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Merck
CN

519324

1-(tert-Butyldimethylsilyloxy)-1-methoxyethene

97%

Synonym(s):

(1,1-Dimethylethyl)[(1-methoxyethenyl)oxy]dimethylsilane, (tert-Butyl)[(1-methoxyethenyl)oxy]dimethylsilane, 1-Methoxy-1-(tert-butyldimethylsiloxy)ethylene, 1-Methoxy-1-[(tert-butyldimethylsilyl)oxy]ethene, 1-Methoxy-1-[(tert-butyldimethylsilyl)oxy]ethylene, Ketene methyl t-butyldimethylsilyl acetal, Ketene tert-butyldimethylsilyl methyl acetal, tert-Butyl[(1-methoxyvinyl)oxy]dimethylsilane

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About This Item

Linear Formula:
(CH3)3CSi(CH3)2OC(OCH3)=CH2
CAS Number:
77086-38-5
Molecular Weight:
188.34
MDL number:
MFCD02683524
UNSPSC Code:
12352100
PubChem Substance ID:
24874073
NACRES:
NA.22

Key Documents

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Quality Level

100

Assay

97%

refractive index

n20/D 1.429 (lit.)

bp

62 °C/9 mmHg (lit.)

density

0.863 g/mL at 25 °C (lit.)

SMILES string

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

InChI

1S/C9H20O2Si/c1-8(10-5)11-12(6,7)9(2,3)4/h1H2,2-7H3

InChI key

UVCCWXJGWMGZAB-UHFFFAOYSA-N

Related Categories

Application

1-(tert-Butyldimethylsilyloxy)-1-methoxyethene may be used in the following
  • Synthesis of β-hydroxy esters via Mukaiyama Aldol reaction with heterocyclic aldehydes in the presence of Lewis acid.
  • Asymmetric Mukaiyama-Mannich reaction with isatin-derived ketimines to synthesize indolyl-β3, 3-aminoacid esters.
  • Broadrup′s synthesis of epothilone D.
  • Preparation of N-benzylidene benzylamine N-oxide.
  • Synthesis of nitroso acetals.

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

125.6 °F - closed cup

Flash Point(C)

52 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
SHBQ7293
SHBP4213
SHBN5077
SHBK0931
SHBJ5606

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Recent developments in the syntheses of the epothilones and related analogues.
Watkins EB, et al.
European Journal of Organic Chemistry, 18, 4071-4084 (2006)
New indenyl phosphinooxazoline complexes of iron and their catalytic activity in the Mukaiyama aldol reaction.
Lenze M, et al.
Tetrahedron Letters, 51(21), 2855-2858 (2010)
Enantioselective addition of ketene silyl acetals to nitrones catalyzed by chiral titanium complexes. Synthesis of optically active ?-amino acids.
Murahashi SI, et al.
Journal of the American Chemical Society, 124(12), 2888-2889 (2002)
Three-step assembly of 4-aminotetrahydropyran-2-ones from isoxazoline-2-oxides.
Naumova AS, et al.
Royal Society of Chemistry Advances, 4(24), 12467-12475 (2014)

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