シクロヘキセン

Cyclohexene

HCID 8079CAS 110-83-8

基本情報

標準SMILES
C1=CCCCC1
InChIKey
HGCIXCUEYOPUTN-UHFFFAOYSA-N
分子式
C6H10
平均分子量
82.14 g/mol
単同位体質量
82.07825032

名称と識別子

優先名称
Cyclohexene
IUPAC
cyclohexene
現地名
シクロヘキセン
英語名
Cyclohexene
分子式
C6H10
分子量
82.14

名称と別名

CYCLOHEXENE110-83-8TetrahydrobenzeneCyclohex-1-eneBenzene tetrahydride1,2,3,4-TetrahydrobenzeneBenzenetetrahydrideHexanaphthyleneCykloheksenBenzene, tetrahydro-3,4,5,6-Tetrahydrobenzene12L0P8F7GN
名称をさらに表示
シクロヘキセンベンゼンテトラヒドリド1-シクロヘキセン1,2,3,4-テトラヒドロベンゼンシクロヘキセン, 99%CyclohexenHXcykloheksen(polish)Cyclohexene, pure, 99%Hxl3ohexeneM100081
DTXSID9038717NSC-24835CHEBI:36404RefChem:129655DTXCID7018717203-807-81-CyclohexeneZyklohexen

データベース識別子

CAS
110-83-8
PubChem CID
8079
DTXSID
DTXSID9038717
ChEMBL
CHEMBL16396
ChEBI
CHEBI:36404
UNII
12L0P8F7GN
EC Number
203-807-8
Nikkaji
J1.313.727G、J1.443.311B、J1.464.503I、J38.186A

物性

構造計算による物性

XLogP
2.9
極性表面積
0 Ų
水素結合供与体数
0
水素結合受容体数
0
回転可能結合数
0
重原子数
6

実験および物理化学的性質

LogP · 2 件

log Kow = 2.86

2.86

OdorSweet odor
Density · 6 件

0.81 (NIOSH, 2024) - Less dense than water; will float

0.8110 at 20 °C/4 °C

Relative density (water = 1): 0.81

0.81

0.8102 @25 °C

0.81

Viscosity0.625 mPa.s at 25 °C
Color/FormColorless liquid
Solubility · 6 件

Insoluble (NIOSH, 2024)

MISCIBLE IN BENZENE, CARBON TETRACHLORIDE, PETROLEUM ETHER

Miscible with ethanol, ether, acetone, and benzene

In water, 213 mg/L at 25 °C

Solubility in water: none

Insoluble

物理化学的性質

融点
-104 °C · -104 °C (lit.)
沸点
83 °C · 83 °C (lit.)
比重(密度)
0.811 g/mL · 0.811 g/mL at 25 °C (lit.)
蒸気密度
2.8 · 2.8 (vs air)
蒸気圧
160 mm · 160 mm Hg ( 20 °C)
屈折率
20 · n20/D 1.446(lit.)

化学的性質

化学的特性Cyclohexene is a colorless liquid (cyclic alkene) with a sweetish odor.

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids];H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral];H304 (95.2%): May be fatal if swallowed and enters airways [Danger Aspiration hazard];H311 (39.4%): Toxic in contact with skin [Danger Acute toxicity, dermal];H411 (57.7%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P210, P233, P240, P241, P242, P243, P262, P264, P270, P273, P280, P301+P316, P301+P317, P302+P352, P303+P361+P353, P316, P321, P330, P331, P361+P364, P370+P378, P391, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 104 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Regulatory Information · 4 件

Chemical: Cyclohexene

Status: Active Update: 09-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/12717

Cyclohexene: HSNO Approval: HSR001113 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelFlammable Liquid
Fire Hazards · 3 件

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:;HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids will float on water. (ERG, 2024)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.;· Vapors may form explosive mixtures with air.;· Vapors may travel to source of ignition and flash back.;· Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.).;· Vapor explosion hazard indoors, outdoors or in sewers.;· Those substances designated with a (P) may polymerize explosively when heated or involved in a fire.;· Runoff to sewer may create fire or explosion hazard.;· Containers may explode when heated.;· Many liquids will float on water.

Highly flammable. Vapour/air mixtures are explosive.

Fire Potential · 2 件

Highly flammable.

Dangerous; keep away from heat and open flame.

Health Hazards · 2 件

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:;May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or asphyxiation, especially when in closed or confined areas. Runoff from fire control or dilution water may cause environmental contamination. (ERG, 2024)

· May cause toxic effects if inhaled or absorbed through skin.;· Inhalation or contact with material may irritate or burn skin and eyes.;· Fire will produce irritating, corrosive and/or toxic gases.;· Vapors may cause dizziness or asphyxiation, especially when in closed or confined areas.;· Runoff from fire control or dilution water may cause environmental contamination.

Hazards Summary · 1 件

TLV Basis = Liver effects; No human studies available; [ACGIH] Exposed laboratory animals show loss of righting reflex and staggering gait. [HSDB] A skin, eye, and respiratory tract irritant; Inhalation of high concentrations may cause CNS effects; [ICSC]

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:;CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient.;SMALL FIRE: Dry chemical, CO2, water spray or regular foam. If regular foam is ineffective or unavailable, use alcohol-resistant foam.;LARGE FIRE: Water spray, fog or regular foam. If regular foam is ineffective or unavailable, use alcohol-resistant foam. Avoid aiming straight or solid streams directly onto the product. If it can be done safely, move undamaged containers away from the area around the fire.;FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. For massive fire, use unmanned master stream devices or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2024)

Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 件

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer for medical attention .

Accidental Release Measures · 2 件

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.;· Keep unauthorized personnel away.;· Stay upwind, uphill and/or upstream.;· Ventilate closed spaces before entering, but only if properly trained and equipped.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.;· All equipment used when handling the product must be grounded.;· Do not touch or walk through spilled material.;· Stop leak if you can do it without risk.;· Prevent entry into waterways, sewers, basements or confined areas.;· A vapor-suppressing foam may be used to reduce vapors.;· Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers.;· Use clean, non-sparking tools to collect absorbed material.;Large Spill;· Dike far ahead of liquid spill for later disposal.;· Water spray may reduce vapor, but may not prevent ignition in closed spaces.

First Aid · 3 件

Excerpt from NIOSH Pocket Guide for Cyclohexene:;Eye: IRRIGATE IMMEDIATELY - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.;Skin: SOAP WASH PROMPTLY - If this chemical contacts the skin, promptly wash the contaminated skin with soap and water. If this chemical penetrates the clothing, promptly remove the clothing and wash the skin with soap and water. Get medical attention promptly.;Breathing: RESPIRATORY SUPPORT - If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform artificial respiration. Keep the affected person warm and at rest. Get medical attention as soon as possible.;Swallow: MEDICAL ATTENTION IMMEDIATELY - If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2024)

General First Aid:;· Call 911 or emergency medical service.;· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.;· Move victim to fresh air if it can be done safely.;· Administer oxygen if breathing is difficult.;· If victim is not breathing:;-- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingested or inhaled the substance.;-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).;-- If no pulse detected or no respiratory medical device available, provide continuous compressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.;· Remove and isolate contaminated clothing and shoes.;· For minor skin contact, avoid spreading material on unaffected skin.;· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.;· For severe burns, immediate medical attention is required.;· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.;· Keep victim calm and warm.;· Keep victim under observation.;· For further assistance, contact your local Poison Control Center.;· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.;Specific First Aid:;· Wash skin with soap and water.

(General first aid procedures);Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.;Skin: Soap wash promptly - If this chemical contacts the skin, promptly wash the contaminated skin with soap and water. If this chemical penetrates the clothing, promptly remove the clothing and wash the skin with soap and water. Get medical attention promptly.;Breathing: Respiratory support;Swallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately.

Safe StorageFireproof. Separated from strong oxidants. Cool. Well closed. Store only if stabilized.
Firefighting Hazards · 2 件

The vapour is heavier than air and may travel along the ground; distant ignition possible. As a result of flow, agitation, etc, electrostatic charges can be generated.

A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C.

毒性情報

Target OrgansEyes, skin, respiratory system, central nervous system
Ecotoxicity Values · 5 件

EC50; Species: Daphnia magna (Water flea); Conditions: freshwater; /conditions of bioassay not specified/; Concentration: = 720 mg/L for 24 hr; Effect: behavior, equilibrium /formulated product/

EC50; Species: Daphnia magna (Water flea); Conditions: freshwater; renewal; Concentration: 2900 ug/L for 15 d; Effect: reproduction, reproduction, general /active ingredient/

EC50; Species: Daphnia magna (Water flea); Conditions: freshwater; static; Concentration: 5300 ug/L for 48 hr; Effect: intoxication, immobile /active ingredient/

LC50; Species: Daphnia magna (Water flea); Conditions: freshwater; static; Concentration: > 50000 ug/L for 24 hr /formulated product/

For more Ecotoxicity Values (Complete) data for CYCLOHEXENE (9 total), please visit the HSDB record page.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 850(SRC), determined from a log Kow of 2.86(2) and a regression-derived equation(3), indicates that cyclohexene is expected to have low mobility in soil(SRC). Volatilization of cyclohexene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 4.55X10-2 atm-cu m/mole(4). Cyclohexene is expected to volatilize from dry soil surfaces(SRC) based upon an extrapolated vapor pressure of 89 mm Hg(5). A 0% theoretical BOD in 4 weeks using an activated sludge inoculum and the Japanese MITI test(6), suggests that biodegradation is not a fast process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 850(SRC), determined from a log Kow of 2.86(2) and a regression-derived equation(3), indicates that cyclohexene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 4.55X10-2 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1 hour and 4 days, respectively(SRC). According to a classification scheme(5), BCF values ranging from 23-45 measured in fish(6), suggests bioconcentration in aquatic organisms is low to moderate(SRC). A 0% theoretical BOD in 4 weeks using an activated sludge inoculum and the Japanese MITI test(6), suggests that biodegradation is not a fast process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cyclohexene, which has a an extrapolated vapor pressure of 89 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase cyclohexene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals, ozone, and nitrate radicals(SRC). The half-life for the reaction with hydroxyl radicals is estimated to be 6 hours(SRC), calculated from its rate constant of 6.77X10-11 cu cm/molecule-sec(3). The half-life for the reaction with ozone is estimated to be 2 hours(SRC), calculated from its rate constant of 2.04X10-16 cu-cm/molec-sec(4). The half-life for the reaction with nitrate radicals is estimated to be 4 hours(SRC), calculated from its rate constant of 1.9X10-12 cu-cm/molec-sec(5).

Adverse EffectsNeurotoxin - Acute solvent syndrome;Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure Routes · 2 件

The substance can be absorbed into the body by inhalation and by ingestion.

inhalation, ingestion, skin and/or eye contact

Signs and Symptoms · 5 件

Cough. Drowsiness.

Redness. Dry skin.

Redness.

Drowsiness. Laboured breathing. Nausea.

irritation eyes, skin, respiratory system; drowsiness

法規制情報

Regulatory Information · 4 件

Chemical: Cyclohexene

Status: Active Update: 09-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/12717

Cyclohexene: HSNO Approval: HSR001113 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

TSCA Requirements · 2 件

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Cyclohexene is included on this list.

Atmospheric Standards · 1 件

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Cyclohexene is produced, as an intermediate or a final product, by process units covered under this subpart.

安全データ

OEB
A
OEL
TWA: 300 ppm (1015 mg/m3)
wgk
1
IDLA
2,000 ppm
tsca
TSCA listed
rtecs
GW2500000

化学と産業

薬理情報

Metabolism/Metabolites · 5 件

Following incubation of Aspergillus niger with cyclohexene, 3 transformation products were isolated: 2-cyclohexen-1-one, (+)-2-cyclohexen-1-ol, and (+)-3-cyclohexene-1,2-cis-diol.

Microsomal oxidases have been detected in the rabbit liver, which readily hydroxylate cyclohexene and a number of related aromatic compounds to the corresponding dihydroxy derivatives.

Hydroxylation of cyclohexene @ allylic position occurred in hepatic microsomes & 9000 g supernatant fractions of rats & rabbits. Formation of product, 2-cyclohexen-1-ol, required presence of NADPH-generating system, was inhibited by CO, and induced by phenobarbital.

In the rabbit, hydroxylation and conjugation occur, with the formation of sulfur-containing metabolites.

Hydroxylated and conjugated metabolites are eliminated in the urine ...

Absorption, Distribution and Excretion · 4 件

Cyclohexene is readily adsorbed following skin, eye, or respiratory exposure or following ingestion.

These hydrocarbons are poorly absorbed from the GI tract and do not cause appreciable systemic toxicity by this route unless aspiration has occurred.

... Two male Holtzman rats were each given 0.1 mL (81.1 mg/kg bw) of cyclohexene by stomach tube ... The urine sample for 24 hr contained 2-cyclohexen-1-one (0.1 % of the oral dose) but 2-cyclohexen-1-ol was not detected even by beta-glucuronidase treatment.

In an inhalation study, male F344/N rats were exposed nose-only to gaseous cyclohexene at 600 ppm (2,015 mg/cu m) for 60 minutes ... During exposure, the blood levels of cyclohexene increased up to 2 ug/g blood.

用途と製造

Uses · 6 件

Used in organic synthesis and as a solvent for oil extraction and catalysts; [ACGIH]

Petroleum Production and Refining [Category: Industry]

ALKYLATION COMPONENT; IN MFR OF ADIPIC ACID, MALEIC ACID, HEXAHYDROBENZOIC ACID AND ALDEHYDE. TO PREPARE BUTADIENE IN THE LABORATORY.

Catalyst solvent; oil extraction

Cyclohexene ... is used as stabilizer for high octane gasoline ...

... Used in the prepn of butadiene in lab ... Inorganic synth ...

U.S. Imports · 3 件

(1972) 3.85X10+7 GRAMS (PRINCPL CUSTMS DISTS)

(1975) 1.2X10+7 GRAMS

(1983) 3.40X10+5 g

U.S. Production · 3 件

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) GREATER THAN 1.4X10+6 GRAMS

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3366]

Methods of Manufacturing · 3 件

Cyclohexene is prepared by dehydration of cyclohexanol by thermal reaction of a ethylene-propylene-butadiene mixture.

Prepared by dehydration of cyclohexanol at high temps over various catalysts.

In Japan, cyclohexene is synthesized in a closed system by catalytic hydrogenation of benzene, isolated by fractionation.

Formulations/Preparations · 3 件

Grade: Technical 95%; 99%; research 99.9 mole%.

CYCLOHEXENE: 99+% (GOLD LABEL), 99%; BOTH INHIBITED WITH 0.01% 2,6-DI-TERT-BUTYL-4 METHYLPHENOL

CYCLOHEXENE: 99.5% ASSAY; INHIBITOR-SODIUM HYDROXIDE

Household ProductsInformation on 1 consumer products that contain Cyclohexene in the following categories is provided:;• Personal Care
応用分野 · 7 件

解説[別用語参照]シクロアルケン森北出版「化学辞典(第2版)

用途シクロヘキサノール等の中間原料、特殊溶剤

用途アルキル化剤。 アジピン酸、マレイン酸、シクロヘキサンカルボン酸、アルデヒドの原料。ハイオクタンガソリンの安定剤。 溶剤、石油の添加剤、化学合成中間体。

説明Cyclohexene is a hydrocarbon, mostly obtained from the hydrogenation of benzene.

使用It occurs in coal tar and is obtained by catalyticdehydration of cyclohexanol and dehydrogenationof cyclohexane. Cyclohexene isused in making adipic acid, maleic acid,and butadiene; in oil extraction; as a stabilizerfor high-octane gasoline; and in organicsynthesis.

一般的な説明A colorless liquid. Insoluble in water and less dense than water. Flash point 20°F. Vapors heavier than air. Inhalation of high concentrations may have a narcotic effect. Used to make other chemicals.

使用用途シクロヘキセンは、他の有機化合物と同様に有機溶媒として用いられるほか、接着剤の溶剤などに利用されています。合成的には、やなど種々の有機化合物の合成原料として用いられる化合物です。 シクロヘキセン誘導体は、農薬や医薬品などさまざまな製品として活用されています。また、特有の悪臭がありながらも硫黄分を含まないことから、都市ガスへの付臭剤としても使用されています。

調製方法 · 2 件

Cyclohexene is prepared by dehydration of cyclohexanol by thermal reaction of an ethylene–propylene–butadiene mixture (1).

純化方法Free cyclohexene from peroxides by washing with successive portions of dilute acidified ferrous sulfate, or with NaHSO3 solution, then with distilled water, drying with CaCl2 or CaSO4, and distilling under N2. Alternative methods for removing peroxides include passage through a column of alumina, refluxing with sodium wire or cupric stearate (then distilling from sodium). The diene is removed by refluxing with maleic anhydride before distilling under vacuum. Treatment with 0.1moles of MeMgI in 40mL of diethyl ether removes traces of oxygenated impurities. Other purification procedures include washing with aqueous NaOH, drying and distilling under N2 through a spinning band column, redistilling from CaH2, storing under sodium wire, and passing through a column of alumina, under N2, immediately before use. Store it at

補足説明

定義ChEBI: A cycloalkene that is cylohexane with a single double bond.

関連反応

885 件

関連ノート

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