| Identification | Back Directory | [Name]
Silane, 1,1'-(1-propyne-1,3-diyl)bis[1,1,1-tris(1-methylethyl)- | [CAS]
82192-59-4 | [Synonyms]
1,3-Bis(triisopropylsilyl)propyne
Silane, 1-propyne-1,3-diylbis[tris(1-methylethyl)-
Silane, 1,1'-(1-propyne-1,3-diyl)bis[1,1,1-tris(1-methylethyl)- | [Molecular Formula]
C21H44Si2 | [MDL Number]
MFCD17013305 | [MOL File]
82192-59-4.mol | [Molecular Weight]
352.75 |
| Hazard Information | Back Directory | [Physical properties]
bp 130–135°C/0.08 mmHg; d 0.846 g cm?3. | [Uses]
1,3-Bis(triisopropylsilyl)propyne is a precursor of a stereoselective bulky C3 nucleophile, functionalized
Peterson reagent.
The main use of the title reagent is as a precursor of the
lithium derivative. 1,3-Bis(triisopropylsilyl)propyne is cleanly
lithiated by treatment with equiv of n-butyllithium in THF at
?20°C (15 min) to what is probably an equilibrium mixture of
propargylic and allenic species (1) and (2) (eq 1).The bulky
triisopropylsilyl (TIPS) group serves as a controlling group in the
addition of (1/2) to electrophiles. | [Preparation]
1,3-bis(TIPS)propyne is prepared in quantitative
yield by silylation of 3-lithio-1-triisopropylsilyl-1-
propyne with triisopropylsilyl trifluoromethanesulfonate. |
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