Di-tert-butyl ether

Di-tert-butyl ether ^[1]

Names
Preferred IUPAC name 2-Methyl-2-[(2-methylpropan-2-yl)oxy]propane
Other names 2-tert-Butoxy-2-methylpropane Di-tert-butyl ether
Identifiers
CAS Number	6163-66-2  Y
3D model (JSmol)	Interactive image
ChemSpider	21138  Y
ECHA InfoCard	100.197.715
PubChem CID	22541
UNII	C3A9UPP65H  Y
CompTox Dashboard (EPA)	DTXSID80210645
InChI InChI=1S/C8H18O/c1-7(2,3)9-8(4,5)6/h1-6H3 Y Key: AQEFLFZSWDEAIP-UHFFFAOYSA-N Y InChI=1/C8H18O/c1-7(2,3)9-8(4,5)6/h1-6H3 Key: AQEFLFZSWDEAIP-UHFFFAOYAT
SMILES O(C(C)(C)C)C(C)(C)C
Properties
Chemical formula	C8H18O
Molar mass	130.231 g·mol−1
Appearance	colorless liquid
Density	0.7658 g/cm3 [2]
Melting point	−61 °C (−78 °F; 212 K) [3]
Boiling point	107.2 °C (225.0 °F; 380.3 K) [2]
Vapor pressure	3730 Pa (at 22 °C) [4]
Thermochemistry
Heat capacity (C)	276.1 J·mol−1·K−1
Std enthalpy of formation (ΔfH⦵298)	−399.6 kJ·mol−1
Hazards
Flash point	−3 °C (27 °F; 270 K)
Autoignition temperature	365 °C (689 °F; 638 K)
Explosive limits	>0.4%
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y  verify  (what is  YN ?) Infobox references

Di-tert-butyl ether is a tertiary ether, primarily of theoretical interest as the simplest member of the class of di-tertiary ethers. Di-tertiary ethers are notoriously challenging to prepare because conventional S_N,2 and dehydration methods favor elimination; as late as 1941, the existence of the molecule remained in doubt. ^[5]

A mediocre-yielding synthesis for di-tert-butyl ether alkylates silver carbonate with tert-butyl chloride. ^[5]

See also

• Ether
• Methyl tert-butyl ether
• Dimethyl ether
• Diethyl ether
• Diisopropyl ether

References

1. Lide, David R. (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, Florida: CRC Press. pp. 3–162, 5–52. ISBN   0-8493-0594-2.
2. David R. Lide (Hrsg.): CRC Handbook of Chemistry and Physics , (90 ed.), CRC Press, Boca Raton, Florida (2009), ISBN   978-1-4200-9084-0, S. 3-148.
3. Alquist; Tower: Nation. Advis. Comm. Aeronautics Rep. MR Nr.E 5 A 04 (1945), Chem. Abstr. 1948, 4736
4. E. J. Smutny, A. Bondi: "DI-t-BUTYL ETHER: STRAIN ENERGY AND PHYSICAL PROPERTIES", in: J. Phys. Chem. , 1961, 65 (3), S. 546–550; doi:10.1021/j100821a038.
5. Erickson, J. L. E.; Ashton, William H. (1 June 1941) [20 May 1941]. "Di-tertiary butyl ether". Journal of the American Chemical Society. 63 (6). doi:10.1021/ja01851a512.