邻氨基苯甲酸异丙酯 | 18189-02-1

• 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: 邻氨基苯甲酸异丙酯
• 英文名称: propan-2-yl 2-aminobenzoate
• 英文别名: isopropyl 2-aminobenzoate；isopropyl anthranilate；2-aminobenzoic acid isopropyl ester；Anthranilsaeure-isopropylester；Isopropyl-2-aminobenzoat
• CAS: 18189-02-1
• 化学式: C₁₀H₁₃NO₂
• mdl: MFCD00060604
• 分子量: 179.219
• InChiKey: XKOZHFJYXAQZJX-UHFFFAOYSA-N

物化性质

• 熔点：
  64-65°C
• 沸点：
  270.5-272.4 °C
• 密度：
  1.099±0.06 g/cm3(Predicted)
• LogP：
  3.042 (est)
• 保留指数：
  1466

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  52.3
• 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
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2922439000

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Isopropyl anthranilate
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: Isopropyl anthranilate
CAS number: 18189-02-1

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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, under −20◦C.
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: C10H13NO2
Molecular weight: 179.2

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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：

  邻氨基苯甲酸异丙酯 在 盐酸 、 sodium nitrite 、 sodium azide 作用下， 以 水 为溶剂， 反应 1.17h， 以71%的产率得到isopropyl 2-azidobenzoate
  参考文献：
  名称：

  光化学合成6-取代的12-氧代-6,12-二氢阿斯庚诺[2,1-b]喹唑啉

  摘要：

  提出了一种通过邻位取代的芳基叠氮化物与2-氨基苯甲酸钠的光引发反应合成6-取代的12-氧代-6,12-二氢氮杂环庚烷[2,1- b ]喹唑啉的方法。在将胺亲核加成至芳族叠氮化物的环状烯酮亚胺的亲核加成过程中，将喹唑啉系统逐步环氧化成氮杂环戊烷，该芳基叠氮化物的光解反应会产生中间体分子间缩合反应。

  DOI：

  10.1007/s10593-016-1951-2
• 作为产物：
  描述：

  isopropyl 2-azidobenzoate 在 水 作用下， 以 邻二甲苯 为溶剂， 反应 1.0h， 生成 邻氨基苯甲酸异丙酯
  参考文献：
  名称：

  Synthesis of 3-phenylbenzo[c]isoxazoles by thermocyclization of 2-azidobenzophenones

  摘要：

  通过 2-叠氮基二苯甲酮在干燥二甲苯中的非催化热分解，定量产率合成了 3-苯基苯并[c]异恶唑。溶剂中痕量的水会降低反应产物的产率。 2-叠氮基苯甲酸酯在指定条件下是稳定的。

  DOI：

  10.1007/s11172-019-2557-5

文献信息

• A Study of the Reactions of 3‐Bromopropenals with Anilines for the Synthesis of α‐Bromo Enaminones
  作者：Sundaram Suresh、Prakash Bhimrao Patil、Pao‐Hsing Yu、Chia‐Chi Fang、Yin‐Zhi Weng、Veerababurao Kavala、Ching‐Fa Yao

  DOI：10.1002/adsc.202100779

  日期：2021.11.9

  The reactions proceed via the p-toluenesulfonic acid monohydrate (TsOH ⋅ H2O) catalyzed reactions of 3-bromopropenals with anilines in dimethyl sulfoxide (DMSO) and does not require an external brominating agent. The chemoselective 1,2-addition was accomplished by employing aniline with a sterically hindered electron-withdrawing group attached at the ortho-position. In addition, the reactions involving

  报道了一种用于合成α-溴烯胺酮的一锅法。反应进行经由所述p -甲苯磺酸一水合物（加入TsOH⋅ħ 2 O）与在二甲亚砜（DMSO），并且不需要外部溴化剂苯胺3- bromopropenals催化的反应。化学选择性 1,2-加成是通过使用在邻位连接有位阻吸电子基团的苯胺来完成的。此外，涉及其他苯胺衍生物作为亲核试剂的反应导致 1,4-加成产物的产量很小。3-溴丙烯醛与苯胺衍生物表现出不同范围的反应性。
• Halogen-substituted anthranilic acid derivatives provide a novel chemical platform for androgen receptor antagonists
  作者：Daniela Roell、Thomas W. Rösler、Wiebke Hessenkemper、Florian Kraft、Monique Hauschild、Sophie Bartsch、Tsion E. Abraham、Adriaan B. Houtsmuller、Rudolf Matusch、Martin E. van Royen、Aria Baniahmad

  DOI：10.1016/j.jsbmb.2018.12.005

  日期：2019.4

  Androgen receptor (AR) antagonists are used for hormone therapy of prostate cancer (PCa). However resistance to the treatment occurs eventually. One possible reason is the occurrence of AR mutations that prevent inhibition of AR-mediated transactivation by antagonists. To offer in future more options to inhibit AR signaling, novel chemical lead structures for new AR antagonists would be beneficial. Here

  雄激素受体（AR）拮抗剂用于前列腺癌（PCa）的激素治疗。然而，最终对治疗产生抵抗力。一个可能的原因是，AR突变的发生阻止了拮抗剂对AR介导的反式激活的抑制。为了将来提供更多抑制AR信号传导的选择，新型AR拮抗剂的新型化学前导结构将是有益的。在这里，我们分析了36种邻氨基苯甲酸甲酯的非甾体结构变体，包括23种合成化合物的电池的结构活性关系。我们确定了导致更有效的AR拮抗剂的结构要求。特定的化合物抑制野生型AR的反式激活以及使突变体对羟基氟他胺，比卡鲁胺和第二代AR拮抗剂enzalutamide产生抗药性的AR突变体。这表明与临床使用的化合物相比，抑制AR的独特模式。竞争测定表明这些化合物与AR配体结合域结合并抑制PCa细胞增殖。而且，尽管抑制了AR介导的反式激活，这表明活性化合物不依赖于反式激活的AR途径，但是活性化合物诱导细胞衰老。与此相符，光漂白后的荧光共振（FRAP）-分析显示AR在
• [EN] METHOD FOR PRODUCING 1-HEXENE<br/>[FR] PROCÉDÉ DE PRODUCTION D'1-HEXÈNE
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2012133937A1

  公开（公告）日：2012-10-04

  Disclosed is a method for producing 1-hexene that is capable of reducing the amount of by-product polymers when 1-hexene is produced through the trimerization reaction of ethylene. The method for producing 1-hexene comprises the following steps 1 and 2: step 1: the step of preparing a catalytic component by bringing a transition metal complex represented by any one of formulae (1-1) to (1-3) into contact with a specific organic aluminum compound in the absence of ethylene; and step 2: the step of trimerizing ethylene in the presence of a catalyst obtainable by bringing the catalytic component obtained in step 1 into contact with a specific boron compound.

  公开了一种生产1-己烯的方法，该方法能够在通过乙烯的三聚反应生产1-己烯时减少副产物聚合物的数量。生产1-己烯的方法包括以下步骤1和2：步骤1：通过将由式（1-1）到（1-3）中的任一表示的过渡金属配合物与特定有机铝化合物接触而制备催化组分，在没有乙烯的情况下；步骤2：在将在步骤1中获得的催化组分与特定硼化合物接触而获得的催化剂存在下，三聚乙烯。
• Synthesis and Antimicrobial Activity of Unsymmetrical Dendrimers With Indazole, Salicylates and Anthranilates as Surface Units
  作者：Mani Jayanthi、Perumal Rajakumar

  DOI：10.1002/jhet.2793

  日期：2017.5

  dendrimers with indazole and methyl/ ethyl/ isopropyl salicylates as surface units and 4‐(bromomethyl)phenol as core unit were synthesized in good yields by O‐alkylation. Similarly unsymmetrical dendrimers with indazole and methyl/ ethyl/ isopropyl anthranilates as surface units and 4‐hydroxybenzoic acid as core unit were synthesized in good yields by amide coupling reaction. The antimicrobial activities

  以吲唑和甲基/乙基/异丙基水杨酸酯为表面单元，以4-（溴甲基）苯酚为核心单元的不对称树状聚合物通过O-烷基化反应以高收率合成。同样，通过酰胺偶联反应以高收率合成了以吲唑和邻氨基苯甲酸甲酯/乙基/异丙基异丙酯为表面单元，以4-羟基苯甲酸为核心单元的不对称树枝状聚合物。新合成的树状聚合物的抗微生物活性对四种人病原性细菌即进行了评价。大肠杆菌，金黄色葡萄球菌，铜绿假单胞菌和枯草芽孢杆菌下在体外条件下通过“杯状板方法”。
• [EN] METHOD FOR PRODUCING THE TRANSITION METAL ION COMPLEX, CATALYST FOR TRIMERIZATION, AND METHOD FOR PRODUCING 1-HEXENE<br/>[FR] PROCÉDÉ DE PRODUCTION D'UN COMPLEXE ION MÉTAL DE TRANSITION, CATALYSEUR DE TRIMÉRISATION, ET PROCÉDÉ DE PRODUCTION DE 1-HEXÈNE
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2012133929A1

  公开（公告）日：2012-10-04

  An object of the present invention is to provide a silicon-bridged Cp-Ar transition metal complex that serves as a catalytic component capable of efficiently and highly selectively producing 1-hexene through the trimerization reaction of ethylene. The present invention provides a transition metal ion complex represented by any of formulae (1-1) to (1-3), etc.: wherein M represents a transition metal atom of Group 4 of the Periodic Table of the Elements; A represents a counter anion; R1, R2, R3, R4, R5, R6, R7, R8, R9, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, X1 and X2 each independently represent a hydrogen atom or the like; R10 and R11 each independently represent a hydrogen atom or the like.

  本发明的一个目的是提供一种硅桥联的Cp-Ar过渡金属配合物，作为一种催化组分，能够通过乙烯三聚反应高效且高选择性地产生1-己烯。本发明提供了一种过渡金属离子配合物，其表示为任一化学式（1-1）至（1-3）等：其中M表示元素周期表第4族的过渡金属原子；A表示反离子；R1、R2、R3、R4、R5、R6、R7、R8、R9、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21、X1和X2每个独立地表示氢原子或类似物；R10和R11每个独立地表示氢原子或类似物。