邻硝基肉桂醛 | 1466-88-2

• 物质功能分类: 化学试剂 - 有机试剂 - 脂肪醛（含缩醛，半缩醛）
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 中文名称: 邻硝基肉桂醛
• 中文别名: 3-(2-硝基苯基)丙烯醛；2-硝基肉桂醛；3-(2-硝基苯基)-2-丙烯醛；2-硝基亚肉桂基醛
• 英文名称: 2-nitrocinnamaldehyde
• 英文别名: o-nitrocinnamaldehyde；o-Nitro-zimtaldehyd；3-(2-nitrophenyl)acrylaldehyde；ortho-nitrocinnamaldehyde；2-nitro-cinnamic aldehyde；2-Nitro-zimtaldehyd；3-(2-nitrophenyl)prop-2-enal
• CAS: 1466-88-2
• 化学式: C₉H₇NO₃
• mdl: MFCD00007188
• 分子量: 177.159
• InChiKey: VMSMELHEXDVEDE-UHFFFAOYSA-N

物化性质

• 熔点：
  127-129 °C(lit.)
• 沸点：
  309.06°C (rough estimate)
• 密度：
  1.3312 (rough estimate)
• 稳定性/保质期：

  如果按照规格使用和储存，通常不会分解，也没有已知的危险反应。应避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38,R36/38,R43
• WGK Germany：
  3
• 海关编码：
  2913000090
• 危险性防范说明：
  P264,P280,P302+P352+P332+P313+P362+P364,P305+P351+P338+P337+P313
• 危险性描述：
  H315,H319
• 储存条件：
  请将贮藏器密封存放于阴凉干燥处，并确保工作环境具有良好的通风或排气设施。

SDS

Name:	o-Nitrocinnamaldehyde Material Safety Data Sheet
Synonym:	None
CAS:	1466-88-2

Section 1 - Chemical Product MSDS Name:o-Nitrocinnamaldehyde Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1466-88-2	o-Nitrocinnamaldehyde	ca. 100	215-988-0

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.Air sensitive.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause 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:
Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. 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 if cough or other symptoms appear.
Notes to Physician:

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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.
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:
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 tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.)

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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# 1466-88-2: 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: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 124 - 126 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: slightly soluble
Specific Gravity/Density:
Molecular Formula: C9H7NO3
Molecular Weight: 177.16

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation, exposure to air.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong bases.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1466-88-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
o-Nitrocinnamaldehyde - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
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# 1466-88-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1466-88-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1466-88-2 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：

  邻硝基肉桂醛 在 双氧水 、 溶剂黄146 作用下， 生成 2-nitrocinnamic acid
  参考文献：
  名称：

  Phenanthridine Syntheses via the Diels-Alder Reaction. A New Route to 6(5)-Phenanthridinone

  摘要：

  DOI：

  10.1021/ja01600a078
• 作为产物：
  描述：

  o-Nitrozimtalkohol 在 2,2,6,6-四甲基哌啶氧化物 、 oxone 、 四乙基溴化铵 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.5h， 以54%的产率得到邻硝基肉桂醛
  参考文献：
  名称：

  使用 TEMPO-Oxone-Et4NBr 反应物系统对烯丙醇进行串联氧化溴化

  摘要：

  烯丙醇可在与 TEMPO、Oxone 和四乙基溴化铵的混合物的单一反应中直接转化为 α-溴-α、β-不饱和酮。该过程首先通过将醇氧化成酮，然后用由 Oxone 和四乙基溴化铵产生的溴对烯烃进行二溴化。然后用三乙胺淬灭反应促进消除并形成溴乙烯。芳环上给电子基团的存在导致更快的反应和更高的产率。或者，在芳环上装饰有吸电子基团的底物氧化较慢。该方法提供了一种使用操作简单的条件和稳定且易于处理的试剂来获取这些溴代烯烃的快速方法。

  DOI：

  10.1016/j.tetlet.2022.153994

文献信息

• A chiral organocatalytic polymer-based monolithic reactor
  作者：Valerio Chiroli、Maurizio Benaglia、Alessandra Puglisi、Riccardo Porta、Ravindra P. Jumde、Alessandro Mandoli

  DOI：10.1039/c4gc00031e

  日期：——

  properly modified enantiomerically pure imidazolidinone inside a stainless steel column in the presence of dodecanol and toluene as porogens afforded the first example of a chiral organocatalyst immobilized onto a monolithic reactor. Organocatalyzed cycloadditions between cyclopentadiene and cinnamic aldehyde were performed under continuous-flow conditions; by optimizing the experimental set up, excellent

  在十二烷基醇和甲苯作为致孔剂的存在下，在不锈钢塔内将二乙烯基苯与适当改性的对映体纯的咪唑啉酮进行自由基共聚反应提供了固定在整体式反应器上的手性有机催化剂的第一个实例。环戊二烯与肉桂醛之间的有机催化环加成反应是在连续流动条件下进行的。通过优化实验设置，可以获得出色的对映选择性（在25°C时为90％ee）和高生产率（高于330），因此表明催化反应器可以有效地连续生产对映体富集的化合物。同样的催化反应器也被用来连续地进行三种不同的立体选择性转化。，依次在手性色谱柱内（Diels–Alder，1，3-偶极硝酮-烯烃环加成和Friedel–Crafts烷基化）；在前两个反应的情况下获得了极好的结果（分别在25°C下达到99％的收率，93％ee和71％的收率，90％ee）。除了简化产物回收之外，整体式反应器在搅拌烧瓶中的性能优于相同的负载型有机催化剂，并且可以连续工作8天以上。
• Chiral Hybrid Inorganic–Organic Materials: Synthesis, Characterization, and Application in Stereoselective Organocatalytic Cycloadditions
  作者：Alessandra Puglisi、Maurizio Benaglia、Rita Annunziata、Valerio Chiroli、Riccardo Porta、Antonella Gervasini

  DOI：10.1021/jo401852v

  日期：2013.11.15

  evaluation of surface areas, pore dimensions, and catalyst loading. They were used in organocatalyzed Diels–Alder cycloadditions between cyclopentadiene and different aldehydes, affording results comparable to those obtained with the nonsupported catalyst (up to 91% yield and 92% ee in the model reaction between cyclopentadiene and cinnamic aldehyde). The catalysts were recovered from the reaction mixture

  据报道，利用两个不同的锚定位点和两个不同的接头，在中孔二氧化硅纳米粒子上合成手性咪唑烷酮。催化剂1 - 4制备来自开始升-苯丙氨酸或升-酪氨酸甲基酯和通过接枝协议或叠氮化物-炔烃铜（I） -催化的环加成支撑所述咪唑啉酮在硅胶上。四种催化剂均通过固态NMR N 2进行了充分表征物理吸附，SEM和TGA，以提供结构评估，包括表面积，孔尺寸和催化剂载量的评估。它们用于环戊二烯与不同醛之间的有机催化Diels-Alder环加成反应，其结果可与无载体催化剂获得的结果相媲美（在环戊二烯与肉桂醛之间的模型反应中，收率高达91％，ee为92％）。通过简单的过滤或离心从反应混合物中回收催化剂。活性最高的催化剂循环使用两次，但催化效率有所降低，而ee的侵蚀也很小。
• Direct construction of carbazoles from 2-methyl-indole-3-carbaldehydes and enals
  作者：Dehai Liu、Jie Huang、Zhenqian Fu、Wei Huang

  DOI：10.1039/c9gc00064j

  日期：——

  The direct and rapid construction of carbazoles was achieved via the reaction of 2-methyl-indole-3-carbaldehydes with enals promoted by LiCl/DBU in a single operation. This mild and green reaction proceeds through a [4 + 2] cycloaddition/dehydration/oxidative aromatization cascade to generate carbazoles in good to excellent yields. The reaction features mild reaction conditions, a broad substrate scope

  通过2-甲基-吲哚-3-甲醛与LiCl / DBU促进的烯醛在一次操作中的反应即可直接快速构建咔唑。这种温和而绿色的反应通过[4 + 2]环加成/脱水/氧化芳构化级联进行，从而生成咔唑，收率好至极佳。该反应具有温和的反应条件，广泛的底物范围和出色的官能团耐受性，使用O 2（1 atm）作为唯一氧化剂，并提供H 2 O作为唯一的副产物。更重要的是，仅需一步就可以从得到的咔唑生成80％收率的重要的生物活性化合物4-氟喹咔唑。
• Synthesis of Indoles by Reductive Cyclization of Nitro Compounds Using Formate Esters as CO Surrogates
  作者：Manar Ahmed Fouad、Francesco Ferretti、Dario Formenti、Fabio Milani、Fabio Ragaini

  DOI：10.1002/ejoc.202100789

  日期：2021.9.14

  A very efficient, general and scalable protocol for the preparation of indoles and other N-heterocycles from suitably substituted nitroarenes using alkyl and phenyl formates as CO surrogates was described. Using phenyl formate, the products were isolated in yields often higher than those previously achieved by using gaseous CO. The mechanism of both the decarbonylation reaction of phenyl formate and

  描述了使用烷基和苯基甲酸酯作为 CO 替代物从适当取代的硝基芳烃制备吲哚和其他N-杂环的非常有效、通用和可扩展的方案。使用甲酸苯酯，产物的分离产率通常高于以前使用气态 CO 实现的产率。通过动力学和机理研究阐明了甲酸苯酯的脱羰反应和环化反应的机理。
• Synthesis and Reactions of (Aroylthiomethyl)-triphenylphosphonium Bromides
  作者：Masaru ISHIDA、Taketoshi IWATA、Masato YOKOI、Kohichi KAGA、Shinzi KATO

  DOI：10.1055/s-1985-36591

  日期：——

  The synthesis of (aroylthiomethyl)-triphenylphosphonium bromides and the applications as an equivalent of (mercaptomethyl)-triphenylphosphonium bromide in the synthesis of aroyl vinyl sulfides (thioenolates) are described.

  报道了合成(芳酰基硫甲基)-三苯基膦溴化物的方法，并介绍了它们作为(巯甲基)-三苯基膦溴化物的等效物在合成芳酰基乙烯硫醚(硫代烯醇盐)中的应用。