2-Methylsuccinic acid

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.

2-Methylsuccinic acid
Names
Preferred IUPAC name
Methylbutanedioic acid
Other names
Pyrotartaric acid; 2-Methylbutanedioic acid; Propane-1,2-dicarboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.144
EC Number
  • 207-857-1
UNII
  • 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
  • CC(CC(=O)O)C(=O)O
Properties
C5H8O4
Molar mass 132.115 g·mol−1
Appearance White solid
Melting point 117.5 °C (243.5 °F; 390.6 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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
  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.
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