2-甲酰基苯基硼酸, 新戊二醇酯 | 95752-86-6

• 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, 新戊二醇酯
• 中文别名: 2-甲酰基苯基硼酸,新戊二醇酯；2-醛基苯硼酸新戊二醇酯；2,2-二甲基丙二醇-2-甲酰基苯硼酸-1,3-新戊二醇酯
• 英文名称: 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzaldehyde
• 英文别名: 2-(2-formylphenyl)-5,5-dimethyl-1,3,2-dioxaborinane；5,5-dimethyl-2-(2-formylphenyl)-1,3,2-dioxaborinane
• CAS: 95752-86-6
• 化学式: C₁₂H₁₅BO₃
• mdl: MFCD04039025
• 分子量: 218.06
• InChiKey: BJRXNDLMZZAOAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 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
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-Formylphenylboronic acid, neopentyl glycol ester
Product Name:
Synonyms: 2-Boronobenzaldehyde, neopentyl glycol 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
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.
2-Formylphenylboronic acid, neopentyl glycol ester
Ingredient name:
CAS number: 95752-86-6

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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, 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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C12H15BO3
Molecular weight: 218.1

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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, 新戊二醇酯 在 葡萄糖 、 水 、 glucose oxidase 作用下， 以 二甲基亚砜 、 硝基苯 、 乙腈 为溶剂， 反应 25.0h， 生成 2-(2-hydroxyphenyl)-1H-anthra[1,2-d]imidazole-6,11-dione
  参考文献：
  名称：

  通过GOx酶促反应基于硼蒽醌衍生物的高特异性葡萄糖荧光传感

  摘要：

  硼酸蒽醌o HAQB和p HAQB已被设计，并被证明可作为葡萄糖的荧光生物传感器。感官分子，ö HAQB，表现出了通过的GOx酶反应的特定葡萄糖感测。在这种贡献，的荧光变化ø HAQB合理对应于在硼酸的至羟基基于传感器的转化葡萄糖的由H浓度2 ö 2从葡萄糖与葡萄糖氧化酶的酶反应而产生。然后，我们的传感系统已成功应用于确定0.08–0.42 mM范围内的葡萄糖浓度。的检测限（LOD）o使用GOx酶探针进行葡萄糖检测的HAQB约为0.011 mM。

  DOI：

  10.1016/j.tet.2012.08.037
• 作为产物：
  描述：

  N-二甲氨基苄叔丁胺 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 4.0h， 生成 2-甲酰基苯基硼酸, 新戊二醇酯
  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

• An efficient synthesis of sterically hindered arylboronic acids
  作者：Hao Fang、Gurpreet Kaur、Jun Yan、Binghe Wang

  DOI：10.1016/j.tetlet.2005.01.064

  日期：2005.3

  variety of applications. In our research, we have found that the synthesis of ortho-substituted arylboronic acids is problematic with the commonly used bis(pinacolato)diboron in palladium-mediated borylation reactions. As a substitute, we have found that bis(neopentyl glycolato)diboron is a much more efficient borylation agent for the synthesis of sterically hindered ortho-substituted arylboronic acids.

  硼酸是广泛应用中的重要中间体和分子识别部分。在我们的研究中，我们发现邻位取代的芳基硼酸的合成对于钯介导的硼化反应中常用的双（频哪醇）二硼是有问题的。作为替代品，我们发现双（新戊基乙二醇基）二硼是用于合成位阻邻位取代的芳基硼酸的更有效的硼化剂。
• End-to-end conformational communication through a synthetic purinergic receptor by ligand-induced helicity switching
  作者：Robert A. Brown、Vincent Diemer、Simon J. Webb、Jonathan Clayden

  DOI：10.1038/nchem.1747

  日期：2013.10

  The long-range communication of information, exemplified by signal transduction through membrane-bound receptors, is a central biochemical function. Reversible binding of a messenger ligand induces a local conformational change that is relayed through the receptor, inducing a chemical effect typically several nanometres from the binding site. We report a synthetic receptor mimic that transmits structural information from a boron-based ligand binding site to a spectroscopic reporter located more than 2 nm away. Reversible binding of a diol ligand to the N-terminal binding site induces a screw-sense preference in a helical oligo(aminoisobutyric acid) foldamer, which is relayed to a reporter group at the remote C-terminus, communicating information about the structure and stereochemistry of the ligand. The reversible nature of boronate esterification was exploited to switch the receptor sequentially between left- and right-handed helices, while the exquisite conformational sensitivity of the helical relay allowed the reporter to differentiate even between purine and pyrimidine nucleosides as ligands. Biological receptors communicate information through ligand-induced conformational changes. A synthetic receptor with a boron-containing binding site that can selectively and reversibly complex a ligand (such as a purine nucleoside) is shown to function in a similar fashion. The resulting conformational change is relayed through the receptor, communicating structural information about the ligand to a spectroscopic reporter more than 2 nm away.

  以通过膜结合受体的信号转导为例的长距离信息通信是一项重要的生化功能。信使配体的可逆结合引起局部构象变化，该变化通过受体传递，通常在距结合位点几纳米的地方引起化学效应。我们报道了一种合成受体模拟物，它将结构信息从基于硼的配体结合位点传输到位于 2 nm 以上的光谱报告基因。二醇配体与 N 端结合位点的可逆结合会在螺旋寡聚（氨基异丁酸）折叠体中诱导螺旋感应偏好，该折叠体被传递到远程 C 端的报告基团，传达有关结构和立体化学的信息配体的。利用硼酸酯化的可逆性质，将受体在左手螺旋和右手螺旋之间顺序切换，而螺旋中继的精致构象敏感性使报告者甚至能够区分作为配体的嘌呤和嘧啶核苷。 生物受体通过配体诱导的构象变化来传递信息。具有含硼结合位点的合成受体可以选择性地、可逆地与配体（例如嘌呤核苷）复合，以类似的方式发挥作用。由此产生的构象变化通过受体传递，将配体的结构信息传递给 2 nm 以外的光谱报告分子。
• Suzuki Cross-Coupling Reaction of Sterically Hindered Aryl Boronates with 3-Iodo-4-methoxybenzoic Acid Methylester
  作者：H. Chaumeil、S. Signorella、C. Le Drian

  DOI：10.1016/s0040-4020(00)00928-5

  日期：2000.12

  The cross-coupling reaction of 3-iodo-4-methoxybenzoic acid methylester with sterically hindered arylboronic esters and especially 5,5-dimethyl-2-mesityl-1,3,2-dioxaborinane, is reported. The optimisation of the process in order to obtain biaryls in good yield by using anhydrous benzene at reflux and sodium phenoxide in the presence of 0.06 equiv. of Pd(PPh3)(4) is described. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Rhodium-Catalyzed Addition–Spirocyclization of Arylboronic Esters Containing β-Aryl α,β-Unsaturated Ester Moiety
  作者：Takanori Matsuda、Satoshi Yasuoka、Shoichi Watanuki、Keisuke Fukuhara

  DOI：10.1055/s-0034-1378691

  日期：——

  In this study, we developed a rhodium(I)-catalyzed spirocyclization. The reaction includes 1,4-rhodium migration and provides a route for forming spirocyclic 1-indanones.
• Lauer, Manfred; Boehnke, Helmut; Grotstollen, Reiner, Chemische Berichte, 1985, vol. 118, # 1, p. 246 - 260
  作者：Lauer, Manfred、Boehnke, Helmut、Grotstollen, Reiner、Salehnia, Mohammad、Wulff, Guenter

  DOI：——

  日期：——