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1,2-エポキシシクロヘキサン

Cyclohexene oxide

HCID 9246
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
286-20-4
標準SMILES
C1CCC2OC2C1
InChIKey
ZWAJLVLEBYIOTI-UHFFFAOYSA-N
分子式
C6H10O
平均分子量
98.14 g/mol
単同位体質量
98.07316494

概要

inhibitor of epoxide hydrase; structure

名称と識別子

優先名称
Cyclohexene oxide
IUPAC
7-oxabicyclo[4.1.0]heptane
現地名
1,2-エポキシシクロヘキサン
英語名
Cyclohexene oxide
分子式
C6H10O
分子量
98.14

名称と別名

Cyclohexene oxide286-20-47-Oxabicyclo[4.1.0]heptane1,2-EPOXYCYCLOHEXANECyclohexene epoxideTetramethyleneoxiraneCyclohexylene oxideCyclohexene 1-oxideCyclohexane oxideCyclohexane, 1,2-epoxy-1,2-Cyclohexene oxideCCHO
名称をさらに表示
1,2-エポキシシクロヘキサン1α,2α-エポキシシクロヘキサン(1α,6α)-7-オキサビシクロ[4.1.0]ヘプタン(1R,1β,6β)-7-オキサビシクロ[4.1.0]ヘプタンcis-シクロヘキセンオキシド(1R,2S)-1,2-エポキシシクロヘキサン7-オキサビシクロ[4.1.0]ヘプタン1β,2β-エポキシシクロヘキサン(1S,6R)-7-オキサビシクロ[4.1.0]ヘプタンテトラメチレンオキシラン7-オキサノルカラン(1R)-1β,2β-エポキシシクロヘキサンシクロヘキセンオキシド(1β,6β)-7-オキサビシクロ[4.1.0]ヘプタン(1R,6S)-7-オキサビシクロ[4.1.0]ヘプタンシクロヘキセンエポキシドエポキシシクロヘキサンシクロヘキセンオキサイド7‐オキサビシクロ[4.1.0]ヘプタン1,2-シクロヘキセンエポキシドEPOXYCYCLOHEXANE1,2-epoxy-cyclohexan(1R,6S)-7-Oxabicyclo[4.1.0]heptaneHXOohexene oxide7-OxanorcaraneCyclohexenoxide
Cyclohexene-1-oxideDTXSID60248807-Oxabicyclo(4.1.0)heptaneCyclohexene, oxideDTXCID404880NSC-5218NSC-1280741XYE04C550

データベース識別子

CAS
286-20-4
PubChem CID
9246
DTXSID
DTXSID6024880
ChEMBL
CHEMBL1361659
EC Number
206-007-7
Nikkaji
J2.980G

物性

構造計算による物性補完中

XLogP
1.2
極性表面積
12.5 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
0
重原子数
7
形式電荷
0
複雑度
70.2

実験および物理化学的性質

PolymersPlastics & Rubber -> Epoxides
SpringerMaterials PropertiesChemical shift
OdorSTRONG ODOR
Density0.967 @ 25 °C/4 °C
Color/FormCOLORLESS LIQUID
Solubility · 2 件

SOL IN ALC, ETHER, ACETONE; INSOL IN WATER

VERY SOL IN BENZENE; SOL IN CHLOROFORM

Flash Point81 °C CC
Boiling Point129-130 °C
Melting PointGREATER THAN -10 °C
Refractive IndexINDEX OF REFRACTION: 1.4503 @ 25 °C/D
Physical DescriptionColorless liquid; [HSDB]

物理化学的性質

安全と法規制

安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 3.2% (5 of 158) of reports.

Danger

H226 (95.6%): Flammable liquid and vapor [Warning Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P318, P321, P330, P361+P364, P362+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 158 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

危険有害性情報

Regulatory Information · 3 件

Chemical: 7-Oxabicyclo[4.1.0]heptane

REACH registered substance: 1,2-epoxycyclohexane (EC: 206-007-7)

Epoxycyclohexane: Does not have an individual approval but may be used under an appropriate group standard

Fire PotentialFLAMMABLE, DANGEROUS FIRE RISK.
Hazards SummaryA tumorigen and mutagen; [RTECS] An irritant; [MSDSonline]
Peroxide Forming Chemical · 4 件

Cyclohexene Oxide

D*: Other compounds that may form peroxides

1 samples had 1 ppm peroxide; age >1 yrs

Management of time-sensitive chemicals (JCHAS)

Hazard Classes and Categories · 2 件

Flam. Liq. 3 (95.6%)

Flammable liquids - Category 3

毒性情報

Interactions

化学と産業

薬理情報

Metabolism/Metabolites · 2 件

RABBIT LIVER MICROSOMES OXIDIZED CYCLOHEXENE OXIDE. THEREFORE, EPOXIDES ARE INTERMEDIATES IN THE OXIDATION OF ALKENES TO GLYCOLS IN LIVER MICROSOMES.

ON INCUBATION WITH RABBIT LIVER MICROSOMES CYCLOHEXENE OXIDE WAS CONVERTED TO THE CORRESPONDING 1,2-GLYCOL BY EPOXIDE HYDRASE.

用途と製造

Uses · 3 件

Used as a chemical intermediate for epoxy resins and photoreactive polymers; [HSDB]

CHEMICAL INTERMEDIATE

CHEM INT, EG, FOR EPOXY RESINS & PHOTOREACTIVE POLYMERS

U.S. Exports · 2 件

(1979) No Data

(1981) No Data

U.S. Imports · 2 件

(1979) 6.26X10+7 GRAMS (PRINCPL CUSTMS DISTS)

(1981) No Data

U.S. Production · 2 件

(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS

(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS

Methods of ManufacturingPROBABLY BY REACTION OF CYCLOHEXENE WITH A PEROXY ACID, EG, PERACETIC ACID
Formulations/PreparationsGRADE: 98% PURE.
General Manufacturing Information7-Oxabicyclo[4.1.0]heptane: ACTIVE
応用分野 · 1 件

使用Cyclohexene oxide has been patented for use as an insecticidal fumigant. Cyclohexene oxide is an important intermediate in the organic industry. It is employed in the manufacture of medicines, pesticides, dyes, and perfumes. In addition, cyclohexene oxide can be used as a monomer in polymerization, chain-cutting agent, flame retardant and diluting agent among other uses. Cyclohexene oxide is useful as a monomer in polymerization with CO2 for production of cyclic carbonates and polycarbonates in the presence of different catalysts.

関連反応

171 件
反応記録を作成
HRID 26248 の反応式
HRID 26248反応物としてuspto-grants-1979_04
HRID 36477 の反応式
HRID 36477反応物としてuspto-grants-1995_05
HRID 73616 の反応式
HRID 73616反応物としてuspto-grants-2014_09
HRID 95203 の反応式
HRID 95203反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 99751 の反応式
HRID 99751反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 129099 の反応式
HRID 129099反応物としてuspto-grants-1995_11
HRID 135852 の反応式
HRID 135852反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 153908 の反応式
HRID 153908反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
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化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す
融点
-40 °C · -40 °C
沸点
129 · 129-130 °C(lit.)
比重(密度)
0.97 g/mL · 0.97 g/mL at 25 °C(lit.)
蒸気圧
12 hPa · 12 hPa (20 °C)
屈折率
20 · n20/D 1.452(lit.)
闪点
81 °F · 81 °F
貯蔵温度
30 °C · Store below +30°C.
外見
液体
色
無色透明～黄色
爆発限界(explosive limit)
1.2 · 1.2-6.5%(V)
水溶解度
不溶性
BRN
383568 · 383568
InChI
1S/C6H10O/c1-2-4-6-5(3-1)7-6/h5-6H,1-4H2
InChIKey
ZWAJLVLEBYIOTI-UHFFFAOYSA-N
SMILES
C1CCC2OC2C1
CAS データベース
286 · 286-20-4(CAS DataBase Reference)
NISTの化学物質情報
Cyclohexene oxide(286-20-4)
EPAの化学物質情報
Cyclohexene oxide (286-20-4)

化学的性質

化学的特性clear colorless to yellow liquid

· 4 件

MODIFIER OF MICROSOMAL EPOXIDE HYDRASE ACTIVITY, CYCLOHEXENE OXIDE, EXERTS DIFFERENTIAL EFFECTS ON CATALYTIC ACTIVITY OF PURIFIED ENZYME FROM RAT LIVER. CYCLOHEXENE OXIDE INHIBITS RATE OF METAB OF BENZO(A)PYRENE 11,12-OXIDE & DIBENZO(A,H)-ANTHRACENE 5,6-OXIDE.

CYCLOHEXENE OXIDE ADMIN IP TO RATS, INHIBITED BILIARY EXCRETION OF METHYL MERCURY. THESE RESULTS PROBABLY REFLECT THE CONJUGATION OF CYCLOHEXENE TO GLUTATHIONE IN THE LIVER.

CO-ADMIN OF CYCLOHEXANE OXIDE AND CHLOROBENZENE REDUCED THE RATE OF METABOLISM OF CHLOROBENZENE AND PREVENTED HEPATIC CENTRILOBULAR NECROSIS CAUSED BY THIS COMPD IN RATS.

INDUCED LUNG HYDROXYLASES HAD KM VALUES OF 1.10 AND 0.52 IN MOUSE AND HAMSTER, RESPECTIVELY. THEY WERE STRONGLY STIMULATED BY CYCLOHEXENE OXIDE.

Ongoing Test Status · 1 件

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=286-20-4]

Human Toxicity ExcerptsCYCLOHEXENE OXIDE IS A CILIA TOXIC AND MUCUS COAGULATING AGENT IDENTIFIED IN AIR POLLUTANTS. /FROM TABLE/
Non-Human Toxicity Excerpts · 4 件

MUTAGENICITY: MUTATION RESEARCH 87: 17 (1981). SISTER CHROMATID EXCHANGE - IN VITRO CHROMOSOMAL EFFECT STUDIES, NON-HUMAN: QUESTIONABLE.

CYCLOHEXANE OXIDE WAS INVESTIGATED USING AMES SALMONELLA TYPHIMURIUM ASSAY WITHOUT ADDN OF LIVER HOMOGENATE FRACTIONS. IT IS FOUND TO BE A WEAK MUTAGEN FOR TA100 & TA1535 STRAINS.

12 EPOXIDE COMPD WERE TESTED FOR CARCINOGENIC ACTIVITY IN RATS AFTER SC INJECTION @ MAX TOLERATED DOSES WITHOUT TOXIC OR ULCERATIVE EFFECTS. 1,2-EPOXYCYCLOHEXANE WAS INACTIVE.

CYCLOHEXENE OXIDE EXERTED DIFFERENTIAL EFFECTS ON NUCLEAR AND MICROSOMAL EPOXIDE HYDRASE WHICH WERE DEPENDENT ON SUBSTRATE AND ON THE ORGANELLE.

Toxicity DataLCLo (rat) = 2,000 ppm/4h

安全データ

wgk
1
tsca
TSCA listed
rtecs
RN7175000
ridadr
UN 2924 3/PG 3
毒性
LD50 orally in Rabbit: 1060 mg/kg LD50 dermal Rabbit 612 mg/kg
hs_code
29109000
risk_code
10-20/21/22-34
化審法
(3)-3263
消防法
危-4-2-III
hazard_code
C
safety_code
26-36/37/39-45-16
hazard_class
8
packing_group
II
自然発火温度
703 °F
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 4 OralEye Dam. 1Flam. Liq. 3Muta. 2Skin Corr. 1B
ストレージクラス
3 - Flammable liquids
有毒物質データの
286-20-4(Hazardous Substances Data)
調製方法 · 1 件

純化方法Fractionate the oxide through an efficient column. The main impurity is probably H2O. Dry it over MgSO4, filter and distil it several times (b 129-134o/760mm). The residue is sometimes hard to remove from the distilling flask. To avoid this difficulty, add a small amount of a mixture of ground NaCl and Celite (1:1) to help break up the residue particularly if H2O is added. [Osterberg Org Synth Coll Vol I 185 1948, Beilstein 17 H 21, 17/1 V 203.]

上流・下流製品情報

上流原料

酸化ほう素トリメチルアンチモン(III)シクロヘキセンオキシドールジエチレングリコールジメチルエーテル1,4-ジオキサンヘキサカルボニルタングステン2-シクロヘキセン-1-オールシクロヘキサン

下流製品

Propargite E.C.亜硫酸2-(p-tert-ブチルフェノキシ)シクロヘキシル2-プロピニル2-(4-TERT-BUTYLPHENOXY)CYCLOHEXANOLヨードシクロヘキサン1,2-シクロヘキサンジオール (cis-, trans-混合物)1,2,3,4-テトラヒドロフェナジンシクロペンタンメタノール2-(3-メトキシフェニル)シクロヘキサノンアジポアルデヒドtrans-1,2-ジクロロシクロヘキサン(±)-trans-1,2-ジブロモシクロヘキサン1,3-dioxepan-2-one