4-异丙氧基甲酰苯基硼酸 | 342002-82-8

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 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-异丙氧基甲酰苯基硼酸
• 中文别名: 4-(异丙氧基羰基)苯硼酸；对-(异丙氧基羰基)苯硼酸
• 英文名称: 4-(isopropoxycarbonyl)phenylboronic acid
• 英文别名: 4-Isopropoxycarbonylphenylboronic acid；(4-propan-2-yloxycarbonylphenyl)boronic acid
• CAS: 342002-82-8
• 化学式: C₁₀H₁₃BO₄
• mdl: MFCD02259385
• 分子量: 208.022
• InChiKey: NIQHFKWRHJZMQU-UHFFFAOYSA-N

物化性质

• 熔点：
  111 °C
• 沸点：
  359.0±44.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  避酸、氧化物以及不相容的材料

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

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：
  2931900090
• 危险性防范说明：
  P233,P260,P261,P264,P270,P271,P280,P301+P312,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P330,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

SDS

Name:	4-Isopropoxycarbonylphenylboronic acid Material Safety Data Sheet
Synonym:	None Known
CAS:	342002-82-8

Section 1 - Chemical Product MSDS Name:4-Isopropoxycarbonylphenylboronic acid Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
342002-82-8	4-Isopropoxycarbonylphenylboronic acid	ca. 100	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 tightly closed container. Store in a dry area. Keep refrigerated. (Store below 4C/39F.)

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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# 342002-82-8: 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 to off-white
Odor: odorless
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 111 deg C(decom)
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: C10H13BO4
Molecular Weight: 280.02

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, boron oxides.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 342002-82-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Isopropoxycarbonylphenylboronic 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# 342002-82-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 342002-82-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 342002-82-8 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

反应信息

• 作为反应物：
  描述：

  4-异丙氧基甲酰苯基硼酸 在 异吲哚啉 、 十二羰基三钌 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙醚 为溶剂， 反应 86.0h， 生成 isopropyl 6'-(pyridin-2-yl)-2',3',4',5'-tetrahydro-[1,1'-biphenyl]-4-carboxylate
  参考文献：
  名称：

  通过裂解原位生成的烯胺的烯基 C-N 键，钌催化酮类作为烯基亲电子试剂与有机硼的交叉偶联

  摘要：

  开发了一种钌催化的酮与有机硼酸酯的交叉偶联反应。在该反应中，具有吡啶导向基团的酮在吡咯烷和钌催化剂存在下直接充当烯基亲电试剂，与有机硼酸酯偶联。该反应通过用吡咯烷、苄胺或异吲哚啉催化裂解由酮原位生成的烯胺中的烯基碳氮键进行。

  DOI：

  10.1021/acs.orglett.2c03765

文献信息

• Fourfold Suzuki-Miyaura and Sonogashira Cross-Coupling Reactions on Tetrahedral Methane and Adamantane Derivatives
  作者：Christine I. Schilling、Oliver Plietzsch、Martin Nieger、Thierry Muller、Stefan Bräse

  DOI：10.1002/ejoc.201001567

  日期：2011.3

  An efficient way to generate a series of rigid tetrahedral organic building units from common methane and adamantane precursors is presented. Suzuki-Miyaura and Sonogashira cross-coupling reactions are used to effectively generate these shape-persistent molecular tectons. Especially the Sonogashira reactions employing the readily available tetrahedral alkynes and commercial iodides and bromides are

  提出了一种从常见的甲烷和金刚烷前体生成一系列刚性四面体有机建筑单元的有效方法。Suzuki-Miyaura 和 Sonogashira 交叉偶联反应用于有效地生成这些形状持久的分子构造。特别是使用容易获得的四面体炔烃和商业碘化物和溴化物的 Sonogashira 反应非常有效。
• <i>N</i>-Methylphenothiazine <i>S</i>-Oxide Enabled Oxidative C(sp²)–C(sp²) Coupling of Boronic Acids with Organolithiums via Phenothiaziniums
  作者：Tatsuki Yoshida、Yuki Honda、Tatsuya Morofuji、Naokazu Kano

  DOI：10.1021/acs.orglett.1c03986

  日期：2021.12.17

  we report the development of a transition-metal-free oxidative C(sp2)–C(sp2) coupling of readily available boronic acids and organolithiums via phenothiazinium ions. Various biaryl, styrene, and diene derivatives were obtained using this reaction system. The key to this process is N-methylphenothiazine S-oxide (PTZSO), which allows efficient conversion of boronic acids to phenothiazinium ions. The mechanism

  在此，我们报告了通过吩噻嗪离子将易得的硼酸和有机锂进行无过渡金属氧化 C(sp 2 )–C(sp 2 ) 偶联的发展。使用该反应体系获得了各种联芳基、苯乙烯和二烯衍生物。该过程的关键是N-甲基吩噻嗪S-氧化物 (PTZSO)，它可以有效地将硼酸转化为吩噻嗪离子。使用理论计算和实验研究了使用 PTZSO 形成吩噻嗪的机制，从而深入了解 PTZSO 的独特反应性。
• Diverse Multi-Functionalized Oligoarenes and Heteroarenes for Porous Crystalline Materials
  作者：Sylvain Grosjean、Zahid Hassan、Christof Wöll、Stefan Bräse

  DOI：10.1002/ejoc.201801232

  日期：2019.2.21

  an advantageous dual‐utility. First, these compounds can serve as useful molecular bricks (ditopic organic linkers) in the construction of complex porous crystalline materials. Second, after the assembly into the crystalline coordination networks, orthogonal functional sites within the linker‐backbone offer tremendous potential from application perspectives as they can be modified by a wide range of

  描述了通过逐步钯催化硼酸化/Suzuki-Miyaura 交叉偶联反应模块化合成多功能联苯、三联苯和更高级的线性低聚苯二甲酸和吡啶封端的低聚芳烃。几个不同的官能团如叠氮化物、羟基和炔烃，以及在战略位置结合在单个低聚芳烃分子单元中的配位官能端基团（羧酸或吡啶）的存在提供了有利的双重用途。首先，这些化合物可以在复杂多孔晶体材料的构建中用作有用的分子砖（双位有机连接体）。其次，组装成晶体配位网络后，连接子骨架内的正交功能位点从应用角度提供了巨大的潜力，因为它们可以通过广泛的合成后修饰进行修饰，包括叠氮化物-炔烃点击化学。这允许进一步定制超分子组件以产生新型多功能材料。
• Palladium-Catalyzed One-Pot Reaction of Hydrazones, Dihaloarenes, and Organoboron Reagents: Synthesis and Cytotoxic Activity of 1,1-Diarylethylene Derivatives
  作者：Maxime Roche、Salim Mmadi. Salim、Jérôme Bignon、Hélène Levaique、Jean-Daniel Brion、Mouad Alami、Abdallah Hamze

  DOI：10.1021/acs.joc.5b00880

  日期：2015.7.2

  products in high yields, offers an expansive substrate scope, and can address a broad range of aryl, styrene, vinyl, and heterocyclic olefinic targets. The scope of this one-pot coupling has been also extended to the synthesis of the 1,1-diarylethylene skeleton of the natural product ratanhine. The new compounds were evaluated for their cytotoxic activity, and this allowed the identification of compound

  开发了N-甲苯磺酰基,、二卤代芳烃和硼酸或硼酸酯之间的新的三组分组装反应，以高收率生产了高度取代的1,1-二芳基乙烯。通过这种偶联形成的两个C–C键已被单一的Pd催化剂以一锅法进行了催化。应当指出，一锅法频哪醇硼酸酯的交叉偶联反应通常以高收率提供产物，提供了扩大的底物范围，并且可以解决广泛范围的芳基，苯乙烯，乙烯基和杂环烯烃目标。这种一锅耦合的范围也已扩展到天然产物藤黄的1,1-二芳基乙烯骨架的合成。对新化合物的细胞毒性活性进行了评估，从而可以鉴定化合物在纳摩尔浓度范围内对HCT116癌细胞系表现出优异的抗增殖活性的4ab。
• Discovery of a novel highly potent broad-spectrum heterocyclic chemical series of arenavirus cell entry inhibitors
  作者：Michael B. Plewe、Vidyasagar Reddy Gantla、Nadezda V. Sokolova、Young-Jun Shin、Shibani Naik、Eric R. Brown、Alexandra Fetsko、Lihong Zhang、Birte Kalveram、Alexander N. Freiberg、Greg Henkel、Ken McCormack

  DOI：10.1016/j.bmcl.2021.127983

  日期：2021.6

  stability in human and most nonhuman liver microsomes as well as a lack of hERG K + channel or CYP enzyme inhibition. Moreover, the straightforward synthesis of several lead compounds (e.g., the simple high yield 3-step synthesis of imidazo[1,2-a]pyridine 37) could provide a cost-effective broad-spectrum arenavirus therapeutic that may help to minimize the cost-prohibitive burdens associated with treatments

  我们确定并探索了一种新型杂环化学系列的沙粒病毒细胞进入抑制剂的构效关系 (SAR)。优化的先导化合物，包括二苯基取代的咪唑并 [1,2-a] 吡啶、苯并咪唑和苯并三唑，对假型和传染性旧世界和新世界沙粒病毒均表现出低至亚纳摩尔的效力，在人类和大多数非人类肝微粒体中具有良好的代谢稳定性以及缺乏 hERG K + 通道或 CYP 酶抑制。此外，几种先导化合物的直接合成（例如咪唑的简单高产率三步合成[1,