Chemistry:2-Methylsuccinic acid

2-Methylsuccinic acid

Names
Preferred IUPAC name Methylbutanedioic acid
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
EC Number	207-857-1
PubChem CID	10349
UNII	H1547KG7UZ
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. 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. Alternatively, hydrocyanation of ethyl crotonate affords an intermediate, which converts to 2-methylsuccinic acid after hydrolysis of the ester and nitrile substituents.