Cyclohexene
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Names | |||
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Preferred IUPAC name
Cyclohexene | |||
Other names
Tetrahydrobenzene, 1,2,3,4-Tetrahydrobenzene, Benzenetetrahydride, Cyclohex-1-ene, Hexanaphthylene, UN 2256
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Identifiers | |||
3D model (
JSmol ) |
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906737 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard
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100.003.462 | ||
EC Number |
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1659 | |||
PubChem CID
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RTECS number
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UNII | |||
CompTox Dashboard (EPA)
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Properties | |||
C6H10 | |||
Molar mass | 82.143 g/mol | ||
Appearance | colorless liquid | ||
Odor | sweet | ||
Density | 0.8110 g/cm3 | ||
Melting point | −103.5 °C (−154.3 °F; 169.7 K) | ||
Boiling point | 82.98 °C (181.36 °F; 356.13 K) | ||
slightly soluble in water | |||
Solubility | miscible with organic solvents | ||
Vapor pressure | 8.93 kPa (20 °C)
11.9 kPa (25 °C) | ||
Henry's law
constant (kH) |
0.022 mol·kg−1·bar−1 | ||
-57.5·10−6 cm3/mol | |||
Refractive index (nD)
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1.4465 | ||
Hazards | |||
GHS labelling: | |||
Danger | |||
H225, H302, H305, H311, H411 | |||
P210, P233, P240, P241, P242, P243, P264, P270, P273, P280, P301+P310, P301+P312, P302+P352, P303+P361+P353, P312, P322, P330, P331, P361, P363, P370+P378, P391, P403+P235, P405, P501 | |||
NFPA 704 (fire diamond) | |||
Flash point | −12 °C (10 °F; 261 K) | ||
244 °C (471 °F; 517 K) | |||
Explosive limits
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0.8–5 % | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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1407 mg/kg (oral, rat) | ||
LCLo (lowest published)
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13,196 ppm (mouse, 2 hr)[2] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible)
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TWA 300 ppm (1015 mg/m3)[1] | ||
REL (Recommended)
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TWA 300 ppm (1015 mg/m3)[1] | ||
IDLH (Immediate danger) |
2000 ppm[1] | ||
Safety data sheet (SDS) | External MSDS | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cyclohexene is a hydrocarbon with the formula (CH2)4C2H2. It is the smallest possible cycloalkene. At room temperature, cyclohexene a colorless liquid with a sharp odor. It has few practical applications.
Production and uses
Cyclohexene is produced by the partial
In the laboratory, it can be prepared by dehydration of cyclohexanol.[4]
- C6H11OH → C6H10 + H2O
Reactions and uses
Benzene is converted to cyclohexylbenzene by acid-catalyzed alkylation with cyclohexene.[5] Cyclohexylbenzene is a precursor to both phenol and cyclohexanone.[6]
Hydration of cyclohexene gives cyclohexanol, which can be dehydrogenated to give cyclohexanone, a precursor to caprolactam.[7]
The
Bromination gives 1,2-dibromocyclohexane.[9]
Structure
Cyclohexene is most stable in a half-chair conformation,[10] unlike the preference for a chair form of cyclohexane. One basis for the cyclohexane conformational preference for a chair is that it allows each bond of the ring to adopt a staggered conformation. For cyclohexene, however, the alkene is planar, equivalent to an eclipsed conformation at that bond.
See also
- Diels-Alder reaction
- Cyclohexa-1,3-diene
- Cyclohexa-1,4-diene
References
- ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0167". National Institute for Occupational Safety and Health (NIOSH).
- ^ "Cyclohexene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ US 9771313, Narisawa, Naoki & Tanaka, Katsutoshi, "Cyclohexanol, method for producing cyclohexanol, and method for producing adipic acid", published 26 Sep 2017
- .
- .
- ^ Plotkin, Jeffrey S. (2016-03-21). "What's New in Phenol Production?". American Chemical Society. Archived from the original on 2019-10-27. Retrieved 2018-01-02.
- ISBN 978-3527306732.
- .
- .
- .
External links
- International Chemical Safety Card 1054
- NIOSH Pocket Guide to Chemical Hazards. "#0167". National Institute for Occupational Safety and Health (NIOSH).
- Material Safety Data Sheet for cyclohexene
- Safety MSDS data
- Reaction of Cyclohexene with Bromine and Potassium Permanganate
- Cyclohexene synthesis
- Data sheet at inchem.org