3-苯基异氰酸丙酯 | 111944-21-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-苯基异氰酸丙酯
• 英文名称: (3-isocyanopropyl)benzene
• 英文别名: 3-phenylpropyl isocyanide；3-Phenylpropylisocyanide；3-isocyanopropylbenzene
• CAS: 111944-21-9
• 化学式: C₁₀H₁₁N
• mdl: MFCD02664668
• 分子量: 145.204
• InChiKey: ZQMZCHTXHCEALS-UHFFFAOYSA-N

物化性质

• 沸点：
  90 °C (7.501 mmHg)
• 密度：
  0.94

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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,S36/37/39
• 危险类别码：
  R36/37/38

SDS

Name:	3-Phenylpropyl isocyanide 96% Material Safety Data Sheet
Synonym:	(3-Isocyanopropyl)benzen
CAS:	111944-21-9

Section 1 - Chemical Product MSDS Name:3-Phenylpropyl isocyanide 96% Material Safety Data Sheet
Synonym:(3-Isocyanopropyl)benzen

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
111944-21-9	3-Phenylpropyl 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# 111944-21-9: 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: yellow
Odor: unpleasant odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 90 deg C @10hPa
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: 0.940
Molecular Formula: C10H11N
Molecular Weight: 145.2

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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# 111944-21-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-Phenylpropyl 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# 111944-21-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 111944-21-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 111944-21-9 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：

  3-苯基异氰酸丙酯 在 吡啶 、 磷酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-(N-(4-(tert-butyl)phenyl)vinylsulfonamido)-N-(3-phenylpropyl)-2-(pyridin-3-yl)acetamide
  参考文献：
  名称：

  新型 SARS-CoV-2 3CLpro 共价抑制剂的设计、合成和体外评价

  摘要：

  当前的 COVID-19 大流行以及之前的 SARS 和 MERS 爆发等严重疾病都是冠状病毒感染的结果，并表明迫切需要抗病毒药物来对抗这些致命病毒。由于其在病毒复制和功能中的重要作用，3CL pro （主要冠状病毒半胱氨酸蛋白酶）已被确定为开发抗病毒药物的有希望的靶标。之前报道的 SARS-CoV 3CL pro非共价抑制剂被用作开发 SARS-CoV-2 3CL pro共价抑制剂的起点。我们在此报告了当使用病毒蛋白酶的酶活性作为筛选平台时，我们在设计和合成亚微摩尔共价抑制剂方面所做的努力。

  DOI：

  10.1016/j.ejmech.2021.114046
• 作为产物：
  描述：

  3-苯基-1-丙胺 在 三光气 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 3-苯基异氰酸丙酯
  参考文献：
  名称：

  加快合理设计非共价 SARS-CoV-2 主要蛋白酶抑制剂的方法

  摘要：

  SARS-CoV-2 的主要蛋白酶 (M pro ) 是经过验证的抗病毒药物靶点。据报道，几种 M pro抑制剂具有有效的酶抑制和细胞抗病毒活性，包括GC376 、 boceprevir 、钙蛋白酶抑制剂 II和XII ，每种抑制剂都含有共价修饰催化 Cys145 的反应弹头。将基于结构的药物设计与一锅 Ugi 四组分反应相结合，我们发现了最有效的非共价抑制剂之一23R ( Jun8-76-3A )，其结构与典型的 M pro抑制剂GC376不同。值得注意的是，与GC376等共价抑制剂相比， 23R具有高度选择性，尤其是针对宿主蛋白酶。 SARS-CoV-2 M pro与23R的共晶结构揭示了位于 S2 和 S4 口袋之间的先前未探索的结合位点。总体而言，这项研究发现了23R ，这是迄今为止报道的最有效和选择性最强的非共价 SARS-CoV-2 M pro抑制剂之一，以及 M pro中的一个新的结合口袋，可用于抑制剂设计。

  DOI：

  10.1021/acs.jmedchem.1c00509

文献信息

• Cyanation of Alcohols with Diethyl Cyanophosphonate and 2,6-Dimethyl-1,4-benzoquinone by a New Type of Oxidation–Reduction Condensation
  作者：Kouta Masutani、Tomofumi Minowa、Yoshiaki Hagiwara、Teruaki Mukaiyama

  DOI：10.1246/bcsj.79.1106

  日期：2006.7

  Cyanation of various alcohols by a new type of oxidation–reduction condensation is described. Primary alkyl diphenylphosphinites, 2,6-dimethyl-1,4-benzoquinone (DMBQ), and diethyl cyanophosphonate ...

  描述了通过新型氧化还原缩合对各种醇进行氰化。伯烷基二苯基次膦酸盐、2,6-二甲基-1,4-苯醌 (DMBQ) 和氰基膦酸二乙酯 ...
• Regioselective one-pot three component synthesis of chiral 2-iminoselenazolines under sonication
  作者：Wong-Jin Chang、Manohar V. Kulkarni、Chung-Ming Sun

  DOI：10.1039/c5ra18763j

  日期：——

  A one-pot multi component reaction of selenoureas, which are in situ generated from l-amino esters and isoselenocyanates, with α-bromoketone under ultrasonication.

  一锅多组分反应，利用从l-氨基酯和异硒氰酸酯生成的硒脲类化合物，在超声波作用下与α-溴酮发生反应。
• Microwave-Assisted Synthesis of Isonitriles:  A General Simple Methodology
  作者：Andrea Porcheddu、Giampaolo Giacomelli、Margherita Salaris

  DOI：10.1021/jo047924f

  日期：2005.3.1

  A facile conversion of formamides to isonitriles under very mild conditions and microwave irradiation is described. This simple and efficient method has been applied for the synthesis of both aliphatic and aromatic isonitriles in high yields.

  描述了在非常温和的条件下和微波辐射下甲酰胺向异腈的容易转化。这种简单而有效的方法已被用于高产率地合成脂族和芳族异腈。
• 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
• Synthesis of N-methyl alkylaminomethane-1,1-diphosphonic acids and evaluation of their complex-formation abilities towards copper(II)
  作者：Barbara Kurzak、Waldemar Goldeman、Magdalena Szpak、Ewa Matczak-Jon、Anna Kamecka

  DOI：10.1016/j.poly.2014.09.031

  日期：2015.1

  can be attributed to the steric effect imposed by cycloheptyl ring attached directly to the N atom. In addition to the main [Cu(HL) 2 ] complexes, with well-known O, O} chelating binding mode, [Cu(HL)L] and [CuL 2 ] species with the O, N} donor set, protonated dinuclear [Cu 2 H x L 3 ] ( x = 4, 5, 6) species have been detected in all studied systems. The nitrogen coordination in the [Cu(HL)L] and

  摘要在反应中合成了一系列具有共同叔氮原子（CH 3 –NR）的带有直链或支链烷基，环庚基或苯基烷基R取代基的N-甲基烷基氨基甲烷-1,1-二膦酸（3a-g）用原甲酸三乙酯和仲胺合成二乙基膦酸酯，然后水解，然后用甲酸和甲醛对烷基氨基甲烷-1,1-二膦酸进行Eschweiler-Clarke甲基化反应。通过pH电位法，ESI-MS光谱法，UV-Vis和EPR方法研究了3a-g对溶液中铜（II）的络合物形成能力。对3a-g的Cu（II）配合物的稳定常数的评估表明，它们依赖于R取代基施加的空间效应和电子效应的组合。已经证明，在N原子（3a，3d，3e）上具有直链或支链烷基的化合物与Cu（II）形成最稳定的配合物，最不稳定的是3f的配合物，这可以归因于所施加的空间效应通过直接与N原子连接的环庚基环 除了主要的[Cu（HL）2]配合物外，还有众所周知的O，O}螯合结合模式，具有[O，N}供体的[Cu（HL）L]和[CuL