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Chloroacetic acid information


Chloroacetic acid
Chloroacetic acid
Chloroacetic acid
Names
Preferred IUPAC name
Chloroacetic acid
Systematic IUPAC name
Chloroethanoic acid
Other names
2-Chloroacetic acid
2-Chloroethanoic acid
Identifiers
CAS Number
  • 79-11-8 checkY
3D model (JSmol)
  • Interactive image
3DMet
  • B02139
ChEBI
  • CHEBI:27869 checkY
ChEMBL
  • ChEMBL14090 checkY
ChemSpider
  • 10772140 checkY
ECHA InfoCard 100.001.072 Edit this at Wikidata
EC Number
  • 201-178-4
KEGG
  • D07677 checkY
  • C06755
PubChem CID
  • 300
RTECS number
  • AF8575000
UNII
  • 5GD84Y125G checkY
CompTox Dashboard (EPA)
  • DTXSID4020901 Edit this at Wikidata
InChI
  • InChI=1S/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5) checkY
    Key: FOCAUTSVDIKZOP-UHFFFAOYSA-N checkY
  • InChI=1/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5)
    Key: FOCAUTSVDIKZOP-UHFFFAOYAR
SMILES
  • ClCC(O)=O
Properties
Chemical formula
ClCH2CO2H
Molar mass 94.49 g·mol−1
Appearance Colorless or white crystals
Density 1.58 g/cm3
Melting point 63 °C (145 °F; 336 K)
Boiling point 189.3 °C (372.7 °F; 462.4 K)
Solubility in water
85.8 g/(100 mL) (25 °C)
Solubility Soluble in methanol, acetone, diethyl ether, benzene, chloroform, ethanol
log P 0.22
Vapor pressure 0.22 hPa
Acidity (pKa) 2.86[1]
Magnetic susceptibility (χ)
−48.1×10−6 cm3/mol
Refractive index (nD)
1.4351 (55 °C)
Structure
Crystal structure
Monoclinic
Thermochemistry
Heat capacity (C)
144.02 J/(K·mol)
Std enthalpy of
formation fH298)
−490.1 kJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
alkylating agent
GHS labelling:
Pictograms
GHS05: CorrosiveGHS06: ToxicGHS09: Environmental hazard
Signal word
Danger
Hazard statements
H301, H311, H314, H331, H400
Precautionary statements
P260, P261, P264, P270, P271, P273, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P330, P361, P363, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Flash point 126 °C (259 °F; 399 K)
Autoignition
temperature
470 °C (878 °F; 743 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
76 mg/kg.[2]
Safety data sheet (SDS) External MSDS
Related compounds
Related compounds
  • Dichloroacetic acid
  • Trichloroacetic acid
  • Fluoroacetic acid
  • Bromoacetic acid
  • Iodoacetic acid
  • Acetic acid
  • 2-Chloropropionic acid
  • 3-Chloropropanoic acid
  • 2,2-Dichloropropionic acid
  • Sodium chloroacetate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Chloroacetic acid, industrially known as monochloroacetic acid (MCA), is the organochlorine compound with the formula ClCH2CO2H. This carboxylic acid is a useful building block in organic synthesis. It is a colorless solid. Related compounds are dichloroacetic acid and trichloroacetic acid.

  1. ^ Dippy, J. F. J.; Hughes, S. R. C.; Rozanski, A. (1959). "498. The dissociation constants of some symmetrically disubstituted succinic acids". Journal of the Chemical Society. 1959: 2492–2498. doi:10.1039/JR9590002492.
  2. ^ Cite error: The named reference Ullmann was invoked but never defined (see the help page).

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Chloroacetic acid

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Chloroacetic acid, industrially known as monochloroacetic acid (MCA), is the organochlorine compound with the formula ClCH2CO2H. This carboxylic acid...

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Chloroacetic acids

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the chloroacetic acids (systematic name chloroethanoic acids) are three related chlorocarbon carboxylic acids: Chloroacetic acid (chloroethanoic acid),...

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Chloroacetyl chloride

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chloride, or the addition of chlorine to ketene. It may be prepared from chloroacetic acid and thionyl chloride, phosphorus pentachloride, or phosgene. Chloroacetyl...

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Glycolic acid

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of chloroacetic acid with sodium hydroxide followed by re-acidification. Other methods, not noticeably in use, include hydrogenation of oxalic acid, and...

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Trichloroacetic acid

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Blob, a bottle of trichloroacetic acid is tossed at the Blob in a futile attempt to fend it off. Chloroacetic acids NIOSH Pocket Guide to Chemical Hazards...

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Malonic acid

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Standards and Technology. A classical preparation of malonic acid starts from chloroacetic acid: Sodium carbonate generates the sodium salt, which is then...

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Dichloroacetic acid

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chlorine atoms. Like the other chloroacetic acids, it has various practical applications. The salts and esters of dichloroacetic acid are called dichloroacetates...

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Acetic acid

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acids are produced from acetic acid. Some commercially significant derivatives: Chloroacetic acid (monochloroacetic acid, MCA), dichloroacetic acid (considered...

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Ethylenediaminetetraacetic acid

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Ferdinand Münz, who prepared the compound from ethylenediamine and chloroacetic acid. Today, EDTA is mainly synthesised from ethylenediamine (1,2-diaminoethane)...

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Acid

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acetic acid. Fluoroacetic acid Trifluoroacetic acid Chloroacetic acid Dichloroacetic acid Trichloroacetic acid Normal carboxylic acids are the direct union...

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Hydrogen chloride

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Teflon, Freon, and other CFCs, as well as chloroacetic acid and PVC. Often this production of hydrochloric acid is integrated with captive use of it on-site...

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Sodium chloroacetate

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sodium salt of chloroacetic acid. Many of its uses are similar to those of the parent acid. It is prepared by treating chloroacetic acid with sodium carbonate...

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Carbocisteine

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in 1960. Carbocisteine is produced by alkylation of cysteine with chloroacetic acid. Carbocisteine. drugbank.ca Zheng JP, Kang J, Huang SG, Chen P, Yao...

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Iodoacetic acid

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acid is more toxic than bromoacetic acid and much more toxic than chloroacetic acid. Dippy, J. F. J.; Hughes, S. R. C.; Rozanski, A. (1959). "The dissociation...

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Carboxylic acid

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carboxylic acid is an organic acid that contains a carboxyl group (−C(=O)−OH) attached to an R-group. The general formula of a carboxylic acid is often...

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Glycine

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processes are amination of chloroacetic acid with ammonia, giving glycine and ammonium chloride, and the Strecker amino acid synthesis, which is the main...

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Rhodanine

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chemists) and chloroacetic acid in water. Rhodanines can also be prepared by the reaction of carbon disulfide, ammonia, and chloroacetic acid, which proceeds...

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Thioglycolic acid

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thiosulfate with chloroacetic acid: ClCH2CO2H + Na2S2O3 → Na[O3S2CH2CO2H] + NaCl Na[O3S2CH2CO2H] + H2O → HSCH2CO2H + NaHSO4 Thioglycolic acid with a pKa of...

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Dimethyl malonate

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world's largest producer of dimethyl malonate by volume and uses a chloroacetic acid/sodium cyanide process developed in the 1940s. Diethyl malonate Merck...

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MCPA

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synthesized MCPA from the corresponding phenol by exposing it to chloroacetic acid and dilute base in a straightforward substitution reaction: 2-methyl-4-chlorophenol...

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Nitrilotriacetic acid

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coproduct. Older routes to NTA included alkylation of ammonia with chloroacetic acid and oxidation of triethanolamine. The conjugate base of NTA is a tripodal...

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Chloroacetamide

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Cl−CH2−C(=O)−NH2. Chloroacetamide is produced by ammonolysis of esters of chloroacetic acid: ClCH2CO2CH3 + NH3 → ClCH2C(O)NH2 + CH3OH Chloroacetamide has been...

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Phenoxyacetic acid

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nucleophilic attack on the methylene carbon of the chloroacetic acid, forming an ether bond. Phenoxyacetic acid is a white or clear crystalline compound at room...

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Salicylaldehyde

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catechol (1,2-dihydroxybenzene) (Dakin reaction). Etherification with chloroacetic acid followed by cyclisation gives the heterocycle benzofuran (coumarone)...

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Chloroformic acid

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benzyl chloroformate and ethyl chloroformate. Chloroacetic acids Dichloroacetic acid Trichloroacetic acid Nomenclature of Organic Chemistry : IUPAC Recommendations...

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Fluoroacetic acid

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Fluoroacetic acid is a organofluorine compound with the chemical formula FCH2CO2H. It is a colorless solid that is noted for its relatively high toxicity...

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Benzofuran

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laboratory. Notable examples include: O-alkylation of salicylaldehyde with chloroacetic acid followed by dehydration (cyclication) of the resulting ether and decarboxylation...

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Nitroacetic acid

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organic reagent in chemical synthesis. Nitroacetic acid can be synthesized by adding cold chloroacetic acid into a cold, slightly alkaline aqueous solution...

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