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376264

Sigma-Aldrich

Trimethyl(propargyl)silane

contains 500 ppm BHT as stabilizer

Synonym(s):

2-Propynyl-trimethylsilane, 3-(Trimethylsilyl)propyne

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About This Item

Linear Formula:
HC≡CCH2Si(CH3)3
CAS Number:
13361-64-3
Molecular Weight:
112.24
Beilstein/REAXYS Number:
2036316
EC Number:
236-427-6
MDL number:
MFCD00042922
UNSPSC Code:
12352100
PubChem Substance ID:
24863432
NACRES:
NA.22

form

liquid

Quality Level

200

contains

500 ppm BHT as stabilizer
≤20% trimethylallenylsilane (in equilibrium)

refractive index

n20/D 1.413 (lit.)

bp

91-93 °C (lit.)

density

0.753 g/mL at 25 °C (lit.)

storage temp.

−20°C

SMILES string

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

InChI

1S/C6H12Si/c1-5-6-7(2,3)4/h1H,6H2,2-4H3

InChI key

ULYLMHUHFUQKOE-UHFFFAOYSA-N

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General description

Trimethyl(propargyl)silane (2-Propynyl-trimethylsilane) is a clear colorless liquid and contains 500ppm of butylated hydroxytoluene (BHT) as stabilizer. It undergoes GaCl3-catalyzed dehydrogenation reaction with aldimines to afford 4-methylquinoline.

Application

Trimethyl(propargyl)silane is suitable for use in the synthesis of diverse end-functionalized (ω-carboxyl, ω-hydroxy, ω-methyl-vinyl, ω-trimethylsilane, and ω-glycidyl-ether) via ′′click′′ reaction. It may be used in the synthesis of γ-allenyl-GABA (γ-aminobutyric acid), via Lewis acid mediated reaction with ω-ethoxy lactams.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

23.0 °F

flash_point_c

-5 °C

ppe

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

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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GaCl3-catalyzed [4+2] annulations of allyltrimethylsilane and trimethyl (propargyl) silane with aldimines.
Hirashita T, et al.
Tetrahedron Letters, 48(31), 5421-5424 (2007)
High yield synthesis of diverse well-defined end-functionalized polymers by combination of anionic polymerization and ?click? chemistry.
Ho C-C, et al.
Journal of Applied Polymer Science, 111(3), 1571-1580 (2009)
Lewis acid induced reactions of propargyl trimethyl silane with ?-ethoxy lactams synthesis of ?-allenyl-GABA.
Hiemstra H, et al.
Tetrahedron Letters, 25(29), 3115-3118 (1984)

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