2-Methylsuccinic acid (original) (raw)
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2-Methylsuccinic acid
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| Names | |
| Preferred IUPAC name Methylbutanedioic acid | |
| Other namesPyrotartaric 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 labelling: | |
| Pictograms |  |
| Signal word | Warning |
| Hazard statements | H315, H319, H335 |
| Precautionary statements | 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 |
Chemical compound
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.
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]
- ^ Kawamura, Kimitaka; Ikushima, Kouichi (1993). "Seasonal Changes in the Distribution of Dicarboxylic Acids in the Urban Atmosphere". Environmental Science and Technology. 27 (10): 2227–35. Bibcode:1993EnST...27.2227K. 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.