CYCLOOCTENE Property

Melting point:

−16 °C(lit.)

Boiling point:

32-34 °C12 mm Hg(lit.)

Density 

0.848 g/mL at 20 °C(lit.)

vapor pressure 

9.9hPa at 20℃

refractive index 

n20/D 1.470

Flash point:

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

LogP

5 at 25℃

CAS DataBase Reference

931-87-3(CAS DataBase Reference)

EPA Substance Registry System

Cyclooctene, (1Z)- (931-87-3)

Safety

Hazard Codes 

Xn

Risk Statements 

10-65

Safety Statements 

29-33

RIDADR 

UN 3295 3/PG 3

WGK Germany 

3

TSCA 

Yes

HazardClass 

3

PackingGroup 

III

HS Code 

29021990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H226Flammable liquid and vapour

H304May be fatal if swallowed and enters airways

H401Toxic to aquatic life

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P405Store locked up.

CYCLOOCTENE Chemical Properties,Usage,Production

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.