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Sigma-Aldrich

9-Oxabicyclo[6.1.0]non-4-ene

95%

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About This Item

Empirical Formula (Hill Notation):
C8H12O
CAS Number:
637-90-1
Molecular Weight:
124.18
EC Number:
211-308-1
MDL number:
MFCD00086420
UNSPSC Code:
12352100
PubChem Substance ID:
24870776
NACRES:
NA.22

Quality Level

100

Assay

95%

refractive index

n20/D 1.495 (lit.)

bp

195 °C (lit.)

density

1.013 g/mL at 25 °C (lit.)

functional group

ether

SMILES string

C1CC2OC2CCC=C1

InChI

1S/C8H12O/c1-2-4-6-8-7(9-8)5-3-1/h1-2,7-8H,3-6H2/b2-1-

InChI key

YWFPXWMSGJXUFS-UPHRSURJSA-N

Related Categories

General description

9-Oxabicyclo[6.1.0]non-4-ene is an epoxide. It undergoes halofluorination reactions with N-halosuccinimides and triethylamine tris-hydrofluoride or Olah′s reagent.

Application

9-Oxabicyclo[6.1.0]non-4-ene may be used in the following studies:
  • novel bicyclo[4.2.1] and bicyclo[3.3.1] ethers
  • trans, trans-2,6-dibromo-9-oxabicyclo[3.3.1]nonane and trans, trans-2,5-dibromo-9-oxabicyclo[4.2.1]nonane
  • (Z)-2-(cyclooct-4-enyloxy)acetic acid.

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)

158.0 °F - closed cup

Flash Point(C)

70 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBK5757
STBG3039V
STBF4017V
STBD8068V
STBD7461V

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Karl J Bonney et al.
The Journal of organic chemistry, 76(1), 97-104 (2010-12-01)
9-Oxabicyclo[6.1.0]non-4-ene (1) undergoes intramolecular bromonium ion-assisted epoxide ring-opening using N-bromosuccinimide via a presumed oxonium ion that is subject to stereospecific, nonregioselective capture with added external nucleophiles producing novel bicyclo[4.2.1] and bicyclo[3.3.1] ethers. Carboxylic acids (as catalyzed by tetramethylguanidine), alcohols, water
Stereoselective synthesis of cyclic ethers via bromine assistedepoxide ring expansion.
Davies SG, et al.
Tetrahedron Letters, 26(11), 1461-1464 (1985)
Transannular oxygen participation in halofluorination reactions of 9-oxabicyclo [6.1. 0] non-4-ene [1].
Haufe G, et al.
Journal of Fluorine Chemistry, 46(1), 83-95 (1990)
High-yielding, two-step 18F labeling strategy for 18F-PARP1 inhibitors.
Edmund J Keliher et al.
ChemMedChem, 6(3), 424-427 (2011-03-02)

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