Skip to Content
Merck
All Photos(2)

Documents

187437

Sigma-Aldrich

Bis(trimethylsilyl)acetylene

99%

Synonym(s):

BTMSA

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Linear Formula:
(CH3)3SiC≡CSi(CH3)3
CAS Number:
14630-40-1
Molecular Weight:
170.40
Beilstein:
906870
EC Number:
238-671-9
MDL number:
MFCD00008276
UNSPSC Code:
12352100
PubChem Substance ID:
24851275
NACRES:
NA.22

Assay

99%

refractive index

n20/D 1.427 (lit.)

bp

136-137 °C (lit.)

mp

21-24 °C (lit.)

density

0.752 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

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

InChI

1S/C8H18Si2/c1-9(2,3)7-8-10(4,5)6/h1-6H3

InChI key

ZDWYFWIBTZJGOR-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

General description

Bis(trimethylsilyl)acetylene (BTMSA) participates as nucleophile in Friedel-Crafts type acylations and alkylations. BTMSA undergoes rhodium catalyzed addition reaction with diarylacetylenes. It undergoes cycloaddition with 1,5-hexadiynes in the presence of CpCo(CO)2 (Cp=cyclopentadienyl) to form benzocyclobutenes. Structure of BTMSA was characterized by a centre of inversion present on triple bond (length=1.208(3)Å). TiCl4-Et2AlCl catalyzed Diels-Alder reaction of BTMSA with norbornadiene has been reported.

Application

Bis(trimethylsilyl)acetylene (BTMSA) was used as starting reagent in the synthesis of functionalized 4-R-1,2-bis(trimethylsilyl)benzenes. It was also used in the synthesis of (+)-brasilenyne and (β-diketanato)Ag(BTMSA).

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

35.6 °F - closed cup

Flash Point(C)

2 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

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

Visit the Document Library

Bis (trimethylsilyl) acetylene.
Bruckmann J and Kruger C.
Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials, 53(12), 1845-1846 (1997)
Titanium-catalyzed cycloaddition-cycloreversion cascade in the reaction of norbornadiene with bis (trimethylsilyl) acetylene.
Mach K, et al.
Organometallics, 5(6), 1215-1219 (1986)
MOCVD of Silver Thin Films from the (1, 1, 1, 5, 5, 5-Hexafluoro-2, 4-pentanedionato)-silver [bis (trimethylsilyl) acetylene] Complex.
Chi KM and Lu YH.
Chem. Vap. Deposition, 7(3), 117-120 (2001)
Akinobu Horita et al.
Organic letters, 10(9), 1751-1754 (2008-04-10)
The addition of bis(trimethylsilyl)acetylene to diarylacetylenes proceeds efficiently and selectively in a formal anti fashion in the presence of [Rh(OH)(cod)]2/bisphosphine and phenol as catalyst and activator, respectively, accompanied by cleavage of one of the C-Si bonds to produce the corresponding
Scott E Denmark et al.
Journal of the American Chemical Society, 124(51), 15196-15197 (2002-12-19)
The first, total synthesis of (+)-brasilenyne (1) has been achieved in 19 steps from l-(S)-malic acid. The key elements of this approach are a highly diastereoselective ring-opening of a 1,3-dioxolanone with bis(trimethylsilyl)acetylene) promoted by TiCl4 to set a propargylic stereocenter
View All Related Papers

Articles

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. Since the reaction involves the formation of a cyclic product via a cyclic transition state, it is also referred to as a "cycloaddition".

Reagents for C–C Bond Formation

We carry a large variety of electrophiles and nucleophiles that are widely used in C–C bond-forming reactions. This group of products contains many organometallic reagents as well as commonly-used alkylating and acylating reagents.

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