Chloroacetic acid

For chloroacetic acids in general, see Chloroacetic acids.
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
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.072 Edit this at Wikidata
EC Number
  • 201-178-4
KEGG
RTECS number
  • AF8575000
UNII
  • 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
  • ClCC(O)=O
Properties
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)
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]
−48.1×10−6 cm3/mol
1.4351 (55 °C)
Structure
Monoclinic
Thermochemistry
144.02 J/(K·mol)
−490.1 kJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 alkylating agent
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS09: Environmental hazard
Danger
H301, H311, H314, H331, H400
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)
470 °C (878 °F; 743 K)
Lethal dose or concentration (LD, LC):
76 mg/kg.[2]
Safety data sheet (SDS) External MSDS
Related compounds
Related compounds
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 ?)
Not to be confused with Acetyl chloride or Chloroacetyl chloride.

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).