2-肼基-1,3-苯并噁唑 | 15062-88-1

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 中文名称: 2-肼基-1,3-苯并噁唑
• 中文别名: 2-肼基-1,3-苯并恶唑；2-肼基苯并[d]恶唑
• 英文名称: 2-hydrazino-1,3-benzoxazole
• 英文别名: 2-hydrazinobenzoxazole；2-hydrazinylbenzo[d]oxazole；2-hydrazineylbenzo[d]oxazole；2‐hydrazinylbenzo[d]oxazole；1,3-benzoxazol-2-ylhydrazine
• CAS: 15062-88-1
• 化学式: C₇H₇N₃O
• mdl: MFCD00085913
• 分子量: 149.152
• InChiKey: QITJGSMHKVXOFR-UHFFFAOYSA-N

物化性质

• 熔点：
  >136°C (dec.)
• 溶解度：
  可溶于氯仿（少量）、DMSO（少量）、甲醇（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.1
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xn
• 海关编码：
  2934999090
• 危险类别：
  IRRITANT
• 安全说明：
  S22
• 包装等级：
  III
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P310+P330,P302+P352+P312,P304+P340+P312,P305+P351+P338,P337+P313,P363,P405,P501
• 危险品运输编号：
  2811
• 危险性描述：
  H301,H312+H332,H319
• 储存条件：
  -20°C下保存，需避光且在惰性气体中进行。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Hydrazino-1,3-benzoxazole
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: 2-Hydrazino-1,3-benzoxazole
CAS number: 15062-88-1

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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.
Storage: Store in closed vessels, under −20◦C.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C7H7N3O
Molecular weight: 149.2

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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

概述

2-肼基-1,3-苯并恶唑可通过2-氯苯并恶唑与水合肼反应得到，主要用于制备一类吡唑化合物。

用途

2-肼基-1,3-苯并恶唑是一种杂环类有机物，可用作有机中间体。

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
  2-氯苯并恶唑	2-chloro-1,3-benzoxazole	615-18-9	C7H4ClNO	153.568

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	Acetaldehyd-benzoxazolylhydrazon	16586-68-8	C9H9N3O	175.19
  ——	N-(benzoxazol-2-yl)-acetone hydrazone	99742-30-0	C10H11N3O	189.217
  ——	N-(benzoxazol-2-yl)-propionaldehyde hydrazone	99742-31-1	C10H11N3O	189.217
  ——	2-(1,3-Benzoxazol-2-ylhydrazinylidene)acetic acid	1337471-24-5	C9H7N3O3	205.173
  ——	benzaldehyde benzooxazol-2-yl-hydrazone	15166-39-9	C14H11N3O	237.261
  ——	2-[(2E)-2-benzylidenehydrazinyl]-1,3-benzoxazole	——	C14H11N3O	237.26
  ——	ethyl 2‐(benzo[d]oxazol‐2‐yl)hydrazine‐1‐carboxylate	——	C10H11N3O3	221.216
  ——	1-(p-Methoxybenzal)-2-(benzoxazol-2'-yl)-hydrazin	15166-38-8	C15H13N3O2	267.287
  ——	2-[(2E)-2-(4-methoxybenzylidene)hydrazinyl]-1,3-benzoxazole	——	C15H13N3O2	267.28
  苯并噁唑,2-叠氮-	2-azidobenzo[d]oxazole	1680-18-8	C7H4N4O	160.135

反应信息

• 作为反应物：
  描述：

  2-肼基-1,3-苯并噁唑 在 偶氮苯 作用下， 以88%的产率得到苯并恶唑
  参考文献：
  名称：

  Walther reaction in the benzazoles series and preparation of their 2-deutero derivatives

  摘要：

  Reactions of 2-hydrazino-substituted 1-methylbenzimidazole, benzothiazole, and benzoxazole with azobenzene at 160-180 degrees C resulted in hydrazino group elimination and formation of the corresponding 2-H-benzazoles. Under similar conditions the 2-deuterohydrazinobenzazoles prepared from 2-hydrazinobenzazoles and heavy water were converted into 2-deuterobenzazoles.

  DOI：

  10.1134/s107042800212014x
• 作为产物：
  描述：

  2-巯基苯并恶唑 在 五氯化磷 、 一水合肼 作用下， 以 苯 为溶剂， 反应 2.5h， 生成 2-肼基-1,3-苯并噁唑
  参考文献：
  名称：

  n-(硫)磷酰基-n?-2-苯并恶唑氨基脲的合成

  摘要：

  我们通过 2-肼苯并恶唑与异硫氰酸根合（硫代）磷酸盐的加成反应制备了带有（硫代）磷酰基部分的苯并恶唑衍生物，并通过元素分析和 1 H NMR 和 IR 光谱数据表征了它们的结构。从生物活性筛选结果，我们发现这些化合物具有一定的除草和植物生长调节活性，特别是对隐匿柄锈菌具有良好的杀菌活性。© 2001 John Wiley & Sons, Inc. 杂原子化学 12:151–155, 2001

  DOI：

  10.1002/hc.1024
• 作为试剂：
  描述：

  乙酰丙酮 在 盐酸 、 2-肼基-1,3-苯并噁唑 、 乙醇 作用下， 反应 4.0h， 以20%的产率得到N-(2-羟基苯基)氨基甲酸乙酯
  参考文献：
  名称：

  Singh, S. P.; Kumar, Dalip; Kumar, Devinder, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 8, p. 682 - 685

  摘要：

  DOI：

文献信息

• [EN] HETEROCYCLIC HYDRAZONE COMPOUNDS AND THEIR USES TO TREAT CANCER AND INFLAMMATION<br/>[FR] COMPOSÉS HYDRAZONE HÉTÉROCYCLIQUES ET LEURS UTILISATIONS POUR TRAITER LE CANCER ET L'INFLAMMATION
  申请人：NOVARTIS AG

  公开号：WO2011018454A1

  公开（公告）日：2011-02-17

  The invention relates to compounds of formula (I) and salts thereof: wherein the substituents are as defined in the specification; a compound of formula (I) for use in the treatment of the human or animal body, in particular with regard to c-Met tyrosine kinase mediated diseases or conditions; the use of a compound of formula (I) for manufacturing a medicament for the treatment of such diseases; pharmaceutical compositions comprising a compound of the formula (I), optionally in the presence of a combination partner, and processes for the preparation of a compound of formula (I).

  该发明涉及公式(I)的化合物及其盐：其中取代基如规范中所定义；公式(I)的化合物用于治疗人体或动物体，特别是针对c-Met酪氨酸激酶介导的疾病或症状；公式(I)的化合物用于制造治疗此类疾病的药物；包含公式(I)的化合物的药物组合物，可选地与组合伙伴一起，并且公式(I)的化合物的制备方法。
• Synthesis and anti-influenzaactivity of N-substituted-2-benzazol-2-ylhydrazinocarbothioamides
  作者：G. N. Tyurenkova、V. I. Il'enko、N. V. Serebryakova、V. G. Platonov、G. A. Mokrushina、I. I. Mudretsova

  DOI：10.1007/bf00758277

  日期：1988.3

  Scientific Fundamentals of Antibiotics [in Russian], 3rd edition, Moscow (1979), pp. 46-47~ V. I. ll'enko, Methods of Testing and Assessment of the Antiviral Activity of Chemical Compounds against Influenze Virus. Methodology [in Russian], Leningrad (1977). G. A. Mokrushina, S. K. Kotovskaya, and G. A. Yurchenko, Conference on the Chemistry and Technology of Organic Sulfur Compounds and Sulfur-Containing

  NS Egorov，抗生素科学基础 [俄文]，第 3 版，莫斯科（1979 年），第 46-47 页~ VI ll'enko，化合物抗流感病毒抗病毒活性的测试和评估方法。方法论[俄语]，列宁格勒（1977 年）。GA Mokrushina、SK Kotovskaya 和 GA Yurchenko，有机硫化合物和含硫石油化学与技术会议。第 16 号：论文摘要 [俄文]，里加，1984 年，第 1 页。187. GA Mokrushina、SK Kotovskaya、GN Tyurenkova 等人，Khim.-farm。Zh., No. 2, 195 (1988).
• Selective Inhibitors of the Protein Tyrosine Phosphatase SHP2 Block Cellular Motility and Growth of Cancer Cells in vitro and in vivo
  作者：Stefanie Grosskopf、Chris Eckert、Christoph Arkona、Silke Radetzki、Kerstin Böhm、Udo Heinemann、Gerhard Wolber、Jens-Peter von Kries、Walter Birchmeier、Jörg Rademann

  DOI：10.1002/cmdc.201500015

  日期：2015.5

  adenocarcinoma (HPAF) cells, as indicated by a decrease in the minimum neighbor distances of cells. Moreover, 25 inhibited cell colony formation in the non‐small‐cell lung cancer cell line LXFA 526L in soft agar. Finally, 25 was observed to inhibit tumor growth in a murine xenograft model. Therefore, the novel specific compound 25 strengthens the hypothesis that SHP2 is a relevant protein target for the inhibition

  酪氨酸蛋白磷酸酶SHP2（src同源区域2域磷酸酶； PTPN11）的选择性抑制剂是通过化学合成和基于结构的合理设计相结合而产生的，该酶在许多人类肿瘤中均被解除调节。制备了70种吡啶并唑-4-亚甲基肼基苯磺酸盐，并在酶分析中进行了评估。使用新生成的SHP2晶体结构在计算机上模拟了活性抑制剂的结合模式。最强大的化合物GS‐493（4 ‐ （2 Z）‐2‐ [1、3‐双（4‐硝基苯基）‐5‐oxo‐1,5‐二氢‐4 H‐吡唑‐4‐liden]]肼基苯磺酸；25）抑制SHP2，IC 50值为71±15 n M在酶检测中，对SHP2的活性比对相关SHP1和PTP1B的活性高29到45倍。在细胞培养实验中，发现化合物25可以阻断肝细胞生长因子（HGF）刺激的人胰腺癌（HPAF）细胞的上皮-间质转化，这通过最小最小细胞距离的减少来表明。此外，在软琼脂中，有25种抑制了非小细胞肺癌LXFA 526L细
• Condensation and Cyclization Reactions of 2-Hydrazinobenzimidazole, -benzoxazole, and -benzothiazole
  作者：M. Z. A. Badr、A. M. Mahmoud、S. A. Mahgoub、Z. A. Hozien

  DOI：10.1246/bcsj.61.1339

  日期：1988.4

  2-Hydrazinobenzoxazole (1), -benzimidazole (2), and benzothiazole (3) were condensed with ethyl chloroformate and/or diethyl oxalate to produce, 1,2,4-triazolo- and 1,2,4-triazino-fused ketones of the title azoles respectively. Condensation of 1 and 2 with aromatic aldehydes and/or acetic anhydride produced, 3-aryl- and 3-methyl-substituted 1,2,4-triazolo-fused azoles respectively. The hydrazines 1

  2-肼基苯并恶唑 (1)、-苯并咪唑 (2) 和苯并噻唑 (3) 与氯甲酸乙酯和/或草酸二乙酯缩合生成 1,2,4-三唑并和 1,2,4-三嗪酮稠合酮分别为标题唑。1 和 2 与芳香醛和/或乙酸酐缩合，分别产生 3-芳基和 3-甲基取代的 1,2,4-三唑并稠合唑。肼 1 和 2 与乙酰丙酮环化生成相应的 2-(1-吡唑基) 衍生物。2-乙酰噻唑并苯并咪唑与羟胺和/或烷基胺反应生成相应的缩合产物。它也与芳香醛缩合得到查耳酮。与重氮苯盐反应，得到相应的2-芳基偶氮取代化合物。
• Synthesis of novel pyridazinyl benzimidazole, benzothiazole and benzoxazole of Expected Anti-Inflammatory Activity
  作者：Hanan M. Refaat、Omneya M. Khalil、Suzan M. Abuel-Maaty

  DOI：10.3184/030823409x466050

  日期：2009.7

  study, a novel series of 6-oxopyridazinyl benzazoles and 3, 6-dioxopyridazinyl benzazoles were prepared from the starting compounds, 2-hydrazinobenzimidazole, 2-hydrazinobenzothiazole and 2-hydrazinobenzoxazole by reaction with butyric acid derivatives and cyclic anhydrides respectively. The structures of the new compounds were confirmed by elemental analysis as well as 1H NMR, IR and MS data. Some of the

  在本研究中，以起始化合物 2-肼基苯并咪唑、2-肼基苯并噻唑和 2-肼基苯并恶唑为原料，分别与丁酸衍生物和环酐反应，制备了一系列新型 6-氧代哒嗪基苯并唑和 3, 6-二氧代哒嗪基苯并唑。通过元素分析以及1H NMR、IR和MS数据确认了新化合物的结构。使用 100 mg kg-1 剂量的角叉菜胶诱导的爪水肿，使用吲哚美辛作为参考标准，对一些新制备的化合物的抗炎活性进行评估，发现它们具有生物活性。