5-溴-2,3-二甲氧基苯甲酸 | 72517-23-8

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 环羧酸
• 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: 5-溴-2,3-二甲氧基苯甲酸
• 英文名称: 5-bromo-2,3-dimethoxybenzoic acid
• 英文别名: 2,3-dimethoxy-5-bromobenzoic acid
• CAS: 72517-23-8
• 化学式: C₉H₉BrO₄
• 分子量: 261.072
• InChiKey: ZKMWQUDSDYOEJQ-UHFFFAOYSA-N

物化性质

• 熔点：
  120 °C
• 沸点：
  348.1±42.0 °C(Predicted)
• 密度：
  1.571±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
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  室温、避光、干燥密封保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Bromo-2,3-dimethoxybenzoic 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: 5-Bromo-2,3-dimethoxybenzoic acid
CAS number: 72517-23-8

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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：

  5-溴-2,3-二甲氧基苯甲酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.67h， 生成 (-)-(S)-5-溴-2,3-二甲氧基-n-[(1-乙基-2-吡咯烷)甲基]-苯甲酰胺
  参考文献：
  名称：

  (S)-N-[(1-乙基-2-吡咯烷基)甲基]-2,3-二甲氧基-5-(三丁基锡)苯甲酰胺从异瑞莫必利的简便制备：[125I]-和[123I]Epidepride的前体

  摘要：

  摘要 [125I]Epidepride，(S)-(-)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-[125I]iodo-2,3-dimethoxybenzamide ([125I]NCQ 219)，是一种新的、极强的放射性配体，可用于研究大脑中多巴胺 D-2 受体的分布。它的合成需要相应的 5-（三丁基锡）衍生物的放射性碘化。芳基锡前体 (TDP 526) 可以通过四（三苯基膦）钯 (0) 催化的甲锡酰化反应，在三乙胺中使用双（三正丁基锡）从异雷莫昔必利（FLB 457）以高产率方便地制备。开发了一种从邻香兰素制备异瑞莫昔利的改进方法。

  DOI：

  10.1080/00397919108019800
• 作为产物：
  描述：

  苯甲酸,二羟基- 在 溴 、 potassium carbonate 作用下， 以 溶剂黄146 、 丙酮 为溶剂， 生成 5-溴-2,3-二甲氧基苯甲酸
  参考文献：
  名称：

  2-（2,3-二甲氧基苯基）-4-（氨基甲基）咪唑类似物的合成及其对多巴胺D（2）和D（3）受体的结合亲和力。

  摘要：

  制备了一系列的2-（2,3-二甲氧基苯基）-4-（氨基甲基）咪唑衍生物，并使用体外结合试验测量了它们对多巴胺D（2）和D（3）受体的亲和力。还制备了几种恶二唑类似物，并测试了它们对多巴胺D（2）和D（3）受体的亲和力。受体结合研究的结果表明，在苯环和碱性氮之间并入咪唑部分并不会显着增加对多巴胺D（3）受体的选择性，而在同一区域并入恶二唑会导致总的两个多巴胺受体亚型结合位点的亲和力丧失。该系列中选择性最高的化合物是2-（5-溴-2,3-二甲氧基苯基）-4-（6,7-二甲氧基-1,2,3,4-四氢异喹啉甲基）咪唑（5i），具有21nM的D（3）受体亲和力，对D（3）与D（2）受体的选择性是7倍。还测量了对sigma（1）和sigma（2）受体的结合亲和力，结果表明几种类似物是选择性的sigma（1）受体配体。

  DOI：

  10.1016/s0968-0896(01)00175-4

文献信息

• TRIAZOLIUM SALTS AS PAR1 INHIBITORS, PRODUCTION THEREOF, AND USE AS MEDICAMENTS
  申请人：HEINELT Uwe

  公开号：US20110034452A1

  公开（公告）日：2011-02-10

  The invention relates to novel compounds of formula I where X, A − , Q1, Q2 Q3, R2, R3, R4, R5, R6, R7, R8 and R9 are each as defined below. The compounds of formula I have antithrombotic activity and inhibit especially protease-activated receptor 1 (PAR1). The invention further relates to a process for preparing the compound of formula I and to the use thereof as a medicament.

  这项发明涉及公式I的新化合物， 其中X，A − ，Q1，Q2，Q3，R2，R3，R4，R5，R6，R7，R8和R9分别如下定义。公式I的化合物具有抗血栓活性，特别是抑制蛋白酶活化受体1（PAR1）。该发明还涉及制备公式I化合物的方法以及将其用作药物的用途。
• BRIDGED BICYCLIC COMPOUNDS AS FARNESOID X RECEPTOR MODULATORS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20190127358A1

  公开（公告）日：2019-05-02

  The present invention provides compounds of Formula (I): or stereoisomers, tautomers, or pharmaceutically acceptable salts or solvates thereof, wherein all the variables are as defined herein. These compounds modulate the activity of farnesoid X receptor (FXR), for example, as agonists. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating a disease, disorder, or condition associated with FXR dysregulation, such as pathological fibrosis, transplant rejection, cancer, osteoporosis, and inflammatory disorders, by using the compounds and pharmaceutical compositions.

  本发明提供了式（I）的化合物： 或其立体异构体、互变异构体或药学上可接受的盐或溶剂，其中所有变量如本文所定义。这些化合物调节法尼索尔X受体（FXR）的活性，例如作为激动剂。本发明还涉及包括这些化合物的药物组合物以及利用这些化合物和药物组合物治疗与FXR失调相关的疾病、紊乱或病况的方法，例如病理性纤维化、移植排斥、癌症、骨质疏松症和炎症性疾病。
• TRIAZOLOPYRIDAZINES AS PAR1 INHIBITORS, PRODUCTION THEREOF, AND USE AS MEDICAMENTS
  申请人：HEINELT Uwe

  公开号：US20110034451A1

  公开（公告）日：2011-02-10

  The invention relates to novel compounds of formula I where R1, R2, R3, R4, R5, R6, R7, R8, Q1, Q2 and Q3 are each as defined below. The compounds of formula I have antithrombotic activity and inhibit especially protease-activated receptor 1 (PAR1). The invention further relates to a process for preparing the compound of formula I and to the use thereof as a medicament.

  该发明涉及公式I的新化合物，其中R1、R2、R3、R4、R5、R6、R7、R8、Q1、Q2和Q3分别如下定义。公式I的化合物具有抗血栓活性，特别是抑制蛋白酶活化受体1（PAR1）。该发明还涉及制备公式I化合物的方法以及将其用作药物的用途。
• Synthesis and in vitro evaluation of tetrahydroisoquinolines with pendent aromatics as sigma-2 (σ₂) selective ligands
  作者：Mark E. Ashford、Vu H. Nguyen、Ivan Greguric、Tien Q. Pham、Paul A. Keller、Andrew Katsifis

  DOI：10.1039/c3ob42254b

  日期：——

  Sigma-2 selective ligands – a SAR study showing increased potency and selectivity with derivatives showing the potential to be converted into radiolabelled ligands.

  Sigma-2 选择性配体 - 一项结构活性关系研究表明，衍生物的效力和选择性增加，有潜力转化为放射标记配体。
• Design, Synthesis, and Biological Evaluation of Quercetagetin Analogues as JNK1 Inhibitors
  作者：Judith Hierold、Sohee Baek、Rene Rieger、Tae-Gyu Lim、Saman Zakpur、Marcelino Arciniega、Ki Won Lee、Robert Huber、Lutz F. Tietze

  DOI：10.1002/chem.201502475

  日期：2015.11.16

  recent discovery of c‐Jun NH2‐terminal kinase JNK1 suppression by natural quercetagetin (1) is a promising lead for the development of novel anticancer agents. Using both X‐ray structure and docking analyses we predicted that 5′‐hydroxy‐ (2) and 5′‐hydroxymethyl‐quercetagetin (3) would inhibit JNK1 more actively than the parent compound 1. Notably, our drug design was based on the active enzyme–ligand complex

  天然槲皮素（1）抑制c-Jun NH 2末端激酶JNK1的最新发现为新型抗癌药的开发提供了有希望的线索。使用X射线结构和对接分析，我们预测5'-羟基-（2）和5'-羟甲基-槲皮素（3）会比母体化合物1更有效地抑制JNK1 。值得注意的是，我们的药物设计基于活性酶-配体复合物，而不是酶的相对开放的载脂蛋白结构。在本文中，我们通过对接模型实验测试了我们的理论预测，并报告了槲皮素类似物2和3的首次合成和生物学评估。。如所计算的，两种化合物均强烈抑制JNK1活性。该IC 50测定值为3.4μ中号和12.2μ中号，分别，这表明2超过母体化合物的效力1（IC 50 = 4.6μ中号）。化合物2还显示出在紫外线照射后以高特异性抑制基质金属蛋白酶-1的表达。