2-硝基-5-甲氧基苯腈 | 38469-84-0

• 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-硝基-5-甲氧基苯腈
• 中文别名: 5-甲氧基-2-硝基苯腈；5-甲氧基-2-硝基苯甲腈
• 英文名称: 5-methoxy-2-nitrobenzonitrile
• 英文别名: 2-nitro-5-methoxybenzonitrile
• CAS: 38469-84-0
• 化学式: C₈H₆N₂O₃
• 分子量: 178.147
• InChiKey: GCXTYFJQZDWUNU-UHFFFAOYSA-N

物化性质

• 熔点：
  96 °C
• 沸点：
  352.2±32.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  78.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2926909090
• 危险性防范说明：
  P280
• 危险性描述：
  H302+H312+H332
• 储存条件：
  室温且干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Methoxy-2-nitrobenzonitrile
Synonyms: 3-Cyano-4-nitroanisole

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 5-Methoxy-2-nitrobenzonitrile
CAS number: 38469-84-0

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
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.
Store in closed vessels.
Storage:

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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
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C8H6N2O3
Molecular weight: 178.1

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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
Non-harzardous for air and ground transportation.

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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-硝基-5-甲氧基苯腈 在 palladium on activated charcoal potassium peroxomonosulphate 、 氢气 作用下， 生成 5-Methoxy-2-nitrosobenzonitril
  参考文献：
  名称：

  Norris,R.K.; Sternhell,S., Australian Journal of Chemistry, 1972, vol. 25, p. 2621 - 2629

  摘要：

  DOI：
• 作为产物：
  描述：

  5-甲氧基-2-硝基苯甲酸 在 ammonium acetate 、 氧气 、 copper (I) acetate 、 silver sulfate 、 丙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以63%的产率得到2-硝基-5-甲氧基苯腈
  参考文献：
  名称：

  一种以芳基羧酸为原料的芳基氰化物合成方法

  摘要：

  本发明公开了一种以芳基羧酸为原料的芳基氰化物合成方法，通过以芳基羧酸为原料，NH4X和N,N‑二甲基甲酰胺组合为氰源，硫酸银和醋酸铜为催化剂，在酸和氧气的作用下，合成芳基氰化物。与常规的芳基氰化物合成方法相比，本发明方法具有反应原料(芳基羧酸、NH4X和N,N‑二甲基甲酰胺)廉价易得、金属催化剂用量小的优点；同时以氧气为氧化剂具有对环境污染小、对芳环上的多种官能团有良好的容忍性、产率高等明显优势；本发明方法能广泛应用于工业界和学术界的药物、功能材料、天然产物等领域的合成中。

  公开号：

  CN111499539B

文献信息

• Selective reduction of aromatic nitro compounds with stannous chloride in non acidic and non aqueous medium
  作者：F.D. Bellamy、K. Ou

  DOI：10.1016/s0040-4039(01)80041-1

  日期：1984.1

  Aromatic nitro compounds are readily reduced by SnCl2, 2 H2O in alcohol or ethyl acetate or by anhydrous SnCl2 in alcohol where other reducible or acid sensitive groups such as aldehyde, ketone, ester, cyano, halogen and O-benzyl remain unaffected.

  醇或乙酸乙酯中的SnCl 2，2 H 2 O或醇中的无水SnCl 2可以很容易地还原芳香硝基化合物，而醛，酮，酯，氰基，卤素和O-苄基等其他可还原或酸敏感基团则不受影响。
• Metal-free chemoselective reduction of nitroaromatics to anilines via hydrogen transfer strategy
  作者：Qi Shuai、Jun Li、Feng Zhao、Weike Su、Guojun Deng

  DOI：10.1007/s11696-018-0634-0

  日期：2019.4

  A novel protocol for chemoselective reduction of aromatic nitro compounds to aromatic amines has been established. The metal-free reduction goes through a hydrogen transfer process. Various easily reducible functional groups can be well tolerated under the optimized reaction conditions.

  建立了将芳香族硝基化合物化学选择性还原为芳香族胺的新方案。无金属还原通过氢转移过程进行。在优化的反应条件下，各种容易还原的官能团都可以被很好地耐受。
• Copper-Catalyzed One-Pot Synthesis of Quinazolinones from 2-Nitrobenzaldehydes with Aldehydes: Application toward the Synthesis of Natural Products
  作者：Subrata Sahoo、Shantanu Pal

  DOI：10.1021/acs.joc.1c02343

  日期：2021.12.17

  A novel, efficient, and atom-economical approach for the construction of quinazolinones from 2-nitrobenzaldehydes has been unveiled via copper-catalyzed nitrile formation, hydrolysis, and reduction in one pot for the first time. In this reaction, urea is used as a source of nitrogen for nitrile formation, hydrazine hydrate is used for both the reduction of the nitro group and the hydrolysis of nitrile

  首次通过铜催化的腈形成、水解和还原在一个锅中揭示了一种从 2-硝基苯甲醛构建喹唑啉酮的新型、高效和原子经济的方法。在该反应中，尿素用作生成腈的氮源，水合肼用于硝基的还原和腈的水解，大气中的氧气用作唯一的氧化剂。该方法描绘了具有良好官能团耐受性的宽底物范围。此外，该方法还用于合成裂殖菌素、色胺菊酯、phaitanthrin-A、phaitanthrin-B和8 H-喹唑啉[4,3 - b ]quinazolin-8-one。
• A Novel Iron-catalyzed One-pot Synthesis of 3-Amino-1,2,4-triazoles
  作者：Taoufik Rohand、Victor N. Mkpenie、Mohammadine El Haddad、István E. Markó

  DOI：10.1002/jhet.3450

  日期：2019.2

  A novel one‐pot synthesis of 3‐amino‐1,2,4‐triazole developed via iron (III) catalyzed route is reported. The new method is more efficient, simple, and convenient and presents a concise new strategy for the synthesis of 3‐amino‐1,2,4‐triazole derivatives. The iron (III) complex intermediate assisted in the intramolecular bond cyclization owing to its Lewis acidity or oxidizing properties. A series

  据报道，通过铁（III）催化途径开发的一种新型一锅法合成3-氨基1,2,4-三唑。该新方法更加高效，简单和方便，为合成3‐氨基1,2,4‐三唑衍生物提出了一种简洁的新策略。铁（III）配合物中间体由于其路易斯酸度或氧化特性而有助于分子内键的环化。还研究了一系列在对位和/或邻位带有取代的给电子和吸电子基团的芳族腈。取代基的位置影响最终化合物的收率，对位取代的底物收率相对较高。
• Substituted 3-(aminoalkylamino)-1,2-benzisoxazoles and related compounds
  申请人：Hoechst-Roussel Pharmaceutical Incorporated

  公开号：US05494908A1

  公开（公告）日：1996-02-27

  This application relates to compounds of the formula ##STR1## wherein R.sup.1, X, Y and n are as defined in the specification; and pharmaceutically acceptable addition salts thereof and optical and geometric isomers or racemic mixtures thereof; which compounds are useful for the treatment of various memory dysfunctions characterized by a decreased cholinergic function such as Alzheimer's disease. Compounds of this invention also inhibit monoamine oxidase and hence are useful as antidepressants.

  这种应用涉及到式##STR1##的化合物，其中R.sup.1、X、Y和n如规范中所定义；以及其药学上可接受的加合盐和其光学和几何异构体或消旋混合物；这些化合物对于治疗由于胆碱功能降低而表现出的各种记忆功能障碍，如阿尔茨海默病，是有用的。本发明的化合物还抑制单胺氧化酶，因此可用作抗抑郁药。