82192-59-4

Basic information

• Product Name: Silane, 1,1'-(1-propyne-1,3-diyl)bis[1,1,1-tris(1-methylethyl)-
• Synonyms: Silane, 1,1'-(1-propyne-1,3-diyl)bis[1,1,1-tris(1-methylethyl)-;Silane, 1-propyne-1,3-diylbis[tris(1-methylethyl)-;1,3-Bis(triisopropylsilyl)propyne
• CAS NO: 82192-59-4
• Molecular Formula: C₂₁H₄₄Si₂
• Molecular Weight: 352.74506
• Mol File: 82192-59-4.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Solubility: both the reagent and its lithio derivative are soluble in ether or THF.
• CAS DataBase Reference: Silane, 1,1'-(1-propyne-1,3-diyl)bis[1,1,1-tris(1-methylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, 1,1'-(1-propyne-1,3-diyl)bis[1,1,1-tris(1-methylethyl)-(82192-59-4)
• EPA Substance Registry System: Silane, 1,1'-(1-propyne-1,3-diyl)bis[1,1,1-tris(1-methylethyl)-(82192-59-4)

Safety Data

• Hazardous Substances Data: 82192-59-4(Hazardous Substances Data)

Usage

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.

Upstream product

• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 

Downstream Products

• 86197-22-0 1α,2,3,3aα,4,5,5aβ,6α,7,8,9,9aβ-dodecahydro-1-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6-<5-(triiisopropylsilyl)-2(Z)-penten-4-ynyl>pyrrolo<1,2-a>quinoline 
• 86258-59-5 1α,2,3,3aα,4,5,5aβ,6α,7,8,9,9aβ-dodecahydro-1-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6-<5-(triiisopropylsilyl)-2(E)-penten-4-ynyl>pyrrolo<1,2-a>quinoline 
• 344315-40-8 C₅₆H₈₂O₇S₂Si₂ 
• 809285-69-6 (3Z,6S,8S,9E)-8-(4-methoxybenzyloxy)-7,7-dimethyl-1-(triisopropylsilyl)undeca-3,9-dien-1-yn-6-ol 

Relevant articles and documents

USEFUL SYNTHETIC REAGENTS DERIVED FROM 1-TRIISOPROPYLSILYLPROPYNE AND 1,3-BISPROPYNE. DIRECT, STEREOSELECTIVE SYNTHESIS OF EITHER Z OR E ENYNES

Lithio reagents derived from 1-triisopropylsilylpropyne (1) and 1,3-bis-propyne (3) are effective for the synthesis of Z or E terminal enyne units (CH=CH-CCH) and for carbon-carbon bond formation with halides, aldehydes, ketones, epoxides, and α,β-enones.