3-溴-4-羟基-5-甲氧基苯甲酸甲酯 | 108249-43-0

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 3-溴-4-羟基-5-甲氧基苯甲酸甲酯
• 英文名称: methyl 3-bromo-4-hydroxy-5-methoxybenzoate
• 英文别名: 3-bromo-4-hydroxy-5-methoxy-benzoic acid methyl ester；3-Brom-4-hydroxy-5-methoxy-benzoesaeure-methylester
• CAS: 108249-43-0
• 化学式: C₉H₉BrO₄
• 分子量: 261.072
• InChiKey: UIWBPQDQVILUJA-UHFFFAOYSA-N

物化性质

• 熔点：
  152-152.5 °C
• 沸点：
  311.2±37.0 °C(Predicted)
• 密度：
  1.573±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2918990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 3-bromo-4-hydroxy-5-methoxybenzoate
Synonyms: Methyl 5-bromo-4-hydroxy-3-methoxybenzoate

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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: Methyl 3-bromo-4-hydroxy-5-methoxybenzoate
CAS number: 108249-43-0

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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: C9H9BrO4
Molecular weight: 261.1

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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：

  3-溴-4-羟基-5-甲氧基苯甲酸甲酯 在 cesium fluoride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 42.0h， 生成 methyl 3-methoxy-4,5-bis((trifluoromethyl)thio)benzoate
  参考文献：
  名称：

  通过Aryne中间体合成1,2-双（三氟甲硫基）芳烃

  摘要：

  已经开发了合成1,2-双三氟甲基硫代芳烃的通用方法。由甲硅烷基芳基三氟甲磺酸酯或卤化物产生的芳烃与双（三氟甲基）二硫化物反应，得到1,2-双-三氟甲基硫代芳烃。芳基，烷基，酯，卤化物和甲氧基官能团与反应条件相容。使用双（全氟芳基）二硫化物可得到中等产率的芳烃二硫基化或环化成氟化二苯并噻吩。

  DOI：

  10.1021/acs.orglett.7b01901
• 作为产物：
  描述：

  香草酸甲酯 在 双氧水 、 vanadium-containing chloroperoxidase from Curvularia inaequalis 、 potassium bromide 作用下， 以 丙酮 为溶剂， 生成 3-溴-4-羟基-5-甲氧基苯甲酸甲酯
  参考文献：
  名称：

  含钒氯过氧化物酶催化酚和酚酸的多功能增值

  摘要：

  木质素解聚的下游产品转化对于高价值芳香化学品的生产具有重要意义。然而，这种转变常常受到恶劣反应条件下化学氧化的阻碍。在这项研究中，我们证明来自Curvularia inaequalis ( Ci VCPO)的含钒氯过氧化物酶原位产生的次卤酸盐可以卤化各种富电子和缺电子苯酚和酚酸底物。具体而言，C 1 VCPO能够实现脱羧卤化、脱酰基卤化、卤化和直接氧化反应。用于酚类化合物增值的多功能转化路线显示出高达 99% 的转化率和 99% 的选择性，Ci VCPO的周转次数为 60,700，周转频率为 60 s –1。这项研究可能扩展木质素增值的生物催化工具箱。

  DOI：

  10.1021/acscatal.3c05333

文献信息

• [EN] SUBSTITUTED INDOLE MCL-1 INHIBITORS<br/>[FR] INHIBITEURS D'INDOLES MCL-1 SUBSTITUÉS
  申请人：UNIV VANDERBILT

  公开号：WO2017152076A1

  公开（公告）日：2017-09-08

  The present disclosure provides for compounds that inhibit the activity of an anti- apoptotic Bcl-2 family member Myeloid cell leukemia-1 (Mcl-1) protein. The present disclosure also provides for pharmaceutical compositions as well as methods for using compounds for treatment of diseases and conditions (e.g., cancer) characterized by the over- expression or dysregulation of Mcl-1 protein.

  本公开提供了抑制抗凋亡Bcl-2家族成员髓细胞白血病-1（Mcl-1）蛋白活性的化合物。本公开还提供了用于治疗由Mcl-1蛋白过度表达或失调所特征的疾病和病况（例如癌症）的药物组合物以及使用化合物的方法。
• [EN] Btk INHIBITORS WITH IMPROVED DUAL SELECTIVITY<br/>[FR] INHIBITEUR DE BTK AYANT UNE DOUBLE SÉLECTIVITÉ AMÉLIORÉE
  申请人：BEIGENE LTD

  公开号：WO2019034009A1

  公开（公告）日：2019-02-21

  Disclosed herein is a tri-substituted phenyl Btk inhibitors with improved dual selectivity, a method and a composition for inhibiting Btk and treating disease associated with undesirable Btk activity (Btk-related diseases).

  本文披露了一种具有改进的双重选择性的三取代苯基Btk抑制剂，以及用于抑制Btk和治疗与不良Btk活性相关的疾病（Btk相关疾病）的方法和组合物。
• The biosynthesis of ubiquinone: Synthesis and enzymatic modification of biosynthetic precursors
  作者：Jennifer A. Shepherd、Wayne W. Poon、David C. Myles、Catherine F. Clarke

  DOI：10.1016/0040-4039(96)00324-3

  日期：1996.4

  The synthesis of key intermediates in the eukaryotic biosynthetic pathway of ubiquinone (Q) and the biotransformation of these materials with yeast (S. cerevisiae) mitochondria are described. The synthesis of Q aromatic precursors 2,3, and 4 (n = 3 in all cases) relies on the palladium (O) catalyzed coupling of farnesyl tributylstannane with suitably functionalized aryl halides. Preliminary experiments

  描述了泛醌（Q）真核生物合成途径中关键中间体的合成以及酵母线粒体对这些物质的生物转化。Q芳族前体2,3和4（在所有情况下，n = 3）的合成依赖于法呢基三丁基锡烷与适当官能化的芳基卤化物的钯（O）催化偶联。初步实验显示的合成底物的该温育3与来自酵母含有3,4-二羟基-5- hexaprenylbenzoate甲基转移酶基因（线粒体COQ3）和S- [甲基- 3 H]腺苷-L-甲硫氨酸的产率放射性标记4。
• Double <i>N</i>-Arylation of Primary Amines:  Carbazole Synthesis from 2,2‘-Biphenyldiols
  作者：Atsushi Kuwahara、Koji Nakano、Kyoko Nozaki

  DOI：10.1021/jo048472+

  日期：2005.1.1

  The double N-arylation of primary amines with 2,2‘-biphenylylene ditriflates was investigated for the synthesis of multisubstituted carbazoles. Palladium complexes supported by 2-dicyclohexylphosphino-2‘-methylbiphenyl or Xantphos [4,5-bis(diphenylphosphino)-9,9-dimethylxanthene] were found to be efficient catalysts for the reaction. The catalysts allow the use of anilines with an electron-donating

  研究了伯胺与2,2'-联亚苯基二三氟甲磺酸酯的双N-芳基化反应，用于合成多取代的咔唑。发现由2-二环己基膦基-2'-甲基联苯或Xantphos [4,5-双（二苯基膦基）-9,9-二甲基x吨]负载的钯配合物是该反应的有效催化剂。该催化剂允许使用具有给电子或吸电子取代基和多取代的2,2'-联亚苯基二三氟甲磺酸酯的苯胺作为底物。氨当量，如ö -叔丁基氨基甲酸酯，也可用作氮源，得到Ñ -保护的咔唑，可以很容易地得到相应的Ñ-脱保护后的未取代咔唑。通过使用这种方法，咔唑生物碱鼠李糖碱以五个步骤的产率合成为40％，效率与最近的先例相当。
• Bacterial Catabolism of Biphenyls: Synthesis and Evaluation of Analogues
  作者：Sven Nerdinger、Eugene Kuatsjah、Timothy E. Hurst、Inge Schlapp-Hackl、Volker Kahlenberg、Klaus Wurst、Lindsay D. Eltis、Victor Snieckus

  DOI：10.1002/cbic.201800231

  日期：2018.8.16

  Alkylated 2,3‐dihydroxybiphenyls (DHBs) have been prepared on the gram scale by using a Directed ortho Metalation–Suzuki–Miyaura coupling strategy. These compounds were used to investigate the substrate specificity of the meta‐cleavage dioxygenase BphC, a key enzyme in the microbial catabolism of biphenyl. Isolation of the meta‐cleavage products will allow further study of the catabolism of lignin‐derived

  烷基化的2,3-二羟基联苯（地区保健委员会）已通过使用有向制备的克规模邻金属化-铃木-宫浦偶联策略。这些化合物用于研究间位裂解双加氧酶BphC（联苯微生物分解代谢中的关键酶）的底物特异性。分离元裂解产物将有助于进一步研究木质素衍生联苯的分解代谢。