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376175

Sigma-Aldrich

1-(Trimethylsilyl)-1-pentyne

98%

Synonym(s):

1-Pentyn-1-yltrimethylsilane

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About This Item

Linear Formula:
CH3CH2CH2C≡CSi(CH3)3
CAS Number:
Molecular Weight:
140.30
Beilstein/REAXYS Number:
1744218
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:

Quality Level

assay

98%

form

liquid

refractive index

n20/D 1.425 (lit.)

bp

135 °C (lit.)

density

0.765 g/mL at 25 °C (lit.)

SMILES string

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

InChI

1S/C8H16Si/c1-5-6-7-8-9(2,3)4/h5-6H2,1-4H3

InChI key

CABCDUQQPBAHEE-UHFFFAOYSA-N

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Application

1-(Trimethylsilyl)-1-pentyne may be used in the synthesis of the natural products credneramide A and B, via Ruthenium-catalyzed Alder-ene reaction.[1] It may be used in the synthesis of 3,3′-ethynediyl-bis-pyridine.[2]

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Warning

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

86.0 °F - closed cup

flash_point_c

30 °C - closed cup

ppe

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


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Copper-free palladium-catalyzed sonogashira-type coupling of aryl halides and 1-aryl-2-(trimethylsilyl) acetylenes.
S?rensen US and Pombo-Villar E.
Tetrahedron, 61(10), 2697-2703 (2005)
Florian Erver et al.
The Journal of organic chemistry, 77(11), 5215-5219 (2012-05-10)
The first synthesis of the natural products credneramide A and B was accomplished by utilizing Alder-ene reactions between a terminal alkene and an internal alkyne to generate the rather uncommon 1,4-diene substructure of these compounds. Moreover, two different short linear

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