2-羟基-4-氨基苯甲酸甲酯 | 4136-97-4

• 物质功能分类: 医药中间体
• 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-羟基-4-氨基苯甲酸甲酯
• 中文别名: 4-氨基-2-羟基苯甲酸甲酯；对氨基水杨酸甲酯；4-氨基水杨酸甲酯；邻羟基对氨基苯甲酸甲酯
• 英文名称: methyl 4-aminosalicylate
• 英文别名: methyl 4-amino-2-hydroxybenzoate；4-amino-2-hydroxy-benzoic acid methyl ester；methyl p-aminosalicylate；methyl 2-hydroxy-4-amino-benzoate；methyl 2-hydroxy-4-amino-benzate
• CAS: 4136-97-4
• 化学式: C₈H₉NO₃
• mdl: MFCD00088091
• 分子量: 167.164
• InChiKey: QQOXBFUTRLDXDP-UHFFFAOYSA-N

物化性质

• 熔点：
  120-123°C
• 沸点：
  120 °C
• 密度：
  1.305±0.06 g/cm3 (20 ºC 760 Torr)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• 最大波长(λmax)：
  254nm(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2922509090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存放于室温环境中，并请密封保存。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Methyl 4-aminosalicylate
Synonyms: Methyl 4-amino-2-hydroxybenzoate

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
Avoid breathing dust/fume/gas/mist/vapours/spray
P261:
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

---

Section 3. Composition/information on ingredients.
Ingredient name: Methyl 4-aminosalicylate
CAS number: 4136-97-4

---

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.

---

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.

---

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.

---

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.
Storage: Store in closed vessels.

---

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.

---

Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H9NO3
Molecular weight: 167.2

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

制备方法

医药和化工中间体。

用途简介

（该部分暂无内容）

反应信息

• 作为反应物：
  描述：

  2-羟基-4-氨基苯甲酸甲酯 在 N-氯代丁二酰亚胺 、 碳酸氢钠 、 potassium carbonate 作用下， 以 水 、 乙酸乙酯 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 methyl 5-acetylamino-6-chloro-2H-chromene-8-carboxylate
  参考文献：
  名称：

  HETEROARYL COMPOUNDS AS 5-HT4 RECEPTOR LIGANDS

  摘要：

  本发明涉及式(I)的新化合物，以及它们的药用盐和含有它们的组合物。 本发明还涉及制备上述新化合物的方法，以及它们的药用盐。式(I)的化合物在治疗与5-HT 4 受体相关的各种疾病中是有用的。

  公开号：

  US20140187581A1
• 作为产物：
  描述：

  4-氨基水杨酸 在 甲醇 、 硫酸 作用下， 以95.1%的产率得到2-羟基-4-氨基苯甲酸甲酯
  参考文献：
  名称：

  5HT 4激动剂的关键苯并吡喃中间体的合成途径的研究

  摘要：

  葛兰素史克（GlaxoSmithKline）的5HT 4受体激动剂1的供应途径以关键的苯并吡喃片段2的构建为中心。我们通过一系列断开连接来描述为该组件定义最终制造路线的尝试。构造苯并吡喃骨架的系统方法集中在适当前体的环化策略和关键步骤性能的评估上。

  DOI：

  10.1021/op900188v

文献信息

• Synthesis and Radiolabeling of (S)-4-Amino-5-iodo-2-methoxy-N-(1-azabicyclo(2.2.2)oct-3-yl)benzamide, the Active Enantiomer of (125I)Iodozacopride, and Re-evaluation of Its 5-HT3 Receptor Affinity.
  作者：William A. HEWLETT、Tomas DE PAULIS、N. Scott MASON、Dennis E. SCHMIDT、Bakula L. TRIVEDI、Zhang-Jin ZHANG、Michael H. EBERT

  DOI：10.1248/cpb.45.2079

  日期：——

  4-amino-2-methoxybenzoic acid via its corresponding 1-imidazole derivative. Radioiodination to produce (S)-[125I]iodozacopride was accomplished by treatment of deschloro-(S)-zacopride with 5 mCi sodium 125iodide and chloramine-T in hydrochloric acid. Purification of the reaction products using an HPLC system capable of detecting chlorinated side-products revealed a mixture of 2.1 mCi (1.3 nmol) (S)-[125I]iodozacopride

  我们报告了未标记的（S）-碘杂扎必利的合成改进，通过脱氯-（S）-zacopride的放射性标记的（S）-[125I]碘杂扎必利，以及其对5-HT3受体亲和力的重新评估。由4-氨基水杨酸经其4-乙酰胺衍生物的碱水解，分七个步骤制备未标记的（S）-碘杂二十烷酸酯。（S）-碘杂铜甲酸酯的催化加氢得到脱氯-（S）-杂铜甲酸酯，与通过其相应的1-咪唑衍生物从（S）-3-氨基-喹核苷和4-氨基-2-甲氧基苯甲酸获得的脱氯-（S）-zacopride相同。通过用5 mCi 125碘化钠和氯胺-T在盐酸中处理脱氯-（S）-zacopride，完成放射性碘化反应生成（S）-[125I] iodozacopride。使用能够检测氯代副产物的HPLC系统纯化反应产物，发现混合物为2。1 mCi（1.3 nmol）（S）-[125I]碘杂扎克必利和（S）-zacopride（1.5 nmol）。纯化的（S）-[
• [EN] MODULATORS OF HCV REPLICATION<br/>[FR] MODULATEURS DE LA REPLICATION DE HCV
  申请人：ANGELETTI P IST RICHERCHE BIO

  公开号：WO2006038039A1

  公开（公告）日：2006-04-13

  The present invention is directed to the use of compounds of formula (I): 1 R X 3 R Y ( I) 2 R 5 where X, Y, R1, R2 and R3 are defined therein, which can act as modulators of viral replication and/or virus production, especially of the hepatitis C virus (HCV), in a cell based system.

  本发明涉及使用式(I)的化合物：1 R X 3 R Y ( I) 2 R 5，其中X、Y、R1、R2和R3在其中被定义，这些化合物可以作为病毒复制和/或病毒产生的调节剂，特别是对丙型肝炎病毒（HCV）在基于细胞的系统中。
• TYK2 INHIBITORS AND USES THEREOF
  申请人：Nimbus Lakshmi, Inc.

  公开号：US20160251376A1

  公开（公告）日：2016-09-01

  The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of TYK2, and the treatment of TYK2-mediated disorders.

  本发明提供了化合物、其组合物以及使用这些化合物来抑制TYK2并治疗TYK2介导的疾病的方法。
• [EN] SMALL MOLECULE INHIBITORS OF THE MCL-1 ONCOPROTEIN AND USES THEREOF<br/>[FR] INHIBITEURS À PETITES MOLÉCULES DE L'ONCOPROTÉINE MCL-1 ET LEURS UTILISATIONS
  申请人：UNIV MARYLAND

  公开号：WO2017011323A1

  公开（公告）日：2017-01-19

  Compounds that inhibit Myeloid Cell Leukemia-1 (Mcl-1) oncoprotein, and methods of using the same, are provided for treating disease.

  提供抑制髓样细胞白血病-1（Mcl-1）癌蛋白的化合物，以及使用相同化合物治疗疾病的方法。
• A New Series of Salicylic Acid Derivatives as Non-saccharide α-Glucosidase Inhibitors and Antioxidants
  作者：Jiangang Chen、Wenfang Lu、Hao Chen、Xiaoli Bian、Guangde Yang

  DOI：10.1248/bpb.b18-00661

  日期：2019.2.1

  In this study, a series of salicylic acid derivatives were designed and synthesized as novel non-saccharide α-glucosidase inhibitors. Biological evaluation indicated that when compared to acarbose, compounds T9, T10, and T32 exhibited a higher potency of α-glucosidase inhibitory activity with IC50 values of 0.15 ± 0.01, 0.086 ± 0.01 and 0.32 ± 0.02 mM, respectively. Evaluation of the inhibition kinetics

  在这项研究中，设计并合成了一系列水杨酸衍生物作为新型非糖α-葡萄糖苷酶抑制剂。生物学评估表明，与阿卡波糖相比，化合物T9，T10和T32表现出更高的α-葡萄糖苷酶抑制活性能力，IC50值分别为0.15±0.01、0.086±0.01和0.32±0.02 mM。抑制动力学的评估表明，T9，T10，T32和阿卡波糖以非竞争性混合抑制方式与α-葡萄糖苷酶相互作用。此外，T9，T10和T32通过形成抑制剂-α-葡萄糖苷酶复合物而静态地淬灭了α-葡萄糖苷酶的荧光。对接结果表明，在测试化合物和α-葡萄糖苷酶之间产生了氢键。抗氧化剂研究表明，化合物T10通过清除1,1-二苯基-2-吡啶并肼基自由基（DPPH）表现出较高的抗氧化活性，从而抑制了脂质过氧化作用和总还原能力。简而言之，在这项研究中确定的水杨酸衍生物有望作为新型非糖α-葡萄糖苷酶抑制剂的开发。