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376310

Sigma-Aldrich

trans-3-(Trimethylsilyl)allyl alcohol

96%

Synonym(s):

trans-(3-Hydroxy-2-propen-1-yl)trimethylsilane, trans-3-(Trimethylsilyl)-2-propen-1-ol

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About This Item

Linear Formula:
(CH3)3SiCH=CHCH2OH
CAS Number:
Molecular Weight:
130.26
Beilstein:
1902497
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

96%

form

liquid

impurities

<3.5% 3-trimethylsilyl-1-propanol

refractive index

n20/D 1.444 (lit.)

bp

166-168 °C (lit.)

density

0.848 g/mL at 25 °C (lit.)

functional group

aldehyde

storage temp.

−20°C

SMILES string

C[Si](C)(C)C\C=C\O

InChI

1S/C6H14OSi/c1-8(2,3)6-4-5-7/h4-5,7H,6H2,1-3H3/b5-4+

InChI key

JKKTXDCTGMUFBS-SNAWJCMRSA-N

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General description

trans-3-(Trimethylsilyl)allyl alcohol is a 3-silyl allyl alcohol.

Application

trans-3-(Trimethylsilyl)allyl alcohol is suitable for use in the preparation of 1-iodo-3-trimethylsilyl-2-propene, via mesylation followed by iodide displacement.

Pictograms

FlameExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

136.4 °F - closed cup

Flash Point(C)

58 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Minh Pham et al.
The Journal of organic chemistry, 73(2), 741-744 (2007-12-22)
In the presence of indium metal, 3-iodo-2-[(trimethylsilyl)methyl]propene (1) reacts with sequentially added aldehydes to provide cis-2,6-disubstituted tetrahydropyrans in good yields. Evidence suggests that InI, formed upon aldehyde (R1CHO) allylation in aqueous media, acts as a promoter for the silyl-Prins reaction

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