4-溴-3-羟基苯甲醛 | 20035-32-9

• 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: 4-溴-3-羟基苯甲醛
• 英文名称: 4-bromo-3-hydroxybenzaldehyde
• CAS: 20035-32-9
• 化学式: C₇H₅BrO₂
• 分子量: 201.019
• InChiKey: USCBCBWUZOPHNV-UHFFFAOYSA-N

物化性质

• 熔点：
  131.5 °C
• 沸点：
  265.0±25.0 °C(Predicted)
• 密度：
  1.737±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  室温和干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Bromo-3-hydroxybenzaldehyde
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-Bromo-3-hydroxybenzaldehyde
CAS number: 20035-32-9

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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: 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

应用广泛，4-溴-3-羟基苯甲醛可用作有机合成中间体和医药中间体，主要应用于实验室研发和化工生产过程中。

反应信息

• 作为反应物：
  描述：

  4-溴-3-羟基苯甲醛 在 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 28.0h， 生成 ethyl (E)-4-bromo-3-(3'-tert-butoxycarboxamidopropoxy)cinnamate
  参考文献：
  名称：

  杂环金刚烷基类胡萝卜素对 IκB 激酶-β 和 IκB 激酶-α 的抑制作用

  摘要：

  我们最近报道了一系列含有金刚烷基的类视黄醇相关分子，又名金刚烷基类胡萝卜素 (AdArs)，在瞬时转染试验中显示出显着的癌细胞生长抑制活性和活化的 RXRα (NR2B1)，但缺乏 RAR 反式激活能力。我们现在已经探索了这些 AdArs 是否也可以结合和抑制 IKKβ，IKKβ 是一种已知的靶标，通过含有查尔酮官能团的相关 AdArs 介导凋亡诱导和癌细胞生长抑制。此外，我们已经制备并评估了新型 AdArs，它包含一个中心杂环，在极性末端连接金刚烷基苯酚和羧酸。我们的结果表明，大多数 RXRα 激活化合物缺乏 IKKβ 抑制活性。相比之下，

  DOI：

  10.1016/j.bmc.2014.01.006
• 作为产物：
  描述：

  乙酸间甲苯酯 在 磺酰氯 、 偶氮二异丁腈 、 溴 作用下， 以 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 7.0h， 生成 4-溴-3-羟基苯甲醛
  参考文献：
  名称：

  4-（4-溴-3-醛基-苯氧基）-苯甲腈的合成方法

  摘要：

  本发明提供了一种4‑(4‑溴‑3‑醛基‑苯氧基)‑苯甲腈的合成方法，以3‑甲基苯酚为起始原料，与酸酐反应制备3‑甲基‑苯酯化物，3‑甲基‑苯酯化物与磺酰氯反应制备3‑氯甲基‑苯酯化物和3‑二氯甲基‑苯酯化物的混合物，加乌洛托品水解后得到3‑羟基‑苯甲醛，经溴化反应得到4‑溴‑3‑羟基‑苯甲醛，加4‑氟苯甲腈经缩合反应后制得4‑(4‑溴‑3‑醛基‑苯氧基)‑苯甲腈。本发明反应原料价廉易得，反应步骤少，生产成本低，工艺简单，产品纯度高，达99.0％以上，有利于实现工业化生产。

  公开号：

  CN109053443A

文献信息

• Mild, Efficient, and Regioselective Monobromination of Arylamines and Phenols Using [BBIm]Br₃ as a New Reagent
  作者：Sanjay P. Borikar、Thomas Daniel、Vincent Paul

  DOI：10.1080/00397910903009430

  日期：2010.2.12

  synthesis and characterization of the room-temperature ionic liquid 1,3-di-n-butylimidazolium tribromide ([BBIm]Br3) (2) and its application as an efficient reagent and solvent for regioselective bromination of arylamines and phenols under mild conditions. The bromination was carried out in the absence of organic solvents, and in most cases, the only extraction solvent needed was water. The spent 1,3-di-n-butylimidazolium

  我们在此报告了一种合成和表征室温离子液体 1,3-二正丁基咪唑鎓三溴化物 ([BBIm]Br3) (2) 的有效方法及其作为区域选择性溴化的有效试剂和溶剂的应用芳胺和酚类在温和条件下。溴化是在没有有机溶剂的情况下进行的，在大多数情况下，唯一需要的萃取溶剂是水。用过的溴化 1,3-二正丁基咪唑鎓 (1) 很容易回收利用。
• [EN] PYRAZOLE DERIVATIVES, COMPOSITIONS AND THERAPEUTIC USE THEREOF<br/>[FR] DÉRIVÉS DE PYRAZOLE, COMPOSITIONS LES COMPRENANT ET LEUR UTILISATION THÉRAPEUTIQUE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2017191098A1

  公开（公告）日：2017-11-09

  Compounds of Formula (I): and salts thereof, and methods of use as Janus kinase inhibitors are described herein.

  化合物的化学式（I）及其盐，以及作为Janus激酶抑制剂的使用方法在此处描述。
• NOVEL COMPOUND AND PHARMACOLOGICALLY ACCEPTABLE SALT THEREOF
  申请人：MEIJI SEIKA PHARMA CO., LTD.

  公开号：US20190322686A1

  公开（公告）日：2019-10-24

  A compound represented by the general formula (1) below or a pharmacologically acceptable salt thereof: [In the formula (1), R 1 and R 2 may be the same or different and each represents a hydrogen atom, a halogen atom, a hydroxyl group, a carboxy group, a cyano group, an optionally substituted C 1-6 alkyl group et al.; R 3 represents a hydrogen atom; R 4 represents an optionally substituted 4- to 10-membered monocyclic heterocyclic group containing 1 to 4 heteroatoms selected from an oxygen atom, a nitrogen atom, and a sulfur atom; X represents a group represented by the following formula: —CH 2 —, —CH 2 —CH 2 —, —CH 2 —CH 2 —CH 2 —, or —CH 2 —O—CH 2 —; and Z represents a hydrogen atom or a hydroxyl group.]

  通用公式（1）表示的化合物或其药理学上可接受的盐：[在公式（1）中，R1和R2可以相同也可以不同，每个代表氢原子，卤原子，羟基，羧基，氰基，可选择地取代的C1-6烷基等；R3代表氢原子；R4代表可选择地取代的含有1至4个异原子（从氧原子，氮原子和硫原子中选择）的4至10元单环杂环基团；X代表以下式表示的基团：—CH2—，—CH2—CH2—，—CH2—CH2—CH2—，或—CH2—O—CH2—；Z代表氢原子或羟基。]
• Vinylidenation of Organoboronic Esters Enabled by a Pd‐Catalyzed Metallate Shift
  作者：Mark D. Aparece、Chenpeng Gao、Gabriel J. Lovinger、James P. Morken

  DOI：10.1002/anie.201811782

  日期：2019.1.8

  Organoboron "ate" complexes undergo a net vinyl insertion reaction to give 1,1-disubstituted alkenyl boronic esters when treated with stoichiometric allyl acetate and a palladium catalyst. Reactions that employ vinyllithium afforded good to excellent yields after one hour, while reactions that employ vinylmagnesium chloride furnished modest to good yields after 18 hours.

  当用化学计量的乙酸烯丙酯和钯催化剂处理时，有机硼“ate”络合物经历净乙烯基插入反应，得到1,1-二取代的烯基硼酸酯。使用乙烯基锂的反应在一小时后提供良好至优异的产率，而使用乙烯基氯化镁的反应在18小时后提供中等至良好的产率。
• [EN] SMALL-MOLECULE INHIBITORS FOR THE Β-CATENIN/B-CELL LYMPHOMA 9 PROTEIN−PROTEIN INTERACTION<br/>[FR] INHIBITEURS À PETITES MOLÉCULES POUR L'INTERACTION PROTÉINE-PROTÉINE DE LYMPHOME À LYMPHOCYTES T/β-CATÉNINE
  申请人：H LEE MOFFITT CANCER CT & RES

  公开号：WO2021055936A1

  公开（公告）日：2021-03-25

  Disclosed are inhibitors for the β-catenin/B-cell lymphoma 9 interaction. The inhibitors are selective for β-catenin/B-cell lymphoma 9 over β-catenin/ E-cadherin PPI interaction. Methods of using the disclosed compounds to treat cancer are also disclosed.

  本文披露了β-连接蛋白/B细胞淋巴瘤9相互作用的抑制剂。这些抑制剂对β-连接蛋白/B细胞淋巴瘤9的选择性高于β-连接蛋白/E-钙粘蛋白PPI相互作用。还披露了使用这些披露的化合物来治疗癌症的方法。