86318-61-8

Basic information

• Product Name: TERT-BUTYLDIMETHYLSILYLACETYLENE
• Synonyms: Silane,(1,1-diMethylethyl)ethynyldiMethyl-;(tert-Butyldimethylsilyl)acetylene;ETHYNYL-TERT-BUTYLDIMETHYLSILANE;(T-BUTYLDIMETHYLSILYL)ACETYLENE;TERT-BUTYLDIMETHYLSILYLACETYLENE;tert-BUTYLDIMETHYLSILYLACETYLENE 98%;ethynyl-t-butyldimethylsilane;(tert-Butyldimethylsilyl)ethyne
• CAS NO: 86318-61-8
• Molecular Formula: C₈H₁₆Si
• Molecular Weight: 140.3
• Product Categories: Alkynes;Building Blocks;Chemical Synthesis;Organic Building Blocks;Terminal
• Mol File: 86318-61-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 98-102℃ (chloroform hexane )
• Boiling Point: 116-117 °C(lit.)
• Flash Point: 43 °F
• Appearance: /
• Density: 0.751 g/mL at 25 °C(lit.)
• Vapor Pressure: 12mmHg at 25°C
• Refractive Index: n20/D 1.451(lit.)
• Storage Temp.: Flammables area
• Water Solubility: Sparingly soluble in water (0.043 g/L at 25°C).
• BRN: 1921466
• CAS DataBase Reference: TERT-BUTYLDIMETHYLSILYLACETYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYLDIMETHYLSILYLACETYLENE(86318-61-8)
• EPA Substance Registry System: TERT-BUTYLDIMETHYLSILYLACETYLENE(86318-61-8)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 9-16-23-24/25-29-33
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 86318-61-8(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless liquid

Uses

tert-Butyldimethylsilylacetylene may be used in the synthesis of β-alkynylketone and β-alkynyl aldehydes. It participates in Cadiot-Chodkiewicz cross-coupling reaction with various bromoalkynes to afford synthetically useful unsymmetrical diynes.

General Description

(tert-Butyldimethylsilyl)acetylene is a bulky trialkylsilyl-protected alkyne. It participates in Cadiot-Chodkiewicz cross-coupling reaction with various bromoalkynes to afford synthetically useful unsymmetrical diynes.

InChI:InChI=1/C8H16Si/c1-7-9(5,6)8(2,3)4/h1H,2-6H3

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 74-86-2 acetylene 
• 4301-14-8 acetylenemagnesium bromide 

Downstream Products

• 777060-86-3 2-[(tert-butyldimethylsilanyl)-ethynyl]-benzaldehyde 
• 937058-20-3 C₁₄H₂₄Si 
• 866929-82-0 2-(tert-butyldimethylsilylethynyl)-5-bromopyridine 
• 1007224-15-8 (R)-1-(tert-butyl-dimethyl-silanyl)-5-(4-methoxy-benzyloxy)-4-methyl-pent-1-yn-3-one 
• 945772-24-7 2-(t-butyldimethylsilyloxy)-7-isopropoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-benzofuran 
• 247045-08-5 4,5-bis(tert-butyldimethylsilylethynyl)phthalonitrile 
• 1104606-10-1 tert-butyl(dimethyl)(3-methylphenyl)silan 
• 149530-69-8 Dimethyl-(1,1-dimethylethyl)-(4-methylphenyl)-silan 
• 1147846-02-3 (E)-[5-(tert-butyldimethylsilyl)-3-(4-methylphenyl)-2-penten-4-ynyl]diisopropylamine 
• 1147846-07-8 (E)-4-[1-(tert-butyldimethylsilyl)-5-(diisopropylamino)-3-penten-1-yn-3-yl]benzonitrile 
• 1147846-06-7 methyl (E)-4-[1-(tert-butyldimethylsilyl)-5-(diisopropylamino)-pent-3-en-1-yn-3-yl]benzoate 
• 1147846-04-5 (E)-[5-(tert-butyldimethylsilyl)-3-(4-trifluoromethylphenyl)-2-penten-4-ynyl]diisopropylamine 
• 1147845-91-7 (E)-4-[5-(tert-butyldimethylsilyl)-3-phenyl-2-penten-4-ynyl]morpholine 
• 1147845-97-3 (E)-4-[2-benzylidene-4-(tert-butyldimethylsilyl)-3-butynyl]morpholine 

Relevant articles and documents

Synthesis and use of new substituted 1,3,5-hexatrienes in studying thermally induced 6π-electrocyclizations

An acyclic, two heterocyclic, and two bicyclic alkenylstannanes, 3, 4a, 4b, 8 and 11, respectively, were synthesized in yields ranging from 43 to 97 %, and each was subjected to a sequence of Stille and Heck couplings with 2-bromocyclohexenyl triflate (13

Synthesis of 4-Silylcyclobut-2-enethiones and Their Use in Cyclobutadiene Generation

Alkynyl silyl sulfides 2 reacted with ynamines 3 to give 1:1 adducts.The structure of 4-silylcyclobut-2-enethiones 4 was confirmed by X-ray analysis of 4a.A cyclobutadiene intermediate is probably not involved in this reaction; we think that it is initiat

Thioketene Syntheses, VII. Substituent Effects on the Thio-Claisen Rearrangement of Alkynyl Allyl Sulfides

Electron acceptors in the position 2 of the allyl residues in alkynyl allyl sulfides 4, 11, 15 favor the Thio-Claisen rearrangement to give thioketenes 5, 12, 16, but in position 3 impede the reaction.For the substituent on the triple bond, the sequence silyl > alkyl > alkylthio is valid.The results can be understood in terms of a zwitterionic intermediate 19 or a highly polarized transition state of the rearrangement.