4-溴-2-羟基苯乙酮 | 30186-18-6

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类卤化物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-溴-2-羟基苯乙酮
• 中文别名: 2-羟基-4-溴苯乙酮
• 英文名称: 4'-bromo-2'-hydroxyacetophenone
• 英文别名: 1-(4-bromo-2-hydroxyphenyl)ethanone；1-(4-bromo-2-hydroxyphenyl)ethan-1-one；4’-bromo-2’-hydroxyacetophenone；4′-bromo-2′-hydroxyacetophenone
• CAS: 30186-18-6
• 化学式: C₈H₇BrO₂
• mdl: MFCD03428533
• 分子量: 215.046
• InChiKey: LQCMMXGKEGWUIM-UHFFFAOYSA-N

物化性质

• 熔点：
  40.0 to 44.0 °C
• 沸点：
  83°C/7mmHg(lit.)
• 密度：
  1.586±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2914700090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  | 室温 |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
1-(4-Bromo-2-hydroxyphenyl)ethanone
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
1-(4-Bromo-2-hydroxyphenyl)ethanone
Ingredient name:
CAS number: 30186-18-6

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H7BrO2
Molecular weight: 215.0

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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, hydrogen bromide.

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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

4-溴-2-羟基苯乙酮

4-溴-2-羟基苯乙酮是一种芳酮类化合物，在合成精细化工、医药和农药、表面活性剂等领域中作为重要中间体。特别是在抗心律失常药（如盐酸普罗帕酮）、磺酰胺类抗真菌药物、抗过敏性疾病及抗丙型肝炎病毒药物的合成过程中，2-羟基-4-取代基芳酮起着关键作用。

制备方法

1. 硫酸[三乙胺4-磺酸丁基铵][氧化锌]离子液体的制备

   • 将1,4-丁烷磺酸内酯9.4g缓慢滴加到三乙胺7.0g中，80℃下反应2h。
   • 降温至25℃后抽滤，用乙醇洗涤3次并真空干燥，得到三乙胺丁烷磺酸内盐。
   • 冰浴条件下，将三乙胺丁烷磺酸内盐15.8g的去离子水溶液与硫酸6.5g混合，在50℃下反应3h后冷却，真空干燥得到中间体[硫酸][三乙胺4-磺酸丁基铵]。
   • 将氧化锌5.2g和上步所得中间体21.3g加入去离子水中搅拌溶解固体，旋转蒸发去除溶剂后真空干燥，最终得到[硫酸][三乙胺4-磺酸丁基铵][氧化锌]离子液体41g。

2. 3-溴乙酸苯酯的制备

   • 将3-溴苯酚5g溶于30mL二氯甲烷中，加入吡啶2.5g，在温度控制在-5至5℃下缓慢滴加乙酰氯2.7g的二氯甲烷溶液8mL。
   • 滴加完毕后室温反应2h，过滤除去吡啶盐酸盐，将滤液倒入冰水中搅拌10min后静置分层。有机相浓缩、减压蒸馏得到3-溴乙酸苯酯6.0g，计算收率为97%，纯度为99.7%。

3. 2-羟基-4-溴苯乙酮的制备

   • 将3-溴乙酸苯酯6.0g加入装有上步所得离子液体41g的反应瓶中，在搅拌下温度升至100℃，在此条件下搅拌1h。
   • 反应结束后冷却至室温，将反应液加入冰水中搅拌20min后过滤，滤饼用冷水洗涤两次。得到固体经石油醚重结晶后获得2-羟基-4-溴苯乙酮5.9g，收率为99%，纯度为99.1%。
   • 上述第（3）步后的滤液通过真空蒸馏除去水分，回收双酸性离子液体催化剂以重复使用。按照相同步骤制备2-羟基-4-溴苯乙酮，在相同的反应条件下进行5次重复制备得到的收率分别为98.5%、98.0%、97.6%、97.2%和96.5%，回收离子液体重复使用5次后，制备的2-羟基-4-溴苯乙酮收率仍保持在96%以上。这表明双酸性季铵盐离子液体催化剂在Fries重排反应中具有很高的催化活性且可多次重复使用。

反应信息

• 作为反应物：
  描述：

  4-溴-2-羟基苯乙酮 在 硫酸 、 sodium hydride 、 溶剂黄146 作用下， 以 吡啶 为溶剂， 反应 0.75h， 生成 7-bromo-2-(4'-methoxybenzyl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  1-Benzopyran-4-one抗氧化剂作为醛糖还原酶抑制剂。

  摘要：

  从类黄酮槲皮素的抑制活性开始，合成了一系列4H-1-苯并吡喃-4-酮衍生物，并测试了其对醛糖还原酶（一种涉及糖尿病并发症出现的酶）的抑制作用。获得的一些化合物显示出与索比尼尔相似的抑制活性，但是就紧密相关的酶，醛还原酶而言，比槲皮素和索比尼尔更具选择性，并且还具有抗氧化活性。值得注意的是，这些化合物比羧酸具有更高的pKa值，这一特性可能使这些化合物的药代动力学非常有趣。

  DOI：

  10.1021/jm980441h
• 作为产物：
  描述：

  间溴苯酚 在 吡啶 、 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 生成 4-溴-2-羟基苯乙酮
  参考文献：
  名称：

  发现有效的大环 HCV NS5A 抑制剂

  摘要：

  HCV NS5A 抑制剂已在 HCV 复制子测定中显示出令人印象深刻的体外病毒学特征，并在临床上显着降低 HCV RNA 滴度，使其成为治疗 HCV 感染的全口服固定剂量组合 (FDC) 方案中具有吸引力的成分。默克公司在这一领域的努力将 MK-4882 和 MK-8325 确定为早期的开发线索。在此，我们描述了具有 MK-8325 或 MK-4882 核心结构的强效大环 NS5A 抑制剂的发现。

  DOI：

  10.1016/j.bmcl.2016.05.042

文献信息

• BRM TARGETING COMPOUNDS AND ASSOCIATED METHODS OF USE
  申请人：Arvinas Operations, Inc.

  公开号：US20190300521A1

  公开（公告）日：2019-10-03

  The present disclosure relates to bifunctional compounds, which find utility as modulators of SMARCA2 or BRM (target protein). In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a ligand that binds to the Von Hippel-Lindau E3 ubiquitin ligase, and on the other end a moiety which binds the target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein are treated or prevented with compounds and compositions of the present disclosure.

  本公开涉及双功能化合物，其作为SMARCA2或BRM（靶蛋白）的调节剂具有实用性。具体而言，本公开涉及包含一端结合Von Hippel-Lindau E3泛素连接酶的配体，另一端结合靶蛋白的双功能化合物，使得靶蛋白与泛素连接酶靠近以实现靶蛋白的降解（和抑制）。本公开展示了与靶蛋白降解/抑制相关的广泛药理活性。本公开的化合物和组合物用于治疗或预防由靶蛋白聚集或积累导致的疾病或紊乱。
• [EN] FUSED TRICYCLIC COMPOUNDS AND USES THEREOF IN MEDICINE<br/>[FR] COMPOSÉS TRYCICLIQUES CONDENSÉS ET UTILISATIONS CORRESPONDANTES EN MÉDECINE
  申请人：SUNSHINE LAKE PHARMA CO LTD

  公开号：WO2018219356A1

  公开（公告）日：2018-12-06

  The present invention relates to a fused tricyclic compound and use thereof as a medicament, in particular as a medicament for the treatment and/or prevention of hepatitis B. Specifically, the invention relates to a compound having Formula (I) or a stereoisomer, a tautomer, an N-oxide, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof, wherein each variate is as defined in specification. The invention also relates to the use of the compound having Formula (I) or a stereoisomer, a tautomer, an N-oxide, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof as a medicament, especially as a medicament for the treatment and/or prevention of hepatitis B.

  本发明涉及一种融合三环化合物及其作为药物的用途，特别是作为治疗和/或预防乙型肝炎的药物。具体地，本发明涉及具有化学式（I）或其立体异构体、互变异构体、N-氧化物、溶剂合物、代谢物、药学上可接受的盐或其前药的化合物，其中每个变量如规范中所定义。本发明还涉及将具有化学式（I）或其立体异构体、互变异构体、N-氧化物、溶剂合物、代谢物、药学上可接受的盐或其前药用作药物，特别是作为治疗和/或预防乙型肝炎的药物。
• [EN] cGAS ANTAGONIST COMPOUNDS<br/>[FR] COMPOSÉS ANTAGONISTES DU CGAS
  申请人：IMMUNE SENSOR LLC

  公开号：WO2017176812A1

  公开（公告）日：2017-10-12

  Disclosed are novel compounds of Formula (I) that are cGAS antagonists, methods of preparation of the compounds, pharmaceutical compositions comprising the compounds, and their use in medical therapy.

  揭示了一种新型化合物的化学式（I），这些化合物是cGAS拮抗剂，涉及到这些化合物的制备方法、包含这些化合物的药物组合物，以及它们在医学治疗中的应用。
• Pyrrole inhibitors of S-nitrosoglutathione reductase as therapeutic agents
  申请人：N30 Pharmaceuticals, Inc.

  公开号：US09138427B2

  公开（公告）日：2015-09-22

  The present invention is directed to inhibitors of S-nitrosoglutathione reductase (GSNOR), pharmaceutical compositions comprising such GSNOR inhibitors, and methods of making and using the same.

  本发明涉及S-亚硝基谷胱甘肽还原酶（GSNOR）的抑制剂，包括这种GSNOR抑制剂的药物组合物，以及制备和使用这些药物的方法。
• [EN] BENZOFURAN DERIVATIVES USEFUL FOR TREATING HYPER-PROLIFERATIVE DISORDERS<br/>[FR] DERIVES DE BENZOFURANE UTILISES POUR TRAITER DES TROUBLES HYPERPROLIFERANTS
  申请人：BAYER PHARMACEUTICALS CORP

  公开号：WO2005014566A1

  公开（公告）日：2005-02-17

  The invention relates to novel heterocycles of formula (I), processes for their preparation and their use for preparing medicaments for the treatment or prophylaxis of disorders, especially of hyperproliferative disorders.

  这项发明涉及到式(I)的新异环化合物，以及用于制备这些化合物的方法，以及它们用于制备治疗或预防疾病的药物，特别是治疗过度增殖性疾病的药物。