1-(2-异氰乙基)环己烷 | 172223-58-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1-(2-异氰乙基)环己烷
• 中文别名: 2-环己烷-1-异氰乙基
• 英文名称: 1-(2-isocyanoethyl)cyclohex-1-ene
• 英文别名: 1-(2-Isocyanoethyl)cyclohexene
• CAS: 172223-58-4
• 化学式: C₉H₁₃N
• mdl: MFCD02664625
• 分子量: 135.209
• InChiKey: KKAZBUBQJPTCKA-UHFFFAOYSA-N

物化性质

• 沸点：
  52-58 °C (1.5 mmHg)
• 密度：
  0.9
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  4.4
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36,S37,S39
• 危险类别码：
  R36/37/38

SDS

Name:	2-Cyclohexen-1-ylethyl isocyanide 96% Material Safety Data Sheet
Synonym:	1-(2-Isocyanoethyl)cyclohexan
CAS:	172223-58-4

Section 1 - Chemical Product MSDS Name:2-Cyclohexen-1-ylethyl isocyanide 96% Material Safety Data Sheet
Synonym:1-(2-Isocyanoethyl)cyclohexan

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
172223-58-4	2-Cyclohexen-1-ylethyl isocyanide	96%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. Causes respiratory tract irritation.
Chronic:
Not available.

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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.
Ingestion:
Get medical aid. 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. Will burn if involved in a fire.
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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
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# 172223-58-4: Personal Protective Equipment Eyes: Not available.
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: Liquid
Color: light yellow - yellow-brown
Odor: stench
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 52 - 58 deg C @1.5Pa
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Insoluble.
Specific Gravity/Density: 0.900
Molecular Formula: C9H13N
Molecular Weight: 135.21

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 172223-58-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Cyclohexen-1-ylethyl isocyanide - 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: TOXIC LIQUID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
IMO
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
RID/ADR
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
WGK (Water Danger/Protection)
CAS# 172223-58-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 172223-58-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 172223-58-4 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：

  二苯二硫醚 、 1-(2-异氰乙基)环己烷 在 二苯基二硒醚 作用下， 以 氘代苯 为溶剂， 反应 23.0h， 以58%的产率得到N-[2-(1-cyclohexenyl)ethyl]bis(phenylthio)methanimine
  参考文献：
  名称：

  二硫键-二硒键混合系统对异氰酸酯的高选择性双重硫属元素化

  摘要：

  基于对有机二卤化物和硫族元素为中心的自由基的相对反应性的阐明，已开发出一种将硫基和硒代基团引入各种异氰酸酯中的高选择性方法。当芳香族异氰化物（ArNC）同有机二硫化物（R'SSR“）和diselenides（R”“SeSeR”“）的反应是通过照射钨灯通过派热克斯（传导ħ ν> 300纳米），同时引入两者的异氰酸酯中的硫代和硒代基团发生，以提供相应的硫代硒化产物（R'S-C（NAr）-SeR''）的收率高，选择性好。在脂族异氰化物（RCN）的情况下，RNC与二芳基二硫化物（Ar'SSAr'）的新型二硒化物辅助双硫醇化成功进行，得到了相应的双硫醇化产物（Ar'S-C（NR）-SAr'），尽管相同在不存在二硒化物的情况下，RNC与二芳基二硫化物的光辐射反应不会发生。假定这些双硫属化合物化反应是通过异氰酸酯与相对反应性的硫代自由基（与硒代自由基相比）的反应形成酰亚胺基自由基中间体而进行的。通过与乙烯酮当量的正式[2

  DOI：

  10.1021/jo061704f
• 作为产物：
  描述：

  N-(2-cyclohex-1-enylethyl)formamide 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到1-(2-异氰乙基)环己烷
  参考文献：
  名称：

  异氰化物2.0

  摘要：

  异氰酸酯官能团由于其在类胡萝卜素和三键特征之间的二分法而具有亲核和亲电子末端碳，在有机化学中表现出不同寻常的反应性，例如在Ugi反应中。不幸的是，仅按比例使用几种异氰酸酯妨碍了有关该官能团引人入胜的反应性的新发现。具有多个官能团的多种异氰酸酯的合成漫长，效率低下，并使化学家暴露于危险的烟雾中。在这里，我们提出了一种创新的异氰酸酯合成方法，它通过避免在96孔微量滴定板中以0.2 mmol规模在0.5 mol克规模进行平行合成而避免的水后处理，克服了这些问题。我们方法的优势包括提高合成速度，在非常温和的条件下可以使用迄今为止从未有过的未知或高度反应性的异氰酸酯类，可以快速使用大量官能化的异氰酸酯，具有较高的收率，高纯度，经过验证的5个数量级以上的可扩展性，增加的安全性和较少的反应浪费，从而大大减少了环境脚印。例如，迄今为止认为是不稳定的2-异氰基嘧啶，2-酰基苯基异氰酸酯，甚至邻-异氰基苯甲醛

  DOI：

  10.1039/d0gc02722g

文献信息

• Highly Selective Double Chalcogenation of Isocyanides with Disulfide−Diselenide Mixed Systems
  作者：Kaname Tsuchii、Yasunori Tsuboi、Shin-ichi Kawaguchi、Junko Takahashi、Noboru Sonoda、Akihiro Nomoto、Akiya Ogawa

  DOI：10.1021/jo061704f

  日期：2007.1.1

  excellent selectivity. In the cases of aliphatic isocyanides (RCN), a novel diselenide-assisted bisthiolation of RNC with diaryl disulfides (Ar‘SSAr‘) proceeds successfully to give the corresponding bisthiolation products (Ar‘S−C(NR)−SAr‘), although the same photoirradiated reaction of RNC with diaryl disulfides does not occur in the absence of diselenide. These double chalcogenation reactions are assumed

  基于对有机二卤化物和硫族元素为中心的自由基的相对反应性的阐明，已开发出一种将硫基和硒代基团引入各种异氰酸酯中的高选择性方法。当芳香族异氰化物（ArNC）同有机二硫化物（R'SSR“）和diselenides（R”“SeSeR”“）的反应是通过照射钨灯通过派热克斯（传导ħ ν> 300纳米），同时引入两者的异氰酸酯中的硫代和硒代基团发生，以提供相应的硫代硒化产物（R'S-C（NAr）-SeR''）的收率高，选择性好。在脂族异氰化物（RCN）的情况下，RNC与二芳基二硫化物（Ar'SSAr'）的新型二硒化物辅助双硫醇化成功进行，得到了相应的双硫醇化产物（Ar'S-C（NR）-SAr'），尽管相同在不存在二硒化物的情况下，RNC与二芳基二硫化物的光辐射反应不会发生。假定这些双硫属化合物化反应是通过异氰酸酯与相对反应性的硫代自由基（与硒代自由基相比）的反应形成酰亚胺基自由基中间体而进行的。通过与乙烯酮当量的正式[2
• Isocyanide 2.0
  作者：Pravin Patil、Maryam Ahmadian-Moghaddam、Alexander Dömling

  DOI：10.1039/d0gc02722g

  日期：——

  advantages of our methodology include an increased synthesis speed, very mild conditions giving access to hitherto unknown or highly reactive classes of isocyanides, rapid access to large numbers of functionalized isocyanides, increased yields, high purity, proven scalability over 5 orders of magnitude, increased safety and less reaction waste resulting in a highly reduced environmental footprint. For example

  异氰酸酯官能团由于其在类胡萝卜素和三键特征之间的二分法而具有亲核和亲电子末端碳，在有机化学中表现出不同寻常的反应性，例如在Ugi反应中。不幸的是，仅按比例使用几种异氰酸酯妨碍了有关该官能团引人入胜的反应性的新发现。具有多个官能团的多种异氰酸酯的合成漫长，效率低下，并使化学家暴露于危险的烟雾中。在这里，我们提出了一种创新的异氰酸酯合成方法，它通过避免在96孔微量滴定板中以0.2 mmol规模在0.5 mol克规模进行平行合成而避免的水后处理，克服了这些问题。我们方法的优势包括提高合成速度，在非常温和的条件下可以使用迄今为止从未有过的未知或高度反应性的异氰酸酯类，可以快速使用大量官能化的异氰酸酯，具有较高的收率，高纯度，经过验证的5个数量级以上的可扩展性，增加的安全性和较少的反应浪费，从而大大减少了环境脚印。例如，迄今为止认为是不稳定的2-异氰基嘧啶，2-酰基苯基异氰酸酯，甚至邻-异氰基苯甲醛
• Hughes, David J.; Livinghouse, Tom, Journal of the Chemical Society. Perkin transactions I, 1995, # 19, p. 2373 - 2374
  作者：Hughes, David J.、Livinghouse, Tom

  DOI：——

  日期：——
• Diphenyl Diselenide-Assisted Radical Addition Reaction of Diphenyl Disulfide to Unsaturated Bonds upon Photoirradiation
  作者：Yuki Yamamoto、Qiqi Chen、Akiya Ogawa

  DOI：10.3390/molecules28062450

  日期：——

  unsaturated compounds. In this study, by combining an interelement compound with homologous heteroatom compounds as a catalyst, we succeeded in suppressing the polymerization of the unsaturated compounds and in attaining a highly selective carbon-heteroatom bond formation through the desired addition reaction. In this paper, we have examined in detail whether such a "catalytic radical reaction" proceeds

  具有杂原子-杂原子单键的元素间化合物在光辐照下与不饱和键的加成反应是高效、原子经济地构建碳-杂原子键的重要方法。然而，在实践中，由于所需的加成反应效率低或不饱和化合物优先聚合，有时无法按预期进行所需的加成反应。在这项研究中，通过将元素间化合物与同系杂原子化合物结合作为催化剂，我们成功地抑制了不饱和化合物的聚合，并通过所需的加成反应实现了高选择性的碳-杂原子键形成。在本文中，我们详细研究了这种“催化自由基反应”是否 对不饱和化合物进行研究，发现一些不饱和化合物（即乙烯基醚、苯乙烯和异氰化物）的二硫醇化可以在 (PhSe)2 的帮助下在光照下进行。作为碳-杂原子键形成的原子经济方法，本研究中开发的方法有望在自由基化学、杂原子化学、合成有机化学和催化剂化学领域产生重大影响。
• Aryl sulfonium salt electron donor-acceptor complexes for halogen atom transfer: Isocyanides as tunable coupling partners
  作者：Huaibo Zhao、Valentina D. Cuomo、James A. Rossi-Ashton、David J. Procter

  DOI：10.1016/j.chempr.2024.01.020

  日期：2024.4

  (electron donor-acceptor) complexes provides a mild platform for aryl-radical-mediated halogen atom transfer activation of a wide range of functionalized alkyl iodides, including tertiary alkyl iodides. Using an aryl sulfonium salt with carbonate as an inexpensive donor for EDA complex formation, the general reaction platform has been applied in a divergent, metal-free photochemical approach to nitriles

  锍盐 EDA（电子供体-受体）复合物的光活化为芳基介导的卤素原子转移活化各种官能化烷基碘（包括叔烷基碘）提供了温和的平台。使用芳基锍盐和碳酸盐作为 EDA 络合物形成的廉价供体，通用反应平台已应用于腈和酰胺的不同、无金属光化学方法。这种差异是通过调节异氰化物自由基陷阱而成为可能的。例如，鉴定一种易于获得、工作台稳定且含有异氰化物的结晶酰胺，可以完全选择性地获得腈产品。