3-氟-2-甲酰基苯硼酸 | 871126-15-7

• 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: 3-氟-2-甲酰基苯硼酸
• 中文别名: 3-氟-2-甲酰基苯基硼酸(含有数量不等的酸酐)；(3-氟-2-甲酰基苯基)硼酸；3-氟-2-甲酰基苯基硼酸
• 英文名称: (3-fluoro-2-formylphenyl)boronic acid
• CAS: 871126-15-7
• 化学式: C₇H₆BFO₃
• mdl: MFCD10697421
• 分子量: 167.932
• InChiKey: GVHWLCYABLWGIR-UHFFFAOYSA-N

物化性质

• 熔点：
  123-127℃
• 沸点：
  357.4±52.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  12
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  8
• 危险类别码：
  R34
• 危险品运输编号：
  UN 3261 8/PG 2
• 海关编码：
  2931900090
• 安全说明：
  S26,S36/37/39,S45
• WGK Germany：
  3
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H317,H319
• 储存条件：
  存放在惰性气体中，并且避免与空气接触，温度范围为0至10℃。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
(3-Fluoro-2-formylphenyl)boronic acid
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H314: Causes severe skin burns and eye damage
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P310: Immediately call a POISON CENTER or doctor/physician

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Section 3. Composition/information on ingredients.
Ingredient name: (3-Fluoro-2-formylphenyl)boronic acid
CAS number: 871126-15-7

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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
This product should be handled only by, or under the close supervision of, those properly qualified
Handling:
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: C7H6BFO3
Molecular weight: 167.9

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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, hydrogen fluoride.

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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
UN Number: UN3261 Class: 8 Packing group: II
Proper shipping name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S. ((3-Fluoro-2-formylphenyl)boronic acid)

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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

(3-氟-2-甲酰基苯基)硼酸是一种生物化学试剂，可用于生物材料或有机化合物的研究，在生命科学领域具有重要作用。

反应信息

• 作为反应物：
  描述：

  3-氟-2-甲酰基苯硼酸 在 potassium phosphate 、 四(三苯基膦)钯 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.67h， 生成 2-(6-fluoro-5H-imidazo[5,1-a]isoindol-5-yl)-1-(1,4-dioxaspiro[4.5]decan-8-yl)ethanone
  参考文献：
  名称：

  Discovery of Clinical Candidate (1R,4r)-4-((R)-2-((S)-6-Fluoro-5H-imidazo[5,1-a]isoindol-5-yl)-1-hydroxyethyl)cyclohexan-1-ol (Navoximod), a Potent and Selective Inhibitor of Indoleamine 2,3-Dioxygenase 1

  摘要：

  A novel class of 5-substituted 5H-imidazo[5,1-a]isoindoles are described as potent inhibitors of indoleamine 2,3-dioxygenase 1 (IDO1). A structure-based drug design approach was used to elaborate the 5H-imidazo[5,1-a]isoindole core and to improve potency and pharmacological properties. Suitably placed hydrophobic and polar functional groups in the lead molecule allowed improvement of IDO1 inhibitory activity while minimizing off-target liabilities. Structure-activity relationship studies focused on optimizing IDO1 inhibition potency and a pharmacokinetic profile amenable to oral dosing while controlling CYP450 and hERG inhibitory properties.

  DOI：

  10.1021/acs.jmedchem.9b00662
• 作为产物：
  描述：

  2-溴-6-氟苯甲醛 在 正丁基锂 、 硫酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 2.5h， 生成 3-氟-2-甲酰基苯硼酸
  参考文献：
  名称：

  通过1H和19F NMR光谱法测定亚磺酰胺的对映体纯度的三组分衍生化方案。

  摘要：

  已经开发了一种实用的简单的三组分手性衍生方案，通过1H和19F NMR光谱分析确定八种S-手性亚磺酰胺的对映体纯度，基于它们用2-甲酰基苯基硼酸模板和对映体纯的pin二醇处理得到的非对映异构体混合物其非对映异构体比率准确反映了母体亚磺酰胺的对映体纯度的磺胺基氨基硼酸酯。

  DOI：

  10.1021/acs.joc.9b02473

文献信息

• Synthesis, Characterisation, and Antifungal Activities of Novel Benzodiazaborines
  作者：Jiyoung Yang、Brandon J. Johnson、Allan A. Letourneau、Christopher M. Vogels、Andreas Decken、Felix J. Baerlocher、Stephen A. Westcott

  DOI：10.1071/ch14534

  日期：——

  Eight new fluoro- and methoxy-substituted benzodiazaborines have been prepared by a simple condensation reaction in high-to-excellent yields. All new compounds have been characterised by several physical methods, including X-ray diffraction studies on three examples. All new compounds were examined for antifungal activities against five species of potentially pathogenic fungi (Aspergillus niger, Aspergillus fumigatus, Rhizoctonia solani, Verticillium albo-atrum, and Verticillium dahliae). While substitution of the aromatic group derived from the 2-formylphenylboronic acid group had an effect on bioactivities, substitution on the parent thioamide C(=S)NH2 group of the starting thiosemicarbazide greatly reduced activities.

  通过简单的缩合反应，我们制备出了八种新的氟代和甲氧基代苯并二氮硼烷，而且产量极高。所有新化合物都通过多种物理方法进行了表征，包括对三个实例进行了 X 射线衍射研究。所有新化合物都对五种潜在致病真菌（黑曲霉、烟曲霉、根瘤菌、轮枝菌和大丽花轮枝菌）进行了抗真菌活性检测。虽然 2-甲酰基苯硼酸基团衍生的芳香基团的取代对生物活性有影响，但起始硫代氨基甲酰肼的母硫酰胺 C(=S)NH2 基团的取代却大大降低了活性。
• An intramolecular <i>ortho</i>-assisted activation of the silicon–hydrogen bond in arylsilanes: an experimental and theoretical study
  作者：Krzysztof Durka、Mateusz Urban、Maja Czub、Marek Dąbrowski、Patryk Tomaszewski、Sergiusz Luliński

  DOI：10.1039/c7dt04858k

  日期：——

  in arylsilanes by selected ortho-assisting functional groups based on boron, carbon and phosphorus was investigated experimentally and by means of theoretical calculations. The major conclusion drawn is that the presence of a negatively charged oxygen atom in the functional group is essential for providing effective chelation to the silicon atom which in turn results in the increased hydridic character

  通过基于理论的计算和实验研究了基于硼，碳和磷的邻位辅助官能团对芳基硅烷中Si-H键的分子内活化作用。得出的主要结论是，在官能团中存在带负电荷的氧原子对于提供与硅原子的有效螯合至关重要，而螯合反过来又导致所得的五配位物质的氢化特性提高。相反，在芳基二甲基硅烷中，氢氧根对硅原子的分子间侵蚀导致硅芳基键的活化。分子内配位的芳基硅烷中Si–H键反应性的提高可归因于显着的反式以首选配置运行的效果。Si–H键的水解裂解会导致二氢消除，并形成各种硅杂环系统，例如苯并硅氧烷基硼酸酯，螺双（硅氧烷）硼酸酯，苯并硅酸内酯和苯并氧杂唑。另外，观察到苯甲醛被邻硼化的芳基硅烷分子间还原，而带有其他可还原官能团（COMe，COOEt，CN和NO 2）的化合物在可比较的条件下是惰性的。具体地，邻位CN基团的分子内还原观察到甲硅烷基化的苄腈衍生物。通过DFT理论计算研究了Si–H键活化的机理。计算表明，硅原子的分子内配位
• SOMATOSTATIN MODULATORS AND USES THEREOF
  申请人：Crinetics Pharmaceuticals, Inc.

  公开号：US20180016252A1

  公开（公告）日：2018-01-18

  Described herein are compounds that are somatostatin modulators, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders that would benefit from modulation of somatostatin activity.

  本文描述了一些肽类调节剂化合物，制备这类化合物的方法，包含这类化合物的药物组合物和药物，以及利用这类化合物治疗需要调节生长抑素活性的疾病、症状或疾病的方法。
• A tautomeric equilibrium between functionalized 2-formylphenylboronic acids and corresponding 1,3-dihydro-1,3-dihydroxybenzo[c][2,1]oxaboroles
  作者：Sergiusz Luliński、Izabela Madura、Janusz Serwatowski、Halina Szatyłowicz、Janusz Zachara

  DOI：10.1039/b611195e

  日期：——

  Functionalized 2-formylphenylboronic acids undergo an unprecedented tautomeric rearrangement in solution to form corresponding 1,3-dihydro-1,3-dihydroxybenzo[c][2,1]oxaboroles. X-Ray analyses of selected examples revealed diverse solid-state molecular structures from a planar open form with a hydrogen-bonded carbonyl group (X = 3-F) through a twisted conformer showing a weak carbonyl–boron interaction

  功能化的2-甲酰基苯基硼酸在溶液中经历前所未有的互变异构重排，以形成相应的1,3-二氢-1,3-二羟基苯并[ c ] [2,1]氧杂硼酸。对选定示例的X射线分析显示，固态分子结构从带有氢键合羰基的平面开放形式（X = 3-F）到扭曲的构象异构体，表现出弱的羰基-硼相互作用（X = 3,5）。 -Br 2）生成环状氧杂硼酸酯衍生物（X = 3-Br）。可变温度1 H NMR光谱用于确定平衡常数以及焓和熵互变异构 在混合溶剂中 [D 6 ]丙酮–d 2 ö（95：5）。还已经通过DFT（B3LYP）和MP2方法对这一过程进行了计算。
• Nickel-catalyzed, ligand-free, diastereoselective synthesis of 3-methyleneindan-1-ols
  作者：Heena Panchal、Christopher Clarke、Charles Bell、Somnath Narayan Karad、William Lewis、Hon Wai Lam

  DOI：10.1039/c8cc06388e

  日期：——

  Nickel-catalyzed, highly diastereoselective annulations between activated allenes and 2-acetylarylboronic acid or 2-formylarylboronic acids are reported. No ligand for nickel is required, and the reactions proceed efficiently at room temperature to give a broad range of substituted 3-methyleneindan-1-ols. Preliminary results of an enantioselective variant are also described.

  据报道，活化的烯与2-乙酰基芳基硼酸或2-甲酰基芳基硼酸之间存在镍催化的高度非对映选择性环。不需要镍的配体，并且反应在室温下有效地进行，从而得到广泛范围的取代的3-亚甲基茚满-1-醇。还描述了对映选择性变体的初步结果。