2,3-二氨基苯甲酸甲酯 | 107582-20-7

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 2,3-二氨基苯甲酸甲酯
• 中文别名: 2.3-二氨基苯甲酸甲酯；4-氨基六氟甲苯
• 英文名称: 2,3-diaminobenzoic acid methyl ester
• 英文别名: methyl 2,3-diaminobenzoate
• CAS: 107582-20-7
• 化学式: C₈H₁₀N₂O₂
• mdl: MFCD04038589
• 分子量: 166.18
• InChiKey: BLJHLOLVEXWHFS-UHFFFAOYSA-N

物化性质

• 熔点：
  68-70°C
• 沸点：
  322.6±22.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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：
  78.3
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 安全说明：
  S26
• 危险类别码：
  R36/37/38
• 海关编码：
  2922499990
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  -20°C 冰箱

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 2,3-diaminobenzoate
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 2,3-diaminobenzoate
CAS number: 107582-20-7

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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: C8H10N2O2
Molecular weight: 166.2

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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

制备方法与用途

应用

2,3-二氨基苯甲酸甲酯是一种医药中间体，可用于制备2-乙氧基-4-甲酸甲酯-3-氢-苯并咪唑，并进一步合成三苯甲基坎地沙坦中间体。

制备

1. 步骤一：2-甲酸甲酯-6-硝基-苯甲酸的制备 将200克3-硝基邻苯二甲酸、1升甲醇加入反应瓶中。在冰水浴下滴加104毫升氯化亚砜，2小时内滴完；然后升温至回流状态并反应24小时。反应混合物浓缩至干，再用石油醚洗涤；过滤后得到2-甲酸甲酯-6-硝基-苯甲酸白色固体210.5克，收率为99%。

2. 步骤二：2-氨基-3-硝基-苯甲酸甲酯的制备 将100克2-甲酸甲酯-6-硝基-苯甲酸、800毫升三氯甲烷和133.3毫升98%硫酸依次加入反应瓶中。室温下分批加入叠氮钠56克，大约100分钟加完；随后升温至50℃并反应22小时。冷却至室温后，滗去溶剂，用三氯甲烷洗涤，并加入400毫升水进行过滤。最终得到黄色固体78.4克，收率为90%。

3. 步骤三：2,3-二氨基苯甲酸甲酯的制备 将5克2-氨基-3-硝基-苯甲酸甲酯、50毫升浓盐酸和25克SnCl₂·2H₂O加入反应瓶中，室温下反应5小时。将反应混合物用饱和碳酸钠溶液调节至pH值8后，使用乙酸乙酯进行萃取；有机相合并并蒸除溶剂，最终得到淡黄色固体2,3-二氨基苯甲酸甲酯4克。

反应信息

• 作为反应物：
  描述：

  2,3-二氨基苯甲酸甲酯 在 4-二甲氨基吡啶 、 sodium hydroxide 、 氯化亚砜 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 2-Amino-3-{[2-(2-benzyloxy-phenyl)-1H-benzoimidazole-4-carbonyl]-amino}-benzoic acid methyl ester
  参考文献：
  名称：

  Synthesis and anticancer evaluation of bis(benzimidazoles), bis(benzoxazoles), and benzothiazoles

  摘要：

  Four classes of UK-1 analogues were synthesized and their cytotoxicity testing against human A-549, BFTC-905, RD, MES-SA, and HeLa carcinoma cell lines was determined. The results revealed that UK-1 and four of these analogues (15-18) are potent against the cancer cell lines. In particular, compound 16 is more potent than UK-1 against A-549 and HeLa cell lines, and compounds 15, 17, and 18 selectively exhibit potent cytotoxic activity against the BFTV-905 cells (IC50 9.6 PM), A-549 cells (IC50 6.6 mu M), and MES-SA cells (IC50 9.2 mu M),respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.007
• 作为产物：
  描述：

  阿齐沙坦酯杂质3 在 tin 、 水 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 4.0h， 生成 2,3-二氨基苯甲酸甲酯
  参考文献：
  名称：

  一种2-乙氧基苯并咪唑-7-羧酸甲酯的合成方 法

  摘要：

  本发明公开了一种2‑乙氧基苯并咪唑‑7‑羧酸甲酯的合成方法，解决现有工艺含量不高，收率极低的问题。本发明是以3‑硝基邻苯二甲酸为原料，经甲酯化、酰化、重氮化后在水溶液中重排，再经锡粉还原，合环，得到2‑乙氧基苯并咪唑‑7‑羧酸甲酯。本发明的合成方法产生杂质极少，含量高，且收率也极高。

  公开号：

  CN104876877B

文献信息

• BENZIMIDAZOLE-2-PIPERAZINE HETEROCYCLIC COMPOUND, PHARMACEUTICAL COMPOSITION CONTAINING THE SAME, PREPARATION METHOD AND USE THEREOF
  申请人：SHANGHAI HUILUN LIFE SCIENCE & TECHNOLOGY CO., LTD

  公开号：US20160159776A1

  公开（公告）日：2016-06-09

  The present invention relates to a class of benzimidazole-2-piperazine heterocyclic derivatives, a preparation method and medical use thereof. Specifically, the present invention relates to a new benzimidazole-2-piperazine heterocyclic derivative of general Formula (I), a preparation method, a pharmaceutical composition containing the same, and use thereof as a therapeutic agent and especially as a poly(ADP-ribose)polymerase (PARP) inhibitor.

  本发明涉及一类苯并咪唑-2-哌嗪杂环衍生物、其制备方法及其医疗用途。具体而言，本发明涉及一种通式（I）的新苯并咪唑-2-哌嗪杂环衍生物、其制备方法、含有该衍生物的药物组合物，以及作为治疗剂特别是作为聚（ADP-核糖）聚合酶（PARP）抑制剂的用途。
• 苯并咪唑-2-哌嗪杂环类化合物、其药物组合物 及其制备方法和用途
  申请人：上海汇伦生命科技有限公司

  公开号：CN104230898B

  公开（公告）日：2016-06-29

  本发明苯并咪唑-2-哌嗪杂环类化合物、其药物组合物及其制备方法和用途，涉及氰基嘧啶化合物、其制备方法及其在医药上的应用。具体的，本发明涉及一种式（19）所示的新的氰基嘧啶化合物、其制备方法及含有该化合物的药物组合物以及其作为治疗剂特别是作为聚（ADP-核糖）聚合酶（PARP）抑制剂的用途。 。
• Design and Synthesis of Poly(ADP-ribose) Polymerase Inhibitors: Impact of Adenosine Pocket-Binding Motif Appendage to the 3-Oxo-2,3-dihydrobenzofuran-7-carboxamide on Potency and Selectivity
  作者：Uday Kiran Velagapudi、Marie-France Langelier、Cristina Delgado-Martin、Morgan E. Diolaiti、Sietske Bakker、Alan Ashworth、Bhargav A. Patel、Xuwei Shao、John M. Pascal、Tanaji T. Talele

  DOI：10.1021/acs.jmedchem.8b01709

  日期：2019.6.13

  Poly(adenosine 5'-diphosphate-ribose) polymerase (PARP) inhibitors are a class of anticancer drugs that block the catalytic activity of PARP proteins. Optimization of our lead compound 1 (( Z)-2-benzylidene-3-oxo-2,3-dihydrobenzofuran-7-carboxamide; PARP-1 IC50 = 434 nM) led to a tetrazolyl analogue (51, IC50 = 35 nM) with improved inhibition. Isosteric replacement of the tetrazole ring with a carboxyl

  聚腺苷5'-二磷酸核糖）聚合酶（PARP）抑制剂是一类抗癌药物，可阻断PARP蛋白的催化活性。优化我们的先导化合物1（（Z）-2-亚苄基-3-氧代-2,3-二氢苯并呋喃-7-羧酰胺; PARP-1 IC50 = 434 nM）产生了四唑基类似物（51，IC50 = 35 nM）具有更好的抑制作用。用羧基等位取代四唑环（60，IC50 = 68 nM）产生了有希望的新先导，随后对其进行了优化，以获得具有有效PARP-1 IC50值（4-197 nM）的类似物。PARP酶谱分析显示，大多数化合物对PARP-2具有选择性，其IC50值可与临床抑制剂媲美。与PARP-1结合的关键抑制剂的X射线晶体结构说明了与向PARP-1腺苷结合袋延伸的类似附件的相互作用方式。化合物81，一种同工型选择性PARP-1 / -2（IC50 = 30 nM / 2 nM）抑制剂，与同基因BRCA1精制细胞相比，对乳腺
• [EN] BI-1H-BENZIMIDAZOLES AS HEPATITIS C VIRUS INHIBITORS<br/>[FR] INHIBITEURS DU VIRUS DE L'HÉPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2010017401A1

  公开（公告）日：2010-02-11

  The present disclosure relates to compounds, compositions and methods for the treatment of Hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.

  本公开涉及化合物、组合物和治疗丙型肝炎病毒（HCV）感染的方法。还公开了含有这些化合物的药物组合物以及在治疗HCV感染中使用这些化合物的方法。
• Regioselective C–H Azidation of Anilines and Application to Synthesis of Key Intermediate for Pharmaceutical
  作者：Masahiko Seki、Yusuke Takahashi

  DOI：10.1021/acs.joc.1c00734

  日期：2021.6.4

  A catalytic system for regioselective C–H azidation of inactive anilines was developed. In the presence of CuSO4·5H2O, simultaneous addition of NaN3 and Na2S2O8 to aq. CH3CN solution of free anilines under weakly acidic conditions (pH 4.5) smoothly underwent C–H azidation to provide corresponding α-azidated products in high yields. Methyl α-azidoanthranilate obtained by this method was readily transformed

  开发了一种用于非活性苯胺的区域选择性 C-H 叠氮化的催化系统。在CuSO 4 ·5H 2 O存在下，同时将NaN 3和Na 2 S 2 O 8 添加到水溶液中。游离苯胺的CH 3 CN 溶液在弱酸性条件下（pH 4.5）顺利地进行 C-H 叠氮化，以高产率提供相应的 α-叠氮化产物。通过这种方法获得的 α-叠氮基邻氨基苯甲酸甲酯很容易通过简单的还原转化为 2-乙氧基苯并咪唑-7-羧酸甲酯，这是抗高血压坎地沙坦酯的关键中间体。