4-溴-3-甲氧基苯甲酸 | 56256-14-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸的卤化、磺化、硝化或亚硝化衍生物
• 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: 4-溴-3-甲氧基苯甲酸
• 中文别名: 3-甲氧基-4-溴苯甲酸
• 英文名称: 4-bromo-3-methoxy-benzoic acid
• 英文别名: 3-methoxy-4-bromobenzoic acid；4-Bromo-3-methoxybenzoic acid
• CAS: 56256-14-5
• 化学式: C₈H₇BrO₃
• 分子量: 231.046
• InChiKey: UEVXVBKBOFGKIN-UHFFFAOYSA-N

物化性质

• 熔点：
  221-224
• 沸点：
  333.7±27.0 °C(Predicted)
• 密度：
  1.625±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2918990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温且干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Bromo-3-methoxybenzoic 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: 4-Bromo-3-methoxybenzoic acid
CAS number: 56256-14-5

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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: C8H7BrO3
Molecular weight: 231.0

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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

用途

4-溴-3-甲氧基苯甲酸是一种重要的精细有机化工产品，广泛应用于医药、农药、香料和石油化工等领域。随着科学技术的发展，它在合成药物及液晶领域也发挥着越来越重要的作用。

合成方法

将828 mg（12 mmol）NaNO₂、1.58 mL（12 mmol）TMS Br 和218 mg（0.8 mmol）苄基三乙基溴化铵溶解于30 mL DMF 中，然后加入669 mg（4 mmol）的4-氨基-3-甲氧基苯甲酸。将反应混合物搅拌2小时后，用水稀释并用EtOAc（三次，每次15 mL）萃取。合并有机层，用水洗涤并以盐水洗涤，然后用无水Na₂SO₄干燥并通过旋转蒸发浓缩。使用己烷/EtOAc（7:3）通过硅胶快速色谱纯化，得到675 mg白色固体4-溴-3-甲氧基苯甲酸，产率为73%。其13C NMR（125 MHz，丙酮-d₆）δ值为：167.0、157.0、134.2、132.3、123.9、117.6、113.6、56.8。

反应信息

• 作为反应物：
  描述：

  4-溴-3-甲氧基苯甲酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-bromo-3-methoxybenzoyl chloride
  参考文献：
  名称：

  发现8-氨基-咪唑并[1,5-a]吡嗪类化合物是可逆的BTK抑制剂，用于治疗类风湿关节炎。

  摘要：

  布鲁顿酪氨酸激酶（BTK）是一种Tec家族激酶，在B细胞受体（BCR）途径中具有明确的作用。它已成为用于选择性B细胞抑制和治疗B细胞相关疾病的有吸引力的激酶靶标。我们报告了一系列基于8-氨基-咪唑并[1,5-a]吡嗪的化合物，它们是有效的可逆BTK抑制剂，具有出色的激酶选择性。通过配体与激酶铰链的特异性相互作用并由氨基吡啶与Ser538和Asp539的氢键键合以及后口袋中三氟吡啶的疏水性相互作用来实现选择性。这些相互作用在与BTK酶形成复合物的先导化合物1和3的X射线晶体结构中很明显。

  DOI：

  10.1021/acsmedchemlett.5b00463
• 作为产物：
  描述：

  3-甲氧基苯甲酸 在 正丁基锂 、 1,2-二溴四氯乙烷 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以45%的产率得到4-溴-3-甲氧基苯甲酸
  参考文献：
  名称：

  通过邻位金属化对取代的甲氧基苯甲酸进行首次常规，直接和区域选择性合成

  摘要：

  在基于邻-金属化位点在芳族化学的新值一般方法邻- ，间- ，和对-茴香酸（1 - 3）（方案1）进行说明。通过改变碱，金属化温度和曝光时间，可以将金属化选择性地定向到任何一个邻位。的金属化邻-茴香酸（1）与小号正丁基锂/ TMEDA在THF中在-78℃下在位置adjacente将羧酸只发生。另一方面，通过n -BuLi / t -BuOK观察到区域选择性的逆转。在LTMP为0°C的情况下，间苯二酸的两个指向矢（2）协同作用以直接将金属引入它们之间，而n - BuLi / t- BuOK优先除去位于甲氧基和羧酸酯（H-4）对位的质子。s- BuLi / TMEDA仅在羧酸酯附近与对茴香酸（3）反应。根据这些方法，已开发出通过多种途径难以达到的，具有多种功能的非常简单的甲氧基苯甲酸的途径（表1）。

  DOI：

  10.1021/jo070082a

文献信息

• N,N-Di-alkyl(phenoxy)benzamide derivatives
  申请人：G. D. Searle & Co.

  公开号：US05223539A1

  公开（公告）日：1993-06-29

  The present invention relates to compounds of the formula: ##STR1## and the pharmaceutically acceptable salts thereof, wherein Z can be: ##STR2## wherein R.sup.3 is alkyl having 1 to 6 carbon atoms and, when n is greater than 1, each R.sup.3 can be the same or different; and n is an integer from 1 to 3; R.sup.1 and R.sup.2 can each independently be hydrogen, straight or branched chain alkyl, or cycloalkyl having 3 to 8 carbon atoms which can optionally be substituted at one or more positions by alkyl of 1 to 6 carbon atoms; X is oxygen, sulfur, NR.sup.4, wherein R.sup.4 is hydrogen or alkyl having 1 to 4 carbon atoms, C.dbd.O, CHOH, or CH.sub.2 ; Y is hydrogen, alkoxy, halogen, alkyl, or hydroxy; and m is an integer from 0 to 3. The compounds are antagonists of platlet-activating factor (PAF).

  本发明涉及以下式的化合物：##STR1##及其药学上可接受的盐，其中Z可以是：##STR2##其中R.sup.3是具有1至6个碳原子的烷基，当n大于1时，每个R.sup.3可以相同或不同；n是1至3之间的整数；R.sup.1和R.sup.2可以分别是氢、直链或支链烷基，或者是具有3至8个碳原子的环烷基，可以在一个或多个位置被1至6个碳原子的烷基取代；X是氧、硫、NR.sup.4，其中R.sup.4是氢或具有1至4个碳原子的烷基，C.dbd.O，CHOH或CH.sub.2；Y是氢、烷氧基、卤素、烷基或羟基；m是0至3之间的整数。这些化合物是血小板活化因子（PAF）的拮抗剂。
• PYRROLOPYRAZINE-SPIROCYCLIC PIPERIDINE AMIDES AS MODULATORS OF ION CHANNELS
  申请人：Hadida Ruah Sara Sabina

  公开号：US20120196869A1

  公开（公告）日：2012-08-02

  The invention relates to pyrrolopyrazine-spirocyclic piperidine amide compounds useful as inhibitors of ion channels. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  这项发明涉及对离子通道具有抑制作用的吡咯吡嘧啶-螺环哌啶酰胺化合物。该发明还提供了包括该发明化合物的药学上可接受的组合物，以及使用这些组合物治疗各种疾病的方法。
• TBK/IKK INHIBITOR COMPOUNDS AND USES THEREOF
  申请人：Merck Patent GmbH

  公开号：US20160376283A1

  公开（公告）日：2016-12-29

  The present invention relates to compounds of Formula I and pharmaceutically acceptable compositions thereof, useful as TBK/IKKε inhibitors.

  本发明涉及式I化合物及其药用可接受的组合物，用作TBK/IKKε抑制剂。
• [EN] CHROMAN - SPIROCYCLIC PIPERIDINE AMIDES AS MODULATORS OF ION CHANNELS<br/>[FR] AMIDES DE PIPÉRIDINE SPIROCYCLIQUE CHROMANIQUE EN TANT QUE MODULATEURS DES CANAUX IONIQUES
  申请人：VERTEX PHARMA

  公开号：WO2012112743A1

  公开（公告）日：2012-08-23

  The invention relates to chroman spirocyclic piperidine amide derivatives useful as inhibitors of ion channels. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  这项发明涉及用于抑制离子通道的螺环色满烷酰胺衍生物。该发明还提供了包含本发明化合物的药用可接受组合物，以及使用这些组合物治疗各种疾病的方法。
• [EN] BIS-(SULFONYLAMINO) DERIVATIVES FOR TREATMENT OF PAIN AND INFLAMMATION<br/>[FR] DÉRIVÉS BIS-(SULFONYLAMINO) DESTINÉS AU TRAITEMENT DE LA DOULEUR ET DE L'INFLAMMATION
  申请人：ASTRAZENECA AB

  公开号：WO2010132016A1

  公开（公告）日：2010-11-18

  The invention provides compounds of formula (I) wherein R1, R2, R3, A and m are as defined in the specification and optical isomers, racemates and tautomers thereof, and pharmaceutically acceptable salts thereof; together with processes for their preparation, pharmaceutical compositions containing them and their use in therapy. The compounds are inhibitors of microsomal prostaglandin E synthase-1.

  该发明提供了式（I）的化合物，其中R1、R2、R3、A和m如规范中定义，并且其光学异构体、消旋体和互变异构体，以及其药学上可接受的盐；以及它们的制备方法、含有它们的药物组合物以及它们在治疗中的应用。这些化合物是微粒体前列腺素E合成酶-1的抑制剂。