2’-氨基联苯-3-羧酸 | 177171-15-2

• 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’-氨基联苯-3-羧酸
• 英文名称: 2'-aminobiphenyl-3-carboxylic acid
• 英文别名: 2-amino-3'-biphenylcarboxylic acid；2-aminobiphenyl-3'-carboxylic acid；3-(2-aminophenyl)benzoic acid；2'-amino-biphenyl-3-carboxylic acid
• CAS: 177171-15-2
• 化学式: C₁₃H₁₁NO₂
• mdl: MFCD03990478
• 分子量: 213.236
• InChiKey: KAOICWOHZSZVKE-UHFFFAOYSA-N

物化性质

• 沸点：
  437.8±28.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2’-Aminobiphenyl-3-carboxylic 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’-Aminobiphenyl-3-carboxylic acid
CAS number: 177171-15-2

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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: C13H11NO2
Molecular weight: 213.2

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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：

  2’-氨基联苯-3-羧酸 在 氯化亚砜 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 168.5h， 生成 Methyl 3-[2-[(2-phenylacetyl)amino]phenyl]benzoate
  参考文献：
  名称：

  Synthesis and Hydrogen Bonding Capabilities of Biphenyl-Based Amino Acids Designed To Nucleate β-Sheet Structure

  摘要：

  The syntheses of 3'-(aminoethyl)-2-biphenylpropionic acid (1) and 2-amino-3'-biphenylcarboxylic acid (2) are described. These residues were designed to nucleate beta-sheet structure in aqueous solution when incorporated into small, amphiphilic peptides in place of the backbone of the i + 1 and i + 2 residues of the beta-turn. N-Benzyl-3'-(2-(benzylamido)ethyl)-2-biphenylpropamide (3) and N-benzyl-(2-benzylamido)-3'-biphenylamide (4) were synthesized and studied as model compounds to investigate the hydrogen-bonding capabilities of residues 1 and 2, respectively. The X-ray crystal structure of 3 indicates that a 13-membered intramolecular hydrogen-bonded ring is formed, while the remaining amide proton and carbonyl are involved in intermolecular hydrogen bonding. Infrared and variable-temperature NMR experiments indicate that, in solution (CH2Cl2), 3 exists as an equilibrium mixture of the 13- and the 15-membered intramolecularly hydrogen-bonded conformers with the 15-membered ring conformer being favored. Amide 4 was shown to exist in solution (CH2Cl2) as an equilibrium mixture of the 11-membered intramolecular hydrogen-bonded ring and a nonbonded conformation. No contribution from the 9-membered hydrogen-bonded ring conformation was observed. The X-ray crystal structure of 4 indicated the absence of intramolecular hydrogen bonding in the solid state.

  DOI：

  10.1021/jo952194k
• 作为产物：
  描述：

  3-溴苯甲酰氯 在 盐酸 、 sodium hydroxide 、 四(三苯基膦)钯 、 硼酸三甲酯 、 叠氮磷酸二苯酯 、 仲丁基锂 、 sodium carbonate 、 三乙胺 、 苯酚 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 128.67h， 生成 2’-氨基联苯-3-羧酸
  参考文献：
  名称：

  Synthesis and Hydrogen Bonding Capabilities of Biphenyl-Based Amino Acids Designed To Nucleate β-Sheet Structure

  摘要：

  The syntheses of 3'-(aminoethyl)-2-biphenylpropionic acid (1) and 2-amino-3'-biphenylcarboxylic acid (2) are described. These residues were designed to nucleate beta-sheet structure in aqueous solution when incorporated into small, amphiphilic peptides in place of the backbone of the i + 1 and i + 2 residues of the beta-turn. N-Benzyl-3'-(2-(benzylamido)ethyl)-2-biphenylpropamide (3) and N-benzyl-(2-benzylamido)-3'-biphenylamide (4) were synthesized and studied as model compounds to investigate the hydrogen-bonding capabilities of residues 1 and 2, respectively. The X-ray crystal structure of 3 indicates that a 13-membered intramolecular hydrogen-bonded ring is formed, while the remaining amide proton and carbonyl are involved in intermolecular hydrogen bonding. Infrared and variable-temperature NMR experiments indicate that, in solution (CH2Cl2), 3 exists as an equilibrium mixture of the 13- and the 15-membered intramolecularly hydrogen-bonded conformers with the 15-membered ring conformer being favored. Amide 4 was shown to exist in solution (CH2Cl2) as an equilibrium mixture of the 11-membered intramolecular hydrogen-bonded ring and a nonbonded conformation. No contribution from the 9-membered hydrogen-bonded ring conformation was observed. The X-ray crystal structure of 4 indicated the absence of intramolecular hydrogen bonding in the solid state.

  DOI：

  10.1021/jo952194k

文献信息

• Pd–EDTA as an efficient catalyst for Suzuki–Miyaura reactions in water
  作者：Dmitrii N. Korolev、Nikolay A. Bumagin

  DOI：10.1016/j.tetlet.2005.06.085

  日期：2005.8

  PdCl2–EDTA complex 1 is an efficient catalyst for the Suzuki–Miyaura reactions of aryl and heteroaryl halides with aryl(heteroaryl)boronic acids in water at 20–100 °C. Aryl iodides and bromides undergo the cross-coupling with turnover numbers (TON) up to 97,000 and turnover frequencies (TOF) up to 582,000 h−1.

  PdCl 2 -EDTA络合物1是在20-100°C的水中，芳基和杂芳基卤化物与芳基（杂芳基）硼酸的Suzuki-Miyaura反应的有效催化剂。芳基碘化物和溴化物进行交叉耦合，其周转数（TON）高达97,000，周转频率（TOF）高达582,000 h -1。
• Transition-metal-catalyzed carbon-nitrogen and carbon-carbon bond-forming reactions
  申请人：Buchwald L. Stephen

  公开号：US20060173186A1

  公开（公告）日：2006-08-03

  One aspect of the present invention relates to ligands for transition metals. A second aspect of the present invention relates to the use of catalysts comprising these ligands in various transition-metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The subject methods provide improvements in many features of the transition-metal-catalyzed reactions, including the range of suitable substrates, number of catalyst turnovers, reaction conditions, and efficiency. For example, improvements have been realized in transition metal-catalyzed: aryl amination reactions; aryl amidation reactions; Suzuki couplings; and Sonogashira couplings. In certain embodiments, the invention relates to catalysts and methods of using them that operate in aqueous solvent systems.

  本发明的一个方面涉及过渡金属配体。本发明的第二个方面涉及在各种过渡金属催化的碳-杂原子和碳-碳键形成反应中使用包含这些配体的催化剂。本方法提供了许多过渡金属催化反应的特征改进，包括适合底物的范围、催化剂周转次数、反应条件和效率。例如，在过渡金属催化的芳基胺化反应、芳基酰胺化反应、Suzuki偶联和Sonogashira偶联中已经实现了改进。在某些实施例中，本发明涉及在水溶剂体系中操作的催化剂及其使用方法。
• Gastrin releasing peptide compounds
  申请人：Cappelletti Enrico

  公开号：US20060018830A1

  公开（公告）日：2006-01-26

  New and improved compounds for use in diagnostic imaging or therapy having the formula M-N—O—P-G, wherein M is a metal chelator having the structure: wherein R1-R5 and FG are as defined herein (in the form complexed with a metal radionuclide or not), N—O—P is the linker containing at least one non-alpha amino acid with a cyclic group, at least one substituted bile acid or at least one non-alpha amino acid, and G is the GRP receptor targeting peptide. In the preferred embodiment, M is an Aazta metal chelator or a derivative thereof. Methods for imaging a patient and/or providing radiotherapy or phototherapy to a patient using the compounds of the invention are also provided. Methods and kits for preparing a diagnostic imaging agent from the compound is further provided. Methods and kits for preparing a radiotherapeutic agent are further provided.

  新的改进化合物用于诊断影像或治疗，其化学式为M-N—O—P-G，其中M是具有以下结构的金属螯合剂： 其中R1-R5和FG的定义如本文所述（以金属放射性核素或未配合的形式），N—O—P是含有至少一个非α氨基酸的连接剂，其中该氨基酸具有一个环形基团，至少一个取代的胆汁酸或至少一个非α氨基酸，而G是GRP受体靶向肽。在首选实施例中，M是Aazta金属螯合剂或其衍生物。还提供了使用该发明的化合物对患者进行成像和/或提供放射治疗或光疗的方法。还提供了制备诊断成像剂的方法和试剂盒。还提供了制备放射治疗剂的方法和试剂盒。
• Transition-Metal-Catalyzed Carbon-Nitrogen and Carbon-Carbon Bond-Forming Reactions
  申请人：Buchwald Stephen L.

  公开号：US20090287016A1

  公开（公告）日：2009-11-19

  One aspect of the present invention relates to ligands for transition metals. A second aspect of the present invention relates to the use of catalysts comprising these ligands in various transition-metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The subject methods provide improvements in many features of the transition-metal-catalyzed reactions, including the range of suitable substrates, number of catalyst turnovers, reaction conditions, and efficiency. For example, improvements have been realized in transition metal-catalyzed: aryl amination reactions; aryl amidation reactions; Suzuki couplings; and Sonogashira couplings. In certain embodiments, the invention relates to catalysts and methods of using them that operate in aqueous solvent systems.

  本发明的一个方面涉及过渡金属的配体。本发明的另一个方面涉及在各种过渡金属催化的碳杂原子和碳-碳键形成反应中使用包含这些配体的催化剂。该方法提供了许多过渡金属催化反应的特征改进，包括适合的底物范围、催化剂周转次数、反应条件和效率等。例如，在过渡金属催化的芳基胺化反应、芳基酰胺化反应、Suzuki 偶联和 Sonogashira 偶联中已经实现了改进。在某些实施例中，本发明涉及在水溶剂体系中操作的催化剂和使用它们的方法。
• Gastrin Releasing Peptide Compounds
  申请人：Cappelletti Enrico

  公开号：US20080008649A1

  公开（公告）日：2008-01-10

  New and improved compounds for use in diagnostic imaging or therapy having the formula M-N—O—P-G, wherein M is a metal chelator having the structure: wherein R 1 -R 5 and FG are as defined herein (in the form complexed with a metal radionuclide or not), N—O—P is the linker containing at least one non-alpha amino acid with a cyclic group, at least one substituted bile acid or at least one non-alpha amino acid, and G is the GRP receptor targeting peptide. In the preferred embodiment, M is an Aazta metal chelator or a derivative thereof. Methods for imaging a patient and/or providing radiotherapy or phototherapy to a patient using the compounds of the invention are also provided. Methods and kits for preparing a diagnostic imaging agent from the compound is further provided. Methods and kits for preparing a radiotherapeutic agent are further provided. Novel methods of treating prostate tumors or of delaying the progression of prostate tumors are also provided, including, methods of treating bone or soft tissue metastases of prostate cancer, methods for treating hormone sensitive and hormone refractory prostate cancer, methods for delaying the progression of hormone sensitive prostate cancer, for facilitating combination therapy in patients with hormone sensitive prostate cancer and for decreasing aberrant vascular permeability in patients with hormone sensitive prostate cancer.

  新的和改进的化合物可用于诊断成像或治疗，其化学式为M-N—O—P-G，其中M是具有以下结构的金属螯合剂： 其中R1-R5和FG如此定义（以金属放射性核素或未配合的形式），N—O—P是含有至少一个非α氨基酸环状基团、至少一个取代胆酸或至少一个非α氨基酸的连接物，而G是GRP受体靶向肽。在首选实施例中，M是Aazta金属螯合剂或其衍生物。本发明还提供了使用该化合物对患者进行成像和/或提供放射治疗或光治疗的方法。还提供了制备诊断成像试剂的方法和试剂盒。还提供了制备放射治疗试剂的方法和试剂盒。还提供了治疗前列腺肿瘤或延缓前列腺肿瘤进展的新方法，包括治疗前列腺癌骨骼或软组织转移的方法，治疗激素敏感和激素难治性前列腺癌的方法，延缓激素敏感前列腺癌进展的方法，促进激素敏感前列腺癌患者联合治疗的方法以及降低激素敏感前列腺癌患者异常血管渗透性的方法。