4-氨基-3-(甲基氨基)苯甲酸甲酯 | 616224-38-5

• 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-氨基-3-(甲基氨基)苯甲酸甲酯
• 中文别名: 4-氨基-3-甲氨基苯甲酸甲酯
• 英文名称: methyl 4-amino-3-(methylamino)benzoate
• CAS: 616224-38-5
• 化学式: C₉H₁₂N₂O₂
• mdl: MFCD15144544
• 分子量: 180.206
• InChiKey: VWGIBJGZLCERFV-UHFFFAOYSA-N

物化性质

• 沸点：
  369.9±32.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2922499990
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8°C，避光，惰性气体保护。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 4-amino-3-(methylamino)benzoate
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: Methyl 4-amino-3-(methylamino)benzoate
CAS number: 616224-38-5

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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, refrigerated.
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: C9H12N2O2
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, nitrogen oxides.

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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：

  4-氨基-3-(甲基氨基)苯甲酸甲酯 在 盐酸 、 水 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 1-甲基-1H-苯并咪唑-6-羧酸
  参考文献：
  名称：

  Synthesis and antiprotozoal activity of nitazoxanide–N-methylbenzimidazole hybrids

  摘要：

  A series of a novel hybrid compounds between nitazoxanide and N-methylbenzimidazole were synthesized starting from the corresponding N-methyl-2-nitroanilines. The new hybrid compounds (1-13) were evaluated in vitro against Giardia intestinalis, Entamoeba histolytica, Trichomonas vaginalis. NTZ, MTZ and ABZ were used as drug standards. Experimental evaluations revealed all of the new compounds (1-13) were active and showed strong activity against the three protozoa, particularly with E. histolytica where the IC50 values ranged between 3 and 69 nM.Overall, compounds 2, 5, 7, 8, 9, 11 and 12 stood out with values lower than 87 nM for all three protozoa, comparatively better than the reference drugs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.011
• 作为产物：
  描述：

  3-(甲基氨基)-4-硝基苯羧酸甲酯 在 铁粉 、 氯化铵 作用下， 以 乙醇 、 水 为溶剂， 以94 %的产率得到4-氨基-3-(甲基氨基)苯甲酸甲酯
  参考文献：
  名称：

  1H-苯并[d]咪唑选择性HDAC6抑制剂的设计和合成，具有治疗多发性骨髓瘤的潜力

  摘要：

  Pan-HDAC抑制剂对多发性骨髓瘤表现出显着的抑制活性，然而，其临床应用却因严重的毒副作用而受到阻碍。相比之下，选择性 HDAC6 抑制剂已被证明可有效治疗多发性骨髓瘤。属于 1 H-苯并[ d ]咪唑异羟肟酸类的化合物已被鉴定为新型 HDAC6 抑制剂，其中苯并咪唑基团充当这些抑制剂的特定连接体。值得注意的是，化合物30 对人多发性骨髓瘤细胞（特别是 RPMI-8226）表现出出色的 HDAC6 抑制活性（IC 50 = 4.63 nM）和卓越的抗增殖作用。此外，它已被证明可以诱导细胞周期停滞在 G2 期，并通过线粒体途径促进细胞凋亡。在骨髓瘤 RPMI-8226 异种移植模型中，化合物30作为独立药物给药时表现出显着的体内抗肿瘤功效 (T/C = 34.8%)，且没有可观察到的细胞毒性。这些发现强调了化合物30作为治疗多发性骨髓瘤的有前途的治疗剂的巨大潜力。

  DOI：

  10.1016/j.ejmech.2023.115833

文献信息

• Reaction of Thiocarbonyl Fluoride Generated from Difluorocarbene with Amines
  作者：Jiao Yu、Jin-Hong Lin、Ji-Chang Xiao

  DOI：10.1002/anie.201710186

  日期：2017.12.22

  The reaction of thiocarbonyl fluoride, generated from difluorocarbene, with various amines under mild conditions is described. Secondary amines, primary amines, and o‐phenylenediamines are converted to thiocarbamoyl fluorides, isothiocyanates, and difluoromethylthiolated heterocycles, respectively. Thiocarbamoyl fluorides were further transformed into trifluoromethylated amines by using a one‐pot process

  描述了在温和条件下由二氟卡宾生成的硫代羰基氟化物与各种胺的反应。仲胺，伯胺和邻苯二胺分别转化为硫代氨基甲酰氟，异硫氰酸酯和二氟甲基硫代杂环。硫氨甲酰氟通过一锅法进一步转化为三氟甲基化胺。硫代羰基氟化物在原位生成，并在温和条件下在一锅中迅速完全转化；因此，不需要特殊的安全预防措施。
• N1-Pyrazolospiroketone Acetyl-CoA Carboxylase Inhibitors
  申请人：BAGLEY SCOTT WILLIAM

  公开号：US20110111046A1

  公开（公告）日：2011-05-12

  The invention provides a compound of Formula (I) or a pharmaceutically acceptable salt of the compound, wherein R 1 , R 2 , R 3 and R 4 are as described herein; pharmaceutical compositions thereof; and the use thereof in treating diseases, conditions or disorders modulated by the inhibition of an acetyl-CoA carboxylase enzyme(s) in an animal.

  该发明提供了化合物I的化合物或其药用可接受的盐，其中R1、R2、R3和R4如本文所述；以及其药物组合物；以及在治疗受乙酰辅酶A羧化酶抑制调节的动物疾病、症状或紊乱中的使用。
• Selective Methylation of Amines with Carbon Dioxide and H₂
  作者：Yuehui Li、Iván Sorribes、Tao Yan、Kathrin Junge、Matthias Beller

  DOI：10.1002/anie.201306850

  日期：2013.11.11

  Put a label on it: Carbon dioxide with H2 is shown to be an efficient and selective methylation reagent for aromatic and aliphatic amines (see scheme; acac=acetylacetonate, triphos = 1,1,1‐tris(diphenylphosphanylmethyl)ethane). A variety of functionalized amines including 13C‐labelled drugs were obtained with good yields and functional‐group tolerance.

  在其上贴上标签：具有H 2的二氧化碳被证明是芳族和脂肪族胺的一种高效且选择性的甲基化试剂（请参阅方案； acac =乙酰丙酮酸酯，三光子= 1,1,1-三（二苯基膦烷基甲基）乙烷）。获得了多种功能化的胺，包括13种C标记的药物，具有良好的收率和官能团耐受性。
• [EN] EXO-AZA SPIRO INHIBITORS OF MENIN-MLL INTERACTION<br/>[FR] INHIBITEURS SPIRO EXO-AZA DE L'INTERACTION MÉNINE-MLL
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2019120209A1

  公开（公告）日：2019-06-27

  Provided are compounds of Formula (I), pharmaceutical compositions comprising such compounds, and their use as menin/MLL protein/protein interaction inhibitors, useful for treating diseases such as cancer, myelodysplastic syndrome (MDS) and diabetes.

  提供的是式（I）的化合物，包括这些化合物的药物组合物，以及它们作为menin/MLL蛋白质/蛋白质相互作用抑制剂的用途，用于治疗癌症、骨髓增生异常综合征（MDS）和糖尿病等疾病。
• [EN] N2-PYRAZOLOSPIROKETONE ACETYL-COA CARBOXYLASE INHIBITORS<br/>[FR] INHIBITEURS DE N2-PYRAZOLOSPIROCÉTONE ACÉTYL-COA CARBOXYLASE
  申请人：PFIZER

  公开号：WO2011058473A1

  公开（公告）日：2011-05-19

  The invention provides a compound of Formula (I) or a pharmaceutically acceptable salt of said compound, wherein R1, R2, R3 and R4 are as described herein; pharmaceutical compositions thereof; and the use thereof in treating diseases, conditions or disorders modulated by the inhibition of an acetyl- CoA carboxylase enzyme(s) in an animal.

  该发明提供了化合物(I)的结构或该化合物的药用盐，其中R1、R2、R3和R4如本文所述；以及其药物组合物；以及在治疗受乙酰辅酶A羧化酶抑制调节的动物疾病、症状或紊乱中的应用。