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208264

Sigma-Aldrich

Allyltrimethylsilane

98%

Synonym(s):

3-(Trimethylsilyl)propene

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About This Item

Linear Formula:
H2C=CHCH2Si(CH3)3
CAS Number:
762-72-1
Molecular Weight:
114.26
Beilstein:
906755
EC Number:
212-104-5
MDL number:
MFCD00008635
UNSPSC Code:
12352103
PubChem Substance ID:
24852502
NACRES:
NA.22
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Quality Level

100

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.[1][2][3] It is used as a reagent in Hosomi−Sakurai reaction.[4][5]

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H315

Hazard Classifications

Flam. Liq. 2 - Skin Irrit. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

60.8 °F - closed cup

Flash Point(C)

16 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS9034
MKCR1766
MKCR1641
MKCP5375
MKCN8829

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Allylation of Imines with Allyltrimethylsilane and Experimental Evidences for a Fluoride-Triggered Autocatalysis Mechanism of the Sakurai- Hosomi Reaction
Wang D, et al.
The Journal of Organic Chemistry, 64(12), 4233-4237 (1999)
Shoji Kobayashi et al.
Carbohydrate research, 343(3), 443-452 (2007-12-11)
An efficient route to the trans-fused tetrahydrooxepin corresponding to the E ring of ciguatoxin was developed. Wide screening of allylation reactions of sulfur or fluoro-substituted tetrahydrooxepin revealed that the optimum method for obtaining the beta-allylation product selectively was the use
Armando Ramirez et al.
Organic letters, 7(21), 4617-4620 (2005-10-08)
[reaction: see text] The annulation reactions of alkenes with peroxycarbenium ions enable the synthesis of a variety of functionalizable 1,2-dioxolanes. Triethysilyl-protected peroxycarbenium ions proved to be optimal for the annulation reaction. Using this method, plakinic acid analogues can be synthesized
Allyltrimethylsilane
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2001)
Thierry Ollevier et al.
Organic & biomolecular chemistry, 4(24), 4440-4443 (2007-02-03)
We report the first catalytic Sakurai reaction of N-alkoxycarbonylamino sulfones with allylsilanes. The allylation reaction of N-alkoxycarbonylamino phenylsulfones with allyltrimethylsilane proceeded smoothly with low catalyst loading of bismuth triflate (2.0 mol%) to afford the corresponding protected homoallylic amines in moderate
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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