CYCLOOCTENE Chemical Properties

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 Information

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

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

CYCLOOCTENE Usage And Synthesis

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.

CYCLOOCTENE(931-87-3)Related Product Information

• HERBAL PROPIONATE
• (+)-Ledene
• HYDROXYDICYCLOPENTADIENE
• Chlorobis(cyclooctene)rhodium(I) dimer
• 3A,4,5,6,7,7A-HEXAHYDRO-4,7-METHANO-5-METHOXY-1(3)H-INDENE
• TRICYCLODECENYL ACETATE
• Dicyclopentenyl acrylate
• Dicyclopentadiene
• FUSICOCCIN
• 3A,4,5,6,7,7A-HEXAHYDRO-4,7-METHANO-1(3)H-INDEN-6-YL ISOBUTYRATE
• 1,2-EPOXY-5-CYCLOOCTENE
• 3A,4,5,6,7,7A-HEXAHYDRO-4,7-METHANO-1(3)H-INDEN-6-YL 2,2-DIMETHYLPROPANOATE
• OPHIOBOLIN A
• 1-METHYLDICYCLOPENTADIENE
• CYCLOOCTENE
• ORGANOCHLORINE PESTICIDE MATRIX SPIKING MIXTURE
• METHYLCYCLOPENTADIENE DIMER
• 6H,12H-5,11-Dioxadibenzo[a,e]cyclooctene-6,12-dione