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Stabilized with 100-200 ppm Irganox® 1076 FD
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.
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.
Hazard Statements: H226-H304
Flammable liquid and vapour. May be fatal if swallowed and enters airways.
Precautionary Statements: P210-P233-P240-P241-P242-P243-P280-P301+P310-P303+P361+P353-P331-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Do NOT induce vomiting. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant