2-甲氧基-3,5-二溴苯甲酸 | 13130-23-9

• 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: 2-甲氧基-3,5-二溴苯甲酸
• 中文别名: 3,5-二溴-2-甲氧基苯甲酸
• 英文名称: 3,5-dibromo-2-methoxybenzoic acid
• 英文别名: 2-Methoxy-3,5-dibrom-benzoesaeure
• CAS: 13130-23-9
• 化学式: C₈H₆Br₂O₃
• mdl: MFCD00016510
• 分子量: 309.942
• InChiKey: GDGFGZWIQSUSAX-UHFFFAOYSA-N

物化性质

• 熔点：
  198-200°
• 沸点：
  373.3±42.0 °C(Predicted)
• 密度：
  1.957

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2918990090
• 危险类别：
  IRRITANT

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3,5-Dibromo-2-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: 3,5-Dibromo-2-methoxybenzoic acid
CAS number: 13130-23-9

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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.
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: C8H6Br2O3
Molecular weight: 309.9

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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-甲氧基-3,5-二溴苯甲酸 在 氯化亚砜 、 magnesium 作用下， 反应 13.5h， 生成 1-(3,5-Dibrom-2-methoxyphenyl)-3-(1,3-dioxan-2-yl)-1-propanon
  参考文献：
  名称：

  Laatsch, Hartmut; Pudleiner, Heinz, Liebigs Annalen der Chemie, 1989, p. 863 - 882

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二溴-2-羟基苯甲酸 在 lithium hydroxide monohydrate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 2-甲氧基-3,5-二溴苯甲酸
  参考文献：
  名称：

  Hydroxybiphenylamide GroEL/ES Inhibitors Are Potent Antibacterials against Planktonic and Biofilm Forms of Staphylococcus aureus

  摘要：

  We recently reported the identification of a GroEL/ES inhibitor (1, N-(4-(benzo[d]thiazol-2-ylthio)-3-chlorophenyl)-3,5-dibromo-2-hydroxybenzamide) that exhibited in vitro antibacterial effects against Staphylococcus aureus comparable to vancomycin, an antibiotic of last resort. To follow up, we have synthesized 43 compound 1 analogs to determine the most effective functional groups of the scaffold for inhibiting GroEL/ES and killing bacteria. Our results identified that the benzothiazole and hydroxyl groups are important for inhibiting GroEL/ES-mediated folding functions, with the hydroxyl essential for antibacterial effects. Several analogs exhibited >50-fold selectivity indices between antibacterial efficacy and cytotoxicity to human liver and kidney cells in cell culture. We found that MRSA was not able to easily generate acute resistance to lead inhibitors in a gain-of-resistance assay and that lead inhibitors were able to permeate through established S. aureus biofilms and maintain their bactericidal effects.

  DOI：

  10.1021/acs.jmedchem.8b01293

文献信息

• Potential neuroleptic agents. 4. Chemistry, behavioral pharmacology, and inhibition of [3H]spiperone binding of 3,5-disubstituted N-[(1-ethyl-2-pyrrolidinyl)methyl]-6-methoxysalicylamides
  作者：Tomas De Paulis、Yatendra Kumar、Lars Johansson、Sten Raemsby、Haakan Hall、Maria Saellemark、Kristina Aengeby-Moeller、Sven Ove Oegren

  DOI：10.1021/jm00151a010

  日期：1986.1

  methyl]-6-methoxysalicylamides was synthesized, starting from the 2,6-dimethoxybenzoic acids, by boron tribromide demethylation of the corresponding 3,5-disubstituted 2,6-dimethoxybenzamides and separation of the two positional isomers. The correct structure assignments were based on selective decoupling studies on their 13C NMR spectra. The salicylamide derivatives were tested for antidopamine activity in vivo

  从2,6-二甲氧基苯甲酸开始，通过相应的3,5-硼的三溴化硼脱甲基，合成了一系列的3,5-二取代的N-[（（1-乙基-2-吡咯烷基）甲基] -6-甲氧基水杨酰胺。二取代2，6-二甲氧基苯甲酰胺和两个位置异构体的分离。正确的结构分配基于对它们的13C NMR光谱进行的选择性去偶联研究。水杨酰胺衍生物通过在大鼠中抑制阿扑吗啡综合征的能力在体内进行了抗多巴胺活性的测试，并在体外从大鼠脑纹状体制剂中置换了[3H]哌酮的能力进行了体外抗多巴胺活性的测试。该活性似乎仅存在于S对映异构体中。几种化合物比氟哌啶醇更有效，特别是在芳环的3-位具有乙基且在5-位具有卤原子的那些。相应的5-烷基-3-卤素取代的化合物的活性低得多。发现最有效的化合物的急性毒性低。一些水杨酰胺在阻止阿扑吗啡诱导的过度活跃和阻止阿朴吗啡引起的刻板印象的剂量之间显示出10-20倍的间隔。一种化合物S-（-）-3,5-二氯-N-[（（1-乙基-2-吡咯烷基）甲基]
• A环三甲氧基黄酮取代水杨酸酯类化合物及 其抗肿瘤作用
  申请人：南华大学

  公开号：CN106699717B

  公开（公告）日：2019-04-09

  本发明涉及医药技术领域。本发明设计合成了新型A环三甲氧基4’‑羟基黄酮化合物和一类A环三甲氧基4’‑羟基黄酮取代水杨酸酯类化合物。图1是A环三甲氧基4’‑羟基黄酮取代水杨酸酯类化合物通式，式中：R1,R2,R3=O 或R2,R3,R4=O ;R5­=O 、CH3、F、Cl、Br或I等。本发明的新型A环三甲氧基4’‑羟基黄酮化合物和一类A环三甲氧基4’‑羟基黄酮取代水杨酸酯类化合物能够对MGC‑803(人胃癌细胞)、HepG2(人肝癌细胞)、MCF‑7（人乳腺癌细胞）具有明显抑制作用，有希望成为得到一类抗肿瘤药物。本发明公开其制备方法。
• Changes in Bone Structure and Mass With Advancing Age in the Male C57BL/6J Mouse
  作者：Bernard P. Halloran、Virginia L. Ferguson、Steven J. Simske、Andrew Burghardt、Laura L. Venton、Sharmila Majumdar

  DOI：10.1359/jbmr.2002.17.6.1044

  日期：——

  To determine whether the mouse loses bone with aging and whether the changes mimic those observed in human aging, we examined the changes in the tibial metaphysis and diaphysis in the male C57BL/6J mouse over its life span using microcomputed tomography (μCT). Cancellous bone volume fraction (BV/TV) decreased 60% between 6 weeks and 24 months of age. Loss was characterized by decreased trabecular number (Tb.N), increased trabecular spacing (Tb.Sp), and decreased connectivity. Anisotropy decreased while the structure model index increased with age. Cortical bone thickness increased between 6 weeks and 6 months of age and then decreased continuously to 24 months (−12%). Cortical bone area (Ct.Ar) remained constant between 6 and 24 months. Fat‐free weight reached a peak at 12 months and gradually declined to 24 months. Total mass lost between 12 and 24 months reached 10%. Overall, the age‐related changes in skeletal mass and architecture in the mouse were remarkably similar to those seen in human aging. Furthermore, the rapid early loss of cancellous bone suggests that bone loss is not just associated with old age in the mouse but rather occurs as a continuum from early growth. We conclude that the C57BL/6J male mouse maybe a useful model to study at least some aspects of age‐related bone loss in humans.

  为了确定小鼠是否在衰老过程中失去骨骼，以及这些变化是否模仿人类衰老过程中观察到的变化，我们使用微计算机断层扫描（μCT）研究了雄性C57BL/6J小鼠在其生命周期内胫骨干骺和干骼的变化。在6周到24个月之间，骨松质体积比（BV/TV）下降了60%。骨量损失的特征表现为小梁数目降低（Tb.N）、小梁间距增加（Tb.Sp）以及连通性下降。随着年龄的增长，各向异性降低，而结构模型指数上升。皮质骨厚度在6周到6个月之间增加，然后持续下降至24个月（下降12%）。皮质骨面积（Ct.Ar）在6到24个月期间保持不变。去脂重在12个月达到顶峰，然后逐渐下降至24个月。12到24个月之间的总体质量损失达到了10%。总体而言，小鼠在骨骼质量和结构方面的年龄相关变化与人类的衰老过程非常相似。此外，骨松质的早期快速损失表明，骨骼丧失并不仅仅与小鼠的老年相关，而是在早期生长阶段就开始发生的连续性过程。我们得出结论，C57BL/6J雄性小鼠可能是研究人类年龄相关骨质流失某些方面的一个有用模型。
• [EN] COMPOUNDS USEFUL AS INHIBITORS OF ALCAT 1<br/>[FR] COMPOSÉS UTILES EN TANT QU'INHIBITEURS D'ALCAT 1
  申请人：PERENNA PHARMACEUTICALS INC

  公开号：WO2018178304A1

  公开（公告）日：2018-10-04

  Inhibitors of ALCAT1 are described having the general formula: (I). These compounds offer a treatment for aging and age-related diseases.

  ALCAT1的抑制剂具有一般公式：(I)。这些化合物提供了治疗衰老和与年龄相关疾病的方法。
• [EN] COMPOUNDS AND METHODS OF INHIBITING BACTERIAL CHAPERONIN SYSTEMS<br/>[FR] COMPOSÉS ET MÉTHODES D'INHIBITION DE SYSTÈMES DE CHAPERONINE BACTÉRIENNE
  申请人：UNIV INDIANA TRUSTEES

  公开号：WO2020092947A1

  公开（公告）日：2020-05-07

  The present disclosure relates to novel compounds and methods of killing or inhibiting the growth of bacteria. In some embodiments, a method of killing or inhibiting the growth of bacteria is provided. The method comprises administering a compound of formula I or a pharmaceutically acceptable salt thereof to bacteria. In some embodiments, a method of killing or inhibiting the growth of bacteria is provided. The method comprises administering an anthelmintic to bacteria.

  本公开涉及新化合物和杀灭或抑制细菌生长的方法。在某些实施方式中，提供了一种杀灭或抑制细菌生长的方法。该方法包括向细菌施用式I的化合物或其药学上可接受的盐。在某些实施方式中，提供了一种杀灭或抑制细菌生长的方法。该方法包括向细菌施用驱虫药。

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