3-氨基-3-(2-硝基苯基)丙酸 | 5678-48-8

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 3-氨基-3-(2-硝基苯基)丙酸
• 中文别名: (RS)-3-氨基-3-(2-硝基苯基)丙酸
• 英文名称: 3-amino-3-(2-nitrophenyl)propionic acid
• 英文别名: 3-amino-3-(2-nitrophenyl)propanoic acid；3-azaniumyl-3-(2-nitrophenyl)propanoate
• CAS: 5678-48-8
• 化学式: C₉H₁₀N₂O₄
• mdl: MFCD00090356
• 分子量: 210.189
• InChiKey: XXBOYULKNZTOMN-UHFFFAOYSA-N

物化性质

• 熔点：
  222 °C
• 沸点：
  423.8±35.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  15
• 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：
  109
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2922499990
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  建议在0-5℃下避光、存放在阴凉干燥处并密封保存。

SDS

Name:	3-Amino-3-(2-nitrophenyl)propanoic acid tech Material Safety Data Sheet
Synonym:	3-Amino-3-(2-nitrophenyl)propionic aci
CAS:	5678-48-8

Section 1 - Chemical Product MSDS Name:3-Amino-3-(2-nitrophenyl)propanoic acid tech Material Safety Data Sheet
Synonym:3-Amino-3-(2-nitrophenyl)propionic aci

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5678-48-8	3-Amino-3-(2-nitrophenyl)propanoic aci		unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 5678-48-8: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 218 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C9H10N2O4
Molecular Weight: 210

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Reducing agents, strong oxidizing agents, acids, bases, acid chlorides.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5678-48-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-Amino-3-(2-nitrophenyl)propanoic acid - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 5678-48-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5678-48-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5678-48-8 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

3-氨基-3-(2-硝基苯基)丙酸可用于医药合成中间体。

反应信息

• 作为反应物：
  描述：

  3-氨基-3-(2-硝基苯基)丙酸 在 hydrazine hydrate 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.5h， 以78%的产率得到吲唑-3-乙酸
  参考文献：
  名称：

  PF74 and Its Novel Derivatives Stabilize Hexameric Lattice of HIV-1 Mature-Like Particles

  摘要：

  一种重要的结构逆转录病毒蛋白，壳蛋白（CA），能够聚合成两种不同的六聚体晶格，使得这种蛋白成为HIV-1复制早期和晚期的关键组成部分。在晚期阶段，作为Gag多蛋白前体的一部分，CA蛋白促进蛋白质-蛋白质相互作用，导致不成熟颗粒的组装。在蛋白酶激活和Gag多蛋白加工之后，CA还推动了成熟病毒核的组装。在感染的早期阶段，CA蛋白的作用是不同的。它控制成熟CA六聚体晶格的解体，即解包装，这对将单链RNA基因组逆转录为双链DNA至关重要。这些特性使得CA成为作为HIV-1颗粒组装和/或解组装抑制剂的小分子非常吸引人的靶点。其中，含有PF74支架的抑制剂已经得到广泛研究。在本研究中，我们报告了对PF74分子的一系列改性及其通过生化和结构方法的表征。我们的数据支持了PF74稳定成熟HIV-1 CA六聚体晶格的假设。我们鉴定出与原始PF74分子相比具有更高体外稳定活性的衍生物。

  DOI：

  10.3390/molecules25081895
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 水 作用下， 生成 3-氨基-3-(2-硝基苯基)丙酸
  参考文献：
  名称：

  Posner, Justus Liebigs Annalen der Chemie, 1912, vol. 389, p. 36,111

  摘要：

  DOI：

文献信息

• Mechanismus der Eintopf-Synthese der 3-Amino-3-(o-nitrophenyl)-propionsäure
  作者：Herbert Oelschläger、Jörg Ogorka、Ingrid Kolbeck

  DOI：10.1002/ardp.19863190603

  日期：——

  Die Eintopf‐Synthese der 3‐Amino‐3‐(o‐nitrophenyl)‐propionsäure (1) aus o‐Nitrobenzaldehyd und Malonsäure in Ammoniumacetat/Eisessig erfolgt in 3 Reaktionsschritten: Kondensation, Addition und Decarboxylierung. Nebenreaktionen wurden geklärt.

  Die Eintopf-Synthese der 3-Amino-3-(o-nitrophenyl)-propionsäure (1) aus o-Nitrobenzaldehyd und Malonsäure in Ammoniumacetat/Eisessig erfolgt in 3 Reaktionsschritten: Kondensation, Addition und Decarboxylierung。Nebenreaktionen wurden geklärt。
• Influence of the aromatic moiety in α- and β-arylalanines on their biotransformation with phenylalanine 2,3-aminomutase from Pantoea agglomerans
  作者：Andrea Varga、Gergely Bánóczi、Botond Nagy、László Csaba Bencze、Monica Ioana Toşa、Ákos Gellért、Florin Dan Irimie、János Rétey、László Poppe、Csaba Paizs

  DOI：10.1039/c6ra02964g

  日期：——

  isomerization of various racemic α- and β-arylalanines catalysed by phenylalanine 2,3-aminomutase from Pantoea agglomerans (PaPAM) was investigated. Both α- and β-arylalanines were accepted as substrates when the aryl moiety was relatively small, like phenyl, 2-, 3-, 4-fluorophenyl or thiophen-2-yl. While 2-substituted α-phenylalanines bearing bulky electron withdrawing substituents did not react, the corresponding

  在这项研究中，Pantoea agloglomerans的苯丙氨酸2，3-氨基变位酶催化的各种外消旋α-和β-芳基丙氨酸的对映异构体选择性异构化（PaPAM）进行了调查。当芳基部分相对较小时，如苯基，2-，3-，4-氟苯基或噻吩-2-基，α-和β-芳基丙氨酸均被接受为底物。尽管带有大量吸电子取代基的2-取代的α-苯丙氨酸没有反应，但相应的取代的β-芳基类似物却被迅速转化。3-和4-取代的α-芳基丙氨酸的转化顺利进行，而相应的β-芳基丙氨酸的转化不良或不存在。在pH 7-9范围内，对外消旋α-或β-（噻吩-2-基）丙氨酸的转化率没有明显影响，而氨的浓度（碳酸铵从50 mM增加到1000 mM）则抑制了异构化逐步减少副产物的量（即（E检测到）-3-（噻吩-2-基）丙烯酸。在所有情况下，产物的高ee值表明优异的对映异构体选择性和异构化的立体特异性，除了来自β-异构体的（S）-2-硝基-α-苯丙氨酸（ee
• Kinetic Resolution of Aromatic β-Amino Acids Using a Combination of Phenylalanine Ammonia Lyase and Aminomutase Biocatalysts
  作者：Nicholas J. Weise、Syed T. Ahmed、Fabio Parmeggiani、Nicholas J. Turner

  DOI：10.1002/adsc.201600894

  日期：2017.5.2

  linked to the first ever proposed biosynthesis of pyloricidin‐like secondary metabolites and was shown to display better β‐lyase activity in many cases. In spite of this, a method combining the higher conversion of EncP with a strict α‐lyase from Anabaena variabilis (AvPAL) was found to be more amenable, allowing kinetic resolution of five racemic substrates and a preparative‐scale reaction with >98% (R)

  已经证明了使用苯丙氨酸氨基变位酶和氨裂合酶（PAM和PAL）酶制备（R）-β-芳基丙氨酸的酶促策略。具有海马链霉菌（EncP）和芽孢杆菌（Bacillus sp。）选择性（S）选择性的候选PAM 。（PabH）通过使用充分研究的模板序列进行序列分析来鉴定。新发现的PabH可能与首次提出的幽门螺杆菌样二级代谢产物的生物合成有关，并在许多情况下显示出更好的β-裂合酶活性。尽管如此，ENCP的较高的转化率具有严格α -裂解酶合成的方法从多变鱼腥藻（AvPAL）被认为是更合适的，它允许五种外消旋底物的动力学拆分以及制备规模的对映体过量> 98％（R）的反应。这项工作代表了对现有生物催化策略的一种改进和对映体互补的方法，它允许简单的产品分离和模块化的伸缩组合，以及使用非手性醛作为原料的先前化学步骤。
• [EN] BREVICAN-BINDING PEPTIDES FOR BRAIN TUMOR IMAGING<br/>[FR] PEPTIDES DE LIAISON AU BRÉVICAN POUR L'IMAGERIE D'UNE TUMEUR CÉRÉBRALE
  申请人：BRIGHAM & WOMENS HOSPITAL INC

  公开号：WO2020072491A1

  公开（公告）日：2020-04-09

  Compositions comprising peptides that bind specifically to BΔg (deglycosylated brevican), and methods of use thereof to deliver therapeutic and diagnostic agents to brevican-expressing cells, e.g., cancerous cells, e.g., brain cancer cells, e.g., glioblastoma cells.

  包含与BΔg（去糖基化的brevican）特异性结合的肽的组合物，以及利用这些肽将治疗和诊断试剂传递到表达brevican的细胞中的方法，例如癌细胞，例如脑癌细胞，例如胶质母细胞瘤细胞。
• Synthesis, Hypoglycemic Effect, Antimicrobial and Molecular Docking Studies of Organotin(IV) Complexes Derived from N-Phthalimido β-Amino Acid Derivatives
  作者：Muhammad Ahmed、Nagina Riaz、Muhammad Kashif、Muhammad Ashfaq、Muhammad Arshad、Muhammad Sajid

  DOI：10.21577/0103-5053.20210011

  日期：——

  N-Phthalimido β-amino acid derivatives, 3-phthalimido-3(2-hydroxyphenyl) propanoic acid (P2HPA) and 3-phthalimido-3(2-nitrophenyl) propanoic acid (P2NPA) with new series of diand triorganotin(IV) complexes (1-12) have been designed and synthesized. All the ligands and organotin(IV) complexes were characterized by elemental analysis, Fourier transform infrared spectroscopy (FTIR), nuclear magnetic resonance

  N-邻苯二甲酰基β-氨基酸衍生物，3-邻苯二甲酰基-3(2-羟基苯基)丙酸（P2HPA）和3-邻苯二甲酰基-3(2-硝基苯基)丙酸（P2NPA）与新系列的二和三有机锡（IV）配合物（1-12）已被设计并合成。所有配体和有机锡（IV）配合物均通过元素分析、傅里叶变换红外光谱（FTIR）、核磁共振（1H、13C、119Sn）光谱和电子电离质谱（EI-MS）进行了表征。合成的配体和配合物经过筛选，以确定抗菌活性，结果显示三有机锡（IV）配合物与二有机锡（IV）配合物和配体相比具有更好的活性。此外，对配体在sortase A的催化口袋（PDB ID 1T2W）上的分子对接分析显示，配体可以结合口袋中的活性氨基酸残基。抗氧化活性也通过DPPH（1,1-二苯基-2-苦基肼自由基）方法进行，配合物的结果比配体更好。这些化合物还在体内进行了测试，以确定对不同组的山梨醇诱导糖尿病兔的降糖活性。配合物（1-6）被发现是更好的降糖剂，因为它们将葡萄糖水平稳定在约175-105毫克/分升，与配体P2HPA相比。