2-溴-3-羟基苯甲醛 | 196081-71-7

• 物质功能分类: 有机原料 - 醛类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-溴-3-羟基苯甲醛
• 英文名称: 2-bromo-3-hydroxybenzaldehyde
• CAS: 196081-71-7
• 化学式: C₇H₅BrO₂
• 分子量: 201.019
• InChiKey: OHXPHMPERMIICA-UHFFFAOYSA-N

物化性质

• 熔点：
  147-148℃
• 沸点：
  252℃
• 密度：
  1.737
• 闪点：
  106℃
• 溶解度：
  可溶于DMSO（少许）、乙酸乙酯（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2913000090
• 危险品标志：
  Xi
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8℃，惰性气体

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Bromo-3-hydroxybenzaldehyde
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302+312+332,: Harmful if swallowed
H335: May cause respiratory irritation
P280: Wear protective gloves/protective clothing/eye protection/face protection

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Bromo-3-hydroxybenzaldehyde
CAS number: 196081-71-7

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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, refrigerated.

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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: C7H5BrO2
Molecular weight: 201.0

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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

理化性质

2-溴-3-羟基苯甲醛在常温常压下为灰白色至浅米色固体粉末，具有微弱的酸性，并且对氧化剂较为敏感。它难溶于水但可溶于乙酸乙酯、二氯甲烷和氯仿等有机溶剂。

应用

在碱性条件下，2-溴-3-羟基苯甲醛的醛基可以与Wittig试剂反应形成烯基化合物。Wittig反应是一种重要的合成方法，可用于引入双键结构，在复杂分子的合成中广泛应用于各种有机化学领域。此外，醛基单元还具有一定的亲电性，可在强亲核试剂如格式试剂或有机锂试剂的作用下发生亲核加成反应。

反应信息

• 作为反应物：
  描述：

  2-溴-3-羟基苯甲醛 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride potassium acetate 、 碳酸氢钠 、 caesium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1-cyclopropyl-6-fluoro-7-{4-[3-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-7-yloxy)-propyl]-piperazin-1-yl}-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid formate
  参考文献：
  名称：

  [EN] BORON CONTAINING SMALL MOLECULES
  [FR] PETITES MOLÉCULES CONTENANT DU BORE

  摘要：

  这项发明提供了用于治疗细菌感染的新化合物，包含这些化合物的药物组合物，以及这些化合物与至少一种其他治疗有效剂的组合。

  公开号：

  WO2011037731A1
• 作为产物：
  描述：

  间羟基苯甲醛 在 溴 、 sodium acetate 、 铁粉 作用下， 以 溶剂黄146 为溶剂， 生成 2-溴-3-羟基苯甲醛
  参考文献：
  名称：

  Bazzanin K的合成研究：区域选择性和化学选择性三组分铃木偶联

  摘要：

  构建了手性环烷天然产物Bazzanin K的三联苯亚结构。关键步骤涉及非对称二溴苯的顺序Suzuki偶联，可通过两步法或一锅三组分偶联进行。关键步骤是二溴苯的区域选择性偶联，以及在氯化苯存在下苯溴化物的化学选择性偶联。三联苯中间体表现出对位非对映异构性，并且通过闭环易位将其转化为单个的菲靶。

  DOI：

  10.1021/acs.joc.9b02043

文献信息

• NOVEL CURCUMIN DERIVATIVE
  申请人：Sugimoto Hachiro

  公开号：US20110082295A1

  公开（公告）日：2011-04-07

  To develop a highly safe measure to treat Alzheimer's disease using a secretase-inhibiting substance, there is provided a compound represented by the following general formula (I) or a salt thereof: wherein A represents a phenyl group or the like, R 1 represents a chlorine atom, a bromine atom, or a nitro group or the like, R 2 , R 3 , R 4 , and R 5 each represent a hydrogen atom or the like, and L represents CH 2 —CH 2 or CH═CH.

  为了开发一种高度安全的措施来治疗阿尔茨海默病，提供了一种由以下一般式（I）或其盐表示的化合物： 其中A代表苯基或类似物，R1代表氯原子、溴原子或硝基团等，R2、R3、R4和R5各自代表氢原子或类似物，L代表CH2—CH2或CH═CH。
• BORON-CONTAINING SMALL MOLECULES
  申请人：Xia Yi

  公开号：US20100256092A1

  公开（公告）日：2010-10-07

  This invention relates to, among other items, 6-substituted benzoxaborole compounds and their use for treating bacterial infections.

  这项发明涉及6-取代苯硼酯化合物等物品，以及它们用于治疗细菌感染的用途。
• Efficient Syntheses of Korupensamines A, B and Michellamine B by Asymmetric Suzuki-Miyaura Coupling Reactions
  作者：Guangqing Xu、Wenzhen Fu、Guodu Liu、Chris H. Senanayake、Wenjun Tang

  DOI：10.1021/ja409669r

  日期：2014.1.15

  Efficient asymmetric Suzuki-Miyaura coupling reactions are employed for the first time in total syntheses of chiral biaryl natural products korupensamine A and B in combination with an effective diastereoselective hydrogenation, allowing ultimately a concise and stereoselective synthesis of michellamine B. Chiral monophosphorus ligands L1-3 are effective for the syntheses of a series of functionalized

  高效的不对称 Suzuki-Miyaura 偶联反应首次用于手性联芳基天然产物 korupensamine A 和 B 的全合成，并结合有效的非对映选择性氢化，最终实现了米歇尔胺 B 的简洁立体选择性合成。 手性单磷配体 L1-3通过不对称 Suzuki-Miyaura 偶联反应以优异的产率和对映选择性（高达 99% ee）合成一系列官能化手性联芳基化合物是有效的。高度极化的 BOP 基团与芳基硼酸偶联物的扩展 π 系统之间存在极性-π 相互作用被认为对于高对映选择性很重要。
• [EN] NEW BICYCLIC DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] NOUVEAUX DÉRIVÉS BICYCLIQUES, LEUR PROCÉDÉ DE PRÉPARATION, ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SERVIER LAB

  公开号：WO2016207217A1

  公开（公告）日：2016-12-29

  Compounds of formula (I); wherein R1, R2, R3, R4, R5, R6, R7, R8, R14, W, A and n are as defined in the description. Medicaments.

  式(I)的化合物；其中R1、R2、R3、R4、R5、R6、R7、R8、R14、W、A和n的定义如描述所示。药物。
• 氮杂环庚烷[4,3,2-cd]异吲哚-2-酮类衍生物及其应用
  申请人：中国药科大学

  公开号：CN113135922B

  公开（公告）日：2023-05-30

  本发明属于医药化学领域，公开了氮杂环庚烷[4,3,2‑cd]异吲哚‑2‑酮类衍生物及其应用。该类化合物或其药学上可接受的盐具有如下通式本发明通过研究BET蛋白的晶体结构模型以及总结BET的构效关系，提供了氮杂环庚烷[4,3,2‑cd]异吲哚‑2‑酮类衍生物，通过药理试验结果标明，本发明的化合物具有良好的BET蛋白抑制活性，具有良好的应用前景，该类化合物与BRD4蛋白结合能力良好，可用于制备预防和/或治疗与BET蛋白有关疾病的药物上的应用。