3-硝基苯硼酸 | 13331-27-6

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类硝化物
• 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: 3-硝基苯硼酸
• 中文别名: 间硝基苯硼酸；3-硝基苯基硼酸；间硝基苯硼酸&amp
• 英文名称: 3-Nitrophenylboronic acid
• 英文别名: m-nitrobenzene boronic acid；m-nitrophenylboronic acid；3-nitrobenzeneboronic acid；meta-nitrophenylboronic acid；3‐nitrophenylboronic acid；(3-nitrophenyl)boronic acid
• CAS: 13331-27-6
• 化学式: C₆H₆BNO₄
• mdl: MFCD00007193
• 分子量: 166.929
• InChiKey: ZNRGSYUVFVNSAW-UHFFFAOYSA-N

物化性质

• 熔点：
  284-285 °C (dec.) (lit.)
• 沸点：
  363.3±44.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)
• 溶解度：
  溶于乙醇、甲醇、乙醚
• 稳定性/保质期：
  在常温常压下保持稳定，应避免接触水分和潮湿的氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.3
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• TSCA：
  T
• 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
• WGK Germany：
  3
• 海关编码：
  29310095
• 危险品运输编号：
  NONH for all modes of transport
• RTECS号：
  CY8980000
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  常温密闭，阴凉通风干燥

SDS

Name:	3-Nitrophenylboronic acid 97% Material Safety Data Sheet
Synonym:	None Known
CAS:	13331-27-6

Section 1 - Chemical Product MSDS Name:3-Nitrophenylboronic acid 97% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13331-27-6	3-Nitrophenylboronic acid	97%	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. May cause chemical conjunctivitis.
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. Can produce delayed pulmonary edema.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately 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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. 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. Do NOT use mouth-to-mouth resuscitation.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
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# 13331-27-6: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: Powder
Color: white - off-white
Odor: odorless
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 289 - 291 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: Soluble in hot water.
Specific Gravity/Density:
Molecular Formula: C6H6BNO4
Molecular Weight: 166.93

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong acids.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, boron oxides.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 13331-27-6: CY8980000 LD50/LC50:
Not available.
Carcinogenicity:
3-Nitrophenylboronic acid - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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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# 13331-27-6: No information available.
Canada
CAS# 13331-27-6 is listed on Canada's DSL List.
CAS# 13331-27-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13331-27-6 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

3-硝基苯硼酸

3-硝基苯硼酸是一种硼酸衍生物，在有机合成中广泛应用，主要用于碳-碳键的形成。在Suzuki偶联反应中，芳基卤化物和硼酸芳基或乙烯基酯可通过四(三苯基膦)钯（Pd(PPb)4）催化进行偶联。

制备

在冰盐浴冷却下，向无色发烟硝酸（50 mL，1.20 M）中加入少量尿素，降温至-15℃。随后，在1-2小时内缓慢滴加苯基硼酸（9.02 g，74 mmol），确保温度不升至-9℃以上。混合物继续搅拌15-30分钟后，倒入冰水中，产物会沉淀出来。通过真空过滤收集硝基苯基硼酸沉淀，并在少量水中重结晶，加入脱色木炭进行热真空过滤以去除杂质。随后用水和甲醇洗涤晶体。原始滤液在冰浴中冷却至室温，用12 N NaOH溶液调pH值至橙红色/红色，再使用硝酸酸化。该混合物通过乙醚萃取，并用水洗涤后，在室温下浓缩。将处理后的两个馏分合并并进行柱色谱分离（洗脱剂：C6H12:CH2Cl2，比例为80:20），除去所有微量杂质。最终以28%的收率得到柠檬棱柱状晶体3-硝基苯硼酸。

用途

3-硝基苯硼酸可催化炔二羰基化合物的烯碳环化反应。

反应信息

• 作为反应物：
  描述：

  3-硝基苯硼酸 在 copper(II) nitrate trihydrate 、 碘 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以40%的产率得到1-碘-3-硝基苯
  参考文献：
  名称：

  一种简单有效的铜催化剂，用于在室温下将芳基硼酸转化为芳基碘化物

  摘要：

  简单的Cu（NO 3）2 ·3H 2 O在室温下具有催化芳基硼酸转化为芳基碘的能力。与先前的铜催化方法相比，本方法避免了使用配体，氧化剂以及加热条件。

  DOI：

  10.1016/j.catcom.2012.11.022
• 作为产物：
  描述：

  3-硝基苯硼酸频哪醇酯 在 盐酸 、 polystyrene boronic acid 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以88%的产率得到3-硝基苯硼酸
  参考文献：
  名称：

  Deprotection of pinacolyl boronate esters by transesterification with polystyrene–boronic acid

  摘要：

  Mild deprotection of pinacolyl boronate esters to the corresponding boronic acids was achieved in the presence of excess polystyrene-boronic acid via a transesterification process. The procedure allows for the cleavage of pinacolyl boronate esters in the presence of sensitive functional groups. Crown Copyright (C) 2004 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.07.014
• 作为试剂：
  描述：

  胆固醇 、 乙酸酐 在 3-硝基苯硼酸 作用下， 反应 15.0h， 以99%的产率得到胆固醇醋酸酯
  参考文献：
  名称：

  A novel 3-nitrobenzeneboronic acid as an extremely mild and environmentally benign catalyst for the acetylation of alcohols under solvent-free conditions

  摘要：

  A novel 3-nitrobenzeneboronic acid is found to catalyse efficiently the acetylation of a wide range of alcohols as well as phenols with acetic anhydride in good to excellent yields at room temperature under solvent-free conditions. The reactions are clean and the catalyst is mild such that highly sensitive functional groups including oximes are stable to the reaction conditions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.046

文献信息

• Site-Selective Ruthenium-Catalyzed C–H Bond Arylations with Boronic Acids: Exploiting Isoindolinones as a Weak Directing Group
  作者：Yu-Chao Yuan、Christian Bruneau、Thierry Roisnel、Rafael Gramage-Doria

  DOI：10.1021/acs.joc.9b01563

  日期：2019.10.18

  functionalization. The reactions exclusively led to monoarylated products, and only ortho selectivity was observed in the aromatic ring connected to the nitrogen atom. Interestingly, no C-H bond functionalization was observed in the other benzene ring in the ortho position with respect to the carbonyl group. This ruthenium-catalyzed reaction displayed a high functional group tolerance, and it employed readily

  在钌催化下，通过CH键官能化作用，与生物学相关的N-芳基异吲哚啉酮可以有效地进行芳基化反应。该反应仅导致单芳基化的产物，并且在与氮原子连接的芳环中仅观察到邻位选择性。有趣的是，在相对于羰基的邻位的另一个苯环中未观察到CH键官能化。该钌催化的反应显示出较高的官能团耐受性，并且使用容易获得的基准稳定的硼酸和芳基三氟硼酸钾衍生物作为偶联伙伴。展示了使用这种方法对吲哚洛芬进行的诱人的后期功能化。
• [EN] SUBSTITUTED PYRAZOLE AND PYRROLE COMPOUNDS AND METHODS FOR USING THEM FOR INHIBITION OF INITIATION OF TRANSLATION AND TREATMENT OF DISEASES AND DISORDERS RELATING THERETO<br/>[FR] COMPOSÉS PYRAZOLE ET PYRROLE SUBSTITUÉS ET PROCÉDÉS D'UTILISATION DE CES DERNIERS POUR L'INHIBITION DE L'INITIATION DE LA TRADUCTION ET LE TRAITEMENT DE MALADIES ET DE TROUBLES ASSOCIÉS À CETTE DERNIÈRE
  申请人：BANTAM PHARMACEUTICAL LLC

  公开号：WO2016196644A1

  公开（公告）日：2016-12-08

  Disclosed are pyrazole compounds, as well as pharmaceutical compositions and methods of use thereof. One embodiment is a compound having the structure (I) and pharmaceutically acceptable salts and /V-oxides thereof, wherein X1, X2, Z1, Z2, the ring system denoted by "a", R1, A1A, L1B, A1B, L1A, L2, Q, L3, R3, A4A, L4B, A4B, L4A, R4, L5, and R5 are as described herein. In certain embodiments, compounds disclosed herein disrupt the elF4E/eiF4G interaction, and can be used to treat hyperproliferative disorder, a neurological disease or disorder, or autism.

  揭示了吡唑化合物，以及其药物组合物和使用方法。其中一种实施例是具有结构（I）及其药用可接受的盐和/或氧化物，其中X1、X2、Z1、Z2、由“a”表示的环系统、R1、A1A、L1B、A1B、L1A、L2、Q、L3、R3、A4A、L4B、A4B、L4A、R4、L5和R5如本文所述。在某些实施例中，本文所披露的化合物破坏elF4E/eiF4G相互作用，并可用于治疗过度增殖性疾病、神经系统疾病或障碍，或自闭症。
• Regioselective Arylation Reactions of Biphenyl-2-ols, Naphthols, and Benzylic Compounds with Aryl Halides under Palladium Catalysis
  作者：Tetsuya Satoh、Jun-ichi Inoh、Yoshiki Kawamura、Yuichiro Kawamura、Masahiro Miura、Masakatsu Nomura

  DOI：10.1246/bcsj.71.2239

  日期：1998.9

  Biphenyl-2-ols undergo regioselective mono- and diarylation upon a treatment with aryl iodides in the presence of a palladium catalyst in DMF using Cs2CO3 as a base to produce 1,1′ : 2′,1″-terphenyl-2-ol and 2′,6′-diphenylbiphenyl-2-ol and their derivatives. The reaction of 1-naphthol selectively occurs at its 8-position to give 8-aryl-1-naphthols. In the reaction of 2-naphthol with aryl bromides, diarylated

  在钯催化剂存在下，在 DMF 中，使用 Cs2CO3 作为碱，用芳基碘化物处理后，联苯 2-醇发生区域选择性单芳基化和二芳基化，生成 1,1': 2',1"-三联苯-2-醇和2',6'-diphenylbiphenyl-2-ol 及其衍生物。1-萘酚的反应选择性地发生在其 8-位，得到 8-芳基-1-萘酚。在 2-萘酚与芳基溴化物的反应中，二芳基化合物 1-(2-芳基苯基)-2-萘酚作为单一的主要产物形成。在类似条件下，苄基酮、苯基乙腈和苯基乙酸甲酯在其苄基位置被芳基化。
• Expanding the Balz-Schiemann Reaction: Organotrifluoroborates Serve as Competent Sources of Fluoride Ion for Fluoro-Dediazoniation
  作者：Tharwat Mohy El Dine、Omar Sadek、Emmanuel Gras、David M. Perrin

  DOI：10.1002/chem.201803575

  日期：2018.10.9

  The Balz–Schiemann reaction endures as a method for the preparation of (hetero)aryl fluorides yet is eschewed due to the need for harsh conditions or high temperatures along with the need to isolate potentially explosive diazonium salts. In a departure from these conditions, we show that various organotrifluoroborates (RBF3−s) may serve as fluoride ion sources for solution‐phase fluoro‐dediazoniation

  Balz-Schiemann反应作为一种制备（杂）芳基氟化物的方法而持久，但由于需要苛刻的条件或高温以及需要分离潜在爆炸性的重氮盐而被避开。与这些条件不同，我们显示了各种有机三氟硼酸盐（RBF 3 - s）可以作为氟离子源，用于在温和条件下在有机溶剂中进行溶液相氟脱氮。该方法成功地扩展到一锅法，避免了芳基重氮盐的分离。受阻位的（杂）苯胺在前所未有的温和条件下以良好至优异的产率进行氟化。综上所述，这项工作扩大了RBF 3的功能范围-在经典的Balz-Schiemann反应的更新中充当氟离子源。
• Novel Diarylurea Based Allosteric Modulators of the Cannabinoid CB1 Receptor: Evaluation of Importance of 6-Pyrrolidinylpyridinyl Substitution
  作者：Thuy Nguyen、Nadezhda German、Ann M. Decker、Tiffany L. Langston、Thomas F. Gamage、Charlotte E. Farquhar、Jun-Xu Li、Jenny L. Wiley、Brian F. Thomas、Yanan Zhang

  DOI：10.1021/acs.jmedchem.7b00707

  日期：2017.9.14

  Allosteric modulators of the cannabinoid CB1 receptor have recently been reported as an alternative approach to modulate the CB1 receptor for therapeutic benefits. In this study, we report the design and synthesis of a series of diarylureas derived from PSNCBAM-1 (2). Similar to 2, these diarylureas dose-dependently inhibited CP55,940-induced intracellular calcium mobilization and [35S]GTP-γ-S binding

  最近有报道称，大麻素CB1受体的变构调节剂是调节CB1受体的另一种治疗方法。在这项研究中，我们报告了一系列源自PSNCBAM-1（2）的二芳基脲的设计和合成。与2相似，这些二芳基脲剂量依赖性地抑制CP55,940诱导的细胞内钙动员和[ 35 S]GTP-γ-S结合，同时增强[ 3 H] CP55,940与CB1受体的结合。结构-活性关系研究表明2的吡啶基环可以被其他芳族环取代，而CB1变构调节不需要吡咯烷基环。34（RTICBM-74）在所有体外测定中的功效均与2相似，但对大鼠肝微粒体的代谢稳定性显着提高。更重要的是，在减轻大鼠熄灭的可卡因寻求行为的恢复方面，34比2更有效，证明了该二芳基脲系列有潜力成为可卡因成瘾复发治疗发展的有希望的候选者。

表征谱图