2-Methylsuccinic acid: Difference between revisions

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| ImageSize =
| ImageSize =
| ImageAlt =
| ImageAlt =
| PIN = Methylbutanedioic acid
| IUPACName =
| OtherNames = Pyrotartaric acid; 2-methylbutanedioic acid; propane-1,2-dicarboxylic acid
| OtherNames = Pyrotartaric acid; 2-Methylbutanedioic acid; Propane-1,2-dicarboxylic acid
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo = 498-21-5
| CASNo = 498-21-5
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| C=5|H=8|O=4
| C=5|H=8|O=4
| MolarMass =
| MolarMass =
| Appearance = white solid
| Appearance = White solid
| Density =
| Density =
| MeltingPtC = 117.5
| MeltingPtC = 117.5
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| AutoignitionPt = }}
| AutoignitionPt = }}
}}
}}
'''2-Methylsuccinic acid''' is an [[organic compound]] with the formula HO<sub>2</sub>CCH(CH<sub>3</sub>)CH<sub>2</sub>CO<sub>2</sub>H. A white solid, it is the simplest [[chiral]] [[dicarboxylic acid]]. It is a recurring component of urban aerosols.<ref>{{cite journal|title=Seasonal Changes in the Distribution of Dicarboxylic Acids in the Urban Atmosphere|authors=Kawamura, Kimitaka; Ikushima, Kouichi|journal=Environmental Science and Technology|year=1993|volume=27|pages=2227-35|doi=10.1021/es00047a033}}</ref> Salts of 2-methylsuccinic acid are called '''2-methylsuccinates'''.
'''2-Methylsuccinic acid''' is an [[organic compound]] with the formula HO<sub>2</sub>CCH(CH<sub>3</sub>)CH<sub>2</sub>CO<sub>2</sub>H. A white solid, it is the simplest [[chiral]] [[dicarboxylic acid]]. It is a recurring component of urban aerosols.<ref>{{cite journal|title=Seasonal Changes in the Distribution of Dicarboxylic Acids in the Urban Atmosphere|author1=Kawamura, Kimitaka |author2=Ikushima, Kouichi|journal=Environmental Science and Technology|year=1993|volume=27|issue=10 |pages=2227–35|doi=10.1021/es00047a033|bibcode=1993EnST...27.2227K }}</ref> Salts and esters of 2-methylsuccinic acid are called '''2-methylsuccinates'''.


==Preparation==
==Preparation==
It can be prepared by partial [[hydrogenation]] of [[itaconic acid]] over [[Raney nickel]].<ref>{{cite journal|title=3-Methylthiophene|authors=R. F. Feldkamp, B. F. Tullar|journal=Org.Synth.|year=1954 |volume=34|page=73|doi=10.15227/orgsyn.034.0073}}</ref> Alternatively, [[hydrocyanation]] of ethyl [[crotonate]] affords an intermediate, which converts to 2-methylsuccinic acid after hydrolysis of the ester and [[nitrile]] substituents.<ref>{{cite journal|journal=Org. Synth.|year=1946|volume=26|page=54|doi=10.15227/orgsyn.026.0054|title=Methylsuccinic acid|author=George Bosworth Brown}}</ref>
It can be prepared by partial [[hydrogenation]] of [[itaconic acid]] over [[Raney nickel]].<ref>{{cite journal|title=3-Methylthiophene|author1=R. F. Feldkamp |author2=B. F. Tullar|journal=Org. Synth.|year=1954 |volume=34|page=73|doi=10.15227/orgsyn.034.0073}}</ref> Alternatively, [[hydrocyanation]] of ethyl [[crotonate]] affords an intermediate, which converts to 2-methylsuccinic acid after hydrolysis of the ester and [[nitrile]] substituents.<ref>{{cite journal|journal=Org. Synth.|year=1946|volume=26|page=54|doi=10.15227/orgsyn.026.0054|title=Methylsuccinic acid|author=George Bosworth Brown}}</ref>


==References==
==References==
<references />
<references />


{{DEFAULTSORT:Methylsuccinic acid, 2-}}
[[Category:Dicarboxylic acids]]
[[Category:Dicarboxylic acids]]
[[Category:Succinates]]

Latest revision as of 22:11, 22 February 2024

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 Edit this at Wikidata
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).

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[edit]

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[edit]

  1. ^ 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.
  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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