Malonic acid

Malonic acid
Names
	Preferred IUPAC name Propanedioic acid
	Other names Methanedicarboxylic acid
Identifiers
CAS Number	141-82-2 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:30794 ;
ChEMBL	ChEMBL7942 ;
ChemSpider	844 ;
DrugBank	DB02175 ;
ECHA InfoCard	100.005.003
PubChem CID	867;
UNII	9KX7ZMG0MK ;
CompTox Dashboard (EPA)	DTXSID7021659 ;
	InChI InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7) Key: OFOBLEOULBTSOW-UHFFFAOYSA-N ; InChI=1/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7) Key: OFOBLEOULBTSOW-UHFFFAOYAJ;
	SMILES O=C(O)CC(O)=O; C(C(=O)O)C(=O)O;
Properties
Chemical formula	C3H4O4
Molar mass	104.061 g·mol−1
Density	1.619 g/cm3
Melting point	135 to 137 °C (275 to 279 °F; 408 to 410 K) (decomposes)
Boiling point	decomposes
Solubility in water	763 g/L
Acidity (pKa)	pKa1 = 2.83 ; pKa2 = 5.69
Magnetic susceptibility (χ)	-46.3·10−6 cm3/mol
Related compounds
Other anions	Malonate
Related carboxylic acids	Oxalic acid; Propionic acid; Succinic acid; Fumaric acid
Related compounds	Malondialdehyde; Dimethyl malonate
Hazards
Safety data sheet (SDS)	External MSDS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH₂(COOH)₂. The ionized form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's diethyl ester. The name originates from the Greek word μᾶλον (malon) meaning 'apple'.

^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 746. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
^ ^a ^b pKa Data Compiled by R. Williams (pdf; 77 kB) Archived 2010-06-02 at the Wayback Machine

[1] International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 746. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

[Williams-2] Ka Data Compiled by R. Williams (pdf; 77 kB) Archived 2010-06-02 at the Wayback Machine

[1]

[2]

Names


Preferred IUPAC name Propanedioic acid^[1]
Other names Methanedicarboxylic acid
Identifiers
CAS Number	141-82-2^Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:30794^Y
ChEMBL	ChEMBL7942^Y
ChemSpider	844^Y
DrugBank	DB02175^Y
ECHA InfoCard	100.005.003
PubChem CID	867
UNII	9KX7ZMG0MK^Y
CompTox Dashboard (EPA)	DTXSID7021659
InChI InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)^Y Key: OFOBLEOULBTSOW-UHFFFAOYSA-N^Y InChI=1/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7) Key: OFOBLEOULBTSOW-UHFFFAOYAJ
SMILES O=C(O)CC(O)=O C(C(=O)O)C(=O)O
Properties
Chemical formula	C₃H₄O₄
Molar mass	104.061 g·mol⁻¹
Density	1.619 g/cm³
Melting point	135 to 137 °C (275 to 279 °F; 408 to 410 K) (decomposes)
Boiling point	decomposes
Solubility in water	763 g/L
Acidity (pK_a)	pK_a1 = 2.83^[2] pK_a2 = 5.69^[2]
Magnetic susceptibility (χ)	-46.3·10⁻⁶ cm³/mol
Related compounds
Other anions	Malonate
Related carboxylic acids	Oxalic acid Propionic acid Succinic acid Fumaric acid
Related compounds	Malondialdehyde Dimethyl malonate
Hazards
Safety data sheet (SDS)	External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Malonic acid

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