2-甲酰基苯基硼酸频哪醇酯 | 380151-85-9

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸酯
• 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-甲酰基苯基硼酸频哪醇酯
• 中文别名: 2-(4,4,5,5-四甲基-1,3,2-二杂氧戊硼烷-2-基)苯甲醛；2-甲酰苯硼酸频哪酯
• 英文名称: 2-(2'-formylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde；2-formylphenylboronic acid pinacol ester
• CAS: 380151-85-9
• 化学式: C₁₃H₁₇BO₃
• mdl: MFCD07363841
• 分子量: 232.087
• InChiKey: SLJMPQLPRHIAOM-UHFFFAOYSA-N

物化性质

• 沸点：
  345.9±25.0 °C(Predicted)
• 密度：
  1.0532 g/mL at 25 °C
• 闪点：
  110 °C
• 稳定性/保质期：

  避免与氧化物和空气接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2934999090
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  保存方法：密封于阴凉、通风干燥处。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Formylphenylboronic acid, pinacol ester
Synonyms: 2-Boronobenzaldehyde, pinacol ester

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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
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Formylphenylboronic acid, pinacol ester
CAS number: 380151-85-9

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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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C13H17BO3
Molecular weight: 232.1

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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.

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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-甲酰基苯基硼酸频哪醇酯 在 三甲基氯硅烷 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.0h， 生成 2-甲酰基苯硼酸
  参考文献：
  名称：

  通过 Pd 催化的 [4 + 2] 环化立体发散进入带有 1,3-不相邻立体中心的 [6.7]-稠合 N-杂环

  摘要：

  我们描述了乙烯基苯并恶嗪酮和七元环状N-磺酰醛亚胺的高效立体发散 [4 + 2] 环化反应，用于通过钯催化合成各种具有 1,3-不相邻立体中心的N-杂环。发现溶剂的极性在非对映选择性的转换中起着关键作用。此外，这些反应的良好对映选择性是通过使用市售的 Wingphos 作为手性配体实现的。

  DOI：

  10.1021/acs.orglett.3c00269
• 作为产物：
  描述：

  N-(苯基亚甲基)-环己胺 在 2,6-二甲基吡啶 、 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 2-甲酰基苯基硼酸频哪醇酯
  参考文献：
  名称：

  瞬态亚胺作为苯甲醛的无金属邻-C-H硼化反应的指导基团

  摘要：

  Organoboron试剂是重要的合成中间体，在合成有机化学中具有广泛的应用。当前使用的选择性硼化策略很大程度上依赖于过渡金属催化剂的使用。因此，非常需要确定更温和的无过渡金属硼化条件。我们在本文中提出了一种统一的策略，该方法使用一种简单的无金属方法，利用一个亚胺瞬态导向基团，对缺电子的苯甲醛衍生物进行选择性C–H硼化。该策略涵盖了广泛的反应，并且（i）即使是高度空间位阻的C–H键也可以顺利地被硼化，（ii）尽管存在其他潜在的导向基团，但该反应还是选择性地在o处发生。苯甲醛部分的-C–H键，以及（iii）附加到苯甲醛衍生物上的天然产物也可以产生适当的硼化产物。此外，该方案的有效性通过以下事实得以证实：即使在一系列外部杂质的存在下，反应也会进行。

  DOI：

  10.1021/jacs.0c13013

文献信息

• Room temperature Pd(0)/Ad3P-catalyzed coupling reactions of aryl chlorides with bis(pinacolato)diboron
  作者：Jie Dong、Hui Guo、Wei Peng、Qiao-Sheng Hu

  DOI：10.1016/j.tetlet.2019.01.042

  日期：2019.3

  Pd(0)/Ad3P-catalyzed cross-coupling reactions of aryl chlorides with bis(pinacolato)diboron are described. The Pd(0)/Ad3P catalyst, generated from Ad3P-coordinated acetanilide-based palladacycle complex, proved to be an efficient catalyst system for the Miyaura borylation reactions of a variety of aryl chlorides with bis(pinacolato)diboron. The mild reaction condition, the easy availability of the catalyst

  描述了室温下Pd（0）/ Ad 3 P催化的芳基氯化物与双（频哪醇）二硼的交叉偶联反应。由Ad 3 P配位的对乙酰苯胺基palladacycle配合物生成的Pd（0）/ Ad 3 P催化剂被证明是一种有效的催化剂体系，用于多种芳基氯化物与双（频哪醇）二硼烷的Miyaura硼酸酯化反应。温和的反应条件，容易获得的催化剂以及良好的偶联收率使得这些反应潜在地可用于有机合成中。
• Modifying aroylhydrazone prochelators for hydrolytic stability and improved cytoprotection against oxidative stress
  作者：Qin Wang、Katherine J. Franz

  DOI：10.1016/j.bmc.2018.11.004

  日期：2018.12

  BSIH ((E)-N′-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene)isonicotinohydrazide) is a prodrug version of the metal chelator SIH ((E)-N′-(2-hydroxybenzylidene)isonicotinohydrazide) in which a boronate group prevents metal chelation until reaction with hydrogen peroxide releases SIH, which is then available for sequestering iron(III) and inhibiting iron-catalyzed oxidative damage. While BSIH

  BSIH（（（E）-N '-（2-（4,4,5,5-tetramethyl-1,3,2-dioxaboroboro-2--2-yl）苄叉基）异烟肼）是金属螯合剂SIH（（E）-N'-（2-羟基亚苄基）异二十二酰肼）中的硼酸酯基团防止金属螯合，直到与过氧化氢反应释放出SIH，然后可用于螯合铁（III）和抑制铁催化的氧化损伤。虽然BSIH已显示出在氧化应激条件下有条件地靶向细胞螯合铁的前景，但由于BSIH以其水解产物异烟肼和2-甲酰基苯基硼酸作为平衡混合物存在于细胞培养基中的事实限制了SIH的产量。在当前的研究中，评估了几种BSIH类似物的水解稳定性，与H 2 O 2的反应结果以及螯合剂到螯合剂的转化效率。值得注意的是，对甲氧基衍生物（p-OMe）BSIH（（E）-N '-（5-甲氧基-2-（4,4,5,5-四甲基-1,3,2-二氧杂硼烷-2-基）亚苄基）异烟肼基）和间位- ，第-double取代的（MD）BSIH（（ë）
• Sterically Controlled Iodination of Arenes via Iridium-Catalyzed C–H Borylation
  作者：Benjamin M. Partridge、John F. Hartwig

  DOI：10.1021/ol303164h

  日期：2013.1.4

  to prepare aryl and heteroaryl iodides by sequential C–H borylation and iodination is reported. The regioselectivity of this process is controlled by steric effects on the C–H borylation step and is complementary to existing methods to form aryl iodides. The iodination of boronic esters has potential for the synthesis of radiolabeled aryl iodides, as demonstrated by the concise synthesis of a potential

  报道了一种通过连续的C–H硼化和碘化制备芳基和杂芳基碘化物的温和方法。该过程的区域选择性由C–H硼化步骤中的空间效应控制，是对现有形成芳基碘化物的方法的补充。硼酸酯的碘化具有放射性标记的芳基碘化物的合成潜力，正如SPECT成像的潜在示踪剂的简明合成所证明的那样。
• An improved procedure for the synthesis of arylboronates by palladium-catalyzed coupling reaction of aryl halides and bis(pinacolato)diboron in polyethylene glycol
  作者：Jie Lu、Zhong-Zhi Guan、Jian-Wu Gao、Zhan-Hui Zhang

  DOI：10.1002/aoc.1799

  日期：2011.7

  A new protocol has been developed for the synthesis of arylboronates by a coupling reaction of aryl halides and bis(pinacolato)diboron using bis(triphenylphosphine)palladium dichloride/sodium acetate/polyethylene glycol 600 [Pd(PPh3)2Cl2/NaOAc/PEG 600] as an efficient catalytic system. Copyright © 2011 John Wiley & Sons, Ltd.

  一种新的协议已经由芳基卤和的偶联反应为arylboronates合成开发双（频哪醇），使用二硼双（三苯基膦）二氯化钯/乙酸钠/聚乙二醇600的Pd（PPh 3）2氯2 /的NaOAc / PEG 600]作为有效的催化体系。版权所有©2011 John Wiley＆Sons，Ltd.
• Remarkably Efficient Iridium Catalysts for Directed C(sp²)–H and C(sp³)–H Borylation of Diverse Classes of Substrates
  作者：Md Emdadul Hoque、Mirja Md Mahamudul Hassan、Buddhadeb Chattopadhyay

  DOI：10.1021/jacs.0c13415

  日期：2021.4.7

  aliphatic substrates for selective C(sp3)–H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C–H bonds. A number of late-stage C–H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)–H and C(sp3)–H borylations enabling the method more general

  在这里，我们描述了一类新的 C-H 硼化催化剂的发现及其在芳族、杂芳族和脂肪族系统的区域选择性 C-H 硼化中的应用。新催化剂具有 Ir-C(噻吩基) 或 Ir-C(呋喃基) 阴离子配体，而不是标准 C-H 硼化条件中使用的二胺型中性螯合配体。据报道，这些新发现的催化剂的使用对不同种类的芳烃底物显示出优异的反应性和邻位选择性，并具有高分离产率。此外，该催化剂被证明对大量脂肪族底物的选择性 C(sp 3)–H 键硼化。杂环分子利用 C-H 键固有的高反应性选择性地硼化。已经使用相同的催化剂描述了许多后期 C-H 功能化。此外，我们表明其中一种催化剂甚至可以在露天用于 C(sp 2 )-H 和 C(sp 3 )-H 硼酸化，从而使该方法更加通用。初步的机理研究表明，活性催化中间体是 Ir(bis)boryl 络合物，连接的配体作为双齿配体。总的来说，这项研究强调了新型 C-H 硼酸化催化剂的发现，这些催化剂应该在