4-苄氧基苯肼盐酸盐 | 52068-30-1

• 物质功能分类: 化学试剂 - 有机试剂 - 肼
• 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: 4-苄氧基苯肼盐酸盐
• 中文别名: 对苄氧基苯肼盐酸盐；4-苄氧苯肼盐酸盐
• 英文名称: 4-benzyloxyphenylhydrazine hydrochloride
• 英文别名: [4-(Phenylmethoxy)phenyl]hydrazine hydrochloride；Hydron;(4-phenylmethoxyphenyl)hydrazine;chloride
• CAS: 52068-30-1
• 化学式: C₁₃H₁₄N₂O*ClH
• 分子量: 250.728
• InChiKey: OVNUPJXMCMTQCN-UHFFFAOYSA-N

物化性质

• 熔点：
  187-189°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  47.3
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R20/21/22,R36/37/38
• 海关编码：
  2928000090
• 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℃ |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Benzyloxyphenylhydrazine, HCl
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: 4-Benzyloxyphenylhydrazine, HCl
CAS number: 52068-30-1

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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.
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: C13H14N2O.ClH
Molecular weight: 250.7

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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, hydrogen chloride.

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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：

  4-苄氧基苯肼盐酸盐 在 palladium on activated charcoal potassium tert-butylate 、 氢气 、 sodium acetate 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 17.33h， 生成 2-[1-(4-氯苯甲酰基)-5-羟基-2-甲基吲哚-3-基]乙酸
  参考文献：
  名称：

  Discovery of Novel Aldose Reductase Inhibitors Using a Protein Structure-Based Approach:  3D-Database Search Followed by Design and Synthesis

  摘要：

  Aldose reductase (AR) has been implicated in the etiology of diabetic complications. Due to the limited number of currently available drugs for the treatment of diabetic complications, we have carried out structure-based drug design and synthesis in an attempt to find new types of AR inhibitors. With the ADAM&EVE program, a three-dimensional database (ACD3D) was searched using the ligand binding site of the AR crystal structure. Out of 179 compounds selected through this search followed by visual inspection, 36 compounds were purchased and subjected to a biological assay. Ten compounds showed more than 40% inhibition of AR at a 15 mug/mL concentration. In a subsequent lead optimization, a series of analogues of the most active compound were synthesized based on the docking mode derived by ADAM&EVE. Many of these congeners exhibited higher activities compared to the mother compound. Indeed, the most potent, synthesized compound showed a -20-fold increase in inhibitory activity (IC50 = 0.21 vs 4.3 muM). Furthermore, a hydrophobic subsite was newly inferred, which would be useful for the design of inhibitors with improved affinity for AR.

  DOI：

  10.1021/jm000483h
• 作为产物：
  描述：

  4-苄氧基-1-硝基苯 在 盐酸 、 tin(II) chloride dihdyrate 作用下， 以 乙醇 为溶剂， 反应 13.5h， 生成 4-苄氧基苯肼盐酸盐
  参考文献：
  名称：

  四氢咔唑衍生物作为潜在降糖药的设计、合成和评价

  摘要：

  基于 ZG02 设计和合成了两个系列的四氢咔唑衍生物，ZG02 是我们之前研究中开发的有前景的候选物。在 HepG2 细胞系中筛选新制备的化合物的葡萄糖消耗活性。氮杂-四氢咔唑化合物12b显示出最有效的降血糖活性，与溶剂对照相比，葡萄糖消耗增加了 45%，其活性比阳性对照化合物（二甲双胍和 ZG02）高约 1.2 倍。对潜在机制的研究表明，12b可能通过激活 AMPK 途径表现出降血糖活性。代谢稳定性分析表明，12b在来自 SD 大鼠的人造胃肠液和血浆中均显示出良好的稳定性。进行了口服葡萄糖耐量试验 (OGTT)，结果进一步证实12b是一种有效的降血糖药。

  DOI：

  10.1016/j.bioorg.2021.105172
• 作为试剂：
  描述：

  4-苯甲氧基苯胺盐酸盐 、 sodium nitrite 、 在 4-苄氧基苯肼盐酸盐 、 乙醇 作用下， 以 水 、 盐酸 为溶剂， 反应 2.0h， 以yielding 52.5 g of p-benzyloxyphenylhydrazine hydrochloride的产率得到4-苄氧基苯肼盐酸盐
  参考文献：
  名称：

  1-(substituted pyridinylamino)-1H-indol-5-yl substituted carbamates

  摘要：

  公开了以下式子的各种化合物，其中，n为0或1；X为氢、卤素、硝基、氨基、三氟甲基、低碳基或低碳氧基；Y为氢、卤素、硝基、氨基、三氟甲基、低碳基或低碳氧基；R.sub.1为氢、低碳基、芳基低碳基、低烯基、低炔基、低碳酰基、芳基低碳酰基、杂芳基低碳基或杂芳基低碳酰基；R.sub.2为氢、低碳基、甲酰基或氰基；R.sub.3为氢或低碳基；R.sub.4为低碳基、芳基低碳基、环烷基、芳基或杂芳基；或者，替代地，--NR.sub.3R.sub.4共同构成##STR2## R.sub.5为氢、低碳基、芳基、芳基低碳基、杂芳基或杂芳基低碳基，这些化合物对于治疗由胆碱能缺陷所特征的各种记忆障碍，如阿尔茨海默病，是有用的。

  公开号：

  US05102891A1

文献信息

• <i>tert-</i> Butyl Iodide Mediated Reductive Fischer Indolization of Conjugated Hydrazones
  作者：Yuta Ito、Masafumi Ueda、Norihiko Takeda、Okiko Miyata

  DOI：10.1002/chem.201504010

  日期：2016.2.18

  available N‐aryl conjugated hydrazones with tert‐butyl iodide has been developed. In this reaction, tert‐butyl iodide is used as anhydrous HI source, and the generated HI acts as a Brønsted acid and a reducing agent. This operationally simple method allows access to various indole derivatives. Furthermore, the procedure can be applied to the synthesis of biologically active compounds.

  已经开发出一种新型的，易于获得的N-芳基共轭与叔丁基碘化物的还原费歇尔吲哚化反应。在该反应中，叔丁基碘化物用作无水HI源，生成的HI用作布朗斯台德酸和还原剂。这种操作简单的方法允许使用各种吲哚衍生物。此外，该方法可以应用于生物活性化合物的合成。
• Carbodiimide coupling reagent
  申请人：Eli Lilly and Company

  公开号：US05998630A1

  公开（公告）日：1999-12-07

  The present invention relates to compounds used for increasing activation of the 5-HT1F receptor.

  本发明涉及用于增加5-HT1F受体激活的化合物。
• Hydrogen peroxide based oxidation of hydrazines using HBr catalyst
  作者：Jian Wang、Zichao Ma、Wanting Du、Liming Shao

  DOI：10.1016/j.tet.2021.132546

  日期：2021.12

  Azo compounds (RN = NR′) are an important class of organic molecules that find wide application in organic synthesis. Herein, we report an efficient, practical and metal-free oxidation of hydrazines (RNH-NHR’) to azo compounds using 5 mol% HBr and hydrogen peroxide as terminal oxidant. This new method has been demonstrated by 40 examples with excellent yields. In addition, we showcased two examples

  偶氮化合物（RN = NR'）是一类重要的有机分子，在有机合成中有着广泛的应用。在此，我们报告了使用 5 mol% HBr 和过氧化氢作为末端氧化剂将肼 (RNH-NHR') 高效、实用且无金属氧化成偶氮化合物的方法。这种新方法已经通过 40 个示例得到了很好的证明。此外，我们展示了两个一锅序反应的例子，包括我们的肼氧化/水解/Heck 反应或铜催化的芳基硼酸 N-芳基化反应。该协议的独特优势包括无金属催化、废物预防和易于操作。
• Use of serotonin 5-HT1F agonists for the prevention of migraine
  申请人：ELI LILLY AND COMPANY

  公开号：EP0832650A3

  公开（公告）日：1998-09-02

  This invention provides methods for the prevention of migraine which comprises administering to a mammal in need thereof a serotonin 5-HT1F agonist.

  这项发明提供了预防偏头痛的方法，包括向需要的哺乳动物施用一种5-HT1F受体激动剂。
• Use of a serotonin 5-HTlf agonist in the manufacture of a medicament for treating or ameliorating the symptoms of common cold or allergic rhinitis
  申请人：ELI LILLY AND COMPANY

  公开号：EP0824917A3

  公开（公告）日：2000-08-30

  This invention provides methods for the treatment or amelioration of the symptoms of the common cold or allergic rhinitis which comprises administering to a mammal in need thereof a serotonin 5-HT1F agonist.

  这项发明提供了治疗或缓解普通感冒或过敏性鼻炎症状的方法，包括向需要的哺乳动物施用一种5-HT1F受体激动剂。