3-氨基-5-硝基吲唑 | 41339-17-7

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 3-氨基-5-硝基吲唑
• 中文别名: 3-氨基-5-硝基-1H-吲唑
• 英文名称: 5-nitro-1H-indazol-3-amine
• 英文别名: 5-Nitro-1H-indazole-3-ylamine
• CAS: 41339-17-7
• 化学式: C₇H₆N₄O₂
• mdl: MFCD00179824
• 分子量: 178.15
• InChiKey: SWZRTDLKPZAFDT-UHFFFAOYSA-N

物化性质

• 熔点：
  254-256°C
• 沸点：
  485.2±25.0 °C(Predicted)
• 密度：
  1.631±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26
• 危险类别码：
  R20/21/22
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  | 2-8°C |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Amino-5-nitroindazole
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: 3-Amino-5-nitroindazole
CAS number: 41339-17-7

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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: C7H6N4O2
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

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
  3-氨基吲唑	3-aminoindazole	874-05-5	C7H7N3	133.153

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	3-Methylamino-5-nitroindazol	80837-91-8	C8H8N4O2	192.177
  ——	2-methyl-5-nitro-2H-indazol-3-ylamine	58890-55-4	C8H8N4O2	192.177
  1-甲基-5-硝基-1H-吲唑-3-胺	1-methyl-5-nitro-1H-indazol-3-ylamine	73105-48-3	C8H8N4O2	192.177
  ——	tert-butyl (5-nitro-1H-indazol-3-yl)carbamate	——	C12H14N4O4	278.268
  ——	N,N,2-trimethyl-5-nitro-2H-indazol-3-amine	77894-82-7	C10H12N4O2	220.231
  ——	N,N,1-trimethyl-5-nitro-1H-indazol-3-amine	77894-76-9	C10H12N4O2	220.231
  ——	(5-nitro-1H-indazol-3-yl)-thiazol-2-yl-methylamine	1027258-98-5	C11H9N5O2S	275.291
  ——	(5-nitro-1H-indazol-3-yl)-oxazol-2-yl-methylamine	1027258-42-9	C11H9N5O3	259.224
  N-(5-硝基-1H-吲唑-3-基)苯甲酰胺	N-(5-nitro-1H-indazol-3-yl)benzamide	599183-43-4	C14H10N4O3	282.258
  ——	3-amino-5-nitro-indazole-2-carboxylic acid ethyl ester	60329-99-9	C10H10N4O4	250.214

反应信息

• 作为反应物：
  描述：

  3-氨基-5-硝基吲唑 在 ammonium cerium (IV) nitrate 、 1,3-二溴-5,5-二甲基海因 、 水 作用下， 以 乙腈 为溶剂， 生成 6-nitrobenzo[d][1,2,3]triazin-4(3H)-one
  参考文献：
  名称：

  通过酸促进苯并三嗪酮的脱氮转环组装苯并[c][1,2]二硫醇-3-酮

  摘要：

  通过苯并三嗪酮的无金属脱氮环环化，开发了苯并[ c ][1,2]二硫醇-3-酮的便捷合成方法，这是酸介导苯并三嗪酮杂环化的第一个例子。这种新发现的苯并三嗪酮的反应活性使得通过使用硫化钠作为硫源在简单的反应条件下能够以良好的产率简化合成各种苯并[ c ][1,2]二硫醇-3-酮。

  DOI：

  10.1021/acs.orglett.2c03638
• 作为产物：
  描述：

  3-氨基吲唑 在 硫酸 、 硝酸 作用下， 反应 3.5h， 生成 3-氨基-5-硝基吲唑
  参考文献：
  名称：

  Gorelik; Lomzakova; Khamidova, Russian Journal of Organic Chemistry, 1996, vol. 32, # 11, p. 1682 - 1689

  摘要：

  DOI：

文献信息

• [EN] SUBSTITUTED TETRAHYDROISOQUINOLINE COMPOUNDS AS FACTOR XIA INHIBITORS<br/>[FR] COMPOSÉS TÉTRAHYDROISOQUINOLINES SUBSTITUÉS EN TANT QU'INHIBITEURS DU FACTEUR XIA
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2013055984A1

  公开（公告）日：2013-04-18

  The present invention provides compounds of Formula (I): or stereoisomers, pharmaceutically acceptable salts thereof, wherein all of the variables are as defined herein. These compounds are inhibitors of factor XIa and/or plasma kallikrein which may be used as medicaments.

  本发明提供了化合物的公式(I)：或其立体异构体，以及其药学上可接受的盐，其中所有变量如本文所定义。这些化合物是XIa因子和/或血浆激肽酶的抑制剂，可用作药物。
• Protein kinase affinity reagents based on a 5-aminoindazole scaffold
  作者：Ratika Krishnamurty、Amanda M. Brock、Dustin J. Maly

  DOI：10.1016/j.bmcl.2010.10.069

  日期：2011.1

  powerful tools for signal transduction research. Here, we describe a general set of kinase ligands based on a 5-aminoindazole scaffold. This scaffold can readily be derivatized with diverse binding elements and immobilized analogs allow selective enrichment of protein kinases from complex mixtures.

  靶向蛋白激酶的亲和试剂是信号转导研究的强大工具。在这里，我们描述了一组基于 5-氨基吲唑支架的通用激酶配体。该支架可以很容易地用不同的结合元件衍生化，并且固定的类似物可以从复杂的混合物中选择性富集蛋白激酶。
• 一种嘧啶并吲唑类化合物的合成方法
  申请人：新乡医学院

  公开号：CN109912606B

  公开（公告）日：2021-05-04

  本发明公开了一种嘧啶并吲唑类化合物的合成方法，属于有机合成技术领域。本发明的技术方案要点为：一种嘧啶并吲唑类化合物的合成方法，具体步骤为：将芳香醛类化合物、3‑氨基吲唑类生物和三乙胺溶于溶剂中，再加入NH4I和氧化剂，然后于110‑150℃反应制得目标产物嘧啶并吲唑类化合物。本发明合成过程简单高效，通过无过渡金属催化的一锅串联反应一步直接制得嘧啶并吲唑类化合物，避免了由于多步反应中多种试剂的使用以及对各步反应中间体的纯化处理等引起的资源浪费和环境污染，合成过程操作方便，原料简单，反应条件温和，底物适用范围广，同时以三乙胺为原料极大地降低了生产成本。
• Aerobic α,β-C(sp³)–H Bond Difunctionalization and C–N Bond Cleavage of Triethylamine: Difunctional Ammonium Iodide Enabling the Regioselective Synthesis of 4-Arylpyrimido[1,2-<i>b</i>]indazoles
  作者：Qinghe Gao、Xinya Han、Peiyuan Tong、Zhiang Zhang、Haotian Shen、Yanrong Guo、Suping Bai

  DOI：10.1021/acs.orglett.9b02218

  日期：2019.8.2

  A novel method for the regioselective synthesis of 4-arylpyrimido[1,2-b]indazoles has been developed via the dual C(sp3)–H bond functionalization and C–N bond cleavage of triethylamine. The elusive acyclic enamine intermediates are effectively in situ generated and captured by aromatic aldehydes to form a wide array of tricyclic products from 3-aminoindazoles under the NH4I-mediated aerobic oxidative

  通过三乙胺的双C（sp 3）-H键官能化和C-N键裂解，开发了一种新的区域选择性合成4-芳基嘧啶[1,2- b ]吲唑的新方法。难以捉摸的无环烯胺中间体可在NH 4 I介导的需氧氧化条件下有效地原位生成并被芳族醛捕获，从而形成多种由3-氨基吲唑形成的三环产物。该反应具有容易获得的原料，绿色和经济条件以及有价值的产品的特点。
• Lewis-acid Promoted Chemoselective Condensation of 2-Aminobenzimidazoles or 3-Aminoindazoles with 3-Ethoxycyclobutanones to Construct Fused Nitrogen heterocycles
  作者：Weiguang Kong、Yao Zhou、Qiuling Song

  DOI：10.1002/adsc.201701641

  日期：2018.5.16

  or 3‐aminoindazoles with 3‐ethoxycyclobutanones is presented. Diverse fused heterocycles benzo[4,5]‐imidazo[1,2‐a]pyrimidine and pyrimido[1,2‐b]‐indazole derivatives were obtained in moderate to high yields under mild conditions, the reaction mechanism of which was in sharp contrast to previous [3+3] annulation reaction of 3‐ethoxycyclobutanones.

  介绍了路易斯酸促进的2-氨基苯并咪唑或3-氨基吲唑与3-乙氧基环丁酮的化学选择性缩合。在温和条件下以中等至高收率获得了多种稠合杂环苯并[4,5]-咪唑并[1,2- a ]嘧啶和嘧啶基[1,2- b ]-吲唑衍生物与以前的3-乙氧基环丁酮的[3 + 3]环化反应形成对比。