2-(4,5-二甲氧基-2-硝基苯基)乙腈 | 17354-04-0

• 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: 2-(4,5-二甲氧基-2-硝基苯基)乙腈
• 中文别名: 4,5-二甲氧基-2-硝基-苯乙腈
• 英文名称: 2-(4,5-dimethoxy-2-nitrophenyl)acetonitrile
• 英文别名: 4,5-dimethoxy-2-nitrophenylacetonitrile；4,5-Dimethoxy-2-nitrobenzylcyanid；4-nitro-5-cyanomethylveratrole；(4,5-dimethoxy-2-nitro-phenyl)-acetonitrile；(4,5-Dimethoxy-2-nitro-phenyl)-acetonitril
• CAS: 17354-04-0
• 化学式: C₁₀H₁₀N₂O₄
• mdl: MFCD00033967
• 分子量: 222.2
• InChiKey: PKDJSFDIQCAPSY-UHFFFAOYSA-N

物化性质

• 熔点：
  110-112℃
• 沸点：
  398.5±37.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 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：
  88.1
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险等级：
  6.1
• 海关编码：
  2926909090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P312,P332+P313,P337+P313
• 危险品运输编号：
  3439
• 危险性描述：
  H302,H311,H315,H319,H332,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(4,5-Dimethoxy-2-nitrophenyl)acetonitrile
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H311: Toxic in contact with skin
H302: Harmful if swallowed
H332: Harmful if inhaled
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P361: Remove/Take off immediately all contaminated clothing
IF exposed or you feel unwell:
P309:
P310: Immediately call a POISON CENTER or doctor/physician

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Section 3. Composition/information on ingredients.
Ingredient name: 2-(4,5-Dimethoxy-2-nitrophenyl)acetonitrile
CAS number: 17354-04-0

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H10N2O4
Molecular weight: 222.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
UN Number: UN3439 Class: 6.1 Packing group: III
Proper shipping name: NITRILES, TOXIC, SOLID, N.O.S. (2-(4,5-Dimethoxy-2-nitrophenyl)acetonitrile)

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-(4,5-二甲氧基-2-硝基苯基)乙腈 在 镍 、 乙酸乙酯 作用下， 生成 (2-amino-4,5-dimethoxy-phenyl)-acetonitrile
  参考文献：
  名称：

  Plieninger; Nogradi, Chemische Berichte, 1955, vol. 88, p. 1961

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二甲氧基苯乙腈 在 硝酸 、 溶剂黄146 作用下， 生成 2-(4,5-二甲氧基-2-硝基苯基)乙腈
  参考文献：
  名称：

  微波辅助Cadogan反应设计和合成吲哚[3,2- c ]香豆素的简便方法

  摘要：

  在水杨醛和2-（4,5-二甲氧基-2-硝基苯基）乙腈中，通过Perkin制备了在香豆素系统的苯环上带有各种取代基的3-（4,5-二甲氧基-2-硝基苯基）香豆素。缩合。这些3-芳基香豆素通过微波辅助的Cadogan反应进一步环化得到相应的吲哚并[3，2- c ]香豆素，收率很好。

  DOI：

  10.1016/j.tetlet.2013.08.030

文献信息

• Active and Recyclable Catalytic Synthesis of Indoles by Reductive Cyclization of 2-(2-Nitroaryl)acetonitriles in the Presence of Co–Rh Heterobimetallic Nanoparticles with Atmospheric Hydrogen under Mild Conditions
  作者：Isaac Choi、Hyunho Chung、Jang Won Park、Young Keun Chung

  DOI：10.1021/acs.orglett.6b02659

  日期：2016.11.4

  cobalt–rhodium heterobimetallic nanoparticle-catalyzed reductive cyclization of 2-(2-nitroaryl)acetonitriles to indoles has been achieved. The tandem reaction proceeds without any additives under the mild conditions (1 atm H2 and 25 °C). This procedure could be scaled up to the gram scale. The catalytic system is significantly stable under these reaction conditions and could be reused more than ten times without

  钴-铑异双金属纳米粒子催化的2-（2-硝基芳基）乙腈还原环化成吲哚。在温和条件下（1 atm H 2和25°C），串联反应在没有任何添加剂的情况下进行。该过程可以按比例放大至克级。在这些反应条件下，催化体系非常稳定，可以重复使用十次以上，而不会损失催化活性。
• Palladium-Catalyzed Dual Annulation: A Method for the Synthesis of Norneocryptolepine
  作者：Li-Hsuan Yeh、Hung-Kai Wang、Gangaram Pallikonda、Yu-Lun Ciou、Jen-Chieh Hsieh

  DOI：10.1021/acs.orglett.9b00287

  日期：2019.3.15

  Pd-catalyzed dual annulation reaction to synthesize the norneocryptolepine derivatives involving the concerted construction of two central heterocycles is reported. The further methylation of the norneocryptolepine to afford its alkaloid analog neocryptolepine implies that synthesis of various neocryptolepine derivatives is feasible. The oxidative addition of Pd(0) is indicated as the key step to activate the

  报道了一种新型的钯催化双环合反应合成壬基隐油菜碱衍生物的新方法，该过程涉及两个中心杂环的协同构建。去甲隐油菜籽进一步的甲基化以提供其生物碱类似物新隐油菜籽暗示了各种新隐油菜籽衍生物的合成是可行的。根据机理研究表明，Pd（0）的氧化加成是激活腈分子内加成的关键步骤。
• A convenient approach to the design and synthesis of indolo[3,2-c]coumarins via the microwave-assisted Cadogan reaction
  作者：Roman A. Irgashev、Arseny A. Karmatsky、Pavel A. Slepukhin、Gennady L. Rusinov、Valery N. Charushin

  DOI：10.1016/j.tetlet.2013.08.030

  日期：2013.10

  prepared from salicylaldehydes and 2-(4,5-dimethoxy-2-nitrophenyl)acetonitrile by means of the Perkin condensation. Further cyclization of these 3-aryl coumarins through the microwave-assisted Cadogan reaction afforded the corresponding indolo[3,2-c]coumarins in good to excellent yields.

  在水杨醛和2-（4,5-二甲氧基-2-硝基苯基）乙腈中，通过Perkin制备了在香豆素系统的苯环上带有各种取代基的3-（4,5-二甲氧基-2-硝基苯基）香豆素。缩合。这些3-芳基香豆素通过微波辅助的Cadogan反应进一步环化得到相应的吲哚并[3，2- c ]香豆素，收率很好。
• INHIBITORS OF HISTONE METHYLTRANSFERASE G9a
  申请人：AbbVie Inc.

  公开号：US20150274660A1

  公开（公告）日：2015-10-01

  Described herein are compounds, pharmaceutical compositions and methods for treating cancer, inflammation, or autoimmune disease in a subject, or for inhibiting histone methyltransferase G9a.

  本文介绍了一种用于治疗癌症、炎症或自身免疫疾病，或用于抑制组蛋白甲基转移酶G9a的化合物、药物组合物和方法。
• Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis–Beirut Reaction
  作者：Jie S. Zhu、Jung-Ho Son、Andrew P. Teuthorn、Makhluf J. Haddadin、Mark J. Kurth、Dean J. Tantillo

  DOI：10.1021/acs.joc.7b01521

  日期：2017.10.20

  Davis–Beirut reaction is described in which an atypical heterocyclic framework (the anthranil or benzo[c]isoxazole framework) is formed as the result of diversion of a key reactive intermediate away from its expected reactivity—a potentially general approach to reaction design and development. Experimental and computational support for the proposed mechanism and origins of altered reactivity are described

  描述了戴维斯-贝鲁特反应的一个新变化形式，发现其中一个非典型的杂环骨架（蒽或苯并[ c ]异恶唑骨架）是由于关键的反应性中间体从其预期的反应性转移而来的结果而形成的-反应设计和开发的潜在通用方法。描述了对所提出的机制和反应性改变的起源的实验和计算支持。