环辛酮肟 | 1074-51-7

• 物质功能分类: 化学试剂 - 有机试剂 - 肟
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 环辛酮肟
• 英文名称: cyclooctanone oxime
• 英文别名: N-cyclooctylidenehydroxylamine
• CAS: 1074-51-7
• 化学式: C₈H₁₅NO
• mdl: MFCD00191967
• 分子量: 141.213
• InChiKey: KTPUHSVFNHULJH-UHFFFAOYSA-N

物化性质

• 熔点：
  43-44 °C (dec.)(lit.)
• 沸点：
  128-129 °C14 mm Hg(lit.)
• 密度：
  0.9938 (rough estimate)
• 闪点：
  128-129°C/14mm
• 稳定性/保质期：
  常温常压下稳定，避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.875
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 安全说明：
  S24/25
• 危险类别码：
  R20/21/22
• WGK Germany：
  3
• 海关编码：
  2928000090
• 危险品运输编号：
  UN 2811
• 储存条件：
  请将容器密封保存，并储存在阴凉、干燥的地方。

SDS

Name:	Cyclooctanone Oxime 98% Material Safety Data Sheet
Synonym:	None Known
CAS:	1074-51-7

Section 1 - Chemical Product MSDS Name:Cyclooctanone Oxime 98% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1074-51-7	Cyclooctanone Oxime	98%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: 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. Wash mouth out with 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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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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. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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 ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1074-51-7: 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:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 128-129 deg C@14 mmHg
Freezing/Melting Point: 36-37 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H15NO
Molecular Weight: 141.21

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen cyanide, carbon monoxide, oxides of nitrogen, carbon dioxide, nitric acid.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1074-51-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Cyclooctanone Oxime - 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: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 1074-51-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1074-51-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1074-51-7 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：

  环辛酮肟 在 acid-treated hierarchical silicalite-1 octahedra comprising highly-branched and orthogonally-stacked nanoplates catalyst 作用下， 以 乙醇 为溶剂， 生成 2-氮杂环壬酮
  参考文献：
  名称：

  Hierarchical silicalite-1 octahedra comprising highly-branched orthogonally-stacked nanoplates as efficient catalysts for vapor-phase Beckmann rearrangement

  摘要：

  设计了一种结构定向剂，用于合成高度分支和正交堆叠的纳米板构成的层级沸石-1八面体，对环氧胺的Beckmann重排反应表现出优异且稳定的活性，且具有高内酰胺选择性。

  DOI：

  10.1039/c6cc05992a
• 作为产物：
  描述：

  环辛烷 在 亚硝酸特丁酯 、 N-羟基邻苯二甲酰亚胺 、 溶剂黄146 作用下， 反应 6.0h， 以65%的产率得到环辛酮肟
  参考文献：
  名称：

  从环烷烃制备内酰胺前体的新途径：使用亚硝酸叔丁酯和N-羟基邻苯二甲酰亚胺直接生产亚硝基环烷烃或环烷酮肟。

  摘要：

  DOI：

  10.1002/anie.200352741

文献信息

• Copper-catalyzed synthesis of thiazol-2-yl ethers from oxime acetates and xanthates under redox-neutral conditions
  作者：Zhongzhi Zhu、Xiaodong Tang、Jinghe Cen、Jianxiao Li、Wanqing Wu、Huanfeng Jiang

  DOI：10.1039/c8cc00445e

  日期：——

  acetates and xanthates for the synthesis of thiazol-2-yl ethers with remarkable regioselectivity has been developed. Various oxime acetates, whether derived from aryl ketones or alkyl ketones, or natural product cores are suitable for this conversion. Unique dihydrothiazoles were also obtained when both reaction sites were methine. Mechanistic studies indicated that imino copper(III) intermediates were involved

  新型的铜催化的肟肟酸酯和黄药酸酯的环化反应用于合成噻唑-2-基醚，具有显着的区域选择性。各种衍生自芳基酮或烷基酮的乙酸肟酯，或天然产物核均适用于该转化。当两个反应位点均为次甲基时，也获得了独特的二氢噻唑。机理研究表明，涉及亚氨基铜（III）中间体。另外，该方案在氧化还原中性条件下进行，不需要添加剂或配体。
• Development of a Gold-Multifaceted Catalysis Approach to the Synthesis of Highly Substituted Pyrroles: Mechanistic Insights via Huisgen Cycloaddition Studies
  作者：Simbarashe Ngwerume、William Lewis、Jason E. Camp

  DOI：10.1021/jo302349k

  日期：2013.2.1

  application of the Huisgen cycloaddition click reaction, which was used to probe the relative stability of substituted O-vinyloximes. The intermediacy of N-alkenylhydroxylamine O-vinyl ethers and imino ketones or imino aldehydes along the reaction pathway were determined by high-temperature 1H, 2H1H}, and 13C1H} NMR experiments. X-ray crystallographic evidence was used to further support the mechanistic hypothesis

  通过独立地优化工艺的两个关键步骤，开发了一种直接从肟和炔烃区域选择性合成高度取代的吡咯的金催化新方法。重要的是，阳离子金（I）物种显示出沿反应路径激活多个步骤，因此可作为多面催化剂。最初由金促进的肟氧向活化的炔烃的添加原位提供了O-乙烯基肟。该Ø随后通过金催化的互变异构，[3,3]-σ重排和环脱水过程将-乙烯基肟转化为吡咯。值得注意的是，该方法提供了酯在3/4位的形式的官能团手柄，以便进一步开发。拟议的机理途径得到了Huisgen环加成点击反应的新应用的支持，该反应被用于探测取代的O-乙烯基肟的相对稳定性。的中间性Ñ -alkenylhydroxylamine ø -乙烯基醚和沿反应途径亚氨基酮或亚氨基醛是由高温测定1 H，2 H ^ 1个H}，和13 C 11 H NMR实验。X射线晶体学证据被用来进一步支持机理假说。
• Facile One-Pot Syntheses of Amidines and Enamines from Oximes via Beckmann Rearrangement Using Trifluoromethanesulfonic Anhydride
  作者：Tomofumi Takuwa、Tomofumi Minowa、Jim Yoshitaka Onishi、Teruaki Mukaiyama

  DOI：10.1246/bcsj.77.1717

  日期：2004.9

  Iminocarbocation intermediates were in situ-generated by treating various oximes with trifluoromethanesulfonic anhydride (Tf2O) in the presence of triethylamine in toluene and nucleophilic trapping with amines or sodium enolates under mild conditions afforded the corresponding amidines and enamines. Some of the thus-obtained enamines were converted to 2-substituted 4-oxo-3-quinolinecarboxylic acid derivatives by subsequent intramolecular Friedel–Crafts acylation.

  通过将各种肟在甲苯中与三氟甲磺酸酐（Tf2O）和三乙胺反应，原位生成亚胺碳正中间体，并在温和条件下用胺或烯醇钠捕捉，得到相应的脒和烯胺。部分获得的烯胺随后通过分子内 Friedel-Crafts 酰基化反应转化为 2-取代的 4-氧代-3-喹啉羧酸衍生物。
• Oxidation of amines over alumina based catalysts
  作者：Karol Rakottyay、Alexander Kaszonyi、Stanislav Vajíček

  DOI：10.1016/j.apcata.2010.01.040

  日期：2010.4.15

  products and byproducts. Coating of γ-Al2O3 with silicotungstic acid or its semisalt can significantly enhance its catalytic activity in amine oxidation. The adsorption of amine on weak acidic sites of catalyst is essential for its oxidation to main reaction products. Cycloalkylamines are oxidized mainly to cyclic oximes (selectivity up to 64%) and Schiff bases of appropriate cycloalkanone and cycloalkylamine

  胺在大气压下在氧化铝和硅钨酸/氧化铝催化剂上被分子氧在气相中氧化。该研究集中在胺的结构和催化剂性能对主要反应产物和副产物的组成的影响上。的涂覆的γ-Al 2 ö 3用硅钨酸或其半盐可以显着增强其在胺氧化中的催化活性。胺在催化剂弱酸性部位的吸附对于其氧化成主要反应产物至关重要。环烷基胺主要被氧化成环状肟（选择性高达64％）和合适的环烷酮和环烷基胺的席夫碱（选择性高达38％）。在伯烷基胺的氧化产物中主要观察到腈（选择性高达55％）和合适的席夫碱（选择性高达54％）。它们的摩尔比取决于催化剂的酸度和反应条件。1,6-己二胺主要被氧化为己内酰胺（收率48％）和其他环状内酰胺和席夫碱以及二腈（收率13％）。
• Highly efficient aerobic oxidation of oximes to carbonyl compounds catalyzed by metalloporphyrins in the presence of benzaldehyde
  作者：Xian-Tai Zhou、Qiu-Lan Yuan、Hong-Bing Ji

  DOI：10.1016/j.tetlet.2009.11.078

  日期：2010.1

  Highly efficient oxidation of oximes to carbonyl compounds by molecular oxygen with benzaldehyde as an oxygen acceptor in the presence of metalloporphyrins has been reported. The simple structural manganese porphyrin showed an excellent activity for the oxidative deoximation reactions of various oximes. Moreover, different factors influencing oximes oxidation, that is, catalyst, solvent, and temperature

  据报道，在金属卟啉存在下，以苯甲醛为氧受体，通过分子氧将肟高效氧化为羰基化合物。简单的结构锰卟啉对各种肟的氧化脱肟反应显示出优异的活性。此外，已经研究了影响肟氧化的不同因素，即催化剂，溶剂和温度。已经提出了脱氧反应的可能机理。

表征谱图