2-Methylsuccinic acid

2-Methylsuccinic acid
Names
	Other names Pyrotartaric acid; 2-methylbutanedioic acid; propane-1,2-dicarboxylic acid
Identifiers
CAS Number	498-21-5;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:91315;
ChemSpider	9922;
ECHA InfoCard	100.007.144
EC Number	207-857-1;
PubChem CID	10349;
UNII	H1547KG7UZ;
CompTox Dashboard (EPA)	DTXSID9025663 ;
	InChI InChI=1S/C5H8O4/c1-3(5(8)9)2-4(6)7/h3H,2H2,1H3,(H,6,7)(H,8,9) Key: WXUAQHNMJWJLTG-UHFFFAOYSA-N;
	SMILES CC(CC(=O)O)C(=O)O;
Properties
Chemical formula	C5H8O4
Molar mass	132.115 g·mol−1
Appearance	White solid
Melting point	117.5 °C (243.5 °F; 390.6 K)
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H315, H319, H335
GHS precautionary statements	P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

2-Methylsuccinic acid is an organic compound with the formula HO₂CCH(CH₃)CH₂CO₂H. A white solid, it is the simplest chiral dicarboxylic acid. It is a recurring component of urban aerosols.[1] Salts and esters of 2-methylsuccinic acid are called 2-methylsuccinates.

Preparation

It can be prepared by partial hydrogenation of itaconic acid over Raney nickel.[2] Alternatively, hydrocyanation of ethyl crotonate affords an intermediate, which converts to 2-methylsuccinic acid after hydrolysis of the ester and nitrile substituents.[3]

References

Kawamura, Kimitaka; Ikushima, Kouichi (1993). "Seasonal Changes in the Distribution of Dicarboxylic Acids in the Urban Atmosphere". Environmental Science and Technology. 27: 2227–35. doi:10.1021/es00047a033.
R. F. Feldkamp; B. F. Tullar (1954). "3-Methylthiophene". Org. Synth. 34: 73. doi:10.15227/orgsyn.034.0073.
George Bosworth Brown (1946). "Methylsuccinic acid". Org. Synth. 26: 54. doi:10.15227/orgsyn.026.0054.

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[1] Kawamura, Kimitaka; Ikushima, Kouichi (1993). "Seasonal Changes in the Distribution of Dicarboxylic Acids in the Urban Atmosphere". Environmental Science and Technology. 27: 2227–35. doi:10.1021/es00047a033.

[2] R. F. Feldkamp; B. F. Tullar (1954). "3-Methylthiophene". Org. Synth. 34: 73. doi:10.15227/orgsyn.034.0073.

[3] George Bosworth Brown (1946). "Methylsuccinic acid". Org. Synth. 26: 54. doi:10.15227/orgsyn.026.0054.