3D Mol Similar

CYCLOOCTENE

Iupac Name：cyclooctene

CAS No.: 931-87-3

Molecular Weight：110.19676

Modify Date.: 2022-11-29 05:50

Introduction:

clear colourless to light brown liquid

Liquid

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1. Names and Identifiers

: 1.1 Name; CYCLOOCTENE; 1.2 Synonyms; (1Z)-Cyclooctene (Z)-cyclooctene 1-Cyclooctene cis-Cyclooctene Cyclooctene, (1Z)- Cyclooctene, (Z)- EINECS 213-245-5 MFCD00001753

1.3 CAS No.: 931-87-3

1.4 CID: 638079

1.5 EINECS(EC#): 213-245-5

1.6 Molecular Formula: C8H14 (isomer)

1.7 Inchi: InChI=1S/C8H14/c1-2-4-6-8-7-5-3-1/h1-2H,3-8H2/b2-1-

1.8 InChIkey: URYYVOIYTNXXBN-UPHRSURJSA-N

1.9 Canonical Smiles: C1CCCC=CCC1

1.10 Isomers Smiles: C1CCC/C=C\CC1

2. Properties

2.1 Density: 0.84

2.1 Melting point: -16℃

2.1 Boiling point: 145-146℃

2.1 Refractive index: n20/D 1.470

2.1 Flash Point: 25℃

2.1 Precise Quality: 110.11000

2.1 PSA: 0.00000

2.1 logP: 2.89680

2.1 Solubility: H2O: insoluble

2.2 Appearance: Clear colorless to light brown Liquid

2.3 Storage: Air Sensitive. Ambient temperatures.

2.4 Chemical Properties: clear colourless to light brown liquid

2.5 Color/Form: Clear colorless to light brown

2.6 Water Solubility: Miscible with alcohol and ether. Immiscible with water.

2.7 StorageTemp: Flammables area

3. Use and Manufacturing

3.1 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 Preparation Products And Raw materials Preparation Products; View all

4. Safety and Handling

4.1 Hazard Codes: Xn

4.1 Risk Statements: R10;R65

4.1 Safety Statements: S16;S23;S62

4.1 Packing Group: III

4.1 Hazard Class: 3

4.1 Hazard Declaration: H226

4.1 RIDADR: UN 3295 3/PG 3

4.1 Caution Statement: P210, P233, P240, P241, P242, P243, P273, P280, P303+P361+P353, P370+P378, P391, P403+P235, P501

4.1 WGK Germany: 3

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Flammable liquids, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H226 Flammable liquid and vapour
Precautionary statement(s)
Prevention	P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking. P233 Keep container tightly closed. P240 Ground and bond container and receiving equipment. P241 Use explosion-proof [electrical/ventilating/lighting/...] equipment. P242 Use non-sparking tools. P243 Take action to prevent static discharges. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P370+P378 In case of fire: Use ... to extinguish.
Storage	P403+P235 Store in a well-ventilated place. Keep cool.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Mass spectrum (electron ionization)

UV/Visible spectrum

7. Synthesis Route

931-87-3Total: 1 Synthesis Route

134357-87-2

931-88-4 28 Suppliers

87922-01-8

931-87-3 18 Suppliers

Literatures:
Journal of the American Chemical Society, , vol. 113, # 12 p. 4712 - 4714
Yield: null

8. Other Information

8.0 Usage: 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.

8.1 Production: 100,000 - 500,000 lb

8.2 Manufacturing Info: Fragrances|Cyclooctene, (1Z)-: ACTIVE|PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.|Cyclooctene: ACTIVE

9. Computational chemical data

Molecular Weight: 110.19676g/mol
Molecular Formula: C₈H₁₄
Compound Is Canonicalized: True
XLogP3-AA: 3.5
Exact Mass: 110.109550447
Monoisotopic Mass: 110.109550447
Complexity: 62.1
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 0
Topological Polar Surface Area: 0
Heavy Atom Count: 8
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBwAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAQAAAAAAAAGAAAAAAACACAAAAAAAAAAACAACBCAAAAAAAgAAAICAAAAAgAAAIAAQAAAAAAgAAIAAMAgIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==