Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

399264

Sigma-Aldrich

(tert-Butyldimethylsilyl)acetylene

99%

Synonym(s):

Ethynyl-tert-butyldimethylsilane

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
(CH3)3CSi(CH3)2C≡CH
CAS Number:
86318-61-8
Molecular Weight:
140.30
Beilstein/REAXYS Number:
1921466
MDL number:
MFCD00191877
UNSPSC Code:
12352100
PubChem Substance ID:
24864798
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

100

assay

99%

refractive index

n20/D 1.451 (lit.)

bp

116-117 °C (lit.)

density

0.751 g/mL at 25 °C (lit.)

SMILES string

CC(C)(C)[Si](C)(C)C#C

InChI

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

InChI key

RTYNRTUKJVYEIE-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
346977187437360031
(tert-Butyldimethylsilyl)acetylene 99%

399264

(tert-Butyldimethylsilyl)acetylene

(Triethylsilyl)acetylene 97%

346977

(Triethylsilyl)acetylene

Bis(trimethylsilyl)acetylene 99%

187437

Bis(trimethylsilyl)acetylene

(Triisopropylsilyl)acetylene 97%

360031

(Triisopropylsilyl)acetylene

assay

99%

assay

97%

assay

99%

assay

97%

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

bp

116-117 °C (lit.)

bp

-

bp

136-137 °C (lit.)

bp

50-52 °C/0.6 mmHg (lit.)

refractive index

n20/D 1.451 (lit.)

refractive index

n20/D 1.433 (lit.)

refractive index

n20/D 1.427 (lit.)

refractive index

n20/D 1.4527 (lit.)

density

0.751 g/mL at 25 °C (lit.)

density

0.783 g/mL at 25 °C (lit.)

density

0.752 g/mL at 25 °C (lit.)

density

0.813 g/mL at 25 °C (lit.)

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.[1]
(tert-Butyldimethylsilyl)acetylene readily undergoes cross-dimerization reaction with various internal phenyl acetylenes in the presence of rhodium dimers and bidentate phosphine ligands to afford enynes.[2]

Application

(tert-Butyldimethylsilyl)acetylene may be used in the synthesis of β-alkynylketone[3] and β-alkynyl aldehydes.[4]

accessory

Product No.
Description
Pricing

pictograms

Flame
GHS02

signalword

Danger

hcodes

H225

pcodes

P210

Hazard Classifications

Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

42.8 °F - closed cup

flash_point_c

6 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

  • Specification Sheet

    • Choose from one of the most recent versions:

    Certificates of Analysis (COA)

    Lot/Batch Number
    SHBL6709
    SHBB4471V
    SHBB1046V
    56296EMV
    56296EM

    Don't see the Right Version?

    If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

    Search for a COA

    Already Own This Product?

    Find documentation for the products that you have recently purchased in the Document Library.

    Visit the Document Library

    Asymmetric synthesis of beta-alkynyl aldehydes by rhodium-catalyzed conjugate alkynylation.
    Takahiro Nishimura et al.
    Angewandte Chemie (International ed. in English), 48(43), 8057-8059 (2009-09-22)
    Trost BM and Li CJ.
    Modern Alkyne Chemistry: Catalytic and Atom-Economic Transformations (2014)
    Joseph P Marino et al.
    The Journal of organic chemistry, 67(19), 6841-6844 (2002-09-14)
    Bulky trialkylsilyl-protected alkynes such as triethylsilyl (TES), tert-butyldimethylsilyl (TBS), and triisopropylsilyl (TIPS) acetylenes underwent the Cadiot-Chodkiewicz cross-coupling reaction with different bromoalkynes to form a variety of synthetically useful unsymmetrical diynes in good yields. The diyne alcohol 10 was transformed regio-
    Steric tuning of silylacetylenes and chiral phosphine ligands for rhodium-catalyzed asymmetric conjugate alkynylation of enones.
    Takahiro Nishimura et al.
    Journal of the American Chemical Society, 130(5), 1576-1577 (2008-01-17)

    Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

    Contact Technical Service