7-溴苯并呋喃-2-甲酸 | 550998-59-9

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 7-溴苯并呋喃-2-甲酸
• 中文别名: 7-溴苯并呋喃-2-羧酸
• 英文名称: 7-bromobenzofuran-2-carboxylic acid
• 英文别名: 7-bromo-1-benzofuran-2-carboxylic acid
• CAS: 550998-59-9
• 化学式: C₉H₅BrO₃
• mdl: MFCD10699647
• 分子量: 241.041
• InChiKey: OPYANDYWSZSRSD-UHFFFAOYSA-N

物化性质

• 沸点：
  370.9±22.0 °C(Predicted)
• 密度：
  1.784±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 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：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2932999099
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 7-Bromobenzofuran-2-carboxylic acid
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: 7-Bromobenzofuran-2-carboxylic acid
CAS number: 550998-59-9

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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: C9H5BrO3
Molecular weight: 241.0

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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

制备方法

1. 3-溴-2-羟基苯甲醛的制备 将20.0克（115.6毫摩尔）的2-溴苯酚加入到500毫升无水乙腈中。依次添加16.84克（176.87毫摩尔）无水氯化镁、23.4克多聚甲醛颗粒以及41.9毫升（300.6毫摩尔）三乙胺。将反应混合物加热回流4小时，冷却至0℃后，加入300毫升2N盐酸。用200毫升二乙醚萃取水相三次。有机相经硫酸镁干燥并真空除去溶剂。分离出目标化合物，无需进一步纯化即可进行下一步反应。产率为24克（理论值的64％，根据HPLC测定纯度为62％）。HPLC（方法1）：Rt=4.25分钟；MS（ESIpos）：m/z=202（M+H）+。

2. 7-溴苯并呋喃-2-甲酸的制备 将13.5克（40.3毫摩尔）3-溴-2-羟基苯甲醛与9.18克（84.62毫摩尔）氯乙酸甲酯、1.49克（4.03毫摩尔）碘化四正丁基铵以及22.28克（161.18毫摩尔）碳酸钾混合，在130℃下加热保持6小时。冷却至室温后，加入100毫升水和100毫升THF，并与13.57克（241.77毫摩尔）氢氧化钾的混合物在室温下搅拌过夜。减压除去溶剂，将残余物溶于400毫升水中，用总共400毫升二乙醚洗涤四次。在冰冷却的同时，用浓盐酸调节pH至0，并用总共700毫升乙酸乙酯萃取五次。用100毫升饱和氯化钠溶液洗涤有机相，经硫酸镁干燥。将粗产物完全除去残余溶剂并与80毫升二乙醚一起搅拌。滤出7-溴苯并呋喃-2-甲酸并用少量冰冷的乙醚洗涤。产率为4.8克（理论值的47％）。1H-NMR（200兆赫，DMSO-d6）：δ=13.5（br.s，1H），7.86-7.72（m，2H），7.79（s，1H），7.31（t，1H）。MS（DCI/NH3）：m/z=258（M+NH4）+。

应用

7-溴苯并呋喃-2-甲酸可用作医药合成中间体。

反应信息

• 作为反应物：
  描述：

  7-溴苯并呋喃-2-甲酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 盐酸 、 sodium hydroxide 、 2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetratetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 DMF (N,N-dimethyl-formamide) 、 水 为溶剂， 生成 7-(2-aminophenyl)-N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-1-benzofuran-2-carboxamide
  参考文献：
  名称：

  [DE] 2-HETEROARYLCARBONSÄUREAMIDE
  [EN] 2-HETEROARYL CARBOXAMIDES
  [FR] 2-HETEROARYLCARBOXAMIDES

  摘要：

  这项发明涉及新的2-杂环芳基羧酰胺及其用于制备用于治疗和/或预防疾病以及改善感知、注意力、学习和/或记忆能力的药物的用途。其中，R1为1-Aza-bicyclo[2.2.2]oct-3-yl，可能通过氮原子与来自C1-C4-烷基、苄基和氧的基团中的一种取代，A为氧或硫，环B为苯并或吡啶，并且可以通过来自卤素、氰基、甲酰基、三氟甲基、三氟甲氧基、硝基、氨基、C1-C6-烷基和C1-C6-烷氧基的基团取代，E为C≡C、芳基和杂环芳基，其中芳基和杂环芳基可以通过来自卤素、氰基、三氟甲基、三氟甲基、三氟甲氧基、硝基、氨基、C1-C6-烷氧基和C1-C6-烷基的基团取代，以及这些化合物的溶剂化合物、盐或盐的溶剂化合物。

  公开号：

  WO2003104227A1
• 作为产物：
  描述：

  3-溴柳醛 在 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 2.0h， 生成 7-溴苯并呋喃-2-甲酸
  参考文献：
  名称：

  含苯并五元杂环结构的化合物及其制备方法与用途

  摘要：

  本发明涉及药物化学领域，公开了一类含苯并五元杂环结构的化合物及其制备方法与用途。本发明还公开了含有所述苯并五元杂环化合物或其药学上可接受的盐及药学上可接受的载体的组合物、及其在制备PARP‑1和ERK抑制剂中的用途。本发明的化合物可用于治疗肿瘤等疾病。

  公开号：

  CN113248482B

文献信息

• [EN] ORAL COMPLEMENT FACTOR D INHIBITORS<br/>[FR] INHIBITEURS ORAUX DU FACTEUR D DU COMPLÉMENT
  申请人：BIOCRYST PHARM INC

  公开号：WO2021072198A1

  公开（公告）日：2021-04-15

  Disclosed are compounds of formula (I), and pharmaceutically acceptable salts thereof, which are inhibitors of the complement system. Also provided are pharmaceutical compositions comprising such a compound, and methods of using the compounds and compositions in the treatment or prevention of a disease or condition characterized by aberrant complement system activity.

  揭示了式(I)的化合物及其药学上可接受的盐，这些化合物是裂解系统的抑制剂。还提供了包含这种化合物的药物组合物，以及使用这些化合物和组合物治疗或预防由异常裂解系统活性特征的疾病或状况的方法。
• 2-CARBOXAMIDE-7-PIPERAZINYL-BENZOFURAN DERIVATIVES 774
  申请人：ANDERSSON Johan

  公开号：US20100331341A1

  公开（公告）日：2010-12-30

  The present invention relates to compounds of formula (I), wherein R 1 is heteroaryl or heterocyclyl, optionally substituted; R 2 is C 1-4 alkyl, heterocyclyl, C 1-4 alkylaryl, C 1-4 alkylheteroaryl, carbocyclyl, C 1-4 alkylheterocyclyl, heterocyclyl-heteroaryl, aryl-heterocyclyl, carbocyclyl-heteroaryl, heterocyclyl-aryl, optionally substituted; R 3 is hydrogen or C 1-4 alkyl, or R 2 and R 3 may together with the nitrogen atom, form a saturated ring system containing 4, 5 or 6 ring forming atoms, and optionally substituted; R 4 is hydrogen, halogen, methyl or methoxy; to pharmaceutical composition containing said compounds and to the use of said compounds in therapy, for instance in treating cognitive disorders. The present invention further relates to new intermediates useful in the preparation thereof.

  本发明涉及公式（I）的化合物，其中R1是杂环芳基或杂环烷基，可选择性取代；R2是C1-4烷基，杂环烷基，C1-4烷基芳基，C1-4烷基杂环芳基，碳环烷基，C1-4烷基杂环烷基，杂环烷基-杂环芳基，芳基-杂环烷基，碳环烷基-杂环芳基，杂环烷基-芳基，可选择性取代；R3是氢或C1-4烷基，或R2和R3可以与氮原子一起形成含有4、5或6个环形成原子的饱和环系统，并可选择性取代；R4是氢，卤素，甲基或甲氧基；含有所述化合物的药物组合物以及所述化合物在治疗中的使用，例如用于治疗认知障碍。本发明还涉及制备中间体的新方法。
• [EN] MODIFIED BENZOFURAN-CARBOXAMIDES AS GLUCOSYLCERAMIDE SYNTHASE INHIBITORS<br/>[FR] BENZOFURAN-CARBOXAMIDES MODIFIÉS COMME INHIBITEURS DU GLUCOSYLCÉRAMIDE SYNTHASE
  申请人：MERCK SHARP & DOHME

  公开号：WO2022060764A1

  公开（公告）日：2022-03-24

  The present invention relates to Compounds of Formula I: and pharmaceutically acceptable salts or prodrug thereof. The present invention also relates to compositions comprising at least one compound of Formula I, and methods of using the compounds of Formula I for treatment or prophylaxis of lysosomal storage diseases, neurodegenerative disease, cystic disease, cancer, or a diseases or disorders associated with elevated levels of glucosylceramide (GlcCer), glucosylsphingosine (GlcSph) and/or other glucosylceramide-based glycosphingolipids (GSLs).

  本发明涉及式I的化合物及其药学上可接受的盐或前药。本发明还涉及包含至少一种式I化合物的组合物，以及使用式I化合物用于治疗或预防溶酶体贮积病、神经退行性疾病、囊性疾病、癌症或与升高的葡糖鞘氨醇脂（GlcCer）、葡糖鞘氨醇（GlcSph）和/或其他基于葡糖鞘氨醇脂（GSLs）的葡糖鞘氨醇脂相关疾病或障碍的方法。
• [DE] 2-HETEROARYLCARBONSÄUREAMIDE<br/>[EN] 2-HETEROARYLCARBOXYLIC ACID AMIDES<br/>[FR] AMIDES D'ACIDE 2-HETEROARYLCARBOXYLIQUE
  申请人：BAYER AG

  公开号：WO2003055878A1

  公开（公告）日：2003-07-10

  Die Erfindung betrifft neue 2-Heteroarylcarbonsäureamide, Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Herstellung von Arzneimitteln zur Behandlung und/oder Prophylaxe von Krankheiten und zur Verbesserung der Wahrnehmung, Konzentrationsleistung, Lernleistung und/oder Gedächtnisleistung.

  该发明涉及新型的2-杂环芳基羧酰胺，其制备方法以及其用于制备用于治疗和/或预防疾病以及改善感知、注意力、学习和/或记忆能力的药物的使用。
• 2-Heteroarylcarboxylic acid amides
  申请人：Hendrix Martin

  公开号：US20050119325A1

  公开（公告）日：2005-06-02

  The invention relates to novel 2-heteroarylcarboxamides, processes for their preparation, and their use for producing medicaments for the treatment and/or prophylaxis of diseases and for improving perception, concentration, learning and/or memory.

  本发明涉及新型2-杂环芳基甲酰胺、其制备方法以及用于制备治疗和/或预防疾病以及改善感知、注意力、学习和/或记忆的药物的用途。