Di-tert-butyl ether

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]

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

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