二苯基甲基异氰化物 | 3128-85-6

• 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: 二苯基甲基异氰化物
• 英文名称: diphenylmethyl isocyanide
• 英文别名: (isocyanomethylene)dibenzene；benzhydryl isocyanide；diphenylmethanisocyanide；[isocyano(phenyl)methyl]benzene
• CAS: 3128-85-6
• 化学式: C₁₄H₁₁N
• mdl: MFCD02664566
• 分子量: 193.248
• InChiKey: REKQCRSUOJRCDV-UHFFFAOYSA-N

物化性质

• 熔点：
  45 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 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
• 危险品运输编号：
  UN 2811
• 海关编码：
  2926909090

SDS

Name:	Diphenylmethyl isocyanide 96% Material Safety Data Sheet
Synonym:	Isocyanodiphenyl methan
CAS:	3128-85-6

Section 1 - Chemical Product MSDS Name:Diphenylmethyl isocyanide 96% Material Safety Data Sheet
Synonym:Isocyanodiphenyl methan

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3128-85-6	Diphenylmethyl 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:
Vacuum or sweep up material and place into a suitable disposal 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# 3128-85-6: 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: Needles
Color: light yellow
Odor: stench
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 45 - 51 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: Insoluble.
Specific Gravity/Density:
Molecular Formula: C14H11N
Molecular Weight: 193.25

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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# 3128-85-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Diphenylmethyl 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 SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
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:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 3128-85-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 3128-85-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3128-85-6 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：

  二苯基甲基异氰化物 在 盐酸 、 sodium hydroxide 、 四丁基溴化铵 作用下， 以 甲醇 、 苯 为溶剂， 反应 26.0h， 生成 2-Amino-1,2,2-triphenyl-ethanol-(1)
  参考文献：
  名称：

  Uminski, Maciej; Jawdosiuk, Mikolaj, Polish Journal of Chemistry, 1983, vol. 57, # 1/3, p. 67 - 73

  摘要：

  DOI：
• 作为产物：
  描述：

  N-benzhydrylformamide 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以871 mg的产率得到二苯基甲基异氰化物
  参考文献：
  名称：

  A cation-directed two-component cascade approach to enantioenriched pyrroloindolines

  摘要：

  已经开发出一种级联方法，用于合成具有全碳四面体立体中心的复杂吡咯并吲哚烷。这一双组分过程使用手性铵盐来控制异构选择性和对映选择性，使异氰酸酯与功能化烯烃的加成反应生成具有多达三个立体中心的吡咯并吲哚烷。文中描述了一种涉及异氰酸酯分子内氢键活化的机理提议。

  DOI：

  10.1039/c4cc06683a

文献信息

• Efficient Assembly of Iminodicarboxamides by a “Truly” Four-Component Reaction
  作者：Kareem Khoury、Mantosh K. Sinha、Tadamichi Nagashima、Eberhardt Herdtweck、Alexander Dömling

  DOI：10.1002/anie.201205366

  日期：2012.10.8

  Mix and match: Similar to a galaxy consisting of millions of stars, a multicomponent reaction (MCR) system can result in millions of compounds. The MCR of α‐amino acids, oxo components, isocyanides, and amines leads to numerous and diverse compounds, thus having enormous potential for drug discovery or catalyst screening.

  混合搭配：类似于由数百万颗恒星组成的星系，多组分反应 (MCR) 系统可以产生数百万种化合物。α-氨基酸、含氧组分、异氰化物和胺的 MCR 导致产生大量不同的化合物，因此在药物发现或催化剂筛选方面具有巨大的潜力。
• β-Elimination of the isonitrile group in alkylation reactions of C–H acids activated by the isonitrile function
  作者：Mikołaj Jawdosiuk、Maciej Umiński

  DOI：10.1039/c39820000979

  日期：——

  During phase-transfer alkylation of the isonitriles R1R2CHNC with X–CH2–Y, where X is a leaving group and Y an electron withdrawing group, some of the alkylation products undergo β-elimination of the isonitrile function to yield R1R2CCHY.

  在异氰酸酯R 1 R 2 CHNC用X–CH 2 –Y进行相转移烷基化的过程中，其中X是一个离去基团，Y是一个吸电子基团，一些烷基化产物会经历β-消除的异腈官能团，从而生成R 1 R 2 C CHY。
• Exploring tertiary enamides as versatile synthons in organic synthesis
  作者：Mei-Xiang Wang

  DOI：10.1039/c4cc10327k

  日期：——

  Tertiary enamides have long been thought of as stable and marginally valuable enamine variants in synthesis. This notion has been challenged, however, in recent years. Enabling the regulation of the cross-conjugation system of the tertiary enamides has been successfully shown to enhance delocalization of the nitrogen lone-pair electrons into a carbon-carbon double, thereby reinvigorating the enaminic

  长期以来一直认为叔酰胺是合成中稳定的和边际上有价值的烯胺变体。但是，近年来，这一概念受到了挑战。已成功地显示出使叔酰胺的交叉缀合系统的调节能够增强氮孤对电子的离域化为碳-碳双键，从而使叔酰胺的烯胺反应性恢复活力。在本文中，我总结了叔酰胺类化合物亲核反应探索的最新进展及其在天然产物和具有生物学和药学意义的杂环化合物的合成中的应用，主要侧重于我们自己的工作。
• Synthesis of Multifunctionalized 1,2,3,4-Tetrahydropyridines, 2,3-Dihydropyridin-4(1H)-ones, and Pyridines from Tandem Reactions Initiated by [5+1] Cycloaddition of N-Formylmethyl-Substituted Enamides to Isocyanides: Mechanistic Insight and Synthetic Appl
  作者：Chuan-Hu Lei、De-Xian Wang、Liang Zhao、Jieping Zhu、Mei-Xiang Wang

  DOI：10.1002/chem.201303221

  日期：2013.12.9

  trans‐3‐hydroxy‐4‐arylamino‐ or ‐alkylamino‐1,2,3,4‐tetrahydropyridines, whereas acylation of the imino group followed by acidic hydrolysis produced 1,6‐disubstituted 3‐acyloxy‐2,3‐dihydropyridin‐4(1H)‐ones. Aerobic oxidation led to the aromatization followed by intermolecular acyl‐group transfer from the pyridinium nitrogen to the 3‐hydroxy moiety, thereby yielding substituted 3‐acyloxy‐4‐aminopyridines. Synthetic

  串联反应可有效合成多功能的1,2,3,4-四氢吡啶，2,3-二氢吡啶-4（1 H）-酮和吡啶衍生物，并研究了反应机理。合成级联反应是由N-甲酰基甲基取代的叔酰胺经Zn（OTf）2介导的[5 + 1]环加成反应成异氰酸酯的，因此导致了多功能的杂环烯胺亚胺中间体。通过用Me 4 NBH（OAc）3非对映选择性还原亚胺官能团来拦截中间体，得到1,6-二取代的反式-3-羟基-4-芳基氨基或烷基氨基1,2,3,4-四氢吡啶，而亚氨基的酰化再进行酸性水解则产生1,6-二取代的3-酰氧基-2,3-二氢吡啶4（ 1 H）-个。有氧氧化导致芳构化，随后分子内的酰基基团从吡啶鎓氮转移到3-羟基部分，从而产生取代的3-酰氧基-4-氨基吡啶。顺式，顺式-4,5--4-二羟基-2-苯基哌啶和反式，反式-4-氨基-5-羟基-2-苯基哌啶化合物的便捷，立体选择性合成证明了所得产物的合成潜力，这很重要。在药物化学中，通过简单而实用的还原反应。
• De Novo Assembly of Highly Substituted Morpholines and Piperazines
  作者：Pravin Patil、Rudrakshula Madhavachary、Katarzyna Kurpiewska、Justyna Kalinowska-Tłuścik、Alexander Dömling

  DOI：10.1021/acs.orglett.6b03807

  日期：2017.2.3

  The morpholine and piperazine with their remarkable physical and biochemical properties are popular heterocycles in organic and medicinal chemistry used in rational property design. However, in the majority of cases these rings are added to an existing molecule in a building block approach thus limiting their substitution pattern and diversity. Here we introduce a versatile de novo synthesis of the

  吗啉和哌嗪具有出色的物理和生化特性，是有机和药物化学中常用的杂环，用于合理的特性设计。然而，在大多数情况下，这些环以构件方式添加到现有分子中，从而限制了它们的取代方式和多样性。在这里，我们介绍了使用多组分反应化学方法对吗啉和哌嗪环进行通用的从头合成。可以在多达四个位置上进一步替代大规模的宜居构建基块，这使其成为一种非常通用的支架合成策略。因此，我们的方法满足了对新型积木设计和以前无法获得的非传统支架的日益增长的需求