2-甲基-1,4-苯二甲酸 | 5156-01-4

• 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-甲基-1,4-苯二甲酸
• 中文别名: 2-甲基对苯二甲酸；2-甲基-1,4-苯二羧酸
• 英文名称: 2-methylterephthalic acid
• 英文别名: 2-methyl-1,4-benzenedicarboxylic acid；Methyl-terephthalsaeure；methylterephthalic acid；2-Methyl-terephthalsaeure；monomethylterephthalic acid
• CAS: 5156-01-4
• 化学式: C₉H₈O₄
• mdl: MFCD09835103
• 分子量: 180.16
• InChiKey: UFMBOFGKHIXOTA-UHFFFAOYSA-N

物化性质

• 熔点：
  323-325 °C
• 沸点：
  388.2±30.0 °C(Predicted)
• 密度：
  1.377
• 闪点：
  202.8℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2917399090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Methylterephthalic 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-Methylterephthalic acid
CAS number: 5156-01-4

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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: C9H8O4
Molecular weight: 180.2

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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.

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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

应用

2-甲基-1,4-苯二甲酸可用作医药化工合成中间体，如用于合成2-甲基对苯二甲酸二甲酯。作为合成乙烯基对苯二甲酸类甲壳型液晶高分子过程中的一种重要化合物，目前大多数采用酸催化合成，但产率较低，只有33%左右，且对原材料的损耗较大。由于2-甲基对苯二甲酸二甲酯在该过程中的必要性，提高其产率具有重要意义。然而，多数酸催化酯化反应存在转化率低的问题。在此过程中，甲醇既是反应试剂也是溶剂，但由于其沸点较低且难以找到合适的带水剂进行油水分离，因此加入吸水性强的无水硫酸铜粉末，在80℃环境下，可以结合3个水分子，从而提高酯化转换率。所得产物通过红外IR和核磁NMR分析确认化合物的正确性，这为下一步大批量合成乙烯基对苯二甲酸类甲壳型液晶高分子的研究奠定了基础。

制备方法

具体制备方法如下：

1. 酯化：在浓硫酸催化下，2-甲基对苯二甲酸与甲醇以1:10的物料比，在80℃下发生酯化反应，时间为8小时至12小时。
2. 吸水：加入无水硫酸铜作为吸水剂，2-甲基对苯二甲酸与无水硫酸铜按重量比20:17~1:1的比例混合。
3. 萃取：使用二氯甲烷为萃取剂，分出下层有机相。
4. 重结晶：将所得粗品在石油醚中进行重结晶，即可得到纯度较高的2-甲基对苯二甲酸二甲酯。

反应信息

• 作为反应物：
  描述：

  2-甲基-1,4-苯二甲酸 在 potassium permanganate 作用下， 生成 1,2,4-苯三甲酸
  参考文献：
  名称：

  Krinos, Chemische Berichte, 1877, vol. 10, p. 1494

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,4-三甲基苯 在 硝酸 作用下， 生成 2-甲基-1,4-苯二甲酸
  参考文献：
  名称：

  Modified water

  摘要：

  讨论了顺势疗法“高倍”在生物学效应方面的现象，并回顾了该主题的最新文献。

  DOI：

  10.1108/03684920110363914

文献信息

• Pyrrolidine derivatives
  申请人：——

  公开号：US20020040146A1

  公开（公告）日：2002-04-04

  The present invention relates to pyrrolidine derivatives useful as inhibitors of metalloproteases, e.g. zinc proteases, and which are effective in treating disease states associated with vasoconstriction.

  本发明涉及吡咯烷衍生物，其作为金属蛋白酶抑制剂，例如锌蛋白酶，在治疗与血管收缩相关的疾病状态中具有有效性。
• Cerium-based metal organic frameworks with UiO-66 architecture: synthesis, properties and redox catalytic activity
  作者：Martin Lammert、Michael T. Wharmby、Simon Smolders、Bart Bueken、Alexandra Lieb、Kirill A. Lomachenko、Dirk De Vos、Norbert Stock

  DOI：10.1039/c5cc02606g

  日期：——

  A series of nine Ce(iv)-based metal organic frameworks with the UiO-66 structure containing linker molecules of different sizes and functionalities were obtained under mild synthesis conditions and short reaction times.

  在温和的合成条件和短的反应时间内，获得了一系列九种基于Ce(IV)的金属有机框架，具有UiO-66结构，并含有不同大小和功能的连接分子。
• Identification and Structure–Activity Relationships of Novel Compounds that Potentiate the Activities of Antibiotics in <i>Escherichia coli</i>
  作者：Keith M. Haynes、Narges Abdali、Varsha Jhawar、Helen I. Zgurskaya、Jerry M. Parks、Adam T. Green、Jerome Baudry、Valentin V. Rybenkov、Jeremy C. Smith、John K. Walker

  DOI：10.1021/acs.jmedchem.7b00453

  日期：2017.7.27

  In Gram-negative bacteria, efflux pumps are able to prevent effective cellular concentrations from being achieved for a number of antibiotics. Small molecule adjuvants that act as efflux pump inhibitors (EPIs) have the potential to reinvigorate existing antibiotics that are currently ineffective due to efflux mechanisms. Through a combination of rigorous experimental screening and in silico virtual

  在革兰氏阴性细菌中，外排泵能够防止多种抗生素达到有效的细胞浓度。充当外排泵抑制剂（EPI）的小分子佐剂有可能使现有的由于外排机制无效的抗生素恢复活力。通过严格的实验筛选和计算机虚拟筛选的组合，我们最近确定了与膜融合蛋白AcrA相互作用的新型EPI，AcrA是大肠杆菌中AcrAB-TolC外排泵的关键组件。在本文中，我们介绍了围绕先前提到的命中之一NSC 60339（1）的初步优化工作以及结构与活性之间的关系。通过这些努力，我们确定了两种化合物，SLUPP - 225（17小时）和SLUPP - 417（170），它表现出良好的特性，如潜在环境绩效指标大肠杆菌细胞，包括渗透外膜的能力，改进的相对流出的抑制作用1新生霉素的活性的，和增强和红霉素。
• 2-Substituted-5-oxo-5H-dibenzo-[A,D]cycloheptenes, the esters and ethers
  申请人：Syntex (U.S.A.) Inc.

  公开号：US03966820A1

  公开（公告）日：1976-06-29

  2-Substituted-5-oxo-5H-dibenzo [a,d]cycloheptenes represented by the following formula: ##SPC1## Where one of R.sup.2 and R.sup.3 is hydrogen, and the other is hydrogen, methyl, or ethyl, or together R.sup.2 and R.sup.3 are methylene; the dotted line represents an optional, additional bond between the carbon atoms at the 10- and 11-positions; and the pharmaceutically acceptable esters and ethers thereof. The compounds have anti-inflammatory, analgesic, and antipyretic activities and, accordingly, are useful in the treatment of inflammation, pain and pyrexia.

  2-取代-5-氧代-5H-二苯并[a,d]环庚烯，由以下公式表示：##SPC1## 其中R.sup.2和R.sup.3之一是氢，另一个是氢、甲基或乙基，或者R.sup.2和R.sup.3共同是亚甲基；虚线表示在10-和11-位置之间的碳原子之间可选的附加键；以及它们的药用可接受酯和醚。这些化合物具有抗炎、镇痛和解热活性，因此可用于治疗炎症、疼痛和发热。
• [EN] NOVEL BEXAROTENE ANALOGS<br/>[FR] ANALOGUES INÉDITS DU BEXAROTÈNE
  申请人：UNIV ARIZONA

  公开号：WO2011103321A1

  公开（公告）日：2011-08-25

  The present invention relates to analogs of bexarotene and methods of use thereof.

  本发明涉及贝沙罗汀的类似物及其使用方法。