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92733

Sigma-Aldrich

Methyl 3-trimethylsiloxy-2-butenoate

technical, ~86% (trans + ~10% cis)

Synonym(s):

3-Trimethylsiloxy-2-butenoic acid methyl ester, Methyl 3-(trimethylsiloxy)crotonate, Methyl acetoacetate enol trimethylsilylether

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About This Item

Empirical Formula (Hill Notation):
C8H16O3Si
CAS Number:
Molecular Weight:
188.30
Beilstein/REAXYS Number:
2356944
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:

grade

technical

assay

~86% (trans + ~10% cis)

refractive index

n20/D 1.447

bp

43-45 °C/0.3 mmHg (lit.)

density

0.966 g/mL at 20 °C (lit.)

storage temp.

2-8°C

SMILES string

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

Other Notes

Mild and efficient silylating agent[1]; Starting material to 1-methoxy-1,3-bis(trimethylsiloxy)butadiene; a diene for Diels-Alder reactions and an equivalent of the dianien of methyl acetoacetate[2][3][4]

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T.H. Chan et al.
Journal of the Chemical Society. Chemical Communications, 578-578 (1979)
K. Yamamoto et al.
Chemistry Letters (Jpn), 649-649 (1978)
P. Brownbridge et al.
Tetrahedron Letters, 4437-4437 (1979)
T. Veysoglu et al.
Tetrahedron Letters, 22, 1303-1303 (1981)

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