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cis-Cyclooctene, 95%, stab., Thermo Scientific Chemicals
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Catalog number A13477.AK
also known as A13477-AK
Price (USD)/ Each
88.50
-
Quantity:
250 mL
Price (USD)/ Each
88.50
cis-Cyclooctene, 95%, stab., Thermo Scientific Chemicals
Catalog numberA13477.AK
Price (USD)/ Each
88.50
-
Chemical Identifiers
CAS931-87-3
IUPAC Name(Z)-cyclooctene
Molecular FormulaC8H14
InChI KeyURYYVOIYTNXXBN-UPHRSURJSA-N
SMILESC1CCCC=C/CC1
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Specifications
Specification Sheet
Specification SheetFormLiquid
CommentStabilized with 100-200 ppm Irganox® 1076 FD
Appearance (Color)Clear colorless
Assay (GC)≥94.0%
Refractive Index1.4660-1.4720 @20?C
cis-Cyclooctene is used as a displaced ligand in chlorobis(cyclooctene)rhodium dimer and chlorobis(cyclooctene)iridium dimer in organometallic chemistry. It acts as a monomer used in synthetic chemistry. It is used to prepare 1-chloro-4-(trichloromethyl) cyclooctane by reaction with carbon tetrachloride using dichlorotris(triphenylphosphine) ruthenium(II) as a catalyst. Further, it is used to study the alkenes chemisorbed on silicon(100) by scanning tunneling microscopy.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
cis-Cyclooctene is used as a displaced ligand in chlorobis(cyclooctene)rhodium dimer and chlorobis(cyclooctene)iridium dimer in organometallic chemistry. It acts as a monomer used in synthetic chemistry. It is used to prepare 1-chloro-4-(trichloromethyl) cyclooctane by reaction with carbon tetrachloride using dichlorotris(triphenylphosphine) ruthenium(II) as a catalyst. Further, it is used to study the alkenes chemisorbed on silicon(100) by scanning tunneling microscopy.
Solubility
Miscible with alcohol and ether. Immiscible with water.
Notes
Air sensitive. Incompatible with strong oxidizing agents.
cis-Cyclooctene is used as a displaced ligand in chlorobis(cyclooctene)rhodium dimer and chlorobis(cyclooctene)iridium dimer in organometallic chemistry. It acts as a monomer used in synthetic chemistry. It is used to prepare 1-chloro-4-(trichloromethyl) cyclooctane by reaction with carbon tetrachloride using dichlorotris(triphenylphosphine) ruthenium(II) as a catalyst. Further, it is used to study the alkenes chemisorbed on silicon(100) by scanning tunneling microscopy.
Solubility
Miscible with alcohol and ether. Immiscible with water.
Notes
Air sensitive. Incompatible with strong oxidizing agents.
RUO – Research Use Only
General References:
- For example of the addition of NOCl to an alkene and subsequent cleavage of the ɑ-chloro oxime by the abnormal Beckmann reaction to the ω-cyanoaldehyde, see: Org. Synth. Coll., 5, 266 (1973).
- Addition of dibromocarbene (see Bromoform, A11904) and ring-opening by reaction with MeLi leads to the cyclic allene 1,2-cyclononadiene: Org. Synth. Coll., 5, 306 (1973).
- The epoxidation of alkenes by H2O2 in methanol in the presence of acetonitrile is described for cyclooctene. The active species is the peroxyimidic acid, and the reaction is, with proper precautions, suitable for scale-up: Org. Synth. Coll., 7, 126 (1990).
- Bai, L.; Yao, L.; Yang, Y.; Lee, J. M. Microspheres with Au@SiO2 core and mesoporous aluminosilica shell as superior heterogeneous catalysts for the aerobic epoxidation of cis-cyclooctene. Chem. Commun. 2015, 51 (20), 4259-4262.
- Yang, J. X.; Cui, J.; Long, Y. Y.; Li, Y. G.; Li, Y. S. Synthesis of novel cyclic olefin polymers with excellent transparency and high glass-transition temperature via gradient copolymerization of bulky cyclic olefin and cis-cyclooctene. J. Polym. Sci. A Polym. Chem. 2014, 52 (22), 3240-3249.