2,2,3,3-Tetramethylsuccinic acid

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2,2,3,3-Tetramethylsuccinic acid
Names
Preferred IUPAC name
Tetramethylbutanedioic acid
Other names
2,2,3,3-Tetramethylbutane-1,4-dioic acid; 2,2,3,3-Tetramethylsuccinic acid; tetramethyl succinic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.242.673 Edit this at Wikidata
EC Number
  • 811-900-5
UNII
  • InChI=1S/C8H14O4/c1-7(2,5(9)10)8(3,4)6(11)12/h1-4H3,(H,9,10)(H,11,12)
    Key: CDPPYCZVWYZBJH-UHFFFAOYSA-N
  • CC(C)(C(=O)O)C(C)(C)C(=O)O
Properties
C8H14O4
Molar mass 174.196 g·mol−1
Density 1.161 g/cm3 [1]
Melting point 204–206 °C (399–403 °F; 477–479 K)[1]
Boiling point 259.6 °C (499.3 °F; 532.8 K) 760 mmHg [1]
1.474 [1]
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H312, H315, H318, H332, H335
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P362, P363, P403+P233, P405, P501
Flash point 125.1 °C (257.2 °F; 398.2 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

In chemistry, 2,2,3,3-tetramethylsuccinic acid or 2,2,3,3-tetramethylbutane-1,4-dioic acid is a dicarboxylic acid with the formula C
8H
14O
4, or HOOC-C(CH3)2-C(CH3)2-COOH.[1][2]

It can be seen as derivative of succinic acid (butane-1,4-dioic acid) with two methyl groups replacing two hydrogen atoms on each of the central carbon atoms of the chain.[1]

Synthesis and chemistry[edit]

The compound can also be obtained by thermal decomposition of 2,2,3,3-tetramethyl-4-one-glutaric acid with release of a carbon monoxide molecule.[3]

On heating it forms a heterocyclic anhydride, 3,3,4,4-tetramethyltetrahydrofuran-2,5-dione, with loss of one molecule of water.[4]

References[edit]

  1. ^ a b c d e f g " 2,2,3,3-tetramethylbutanedioic acid" at Molbase. Accessed on 2015-08-031.
  2. ^ 2,2,3,3-tetramethylsuccinic acid at the ChemBook site. Accessed on 2015-08-03.
  3. ^ Francis Francis and Francis George Willson (1913), Some derivatives of phorone. Part I. Journal of the Chemical Society, Transactions (UK), volume 103, article CCXXXIII, pages 2238-2247. doi:10.1039/CT9130302238
  4. ^ Eugene Rothstein, Charles William Shoppee (1927), Ring-chain tautomerism. Part XV. The hydroxy-lactone type. Journal of the Chemical Society (UK; Resumed), article LXXVIII, pages 531-534. doi:10.1039/JR9270000531.
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