1-甲基-5-硝基-1H-吲哚 | 29906-67-0

• 物质功能分类: 医药中间体 - 杂环化合物 - 吲哚类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1-甲基-5-硝基-1H-吲哚
• 中文别名: 1-甲基-5-硝基吲哚
• 英文名称: 1-methyl-5-nitro-1H-indole
• 英文别名: 1-methyl-5-nitroindole；N-methyl-5-nitroindole；5-nitro-N-methylindole；5-nitro-1-methylindole
• CAS: 29906-67-0
• 化学式: C₉H₈N₂O₂
• 分子量: 176.175
• InChiKey: PXBQSCHRKSBGKV-UHFFFAOYSA-N

物化性质

• 熔点：
  167 °C
• 沸点：
  339.2±15.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S26,S39
• 危险类别码：
  R22,R41
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Methyl-5-nitro-1h-indole
Synonyms:

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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: 1-Methyl-5-nitro-1h-indole
CAS number: 29906-67-0

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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, refrigerated.
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: C9H8N2O2
Molecular weight: 176.2

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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
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

制备方法与用途

简介

1-甲基-5-硝基-1H-吲哚是一种吲哚类化合物。吲哚类化合物广泛存在于具有生物活性的天然产物中，是自然界中最为丰富的杂环化合物之一。1866年，德国化学家Adolf von Baeyer首次通过人工方法合成了吲哚，并证实了其化学结构。最初，尽管已能合成和应用吲哚类杂环化合物，但并没有引起广泛关注。

用途

1-甲基-5-硝基-1H-吲哚主要用于医药中间体的制备。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  5-硝基吲哚	5-nitroindole	6146-52-7	C8H6N2O2	162.148
  6-硝基吲哚	6-nitroindole	4769-96-4	C8H6N2O2	162.148

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  1-甲基-1H-吲哚-5-胺	1-methyl-1H-indol-5-amine	102308-97-4	C9H10N2	146.192
  ——	N-(1-methyl-1H-indol-5-yl)phenylamine	——	C15H14N2	222.29
  ——	N-(1-methyl-1H-indol-5-yl)formamide	——	C10H10N2O	174.202
  1,4-二甲基-5-硝基吲哚	1,4-dimethyl-5-nitroindole	143797-99-3	C10H10N2O2	190.202
  ——	1-methyl-N-(naphthalen-1-yl)-1H-indol-5-amine	——	C19H16N2	272.349
  ——	1-methyl-5-nitro-1H-indole-3-carbonitrile	——	C10H7N3O2	201.184
  ——	1-methyl-5-nitro-1H-indole-3-carbaldehyde	3558-10-9	C10H8N2O3	204.185
  ——	N-benzyl-1-methyl-1H-indol-5-amine	114650-53-2	C16H16N2	236.316
  N-(1-甲基-1H-吲哚-5-基)肼羧酰胺	N-(1-methyl-1H-indol-5-yl)-semicarbazide	958888-24-9	C10H12N4O	204.231
  ——	N-(4-methoxyphenyl)-1-methyl-1H-indol-5-amine	1369116-47-1	C16H16N2O	252.316

反应信息

• 作为反应物：
  描述：

  1-甲基-5-硝基-1H-吲哚 在 N-甲基吗啉 、 palladium 10% on activated carbon 、 氢气 、 silver(l) oxide 作用下， 以 1,4-二氧六环 为溶剂， 20.0~100.0 ℃ 、350.01 kPa 条件下， 生成 扎鲁司特
  参考文献：
  名称：

  抗哮喘药物扎鲁司特的简明替代合成

  摘要：

  摘要 描述了扎鲁司特 (1) 的简洁和替代合成。该合成具有步骤少、合成收敛、中间体新颖等特点。图形概要

  DOI：

  10.1080/00397911.2011.603875
• 作为产物：
  描述：

  1-甲基-5-硝基吲哚啉 在 4-二甲氨基吡啶 、 ethyl 2-(4-nitrophenyl)hydrazinecarboxylate 、 氧气 、 copper(l) chloride 作用下， 以 乙腈 为溶剂， 以18 %的产率得到1-甲基-5-硝基-1H-吲哚
  参考文献：
  名称：

  偶氮/酰肼氧化还原铜催化叔吲哚有氧氧化脱氢生成吲哚

  摘要：

  偶氮化合物用途广泛，用途广泛。它们是光延反应和脱氢反应中的关键试剂。然而，偶氮化合物或其相应的酰肼从未在叔胺催化脱氢中进行过研究。在此，我们报道了一种使用 CuCl、4-(二甲基氨基)吡啶 (DMAP) 和 2-(4-硝基苯基)肼-1-羧酸酯的共催化系统，用于将叔吲哚啉有氧氧化脱氢为其相应的吲哚。

  DOI：

  10.1039/d3nj05172b
• 作为试剂：
  描述：

  4-溴甲基-3-甲氧基苯甲酸甲酯 、 1-甲基-5-硝基-1H-吲哚 在 1-甲基-5-硝基-1H-吲哚 作用下， 以62的产率得到3-甲氧基-4-(1-甲基-5-硝基-1H-吲哚-3-甲基)苯甲酸
  参考文献：
  名称：

  Org. Process Res. Dev. 2004, 8, 952-954

  摘要：

  DOI：

文献信息

• Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20150231142A1

  公开（公告）日：2015-08-20

  The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

  本发明涉及含有上皮钠通道活性抑制剂与至少一种ABC转运蛋白调节剂化合物（A式、B式、C式或D式）的药物组合物。该发明还涉及这些药物配方，以及使用这些组合物治疗CFTR介导的疾病，特别是囊性纤维化的方法。
• Chemoselective transfer hydrogenation of nitroarenes by highly dispersed Ni-Co BMNPs
  作者：Jia-wei Zhang、Guo-ping Lu、Chun Cai

  DOI：10.1016/j.catcom.2016.05.023

  日期：2016.9

  Highly dispread Ni-Co bimetallic nanoparticles (Ni-Co BMNPs) are synthesized and applied as an efficient catalyst in the chemoselective transfer hydrogenation of nitroarenes (CTH) using hydrazine hydrate as the hydrogen donor. The BMNPs can efficiently catalyze the reduction reaction without any additives under mild conditions with high TOF. Significantly higher activity is achieved when compared with

  合成了高度分散的Ni-Co双金属纳米颗粒（Ni-Co BMNPs），并使用水合肼作为氢供体，将其作为有效的催化剂用于硝基芳烃（CTH）的化学选择性转移加氢。在高TOF的温和条件下，无需任何添加剂，BMNP即可有效催化还原反应。与相应的单组分催化剂相比，可以显着提高活性，筛选出Ni-Co BMNPs的最佳组成，事实证明这对选择性和收率都至关重要。Ni-Co BMNP的出色性能归因于BMNPs表面活性位点的改善分散性（与Ni NPs相比）以及电子从钴到镍的转移。
• Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications
  作者：Lixing Zhao、Chenyang Hu、Xuefeng Cong、Gongda Deng、Liu Leo Liu、Meiming Luo、Xiaoming Zeng

  DOI：10.1021/jacs.0c12318

  日期：2021.1.27

  Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for

  利用 N-杂环卡宾作为非无害配体促进转化的过渡金属催化尚未得到很好的研究。我们在这里报告了具有成本效益的铬催化的环状（烷基）（氨基）卡宾（CAAC）配体促进的硝基脱氧硼氢化反应。使用 1 mol % 的 CAAC-Cr 预催化剂，将 HBpin 添加到硝基支架上会导致脱氧，从而保留各种可还原的官能团和敏感基团对硼氢化的相容性，从而提供一种温和、化学选择性和易于形成的策略苯胺，以及杂芳基和脂肪胺衍生物，具有广泛的范围和特别高的转换数（高达 1.8 × 106）。基于理论计算的机械研究，表明CAAC配体在促进HBpin氢化物极性反转中起重要作用；它用作 H 穿梭以促进脱氧硼氢化。通过这种策略制备的几种市售药物突出了其在药物化学中的潜在应用。
• COMPOSITIONS FOR TREATMENT OF CYSTIC FIBROSIS AND OTHER CHRONIC DISEASES
  申请人：Van Goor Fredrick F.

  公开号：US20110098311A1

  公开（公告）日：2011-04-28

  The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

  本发明涉及包含上皮钠通道活性抑制剂与至少一种ABC转运蛋白调节剂化合物（A式、B式、C式或D式）的药物组合物。该发明还涉及这些药物配方，以及使用这些组合物治疗CFTR介导的疾病，特别是囊性纤维化的方法。
• Cyanation of indoles with benzyl cyanide as the cyanide anion surrogate
  作者：Lianpeng Zhang、Qiaodong Wen、Jisong Jin、Chen Wang、Ping Lu、Yanguang Wang

  DOI：10.1016/j.tet.2013.03.089

  日期：2013.5

  A copper-mediated direct cyanation of indoles with benzyl cyanide as the cyanide anion surrogate has been achieved. The cascade reaction furnished 3-cyanoindoles under mild reaction conditions in good to excellent yields with various functional groups tolerance.

  已经实现了用苄基氰化物作为氰化物阴离子替代物对吲哚进行铜介导的直接氰化。该级联反应在温和的反应条件下提供了3-氰基吲哚，具有良好的收率和优异的产率，并具有各种官能团耐受性。