氧化环辛烯 | 286-62-4

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 环烃
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 中文名称: 氧化环辛烯
• 中文别名: 1,2-环氧环辛烷；环氧化环辛烷
• 英文名称: Cyclooctene oxide
• 英文别名: 9-oxabicyclo[6.1.0]nonane；cyclooctene epoxide；1,2-epoxycyclooctane；epoxycyclooctane
• CAS: 286-62-4
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: MELPJGOMEMRMPL-UHFFFAOYSA-N

物化性质

• 熔点：
  53-56 °C(lit.)
• 沸点：
  55 °C5 mm Hg(lit.)
• 密度：
  0.9090 (rough estimate)
• 闪点：
  133 °F
• 溶解度：
  溶于甲醇
• 稳定性/保质期：
  存在于主流烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  4.1
• 危险品标志：
  Xn
• 安全说明：
  S26,S37/39
• 危险类别码：
  R22,R36/38
• WGK Germany：
  2
• 海关编码：
  2932999099
• 包装等级：
  III
• 危险类别：
  4.1
• 危险品运输编号：
  UN 1325 4.1/PG 3
• 危险性防范说明：
  P210,P305+P351+P338
• 危险性描述：
  H228,H302,H315,H319
• 储存条件：
  贮存温度为4°C。

SDS

Name:	Cyclooctene Oxide 99% Material Safety Data Sheet
Synonym:	None known
CAS:	286-62-4

Section 1 - Chemical Product MSDS Name:Cyclooctene Oxide 99% Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
286-62-4	Cyclooctene Oxide	99	206-010-3

Hazard Symbols: XN
Risk Phrases: 22 36/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed. Irritating to eyes and skin.Moisture sensitive.
Potential Health Effects
Eye:
Causes eye irritation. May cause lacrimation (tearing), blurred vision, and photophobia. May cause chemical conjunctivitis and corneal damage.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated. May cause nausea, vomiting, abdominal pain, and increased salivation.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Olfactory fatigue may occur. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Use water spray to keep fire-exposed containers cool. Dust can be an explosion hazard when exposed to heat or flame. Flammable solid. May burn rapidly with flare burning effect. May re-ignite after fire is extinguished. Containers may explode when heated.
Extinguishing Media:
Do NOT use water directly on fire. Do NOT get water inside containers. For large fires, use water spray, fog or regular foam.
Contact professional fire-fighters immediately. For small fires, use dry chemical, carbon dioxide, sand, earth, water spray or regular foam. Cool containers with flooding quantities of water until well after fire is out.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Scoop up with a nonsparking tool, then place into a suitable container for disposal. Avoid generating dusty conditions. Remove all sources of ignition. Provide ventilation. Do not get water inside containers.

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Section 7 - HANDLING and STORAGE
Handling:
Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation.
Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Keep away from heat, sparks and flame.
Avoid ingestion and inhalation. Do not allow contact with water. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames. Keep from contact with moist air and steam.
Storage:
Keep away from heat, sparks, and flame. Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep away from water. Keep refrigerated. (Store below 4C/39F.) Store protected from moisture.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate general or local explosion-proof ventilation to keep airborne levels to acceptable levels.
Exposure Limits CAS# 286-62-4: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: colorless to white
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 189 deg C @ 760.00mm Hg
Freezing/Melting Point: 53 - 56 deg C
Autoignition Temperature: Not applicable.
Flash Point: 56 deg C ( 132.80 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H14O
Molecular Weight: 126.20

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, ignition sources, dust generation, moisture, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Moisture, strong oxidizing agents, acids, bases.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 286-62-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Cyclooctene Oxide - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: FLAMMABLE SOLID, ORGANIC, N.O.S.*
Hazard Class: 4.1
UN Number: 1325
Packing Group: II
IMO
Shipping Name: FLAMMABLE SOLID, ORGANIC, N.O.S.
Hazard Class: 4.1
UN Number: 1325
Packing Group: II
RID/ADR
Shipping Name: FLAMMABLE SOLID, ORGANIC, N.O.S.
Hazard Class: 4.1
UN Number: 1325
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 22 Harmful if swallowed.
R 36/38 Irritating to eyes and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 37/39 Wear suitable gloves and eye/face
protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 286-62-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 286-62-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 286-62-4 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  氧化环辛烯 在 三氯异氰尿酸 、 三苯基膦 作用下， 以 水 、 乙腈 为溶剂， 以88%的产率得到2-chlorocyclooctane-1-ol
  参考文献：
  名称：

  三卤代异氰尿酸/三苯膦：在温和条件下将环氧化物选择性转化为邻卤代醇和邻二卤化物的有效系统

  摘要：

  摘要 通过在温和中性条件下与三卤代异氰尿酸/三苯基膦体系反应，已开发出一种新的合成方法，用于将环氧化物区域选择性转化为邻位氯-/溴代醇和邻位二卤化物。反应分别在室温和回流下以高收率顺利进行， 在短时间内。 通过在温和中性条件下与三卤代异氰尿酸/三苯基膦体系反应，已开发出一种新的合成方法，用于将环氧化物区域选择性转化为邻位氯-/溴代醇和邻位二卤化物。反应分别在室温和回流下以高收率顺利进行， 在短时间内。

  DOI：

  10.1055/s-0035-1560408
• 作为产物：
  描述：

  1,5-cis,cis-cyclooctadiene 在 platinum(IV) oxide molybdenyl acetylacetonate 、 氢气 、 氧气 作用下， 以 乙醇 为溶剂， 反应 28.0h， 生成 氧化环辛烯
  参考文献：
  名称：

  Giezynski, Roman; Pala, Magdalena, Polish Journal of Chemistry, 1982, vol. 56, # 10-12, p. 1349 - 1355

  摘要：

  DOI：

文献信息

• Biphasic copper-catalyzed C–H bond activation of arylalkanes to ketones with tert-butyl hydroperoxide in water at room temperature
  作者：Md. Munkir Hossain、Shin-Guang Shyu

  DOI：10.1016/j.tet.2016.05.066

  日期：2016.7

  A facile C–H bond activation of arylalkanes to their corresponding ketones catalyzed by copper salts using tert-butyl hydroperoxide as an oxidant in water at room temperature is described. Easy product separation, simple reaction procedures (without using base or phase transfer catalysis), and catalyst recycling make the catalytic system attractive. It is also active beyond activated benzylic methylene

  描述了在室温下水中叔丁基过氧化氢作为氧化剂，通过铜盐催化的芳基烷烃轻松实现C–H键与相应酮的活化反应。容易的产品分离，简单的反应程序（不使用碱或相转移催化）和催化剂循环利用，使催化体系具有吸引力。它在活化的苄基亚甲基位置以外也具有活性，并且可以耐受具有不同基团的派系化芳基烷烃。
• Kinetics of C–H bond and alkene oxidation by trans-dioxoruthenium(<scp>VI</scp>) porphyrins
  作者：Clare Ho、Wa-Hung Leung、Chi-Ming Che

  DOI：10.1039/dt9910002933

  日期：——

  characterized, and the kinetics and mechanism of oxidation of the C–H bond and alkenes investigated. The complexes were selective towards tertiary C–H bonds in saturated alkanes but were almost inactive towards secondary C–H bonds. However, they were reactive towards aromatic hydrocarbons and the second-order rate constants (k2) for the oxidation of ethylbenzene and cumene by [Ru(tpp)O2](tpp = 5, 10, 15, 20-te

  A.合成并表征了一系列[Ru VI LO 2 ]配合物（H 2 L =对位取代的四苯基卟啉），并研究了C–H键和烯烃的氧化动力学和机理。该络合物对饱和烷烃中的C–H键具有选择性，但对C–H二级键几乎没有活性。但是，它们对芳烃有反应性，[Ru（tpp）O 2 ]（tpp = 5，10，15，20-四苯基卟啉）氧化乙苯和枯烯的二级速率常数（k 2）为2.21。 ×10 –4和3.16×10 –4 dm 3 mol –1s –1分别。发现环己烯被[Ru（tpp）O 2 ]烯丙基氧化的动力学同位素效应（K H / K D）为11.7 。CH 2 Cl 2 -MeOH混合物中烯烃氧化的主要有机产物是环氧化物，[Ru（tpp）O 2 ]得到的单体产物为[Ru IV（tpp）O]·EtOH。或[Ru IV（tpp）（OH）2 ·] EtOH。与[Ru VI（oep）O 2 ]（oep = 2,3,7,8
• Mn(III)-Iodosylarene Porphyrins as an Active Oxidant in Oxidation Reactions: Synthesis, Characterization, and Reactivity Studies
  作者：Mian Guo、Yong-Min Lee、Mi Sook Seo、Yong-Ju Kwon、Xiao-Xi Li、Takehiro Ohta、Won-Suk Kim、Ritimukta Sarangi、Shunichi Fukuzumi、Wonwoo Nam

  DOI：10.1021/acs.inorgchem.8b01426

  日期：2018.8.20

  + species were then investigated in the epoxidation of olefins under stoichiometric conditions. In the epoxidation of olefins by the Mn(III)-iodosylarene porphyrin species, epoxide was formed as the sole product with high chemoselectivities and stereoselectivities. For example, cyclohexene oxide was formed exclusively with trace amounts of allylic oxidation products; cis- and trans-stilbenes were oxidized

  Mn（III）-碘亚芳基卟啉加合物[Mn（III）（ArIO）（Porp）] +通过使缺电子的Mn（III）卟啉配合物与碘亚芳基（ArIO）在-60°C下反应而合成光谱方法。然后在化学计量条件下在烯烃的环氧化中研究了[Mn（III）（ArIO）（Porp）] +物质。在Mn（III）-碘亚芳基卟啉物种对烯烃的环氧化中，形成环氧化物作为具有高化学选择性和立体选择性的唯一产物。例如，环己烯氧化物仅与痕量的烯丙基氧化产物形成；顺式-和反式-斯蒂尔苯被氧化成相应的顺式和反式-二苯乙烯氧化物。缺电子的Mn（III）卟啉配合物和s在环己烯的催化环氧化中在低温（例如-60°C）下的PhIO中，Mn（III）-碘亚芳基卟啉物种被证明是一种有效的氧化剂，可影响烯烃的环氧化以提供环氧化物作为产物。但是，在高温（例如0°C）下或在使用富电子的锰（III）卟啉催化剂的情况下，会生成烯丙基氧化产物以及环己烯氧化物，
• Effect of Ligand Fields on the Reactivity of O ₂ ‐Activating Iron(II)‐Benzilate Complexes of Neutral N5 Donor Ligands
  作者：Shrabanti Bhattacharya、Reena Singh、Tapan Kanti Paine

  DOI：10.1002/asia.202000142

  日期：2020.4.17

  Three new iron(II)-benzilate complexes [(N4Py)FeII (benzilate)]ClO4 (1), [(N4PyMe2 )FeII (benzilate)]ClO4 (2) and [(N4PyMe4 )FeII (benzilate)]ClO4 (3) of neutral pentadentate nitrogen donor ligands have been isolated and characterized to study their dioxygen reactivity. Single-crystal X-ray structures reveal a mononuclear six-coordinate iron(II) center in each case, where benzilate binds to the iron

  三种新的铁（II）-苯甲酸酯络合物[（N4Py）FeII（苯甲酸酯）] ClO4（1），[（N4PyMe2）FeII（苯甲酸酯）] ClO4（2）和[（N4PyMe4）FeII（苯甲酸酯）] ClO4（3）已分离出中性的五齿氮供体配体，并对其特征进行了研究以研究其双氧反应性。单晶X射线结构在每种情况下都显示一个单核六坐标铁（II）中心，其中苯甲酸酯通过一个羧酸氧以单齿模式结合到铁中心。与母体N4Py配体相比，在吡啶环的6位引入甲基使得N4PyMe2和N4PyMe4配体场更弱。所有的配合物（1-3）与双氧反应以将配位的苯甲酸酯定量地脱羧为二苯甲酮。对于位阻更强的配体的配合物，脱羧速度更快，并且遵循3> 2>的顺序 1.配合物显示出与硫代苯甲醚的氧原子转移反应性，并且还与含有弱CH键的底物发生氢原子转移反应。基于与外部底物的拦截研究，标记实验和Hammett分析，提出了一种亲核性铁（II）-氢
• Synthesis, characterization, and reactivity of oxoiron(IV) porphyrin π-cation radical complexes bearing cationic N-methyl-2-pyridinium group
  作者：Yuna Suzuki、Masahiko Hada、Hiroshi Fujii

  DOI：10.1016/j.jinorgbio.2021.111542

  日期：2021.10

  reactivity of metalloenzymes. Here, to investigate the effect of the cationic charge near the heme in heme proteins, we synthesized new iron porphyrin complexes (1 and 2) having cationic 3-methyl-N-methyl-2-pyrdinium group and N-methyl-2-pyridinium group at one of the four meso-positions, respectively. The N-methyl-2-pyridinium groups could be introduced by Stille coupling used palladium catalysts. Oxoiron(IV)

  活性位点附近的电子电荷是控制金属酶反应性的重要因素。在这里，为了研究血红素蛋白中靠近血红素的阳离子电荷的影响，我们合成了具有阳离子 3-甲基-N-甲基-2-吡啶鎓和N-甲基-2-吡啶鎓的新型铁卟啉配合物（ 1和2 ）。分别在四个中间位置之一分组。N-甲基-2-吡啶鎓基团可以通过Stille偶联使用的钯催化剂引入。1 ( 1-CompI ) 和2 ( 2-CompI )的氧代铁 (IV) 卟啉π-阳离子自由基配合物 (Compound I)) 可溶于大多数有机溶剂，从而可以在相同条件下直接比较它们的电子结构和与四苯甲基卟啉 ( 3-CompI ) 和四-(2,6-二氯苯基)卟啉 ( 4-CompI ) 的化合物 I 的反应性。1-CompI的光谱数据与3 -CompI 的光谱数据接近，但1-CompI的氧化还原电位与4-CompI的接近。环氧化反应的动力学分析表明，1-CompI和2-Com

表征谱图