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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:
Molecular Weight:
230.45
Beilstein:
1367530
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

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

Signal Word

Warning

Hazard Statements

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

293830-5G:
293830-BULK:
293830-VAR:
293830-1G:


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Organic Syntheses, 7, 112-112 (1990)
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)
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)
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)

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