2,2,5,5-Tetramethyltetrahydrofuran

2,2,5,5-Tetramethyltetrahydrofuran
Names
Preferred IUPAC name
2,2,5,5-Tetramethyloxolane
Other names
TMO, Tetrahydro-2,2,5,5-tetramethylfuran, TMTHF, Me4THF
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.035.547
EC Number
  • 239-117-9
UNII
  • InChI=1S/C8H16O/c1-7(2)5-6-8(3,4)9-7/h5-6H2,1-4H3
    Key: BBLDTXFLAHKYFJ-UHFFFAOYSA-N
  • CC1(CCC(O1)(C)C)C
Properties
C8H16O
Molar mass 128.21
Appearance clear colorless
Density 0.811 g/cm3 (25 C)
Melting point −92 °C (−134 °F; 181 K)
Boiling point 112 °C (234 °F; 385 K)
water: 1627 mg/L at 25 C
log P 2.39
1.405
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 highly flammable
Flash point 4 °C; 39 °F; 277 K
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

2,2,5,5-tetramethyltetrahydrofuran (TMTHF) or 2,2,5,5-tetramethyloxolane (TMO) is a heterocyclic compound with the formula C
8H
16O, or (CH3)2(C(CH2)2OC)(CH3)2. It can be seen as derivative of tetrahydrofuran (oxolane) with four methyl groups replacing four hydrogen atoms on each of the carbon atoms in the ring that are adjacent to the oxygen. The absence of hydrogen atoms adjacent to the oxygen means that TMTHF (TMO) does not form peroxides, unlike other common ethers such as tetrahydrofuran, diethyl ether and CPME.

The compound has been demonstrated as a non-polar solvent in research chemistry, having similar properties to toluene and as a reagent in chemical synthesis.

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