| Identification | More | [Name]
CYCLOOCTENE | [CAS]
931-87-3 | [Synonyms]
CIS-CYCLOOCTENE
CYCLOOCTENE
(Z)-cyclooctene
1-Cyclooctene
Cyclooctene, (Z)-
cis-Cyclooctene,94%
cis-Cyclooctene, stabilized, 95%
Cyclooctene, (1Z)-
(Z)-Cycloocten
cis-Cyclooctene, 95%, stab.
Cis-Cyclooctene, 95%, stabilized
(Z)-1-Cyclooctene | [EINECS(EC#)]
213-245-5 | [Molecular Formula]
C8H14 | [MDL Number]
MFCD00001753 | [Molecular Weight]
110.2 | [MOL File]
931-87-3.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colourless to light brown liquid | [Melting point ]
−16 °C(lit.) | [Boiling point ]
32-34 °C12 mm Hg(lit.) | [density ]
0.848 g/mL at 20 °C(lit.)
| [refractive index ]
n20/D 1.470
| [Fp ]
77 °F
| [storage temp. ]
Flammables area | [solubility ]
H2O: insoluble | [form ]
Liquid | [color ]
Clear colorless to light brown | [Water Solubility ]
Miscible with alcohol and ether. Immiscible with water. | [Sensitive ]
Air Sensitive | [BRN ]
1280166 | [CAS DataBase Reference]
931-87-3(CAS DataBase Reference) | [EPA Substance Registry System]
Cyclooctene, (1Z)- (931-87-3) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R10:Flammable.
R65:Harmful: May cause lung damage if swallowed. | [Safety Statements ]
S29:Do not empty into drains .
S33:Take precautionary measures against static discharges . | [RIDADR ]
UN 3295 3/PG 3
| [WGK Germany ]
3
| [TSCA ]
Yes | [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29021990 |
| Hazard Information | Back Directory | [Chemical Properties]
clear colourless to light brown liquid | [Uses]
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. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 102, p. 2693, 1980 DOI: 10.1021/ja00528a029
The Journal of Organic Chemistry, 40, p. 2555, 1975 DOI: 10.1021/jo00905a040
Tetrahedron Letters, 14, p. 2667, 1973 | [General Description]
cis-Cyclooctene undergoes addition reaction with carbon tetrachloride catalyzed by dichlorotris(triphenylphosphine) ruthenium(II) to yield 1-chloro-4-(trichloromethyl) cyclooctane (1,4-adduct). It undergoes epoxidation catalyzed by molybdenum oxide nanoparticles incorporated in a mesoporous silica shell coated on dense silica-coated magnetite nanoparticles. | [Purification Methods]
The cis-isomer is freed from the trans-isomer by fractional distillation through a spinning-band column, followed by preparative gas chromatography on a Dowex 710-Chromosorb W GLC column. It is passed through a short alumina column immediately before use [Collman et al. J Am Chem Soc 108 2588 1986]. It has also been distilled in a dry N2 glove box from powdered fused NaOH through a Vigreux column (p 11), then passed through activated neutral alumina before use [Wong et al. J Am Chem Soc 109 4328 1987]. Alternatively it can be purified via the AgNO3 salt. This salt is obtained from crude cyclooctene (40 mL) by shaking at 70-80o with 50% w/w AgNO3 (2 x 15 mL) to remove cyclooctadienes (aqueous layer). Extraction is repeated at 40o (4 x 20 mL, of 50% AgNO3). Three layers are formed each time. The middle layer contains the AgNO3 adduct of cyclooctene which crystallises on cooling the layer to room temperature. The adduct (complex 2:1) is highly soluble in MeOH (at least 1g/mL) from which it crystallises in large flat needles when cooled at 0o. It is dried under slight vacuum for 1 week in the presence of CaCl2 and paraffin wax soaked in cyclooctene. It has m 51o and loses hydrocarbon on exposure to air. cis-Cyclooctene can be recovered by steam distillation of the salt, collected, dried (CaCl2) and distilled in vacuum. [Braude et al. J Chem Soc 4711 1957, AgNO3: Jones J Chem Soc 1808 1954, Cope & Estes J Am Chem Soc 72 1128 1950, Beilstein 5 I 35, 5 IV 263.] FLAMMABLE LIQUID. |
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