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Merck
CN

293830

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24857681
MDL number:
MFCD00010798
Beilstein/REAXYS Number:
1367530
Assay:
≥95%

Key Documents

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Product Name

1,2-Bis(trimethylsiloxy)cyclobutene, ≥95%

InChI

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

SMILES string

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

InChI key

WOBRFSDEZREQAB-UHFFFAOYSA-N

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.)

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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
  • angularly substituted bicyclo[4.3.0]nona-2,5-diones and bicyclo-[4.4.0]deca-2,5-diones
  • 3-methoxyestra-1,3,5,8,14-pentaen-17-one

General description

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

141.8 °F - closed cup

flash_point_c

61 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
04126CJ
02808CE
16724MI
16518DR
14113DI

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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)
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)

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