 |
cis-Cyclooctene
- Iupac Name：cyclooctene
- CAS No.: 931-88-4
- Molecular Weight：110.2
- Modify Date.: 2023-11-06 06:55
- Introduction:
cis-Cyclooctene, with the chemical formula C8H14 and CAS registry number 931-88-4, is a compound known for its applications in various chemical processes. This colorless liquid is characterized by its cycloalkene structure, consisting of a ring of eight carbon atoms with a double bond between two adjacent carbons. It is commonly used as a starting material in organic synthesis, offering a versatile platform for the introduction of various functional groups into different molecules. cis-Cyclooctene is also known for its ability to undergo ring-opening reactions, leading to the formation of different compounds with diverse properties. Furthermore, it is used as a ligand in coordination chemistry, forming complexes with transition metals. Overall, cis-Cyclooctene plays a crucial role in the field of organic chemistry, serving as a valuable building block for the synthesis of numerous compounds.
View more+
1. Names and Identifiers
- 1.1 Name
- cis-Cyclooctene
- 1.2 Synonyms
5-cyclooctadiene cis-cyclo-octene cyclooctaene CYCLOOCTENE cyclo-octene Cyclooctene >cis-Cyclooctene ISO 9001：2015 REACH CYCLOOCTENE, STANDARD FOR GC CYCLOOCTENE,STANDARD FOR GC EINECS 213-245-5 MFCD00001753 trans-cyclooctene
- View all
- 1.3 CAS No.
- 931-88-4
- 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
- C1CCC\C=C/CC1
- 1.10 Isomers Smiles
- C1CCC/C=C\CC1
2. Properties
- 2.1 Density
- 0.848?g/mL?at 20?°C(lit.)
- 2.1 Melting point
- ?16?°C(lit.)
- 2.1 Boiling point
- 32-34?°C12?mm Hg(lit.)
- 2.1 Refractive index
- 1.469
- 2.1 Flash Point
- 77?°F
- 2.1 Precise Quality
- 110.11000
- 2.1 PSA
- 0.00000
- 2.1 logP
- 2.89680
- 2.1 Appearance
- Liquid
- 2.2 Color/Form
- Colorless to Almost colorless
- 2.3 Water Solubility
-
- 2.4 Stability
- Stable under normal temperatures and pressures.
- 2.5 StorageTemp
- Keep away from heat, sparks, and flame.
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. cis-CycloocteneSupplier
- View all
4. Safety and Handling
- 4.1 Symbol
- GHS02, GHS08
- 4.1 Hazard Codes
- Xn
- 4.1 Signal Word
- Danger
- 4.1 Risk Statements
- 10-65
- 4.1 Safety Statements
- 29-33-62-16
- 4.1 Packing Group
- III
- 4.1 Hazard Class
- 3.2
- 4.1 Hazard Declaration
- H226-H304
- 4.1 RIDADR
- UN 3295 3/PG 3
- 4.1 Caution Statement
- P301 + P310-P331
- 4.1 WGK Germany
- 3
- 4.1 Specification
-
The cis-Cyclooctene with cas registry number of 931-88-4, is also called NSC 72425; Cyclooctene,99%. The cis-Cyclooctene belongs to the following product categories: (1)Alpha Sort; (2)CAlphabetic; (3)CO - CZChemical Class; (4)Hydrocarbons; (5)NeatsGasoline, Diesel,&Petroleum; (6)Olefins; (7)Substance classes; (8)Volatiles/ Semivolatiles.
Physical properties of cis-Cyclooctene: (1)ACD/LogP: 4.02; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.02; (4)ACD/LogD (pH 7.4): 4.02; (5)ACD/BCF (pH 5.5): 672.65; (6)ACD/BCF (pH 7.4): 672.65; (7)ACD/KOC (pH 5.5): 3679.04; (8)ACD/KOC (pH 7.4): 3679.04; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 0 Å2; (13)Index of Refraction: 1.452; (14)Molar Refractivity: 36.49 cm3; (15)Molar Volume: 135.2 cm3; (16)Polarizability: 14.46×10-24cm3; (17)Surface Tension: 28.2 dyne/cm; (18)Enthalpy of Vaporization: 36.47 kJ/mol; (19)Vapour Pressure: 6.76 mmHg at 25°C.
You can still convert the following datas into molecular structure: (1)SMILES:C\1=C\CCCCCC/1; (2)InChI:InChI=1/C8H14/c1-2-4-6-8-7-5-3-1/h1-2H,3-8H2/b2-1-; (3)InChIKey:URYYVOIYTNXXBN-UPHRSURJBT; (4)Std. InChI:InChI=1S/C8H14/c1-2-4-6-8-7-5-3-1/h1-2H,3-8H2/b2-1-; (5)Std. InChIKey:URYYVOIYTNXXBN-UPHRSURJSA-N.
- View all
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Flammable liquids, Category 3
Aspiration hazard, Category 1
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |   |
| Signal word | Danger |
| Hazard statement(s) | H226 Flammable liquid and vapour H304 May be fatal if swallowed and enters airways |
| 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. P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P331 Do NOT induce vomiting. |
| Storage | P403+P235 Store in a well-ventilated place. Keep cool. P405 Store locked up. |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
931-88-4Total: 187 Synthesis Route
9. Other Information
- 9.0 BRN
- 1901031
- 9.1 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.
- View all
10. Computational chemical data
- Molecular Weight: 110.2g/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==
11. Question & Answer
-
How does trans-cyclooctene exhibit chirality if there are no stereocenters? Related follow-on questions: Are all higher cycloalkenes chiral? Do more double bonds cause a bigger number of stereoisomer..
12. Recommended Suppliers
-
- Products:Pharmaceutical, chemical technology research and development
- Tel:086-0532-80960264
-
- Products:epibrassinolide Propionamide Trisodium thiophosphate 4,4 -Biphenol magnesium aluminosilicate
- Tel:+86-531-58668191 58668193 58668196 58661173
-
- Products:Shanghai Forever Synthesis Co.,Ltd. is a professional chemical supplier for API, intermediates, fine chemicals, and customized synthesis.
- Tel:86-21-61124658
-
- Products:API Intermediate Plant extracts Pigments and dyes Food and feed additives Reagent Customization synthesisOther products
- Tel:86-571-86960370
-
- Tel:021-67121386 800-988-0390
13. Realated Product Infomation
skype
![Dibenzo[a,e]cyclooctene](https://structimg.guidechem.com/12/12/298331.png)
