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3,3,4,4-Tetramethyltetrahydrofuran-2,5-dione

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3,3,4,4-Tetramethyltetrahydrofuran-2,5-dione
Names
Preferred IUPAC name
3,3,4,4-Tetramethyloxolane-2,5-dione
Other names
Tetrahydro-3,3,4,4-tetramethylfuran-2,5-dione; 3,3,4,4-tetramethytetrahydrofuran-2,5-quinone; dihydro-3,3,4,4-tetramethyl-2,5-furandione; tetramethylsuccinic anhydride; TMSA
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C8H12O3/c1-7(2)5(9)11-6(10)8(7,3)4/h1-4H3
    Key: KYZIXHLDWJBHDI-UHFFFAOYSA-N
  • CC1(C(=O)OC(=O)C1(C)C)C
Properties
C8H12O3
Molar mass 156.181 g·mol−1
Appearance White crystalline[1]
Density 1.044 g/cm3[2]
Melting point 147 °C (297 °F; 420 K)[1]
Boiling point 226.1 °C (439.0 °F; 499.2 K) 760mmHg[2]
1.434[2]
Hazards
Flash point 93.2 °C (199.8 °F; 366.3 K)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

In chemistry, 3,3,4,4-tetramethyltetrahydrofuran-2,5-dione is a heterocyclic compound with the formula C
8H
12O
3, or (CH3)2(COC2COO)(CH3)2. It is a white crystalline solid with a pungent camphoraceous odor.[1]

The compound is also called 3,3,4,4-tetramethyloxolane-2,5-dione (its IUPAC name) or 3,3,4,4-tetramethylsuccinic anhydride,[2] namely the anhydride of 2,2,3,3-tetramethylsuccinic acid, and sometimes abbreviated as TMSA.[3] It can be seen as derivative of tetrahydrofuran-2,5-dione (oxolane-2,5-dione) with two methyl groups replacing two hydrogen atoms on each of the carbon atoms in the ring that are not adjacent to the ring oxygen.[2]

Synthesis and chemistry

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The compound is soluble in petroleum ether.[1][4]

The compound was described in 1890 by Karl von Auwers and Victor Meyer who obtained it by thermal decomposition of 2,2,3,3-tetramethylsuccinic acid.[1][5] It can also be obtained, in > 50% yield, from 3,3,4,4-tetramethylpyrrolidine-2,5-dione[4] Other synthesis routes include

See also

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References

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  1. ^ a b c d e Karl von Auwers, Victor Meyer (1890), Ueber Tetramethylbernsteinsäure und Trimethylglutarsäure. Berichte der deutschen chemischen Gesellschaft, volume 23, issue 1, pages 293,301,304–305. doi:10.1002/cber.18900230151
  2. ^ a b c d e f "3,3,4,4-tetramethyloxolane-2,5-dione" at Molbase. Accessed on 2015-08-01.
  3. ^ Subat Turdi, Peisheng Xu, Qun Li, Youqing Shen, Parhat Kerram, and Jun Ren (2008), Amidization of Doxorubicin Alleviates Doxorubicin-Induced Contractile Dysfunction and Reduced Survival in Murine Cardiomyocytes. Toxicology Letters volume 178, issue 3, pages 197–201. doi:10.1016/j.toxlet.2008.03.010
  4. ^ a b Snezna Bizilj, David P. Kelly, Algirdas K. Serelis, David H. Solomon, Kathleen E. White (1985). The Self-Reactions of 1-Methoxycarbonyl-1-methylethyl and Higher Ester Radicals: Combination vs Disproportionation and Oligomeric Products from Secondary Reactions. Australian Journal of Chemistry, volume 38, issue 11, pages 1657–1673. doi:10.1071/CH9851657
  5. ^ Karl von Auwers, O. Ungemach (1935) Zur Zerreißbarkeit der Kohlenstoffkette in Bernsteinsäure-Derivaten. Berichte der deutschen chemischen Gesellschaft, volume 68, pages 23, 349–351. doi:10.1002/cber.19350680228
  6. ^ J. Thiele, K. Heuser (1896). Ueber Hydrazinderivate der Isobuttersäure. Justus Liebigs Annalen der Chemie, volume 290, pages 1–43.
  7. ^ 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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