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 ;
3D model (JSmol)	Interactive image;
3DMet	B02139;
ChEBI	CHEBI:27869 ;
ChEMBL	ChEMBL14090 ;
ChemSpider	10772140 ;
ECHA InfoCard	100.001.072
EC Number	201-178-4;
KEGG	D07677 ; C06755;
PubChem CID	300;
RTECS number	AF8575000;
UNII	5GD84Y125G ;
CompTox Dashboard (EPA)	DTXSID4020901 ;
	InChI InChI=1S/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5) Key: FOCAUTSVDIKZOP-UHFFFAOYSA-N ; 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
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 (ΔfH⦵298)	−490.1 kJ/mol
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	alkylating agent
	GHS labelling:
Pictograms
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)	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.
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). verify (what is ?) Infobox references

Chloroacetic acid, industrially known as monochloroacetic acid (MCA), is the organochlorine compound with the formula Cl C H₂CO₂H. This carboxylic acid is a useful building block in organic synthesis. It is a colorless solid. Related compounds are dichloroacetic acid and trichloroacetic acid.

^ 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.
^ Cite error: The named reference Ullmann was invoked but never defined (see the help page).

[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.

[Ullmann-2] Cite error: The named reference Ullmann was invoked but never defined (see the help page).

[1]

[2]

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^Y
3D model (JSmol)	Interactive image
3DMet	B02139
ChEBI	CHEBI:27869^Y
ChEMBL	ChEMBL14090^Y
ChemSpider	10772140^Y
ECHA InfoCard	100.001.072
EC Number	201-178-4
KEGG	D07677^Y C06755
PubChem CID	300
RTECS number	AF8575000
UNII	5GD84Y125G^Y
CompTox Dashboard (EPA)	DTXSID4020901
InChI InChI=1S/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5)^Y Key: FOCAUTSVDIKZOP-UHFFFAOYSA-N^Y 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 (pK_a)	2.86^[1]
Magnetic susceptibility (χ)	−48.1×10⁻⁶ cm³/mol
Refractive index (n_D)	1.4351 (55 °C)
Structure
Crystal structure	Monoclinic
Thermochemistry
Heat capacity (C)	144.02 J/(K·mol)
Std enthalpy of formation (Δ_fH^⦵₂₉₈)	−490.1 kJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	alkylating agent
GHS labelling:
Pictograms
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)	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 ^YN ?) Infobox references