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293830

Sigma-Aldrich

1,2-Bis(trimethylsiloxy)cyclobutene

≥95%

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About This Item

Empirical Formula (Hill Notation):
C10H22O2Si2
CAS Number:
17082-61-0
Molecular Weight:
230.45
Beilstein:
1367530
MDL number:
MFCD00010798
UNSPSC Code:
12352100
PubChem Substance ID:
24857681
NACRES:
NA.22
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Assay

≥95%

refractive index

n20/D 1.435 (lit.)

bp

58-59 °C/2 mmHg (lit.)

density

0.897 g/mL at 25 °C (lit.)

SMILES string

C[Si](C)(C)OC1=C(CC1)O[Si](C)(C)C

InChI

1S/C10H22O2Si2/c1-13(2,3)11-9-7-8-10(9)12-14(4,5)6/h7-8H2,1-6H3

InChI key

WOBRFSDEZREQAB-UHFFFAOYSA-N

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General description

Photocycloaddition of 2-cyclohexenones to 1,2-bis(trimethyl-siloxy)cyclobutene has been studied[1]. It undergoes Aldol condensation reaction with carbonyl compounds[2]. It reacts with Br2 to give cyclobutanedione[3].

Application

1,2-Bis(trimethylsiloxy)cyclobutene has been used in the synthesis of:
  • functionalized decalins, required for the total synthesis of various sesquiterpenes and diterpenes[1]
  • angularly substituted bicyclo[4.3.0]nona-2,5-diones and bicyclo-[4.4.0]deca-2,5-diones[4]
  • 3-methoxyestra-1,3,5,8,14-pentaen-17-one[5]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

141.8 °F - closed cup

Flash Point(C)

61 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
04126CJ
02808CE
16111KG
04307JZ
00519JF

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Journal of the American Chemical Society, 106, 1759-1759 (1984)
A very short synthesis of 3-methoxyestra-1, 3, 5, 8, 14-pentaen-17-one.
Burnell DJ and Wu Y-J.
Canadian Journal of Chemistry, 67(5), 816-819 (1985)
Organic Syntheses, 7, 112-112 (1990)
A (Π2+ Π2) photocycloaddition reaction as a facile route to angularly substituted cis-hydrindanes and cis-decalanes.
Van Audenhove M, et al.
Tetrahedron Letters, 21(20), 1979-1982 (1980)
Photoaddition with 1, 2-bis (trimethylsiloxy) cyclobutene: a versatile entry to the stereocontrolled total synthesis of various sesquiterpenes and diterpenes.
de Keukeleire D, et al.
Journal of Photochemistry, 28(2), 165-174 (1985)

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