4-羧基-2-硝基苯硼酸 | 85107-54-6

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 环羧酸
• 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-羧基-2-硝基苯硼酸
• 中文别名: 4-羧基-2-硝基苯基硼酸；2-硝基-4-羧基苯硼酸
• 英文名称: (4-carboxy-2-nitro phenyl)dihydroxy borane
• 英文别名: 2-nitro-4-carboxyphenylboronic acid；4-carboxy-2-nitrophenylboronic acid；4-dihydroxyboranyl-3-nitro-benzoic acid；4-Dihydroxyboryl-3-nitro-benzoesaeure；2-nitro-4-carboxybenzeneboronic acid；4-borono-3-nitrobenzoic acid
• CAS: 85107-54-6
• 化学式: C₇H₆BNO₆
• mdl: MFCD00448780
• 分子量: 210.939
• InChiKey: APBXPKJLXBBPQJ-UHFFFAOYSA-N

物化性质

• 熔点：
  265-268
• 沸点：
  487.1±55.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.11
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• TSCA：
  No
• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R20/21/22,R36/37/38
• 海关编码：
  2931900090
• 安全说明：
  S26,S36
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4-Carboxy-2-nitrophenylboronic acid
Product Name:
Synonyms: 4-Borono-3-nitrobenzoic acid

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
4-Carboxy-2-nitrophenylboronic acid
Ingredient name:
CAS number: 85107-54-6

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C7H6BNO6
Molecular weight: 210.9

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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

简介

4-羧基-2-硝基苯硼酸是一种灰白色的结晶物，密度为1.62 g/cm³，沸点为487.1°C（在760 mmHg下），熔点为265-268°C。

制备

在带有回流冷凝管和温度计的三口瓶中加入4-羧基-苯硼酸、浓硫酸和硝酸，磁力搅拌进行反应。当温度升至103℃时，4-羧基-苯硼酸开始溶解，继续升温至120℃并保持反应2小时。通过薄层色谱检测反应进程，在反应完成后冷却，过滤，并用乙醚洗涤滤饼，抽滤、烘干以获得所需的灰色针状晶体4-硝基-2-硝基苯硼酸。

反应信息

• 作为反应物：
  描述：

  4-羧基-2-硝基苯硼酸 在 乙醇 、 镍 作用下， 生成 3-氨基-4-硼苯甲酸
  参考文献：
  名称：

  Torssell et al., Arkiv foer Kemi, 1957, vol. 10, p. 479,504

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羧基苯硼酸 生成 4-羧基-2-硝基苯硼酸
  参考文献：
  名称：

  苯硼酸的稳定性与合成1

  摘要：

  描述了几种取代的羧基苯基硼酸的制备。注意到此类化合物中碳-硼键的显着稳定性。已经合成了三种具有潜在致癌性的含硼化合物。（授权）

  DOI：

  10.1021/ja01521a025

文献信息

• Synthesis of 2-amino-4-(methoxycarbonyl)Phenylboronic Acid Hydrochloride, a key Intermediate for the Synthesis of Quinolines Derivatives
  作者：Feng Xue、Chang-Gong Li、Yong Zhu、Tian-Jun Lou

  DOI：10.3184/174751914x14175346572646

  日期：2014.12

  A practical and efficient process for the synthesis in good yield of 2-amino-4-(methoxycarbonyl)phenylboronic acid hydrochloride from p-bromo toluene has been developed via borylation, oxidation, nitration, esterification and hydrogenation.

  通过硼酸化、氧化、硝化、酯化和加氢，开发了一种从对溴甲苯中高产率合成2-氨基-4-(甲氧基羰基)苯基硼酸盐酸盐的实用且有效的方法。
• Rapid nickel(<scp>ii</scp>)-promoted cysteine <i>S</i>-arylation with arylboronic acids
  作者：Kengo Hanaya、Jun Ohata、Mary K. Miller、Alicia E. Mangubat-Medina、Michael J. Swierczynski、David C. Yang、Reece M. Rosenthal、Brian V. Popp、Zachary T. Ball

  DOI：10.1039/c9cc00159j

  日期：——

  proteins, providing novel structure and electronic perturbation. The present work demonstrates an operationally-simple cysteine arylation reaction 2-nitro-substituted arylboronic acids, promoted by a simple nickel(II) salt. The process exhibits strikingly fast reaction rates under physiological conditions in purely aqueous media with excellent selectivity toward cysteine residues. Cysteine arylation of

  半胱氨酸残基的S-酰化是蛋白质位点特异性修饰的一种越来越强大的工具，它提供了新颖的结构和电子扰动。本工作证明了操作上简单的半胱氨酸芳基化反应2-硝基取代的芳基硼酸，由简单的镍（II）盐促进。该方法在生理条件下，在纯水介质中对半胱氨酸残基具有优异的选择性，显示出惊人的快速反应速率。天然蛋白质和肽的半胱氨酸芳基化反应可以连接有用的反应性手柄，用于装订，成像或进一步偶联。
• Boronic Acid Pairs for Sequential Bioconjugation
  作者：Mary K. Miller、Michael J. Swierczynski、Yuxuan Ding、Zachary T. Ball

  DOI：10.1021/acs.orglett.1c01624

  日期：2021.7.16

  Boronic acids can play diverse roles when applied in biological environments, and employing boronic acid structures in tandem could provide new tools for multifunctional probes. This Letter describes a pair of boronic acid functional groups, 2-nitro-arylboronic acid (NAB) and (E)-alkenylboronic acid (EAB), that enable sequential cross-coupling through stepwise nickel- and copper-catalyzed processes

  硼酸在生物环境中可以发挥多种作用，串联使用硼酸结构可以为多功能探针提供新的工具。这封信描述了一对硼酸官能团，2-硝基-芳基硼酸 (NAB) 和 ( E )-烯基硼酸 (EAB)，它们能够通过逐步的镍和铜催化过程进行顺序交叉偶联。NAB 基团的选择性偶联能够制备钉合肽、蛋白质-蛋白质偶联物和其他生物偶联物。
• Nickel(II)-Promoted Amide N–H Arylation of Pyroglutamate–Histidine with Arylboronic Acid Reagents
  作者：Kengo Hanaya、Mary K. Miller、Zachary T. Ball

  DOI：10.1021/acs.orglett.9b00759

  日期：2019.4.5

  Small and simple bioorthogonal reactive handles that can be readily encoded by natural processes are important for bioconjugation. A rapid nickel-promoted N–H arylation of pyroglutamate–histidine sequences with 2-nitroarylboronic acids proceeds under mild aqueous conditions. Chemoselective activation of a lactam amide N–H within a peptide or protein provides a new approach to selective conjugation

  可以通过自然过程轻松编码的小而简单的生物正交反应手柄对于生物缀合非常重要。焦谷氨酸-组氨酸序列与2-硝基芳基硼酸的快速镍促进NH芳基化反应在温和的水性条件下进行。肽或蛋白质中内酰胺酰胺N–H的化学选择性活化为聚酰胺结构的选择性偶联提供了一种新方法。
• Protection-Free Strategy for the Synthesis of Boro-Depsipeptides in Aqueous Media under Microwave-Assisted Conditions
  作者：Shuo-Bei Qiu、Pei-Yao Liu、Bo-Cheng Wang、Pin-Rui Chen、Jing-Han Xiao、Ting-Yu Hsu、Kuan-Lin Pan、Zhi-Yin Lai、Yi-Wei Chen、Ying-Chuan Chen、Jen-Kun Chen、Po-Shen Pan

  DOI：10.3390/molecules27072325

  日期：——

  In this report, 19 boron-containing depsipeptides were synthesized via microwave-assisted Passerini three-component reaction (P-3CR) in an aqueous environment. The linker-free DAHMI fluorescent tagging approach was used on selected boron-containing compounds to study the relationship between their structures and their level of cellular uptake of HEK293 cells. The biological data retrieved from the

  在本报告中，通过微波辅助 Passerini 三组分反应 (P-3CR) 在水环境中合成了 19 种含硼缩肽。无接头的 DAHMI 荧光标记方法用于选定的含硼化合物，以研究其结构与 HEK293 细胞的细胞摄取水平之间的关系。从 DAHMI 实验中检索到的生物学数据表明，虽然测试化合物的结构可能高度相似，但它们的生物分布曲线可能非常不同。报道的优化的一锅法合成策略沿着无接头体外测试方案可以提供一个有效的平台来加速含硼药物的开发。