1,3-Bis(triisopropylsilyl)propyne
Basic information
- CAS
82192-59-4- Standard SMILES
CC(C)[Si](C#CC[Si](C(C)C)(C(C)C)C(C)C)(C(C)C)C(C)C- InChIKey
JFDDOGUVACDNTR-UHFFFAOYSA-N- Molecular formula
- C21H44Si2
- Average molar mass
- 352.7 g/mol
- Monoisotopic mass
- 352.29815447
Names & identifiers
- Preferred name
- 1,3-Bis(triisopropylsilyl)propyne
- IUPAC
- tri(propan-2-yl)-[3-tri(propan-2-yl)silylprop-1-ynyl]silane
- English name
- 1,3-Bis(triisopropylsilyl)propyne
- Molecular formula
- C21H44Si2
- Molecular weight
- 352.75
Names & synonyms
1,3-BIS(TRIISOPROPYLSILYL)PROPYNE82192-59-4DTXSID00326813RefChem:218129DTXCID90277926tri(propan-2-yl)-[3-tri(propan-2-yl)silylprop-1-ynyl]silaneNSC617303NSC-617303(Prop-1-yne-1,3-diyl)bis[tri(propan-2-yl)silane]Silane, 1-propyne-1,3-diylbis[tris(1-methylethyl)-Silane, 1,1'-(1-propyne-1,3-diyl)bis[1,1,1-tris(1-methylethyl)-
Database identifiers
- CAS
82192-59-4- PubChem CID
- 357780
- DTXSID
DTXSID00326813- Nikkaji
- J1.386.442J
Properties
Computed structural properties
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 8
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 372
Physicochemical properties
- Boiling point
- 130 · 130-135 °C(Press: 0.08 Torr)
- Density
- 0.816 · 0.816±0.06 g/cm3(Predicted)
- solubility
- both the reagent and its lithio derivative are soluble in ether or THF.
Chemistry & industry
Applications
Uses1,3-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 methods
Preparation1,3-bis(TIPS)propyne is prepared in quantitative yield by silylation of 3-lithio-1-triisopropylsilyl-1- propyne with triisopropylsilyl trifluoromethanesulfonate.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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