2-溴-5-羟基苯甲酸 | 58380-11-3

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-溴-5-羟基苯甲酸
• 中文别名: 2-溴-5-羟基-4-甲氧基苯甲酸
• 英文名称: 2-bromo-5-hydroxybenzoic acid
• CAS: 58380-11-3
• 化学式: C₇H₅BrO₃
• 分子量: 217.019
• InChiKey: HTCSAMJZDHWTKD-UHFFFAOYSA-N

物化性质

• 熔点：
  185 °C (decomp)
• 沸点：
  374.5±32.0 °C(Predicted)
• 密度：
  1.861±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

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：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2918290000
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  室温且干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Bromo-5-hydroxybenzoic 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: 2-Bromo-5-hydroxybenzoic acid
CAS number: 58380-11-3

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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.
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: C7H5BrO3
Molecular weight: 217.0

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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

反应信息

• 作为反应物：
  描述：

  2-溴-5-羟基苯甲酸 在 咪唑 、 lithium aluminium tetrahydride 、 二苯基膦叠氮化物 、 硼烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 21.0h， 生成 [2-bromo-5-(tert-butyldiphenylsilyloxy)-phenyl]methylamine
  参考文献：
  名称：

  3-Aminopyrrolidinone Farnesyltransferase Inhibitors:  Design of Macrocyclic Compounds with Improved Pharmacokinetics and Excellent Cell Potency

  摘要：

  A series of macrocyclic 3-aminopyrrolidinone farnesyltransferase inhibitors (FTIs) has been synthesized. Compared with previously described linear 3-aminopyrrolidinone FTIs such as compound 1, macrocycles such as 49 combined improved pharmacokinetic properties with a reduced potential for side effects. In dogs, oral bioavailability was good to excellent, and increases in plasma half-life were due to attenuated clearance. It was observed that in vivo clearance correlated with the flexibility of the molecules and this concept proved useful in the design of FTIs that exhibited low clearance, such as FTI 78. X-ray crystal structures of compounds 49 and 66 complexed with farnesyltransferase (FTase)-farnesyl diphosphate (FPP) were determined, and they provide details of the key interactions in such ternary complexes. Optimization of this 3-aminopyrrolidinone series of compounds led to significant increases in potency, providing 83 and 85, the most potent inhibitors of FTase in cells described to date.

  DOI：

  10.1021/jm010531d
• 作为产物：
  描述：

  2-溴-5-甲氧基苯甲酸 在 aluminum (III) chloride 作用下， 以 氯苯 为溶剂， 反应 16.0h， 生成 2-溴-5-羟基苯甲酸
  参考文献：
  名称：

  Gut Microbiota Conversion of Dietary Ellagic Acid into Bioactive Phytoceutical Urolithin A Inhibits Heme Peroxidases

  摘要：

  大量研究表明，富含植物化学物质的膳食具有许多有益功能，尤其是在病理状态下，但由于个体间的差异，其效果往往并不一致。宿主肠道微生物群及其对膳食植物化学物质的调节作用已成为对植物药干预效果产生重大影响的因素。在这里，我们研究了从鞣花酸（EA）中提取的一种活性微生物代谢产物--尿囊素 A（UA 或 3,8-二羟基苯并[c]色烯-6-酮）的生物活性。我们的研究表明，与母体化合物 EA 相比，UA 能有效抑制血红素过氧化物酶，即髓过氧化物酶（MPO）和乳过氧化物酶（LPO）。此外，铬偶氮呋喃 S（CAS）检测表明，EA（而非 UA）因其儿茶酚样结构而能够与 Fe3+ 结合，尽管其适度的血红素过氧化物酶抑制活性在与 Fe3+ 结合后会减弱。有趣的是，UA 介导的 MPO 和 LPO 抑制作用可被先天性免疫蛋白人 NGAL 或其鼠类同源物脂钙蛋白 2（Lcn2）所阻止，这意味着宿主先天性免疫与微生物群相互作用的复杂性。光谱分析表明，UA 能抑制血红素过氧化物酶催化的反应，使过氧化物酶恢复到无活性的原生状态。为支持这些体外实验结果，UA 能显著减少中性粒细胞中由磷酸果胶肉豆蔻酸醋酸酯（PMA）诱导的超氧化物生成，而 EA 却不能阻止超氧化物的生成。与 EA 处理的小鼠相比，UA 能明显减轻 PMA 诱导的小鼠耳水肿和 MPO 活性。总之，我们的研究结果表明，微生物区系介导的 EA 向 UA 的转化对宿主和微生物区系都有利，即 UA 介导的促氧化酶抑制可减轻组织炎症，减轻肠道细菌的非特异性杀灭，并削弱 EA 的铁结合特性，从而为微生物区系获取限制性营养铁和在肠道中茁壮成长提供竞争优势。

  DOI：

  10.1371/journal.pone.0156811

文献信息

• Ruthenium-Catalyzed Hydroarylation and One-Pot Twofold Unsymmetrical C−H Functionalization of Arenes
  作者：Koushik Ghosh、Raja K. Rit、E. Ramesh、Akhila K. Sahoo

  DOI：10.1002/anie.201600649

  日期：2016.6.27

  excellent yields. A one‐pot, unsymmetrical, twofold C−H functionalization involving intramolecular C−C and intermolecular C−C/C−N bond formations is successfully demonstrated by using a single set of catalytic reaction conditions, which is unprecedented thus far. A novel isoquinolone‐bearing dihydrobenzofuran is constructed through an unsymmetrical twofold C−H functionalization.

  甲基苯基硫肟亚胺（MPS）用作链烯基苯甲酸衍生物在钌催化的分子内氢芳基化反应中的导向基团，从而以良好或优异的收率提供二氢苯并呋喃和二氢吲哚。通过使用一组催化反应条件成功地证明了涉及分子内C-C和分子间C-C / C-N键形成的单锅，不对称，双重CH功能化，这是迄今为止前所未有的。通过不对称的双重CH官能团构建了一种新型的带有异喹诺酮的二氢苯并呋喃。
• Synthesis of Polysubstituted Isoindolinones via Radical Cyclization of 1,3-Dicarbonyl Ugi-4CR Adducts Using Tetrabutylammonium Persulfate and TEMPO
  作者：Andrés Borja-Miranda、Fabiola Valencia-Villegas、J. Armando Lujan-Montelongo、Luis A. Polindara-García

  DOI：10.1021/acs.joc.0c02441

  日期：2021.1.1

  The development of an efficient method for the synthesis of polysubstituted isoindolinones from 1,3-dicarbonyl Ugi-4CR adducts, employing an aromatic radical cyclization process promoted by tetrabutylammonium persulfate and 2,2,6,6-tetramethyl-1-piperidine 1-oxyl (TEMPO), is described. The protocol allowed the construction of a library of isoindolinones bearing a congested carbon in good to excellent

  开发一种由1,3-二羰基Ugi-4CR加合物合成多取代异吲哚啉酮的有效方法，该方法采用了过硫酸四丁铵和2,2,6,6-四甲基-1-哌啶1-氧基所促进的芳族自由基环化工艺说明（TEMPO）。该方案允许在温和的条件下和较短的反应时间内以良好的收率构建具有拥挤碳的异吲哚啉酮文库。
• 3-(3-aryloxyphenyl)-1-(substituted methyl)-s-triazine-2,4,6-oxo or
  申请人：American Cyanamid Co.

  公开号：US05519133A1

  公开（公告）日：1996-05-21

  There is provided a 3-(3-aryloxyphenyl)-1-(substituted methyl)-s-triazine-2,4,6-oxo or thiotrione compound having the structural formula I ##STR1## Further provided are a composition and a method comprising that compound for the control of undesirable plant species.

  提供一种具有结构式 I 的 3-(3-芳氧基苯基)-1-(取代甲基)-s-三嗪-2,4,6-酮或硫代三嗪化合物。进一步提供了一种包含该化合物的组合物和方法，用于控制不良植物物种。
• Synthesis, Characterization, Molecular Docking, and Biological Activities of Some Natural and Synthetic Urolithin Analogs
  作者：Bahareh Noshadi、Tugba Ercetin、Chiara Luise、Mine Yarim Yuksel、Wolfgang Sippl、Mustafa Fethi Sahin、Mustafa Gazi、Hayrettin Ozan Gulcan

  DOI：10.1002/cbdv.202000197

  日期：2020.8

  as well as some synthetic urolithin analogues have been synthesized and screened for their biological activities in various enzyme inhibition (acetylcholinesterase, butyrylcholinesterase, monoamine oxidase B, cyclooxygenase 1, and cyclooxygenase 2) and antioxidant (DPPH radical scavenging) assay systems. The results, for the first time, pointed out the possible mechanisms of the activities of the urolithins

  尿石素（即羟基取代的苯并[c]色烯-6-酮衍生物）是在接触各种富含鞣花单宁的饮食后在胃肠道内形成的，特别是涉及石榴、坚果和浆果。关于鞣花单宁的生物利用度不足，通过这些膳食提取物获得的生物活性归因于尿石素化合物，因为它们是生物可利用的。特别是，有研究表明富含鞣花单宁的食物对于阿尔茨海默病 (AD) 的保护性和替代性治疗的重要性。从这个角度来看，在本研究中，主要的尿石素（即尿石素 A 和 B）、它们的甲醚代谢物、以及一些合成的尿石素类似物已经合成并筛选了它们在各种酶抑制（乙酰胆碱酯酶、丁酰胆碱酯酶、单胺氧化酶 B、环氧合酶 1 和环氧合酶 2）和抗氧化剂（DPPH 自由基清除）测定系统中的生物活性。该结果首次指出了尿石素治疗AD的活性与相应的构效关系的可能机制。还进行了对接研究以研究与相应受体的可能相互作用。指出了尿石素活性治疗AD的可能机制及其相应的构效关系。还进行了对接研究以研究与相应受体
• Urolithin A and B Derivatives as ON-OFF Selective Fluorescent Sensors for Iron(III)
  作者：Amirhossein Fallah、Bahareh Noshadi、Mustafa Gazi、Hayrettin Ozan Gülcan

  DOI：10.1007/s10895-019-02475-0

  日期：2020.1

  been of great significance in various fields such as biological and environmental cycles. Our previous studies have indicated a new coumarin based lactone, Urolithin B (i.e., 3-Hydroxy[c]chromen-6-one) as a potent fluorescent probe for the selective detection of Iron (III). In order to question the extension of this application to other urolithins, we have synthesized the major urolithins that humans

  对环境至关重要的金属离子的检测和感测在诸如生物和环境循环的各个领域中一直具有重要意义。我们以前的研究表明，一种新的基于香豆素的内酯Urolithin B（即3-Hydroxy [c] chromen-6-one）作为选择性检测铁（III）的有效荧光探针。为了质疑将此应用扩展到其他尿石素，我们合成了人类通过常规饮食所接触的主要尿石素。在进行结构鉴定研究之后，对化合物进行了荧光滴定测试，以研究其与各种金属的相互作用。结果表明，每种标题化合物在开-关模式下选择性地与铁（III）相互作用，而与另一种金属的存在无关。与以前的发现类似，3+仅表明内酯基的重要性。