5-乙酰氧基-6-溴-2-溴甲基-1-甲基吲哚-3-甲酸乙酯 | 110543-98-1

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 5-乙酰氧基-6-溴-2-溴甲基-1-甲基吲哚-3-甲酸乙酯
• 中文别名: 6-溴-5-羟基-1-甲基-2-苯硫甲基吲哚-3-甲酸乙酯；1-甲基-2-(溴甲基)-5-乙酰氧基-6-溴吲哚-3-甲酸乙酯
• 英文名称: 1-methyl-2-bromomethyl-3-ethoxycarbonyl-5-acetoxy-6-bromoindole
• 英文别名: ethyl 5-acetoxy-6-bromo-2-bromomethyl-1-methylindole-3-carboxylate；ethyl 5-acetoxy-6-bromo-2-(bromomethyl)-1-methyl-1H-indole-3-carboxylate；ethyl 5-acetyloxy-6-bromo-2-(bromomethyl)-1-methylindole-3-carboxylate
• CAS: 110543-98-1
• 化学式: C₁₅H₁₅Br₂NO₄
• mdl: MFCD00407019
• 分子量: 433.096
• InChiKey: MESMQGKAVXOGHJ-UHFFFAOYSA-N

物化性质

• 熔点：
  168-171 °C(Solv: carbon tetrachloride (56-23-5))
• 沸点：
  529.8±50.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090
• 储存条件：
  2-8°C，惰性气体

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Ethyl 5-acetoxy-6-bromo-2-(bromomethyl)-1-methyl-1h-indole-3-carboxylate
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: Ethyl 5-acetoxy-6-bromo-2-(bromomethyl)-1-methyl-1h-indole-3-carboxylate
CAS number: 110543-98-1

---

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.

---

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.

---

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.

---

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, refrigerated.

---

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.

---

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: C15H15Br2NO4
Molecular weight: 433.1

---

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 bromide.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-乙酰氧基-6-溴-2-溴甲基-1-甲基吲哚-3-甲酸乙酯 在 盐酸 、 甲醇 、 溶剂黄146 、 potassium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 9.0h， 生成 盐酸阿比朵尔
  参考文献：
  名称：

  一种合成盐酸阿比朵尔中间体的方法

  摘要：

  一种合成盐酸阿比朵尔中间体的方法,其属于医药中间体技术领域。该方法采用5‑羟基‑1，2‑二甲基吲哚‑3‑羧酸乙酯为原料，经酯化、溴代、苯硫酚化和脱保护、Mannich反应、成盐得到盐酸阿比朵尔。在溴代反应生成最重要的中间体5‑乙酰氧基‑6‑溴‑2‑溴甲基‑1‑甲基吲哚‑3‑羧酸过程中，以（对甲基异丙基苯）‑二氯化钌二聚体为催化剂，NBS为溴代试剂，DMA为溶剂代替传统溴素溴代试剂，反应条件温和，反应选择性高以及原料来源方便，同时可以避免溴素对环境的污染，并且新型催化剂不受反应环境影响导致催化活性降低。因此该方法具有副产物少，产率高，生产成本低，安全性高，节省能源等诸多优点，符合绿色反应的现代化工生产要求。

  公开号：

  CN111533677A
• 作为产物：
  描述：

  4-硝基苯基乙酸酯 在 indium(III) bromide 、 溴 、 copper diacetate 、 palladium diacetate 、 铁粉 、 potassium carbonate 、 氯化铵 、 过氧化苯甲酰 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 5-乙酰氧基-6-溴-2-溴甲基-1-甲基吲哚-3-甲酸乙酯
  参考文献：
  名称：

  一种盐酸阿比朵尔一水合物的制备方法

  摘要：

  本发明公开了一种盐酸阿比朵尔的制备方法，本发明创新性的采用原料廉价易得的对硝基苯酚为原料，经乙酰化、硝基还原、吲哚环反应、甲基化反应、溴代、苯硫酚化和脱保护、Mannich反应、成盐得到盐酸阿比朵尔；整个合成过程反应条件温和，原料来源方便，产品性状好，收率高，副产物少，反应选择性和纯度高，对环境友好，生产成本低，适合工业化生产；避免了现有技术中的选择性差、副产物多、收率较低、避免了使用贵重的催化剂以及环境污染大的试剂的弊端。

  公开号：

  CN106083691B

文献信息

• Visible‐Light‐Mediated Click Chemistry for Highly Regioselective Azide–Alkyne Cycloaddition by a Photoredox Electron‐Transfer Strategy
  作者：Zheng‐Guang Wu、Xiang‐Ji Liao、Li Yuan、Yi Wang、You‐Xuan Zheng、Jing‐Lin Zuo、Yi Pan

  DOI：10.1002/chem.202000252

  日期：2020.5.4

  Click chemistry focuses on the development of highly selective reactions using simple precursors for the exquisite synthesis of molecules. Undisputedly, the CuI -catalyzed azide-alkyne cycloaddition (CuAAC) is one of the most valuable examples of click chemistry, but it suffers from some limitations as it requires additional reducing agents and ligands as well as cytotoxic copper. Here, we demonstrate

  Click化学专注于使用简单的前体进行分子的精细合成的高选择性反应的开发。毋庸置疑，CuI催化的叠氮化物-炔烃环加成（CuAAC）是点击化学最有价值的例子之一，但由于需要额外的还原剂和配体以及细胞毒性铜，因此受到一些限制。在这里，我们展示了一种新颖的叠氮化物-炔烃环加成反应的策略，该策略涉及光氧化还原电子转移自由基机理，而不是传统的金属催化配位过程。这种新开发的光催化的叠氮化物-炔烃环加成反应可以在室温下，在空气和可见光存在的条件下，在温和条件下进行，显示出良好的官能团耐受性，优异的原子经济性，高达99％的高收率，和绝对的区域选择性，提供了各种1,4-二取代的1,2,3-三唑衍生物，包括生物活性分子和药物。使用可回收的光催化剂，太阳能和水作为溶剂，使该光催化系统具有可持续性和环境友好性。此外，叠氮化物-炔烃环加成反应可以在具有优异区域选择性的无金属催化剂的存在下进行光催化，这代表了点击化学
• [EN] ARBIDOL ANALOGS WITH IMPROVED INFLUENZA HEMAGGLUTININ POTENCY<br/>[FR] ANALOGUES D'ARBIDOL AYANT UNE PUISSANCE AMÉLIORÉE VIS-À-VIS DE L'HÉMAGGLUTININE D'INFLUENZA
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2018112128A1

  公开（公告）日：2018-06-21

  The invention provides a series of analogs of arbidol having enhanced binding activity with respect to influenza hemagglutinin. Accordingly, the invention can provide a method of inhibiting the bioactivity of viral hemagglutinin activity, which is an essential step in the entry of infectious viral particles into host cells. The invention also can provide a method of treatment of influence, comprising administering an effective amount of a compound of formula (A), wherein X is S or O, to a patient afflicted therewith.

  这项发明提供了一系列与阿比多尔类似物，其在与流感血凝素结合活性方面具有增强的效果。因此，该发明可以提供一种抑制病毒血凝素生物活性的方法，这是感染性病毒颗粒进入宿主细胞的关键步骤。该发明还可以提供一种治疗流感的方法，包括向患者施用化合物(A)的有效剂量，其中X为S或O。
• Synthesis and biological activity of substituted sulfides of indole and benzofuran
  作者：S. A. Zotova、T. M. Korneeva、V. I. Shvedov、V. K. Zavyalova、V. Yu. Mortikov、V. P. Litvinov、N. V. Darinskii、I. S. Nikolaeva、A. N. Fomina

  DOI：10.1007/bf00773200

  日期：1992.1

  indoles and benzofurans. The later Was deacylated by KOH or hydrochloric acid to the corresponding 5-hydroxy derivative. Prepared by this route were 2-(benzoxalyl2 ' ) (Ilia), 2( benzthiazolyl-2 ' ) (IIIb), 2(pyridyl-2 ' ) (lllc), 2( 3 ' -cyano-4 ', 6 ' -dimethylpyridyl-2' )-(llld), 2-(thienyl-2' )-(llIe), 2-(thienyl-3' )-(IIlf), 2-cyclohexyl-(lllg), 2( 3 ', 5 ' -ditert-butyl-4 ' -hydroxyphenyl) (lllh)

  我们之前描述的 2-bromomethyl-3-ethoxycarbonyl-5-acetoxybenzofuran (I) [3] 和 l-methyl2-bromomethyl-3-ethoxycarbonyl-5-acetoxy-6-bromoindole (II) [4] 被用作起始材料. 化合物 I 和 II 与苯并恶唑、苯并噻唑、吡啶、3-氰基-4,6-二甲基吡啶、2-噻吩 [2, 6]、环己烷 [7] 和 3,5-二叔丁基的巯基衍生物缩合4-羟基苯[8]得到相应的吲哚和苯并呋喃的5-乙酰氧基-2-R-硫甲基衍生物。后者用KOH或盐酸脱酰成相应的5-羟基衍生物。通过该路线制备的有2-(苯并二甲酰基2')(IIIa)、2(苯并噻唑基-2')(IIIb)、2(吡啶基-2')(IIIlc)、2(3'-氰基-4'、6'-二甲基吡啶基-2')-(IIId)、2-(噻吩基-2')-(III
• Synthesis and X-ray analysis of 7-bromoarbidol, an impurity standard of arbidol
  作者：Zenta Tetere、Viktors Kumpiņš、Sergey Belyakov、Daina Zicāne、Māris Turks

  DOI：10.1002/jhet.625

  日期：2011.5

  For the first time, synthesis and X‐ray analysis of 7‐bromoarbidol hydrochloride is reported. The latter is a proven impurity of Arbidol which is an antiviral drug marketed in Russia and China. J. Heterocyclic Chem., (2011).

  首次报道了7-溴阿比多盐酸盐的合成和X射线分析。后者是公认的Arbidol的杂质，Arbidol是在俄罗斯和中国销售的抗病毒药物。J.杂环化​​学。（2011）。
• 一种阿比朵尔中间体的制备方法
  申请人：苏州敬业医药化工有限公司

  公开号：CN111269168B

  公开（公告）日：2022-04-01

  本发明公开了一种阿比朵尔中间体的制备方法，以乙酰乙酸乙酯、一甲胺、对苯醌为起始原料，经过甲胺化，环合，乙酰化，溴化，苯硫化制备目标化合物5‑羟基‑6‑溴‑2‑苯基硫甲基‑1‑甲基吲哚‑3‑羧酸乙酯。本发明阿比朵尔中间体的制备方法，操作简便，原材料价廉易得，收率高，成本低，质量好，绿色环保，反应条件温和，安全生产系数高，适合大规模的工业化生产。