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208264

Sigma-Aldrich

Allyltrimethylsilane

98%

Sinónimos:

3-(Trimethylsilyl)propene

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About This Item

Fórmula lineal:
H2C=CHCH2Si(CH3)3
Número de CAS:
762-72-1
Peso molecular:
114.26
Beilstein/REAXYS Number:
906755
EC Number:
212-104-5
MDL number:
MFCD00008635
UNSPSC Code:
12352103
PubChem Substance ID:
24852502
NACRES:
NA.22

assay

98%

form

liquid

refractive index

n20/D 1.407 (lit.)

bp

84-88 °C (lit.)

density

0.719 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C[Si](C)(C)CC=C

InChI

1S/C6H14Si/c1-5-6-7(2,3)4/h5H,1,6H2,2-4H3

InChI key

HYWCXWRMUZYRPH-UHFFFAOYSA-N

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Application

Allyltrimethylsilane is a general reagent to introduce allyl groups across acid chlorides, aldehydes, ketones, iminium ions, enones, and for cross-coupling with other carbon electrophiles. It is used as a reagent in Hosomi−Sakurai reaction.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

hcodes

H225,H315

Hazard Classifications

Flam. Liq. 2 - Skin Irrit. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

60.8 °F - closed cup

flash_point_c

16 °C - closed cup

ppe

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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2-Bromoallyltrimethylsilane technical grade, 90%

Sigma-Aldrich

333530

2-Bromoallyltrimethylsilane

Trimethylsilyl trifluoromethanesulfonate 99%

Sigma-Aldrich

225649

Trimethylsilyl trifluoromethanesulfonate

A general and efficient FeCl3-catalyzed nucleophilic substitution of propargylic alcohols
Zhan Z, et al.
The Journal of Organic Chemistry, 71(21), 8298-8301 (2006)
Roman Schowner et al.
Angewandte Chemie (International ed. in English), 59(2), 951-958 (2019-11-28)
The origin of hydroxyl group tolerance in neutral and especially cationic molybdenum imido alkylidene N-heterocyclic carbene (NHC) complexes has been investigated. A wide range of catalysts was prepared and tested. Most cationic complexes can be handled in air without difficulty
Ming Yu et al.
Organic letters, 5(24), 4639-4640 (2003-11-25)
[reaction: see text] Direct allylation of glycal-derived donor-acceptor cyclopropanes has been achieved with TiCl(4) activation followed by addition of allyltrimethylsilane. The alpha diastereomer is the major product, with selectivities ranging from 3:1 to 10:1 and yields around 80%.
Control of alpha/beta stereoselectivity in Lewis acid promoted C-glycosidations using a controlling anomeric effect based on the conformational restriction strategy.
Satoru Tamura et al.
Angewandte Chemie (International ed. in English), 42(9), 1021-1023 (2003-03-05)
Ionic liquid-promoted, highly regioselective heck arylation of electron-rich olefins by aryl halides
Mo J, et al.
Journal of the American Chemical Society, 127(2), 751-760 (2005)
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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.

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