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244481

Sigma-Aldrich

1-(Trimethylsilyl)propyne

99%

Synonym(s):

Trimethyl-1-propynylsilane

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About This Item

Linear Formula:
CH3C≡CSi(CH3)3
CAS Number:
6224-91-5
Molecular Weight:
112.24
Beilstein:
1071311
EC Number:
228-314-5
MDL number:
MFCD00009271
UNSPSC Code:
12352100
PubChem Substance ID:
24854680
NACRES:
NA.22

vapor density

>1 (vs air)

Assay

99%

form

liquid

refractive index

n20/D 1.417 (lit.)

bp

99-100 °C (lit.)

density

0.758 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

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

InChI

1S/C6H12Si/c1-5-6-7(2,3)4/h1-4H3

InChI key

DCGLONGLPGISNX-UHFFFAOYSA-N

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Application

1-(Trimethylsilyl)propyne was used in the synthesis of highly substituted indenes via palladium-catalyzed carboannulation and indenones via a rhodium-catalyzed reaction with 2-bromophenylboronic acids.

Pictograms

Flame
GHS02

Signal Word

Danger

Hazard Statements

H225

Hazard Classifications

Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

39.2 °F - closed cup

Flash Point(C)

4 °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’.

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Journal of Polymer Science Part A: Polymer Chemistry, 25, 1353-1353 (1987)
Daohua Zhang et al.
The Journal of organic chemistry, 72(1), 251-262 (2006-12-30)
The synthesis of highly substituted indenes has been achieved by three different transition metal-mediated methods. The first method involves the palladium-catalyzed carboannulation of internal alkynes. The second method utilizes a two-step approach, which involves first the palladium/copper-catalyzed cross-coupling of terminal
Tetrahedron Letters, 33, 5969-5969 (1992)
Journal of the American Chemical Society, 105, 7473-7473 (1983)
Yasuyuki Harada et al.
Journal of the American Chemical Society, 129(17), 5766-5771 (2007-04-10)
The Rh-catalyzed reaction of alkynes with 2-bromophenylboronic acids involves carbonylative cyclization to give indenones. The key steps in the reaction involve the addition of an arylrhodium(I) species to an alkyne and the oxidative addition of C-Br bonds on the adjacent

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