhabdomyolysis. CAA by reduction of cellular glutathione can cause oxidative stress. Inhibition of mitochondrial aconitase causes hypoglycemia.
ShippingUN1750 (liquid) & UN1751 (solid) Chloroacetic acid, solid or liquid, Hazard class: 6.1; Labels: 6.1-Poison Inhalation Hazard, 8-Corrosive material.
Purification MethodsCrystallise the acid from CHCl3, CCl4, *benzene or water. Dry it over P2O5 or conc H2SO4 in a vacuum desiccator. Further purification is by distillation from MgSO4, and by fractional crystallisation from the melt. Store it under vacuum or under dry N2. [Bernasconi et al. J Am Chem Soc 107 3621 1985, Beilstein 2 IV 474.]
Toxicity evaluationOccupational exposure to CAA can occur through inhalation and dermal contact with this compound at workplaces where it is produced or used. The general population can be exposed to CAA via ingestion of chlorinated or chloraminated drinking water.
The atmospheric photochemical oxidation of some volatile organochlorine compounds is one source of CAAs in the environment. CAA can be generated during water disinfection processes and during metabolic detoxification of industrial solvents such as trichloroethylene.
IncompatibilitiesCompounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water, and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, sulfides (releasing heat, toxic, and possibly flammable gases), thiosulfates, and dithionites (releasing hydrogen sulfate and oxides of sulfur). The solution in water is a strong acid. Contact with strong oxidizers, strong bases; and strong reducing agents such as hydrides can cause violent reactions. Chloracetic acid decomposes on heating, producing toxic and corrosive hydrogen chloride, phosgene, and carbon monoxide gases. Attacks metals in the presence of moisture.
Waste DisposalIncineration, preferably after mixing with another combustible fuel; care must be exercised to assure complete combustion to prevent the formation of phosgene; an acid scrubber is necessary to remove the halo acids produced.
Tag:Chloroacetic acid(79-11-8) Related Product Information
Chloroacetic acid [(1S,4S)-7-diphenylmethylenebicyclo[2.2.1]heptan-2α-yl] ester Bis(chloroacetic acid)1,5-pentanediyl (+)-Chloroacetic acid (R)-α-methylbenzyl ester Chloroacetic acid 3-allyloxy-2-hydroxypropyl ester Boc-L-Val-L-Pro-L-Arg-Chloroacetic acid Chloroacetic acid (chloromethyl) ester 2-Acetyl-2-chloroacetic acid methyl ester Chlorodifluoroacetic acid CHLORODIFLUOROACETIC ANHYDRIDE Methyl 2-chloropropionate Methyl 2,3-dichloropropionate METHYL OXALYL CHLORIDE METHYL CHLORODIFLUOROACETATE Ethyl oxalyl monochloride Ethyl 2-chloropropionate phosphoric acid Chloroacetic acid 1,1-dimethylethyl Ethyl 2-(Chlorosulfonyl)acetate