3,5-二氟苯硼酸 | 156545-07-2

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟苯硼酸系列
• 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: 3,5-二氟苯硼酸
• 中文别名: 3,5-二氟苯基硼酸；3,5-二氟代苯硼酸
• 英文名称: 3,5-difluorophenylboronic acid
• 英文别名: 3,5-difluorobenzeneboronic acid；3,5‐difluorophenylboronic acid；dihydroxy(3,5-difluorophenyl)borane；(3,5-difluorophenyl)boronic acid
• CAS: 156545-07-2
• 化学式: C₆H₅BF₂O₂
• mdl: MFCD01318138
• 分子量: 157.912
• InChiKey: QWQBQRYFWNIDOC-UHFFFAOYSA-N

物化性质

• 熔点：
  210-217 °C (lit.)
• 沸点：
  266.9±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)
• pKa：
  6.46±0.10 (Predicted,Most Acidic Temp: 25 °C)
• 稳定性/保质期：
  **避氧化物**

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  11
• 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：
  40.5
• 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,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2931900090
• 危险品运输编号：
  NONH for all modes of transport
• 危险类别：
  IRRITANT
• 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

Name:	3 5-Difluorophenylboronic Acid Material Safety Data Sheet
Synonym:	Not Known
CAS:	156545-07-2

Section 1 - Chemical Product MSDS Name:3 5-Difluorophenylboronic Acid Material Safety Data Sheet
Synonym:Not Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
156545-07-2	3,5-Difluorophenylboronic 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.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
Causes respiratory tract irritation. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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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# 156545-07-2: 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: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: > 300 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:
Specific Gravity/Density:
Molecular Formula: C6H5BF2O2
Molecular Weight: 157.8406

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, hydrogen fluoride gas, boron oxides.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 156545-07-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3,5-Difluorophenylboronic 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
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# 156545-07-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 156545-07-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 156545-07-2 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

制备方法与用途

应用

3,5-二氟苯硼酸是一种黄色固体，属于含氟苯硼酸。这类化合物在空气中较为稳定，不易受潮气影响，便于长期保存，并且具有较高的反应活性，常作为有机合成、医药和化工领域的中间体。它与卤代芳烃进行Suzuki偶联反应时表现出良好的位置选择性和立体选择性，多种化学官能团在此过程中不会发生变化，条件温和，产率高，是形成碳-碳键的重要方法。

制备

在5升三口瓶中加入62克（2.6摩尔）的镁屑，以及750毫升四氢呋喃。安装带有干燥管的球形冷凝管和滴液漏斗后，分批滴加482.5克（2.5摩尔）3,5-二氟溴苯和1500毫升四氢呋喃以确认反应开始。待混合物加热回流半小时后，通入氮气保持正压，并在低温浴槽中冷却至约-50℃。随后缓慢滴加850克（3.7摩尔）的硼酸三异丁酯溶解于500毫升四氢呋喃中的溶液，确保反应液温度低于-50℃，并在约1.5小时内完成滴加。滴加完成后，在低温浴槽中搅拌5分钟，然后室温下继续搅拌过夜。次日加入500毫升浓盐酸和1000毫升水进行水解处理，并搅拌1小时后，再用2升乙酸乙酯萃取并分液，使用饱和食盐水洗涤至中性。在水浴条件下减压蒸除溶剂，并冷却至室温后，通过吸滤收集产物，即得3,5-二氟苯硼酸。产品收率为296克（理论值的75%），熔点为210℃。

反应信息

• 作为反应物：
  描述：

  3,5-二氟苯硼酸 在 potassium phosphate 、 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 氢气 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 110.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 恩曲替尼
  参考文献：
  名称：

  一种恩曲替尼的制备方法

  摘要：

  本发明提供了恩曲替尼的制备方法。本发明的路线反应步数少，提高了反应的总收率；并且路线成熟，反应条件温和，不需要进行极低温反应，后处理简便，有利于大量合成目标产物，纯度可达99.5％以上，且有利于实现该产品的工业化生产。

  公开号：

  CN113024522B
• 作为产物：
  描述：

  1-溴-3,5-二氟苯 在 magnesium 、 硼酸三甲酯 、 盐酸 作用下， 以 乙醚 为溶剂， 生成 3,5-二氟苯硼酸
  参考文献：
  名称：

  (Fluoroorgano)fluoroboranes and -fluoroborates I: synthesis and spectroscopic characterization of potassium fluoroaryltrifluoroborates and fluoroaryldifluoroboranes

  摘要：

  A convenient preparation of K[ArBF3] (Ar= 2-C6H4F, 3-C6H4F, 4-C6H4F, 2,6-C6H3F2, 3,5-C6H3F2, 2,4,6-C6H2F3, 3,4,5-C6H2F3, 2,3,4,5-C6HF4 and C6F5) is offered and the IR and multinuclear NMR spectra of these salts are reported. Treatment of the trifluoroborate salts with BF3 in chlorocarbon solvents provides an easy synthetic route to the corresponding aryldifluoroboranes ArBF2. The multinuclear NMR spectra of ArBF2 are presented. The electron substituent effect of the [-BF3](-)-group shows this substituent as one of the strongest sigma-electron donors, while its pi-electron influence is negligible (sigma(I) = - 0.32, sigma(R) = - 0.07). (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(99)00690-7
• 作为试剂：
  描述：

  苯基环丙基甲酮 在 盐酸羟胺 、 sodium acetate 、 3,5-二氟苯硼酸 作用下， 以 乙醇 、 水 、 1,2-二氯乙烷 为溶剂， 反应 18.0h， 生成 N-(1-cyclopropyl-1-phenylbut-3-en-1-yl)hydroxylamine
  参考文献：
  名称：

  Arylboronic Acid-Catalyzed C-Allylation of Unprotected Oximes: Total Synthesis of N-Me-Euphococcine

  摘要：

  O-Unprotected keto- and aldoximes are readily C-allylated with allyl diisopropyl boronate in the presence of arylboronic acid catalysts to yield highly substituted N-alpha-secondary and tertiary homoallylic hydroxylamines. The method was used in the total synthesis of the trace alkaloid N-Me-Euphococcine.

  DOI：

  10.1021/acs.orglett.0c00727

文献信息

• [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。
• 重合性化合物及び光学異方体
  申请人：ＤＩＣ株式会社

  公开号：JP2015110532A

  公开（公告）日：2015-06-18

  【課題】 本発明が解決しようとする課題は、大きな屈折率異方性と、重合性液晶組成物に添加した際に結晶の析出等が起こらず高い保存安定性を有する重合性化合物を提供し、当該重合性化合物を含有する重合性液晶組成物を重合して得られるレンズ状の重合物を作製した際に変色が発生しにくい重合性液晶組成物を提供することである。更に、当該重合性液晶組成物を重合させることで得られる重合体及び当該重合体を用いた光学異方体を提供することである。【解決手段】 本願発明は一般式（Ｉ）【化１】で表される化合物を提供し、併せて当該化合物を含有する重合性組成物、重合性液晶組成物、当該重合性液晶組成物を重合させることにより得られる重合体及び当該重合体を用いた光学異方体を提供する。【選択図】 図１

  本发明旨在解决的问题是提供具有高折射率各向异性和添加到重合液晶组成物中时不会发生晶体析出等现象且具有高保存稳定性的重合性化合物，以及提供制备镜状重合物时不容易发生变色的重合性液晶组成物。此外，本发明还涉及通过重合所述重合性液晶组成物获得的重合体以及使用所述重合体制备的光学各向异性体。本申请发明提供了由通式（I）所表示的化合物，以及包含该化合物的重合性组成物、重合性液晶组成物、通过重合所述重合性液晶组成物获得的重合体以及使用所述重合体制备的光学各向异性体。
• Substrate Activity Screening:  A Fragment-Based Method for the Rapid Identification of Nonpeptidic Protease Inhibitors
  作者：Warren J. L. Wood、Andrew W. Patterson、Hiroyuki Tsuruoka、Rishi K. Jain、Jonathan A. Ellman

  DOI：10.1021/ja0547230

  日期：2005.11.1

  A new fragment-based method for the rapid development of novel and distinct classes of nonpeptidic protease inhibitors, Substrate Activity Screening (SAS), is described. This method consists of three steps: (1) a library of N-acyl aminocoumarins with diverse, low molecular weight N-acyl groups is screened to identify protease substrates using a simple fluorescence-based assay, (2) the identified N-acyl

  描述了一种新的基于片段的方法，用于快速开发新型和不同类别的非肽蛋白酶抑制剂，即底物活性筛选 (SAS)。该方法由三个步骤组成：(1) 筛选具有多种低分子量 N-酰基的 N-酰基氨基香豆素库，以使用简单的基于荧光的测定来鉴定蛋白酶底物，(2) 已鉴定的 N-酰基氨基香豆素底物通过快速类似物合成和评估进行优化，并且 (3) 优化的底物通过用已知机制的药效团直接替换氨基香豆素而转化为抑制剂。SAS 方法已成功应用于与自身免疫性疾病有关的半胱氨酸蛋白酶组织蛋白酶 S。在筛选 N-酰基氨基香豆素文库时鉴定出多种不同类别的非肽底物。两种非肽底物类别针对底物进行了优化，每个类别的切割效率提高了 8000 倍以上。然后将选择的非肽底物直接转化为对组织蛋白酶 S 具有纳摩尔亲和力的低分子量新型醛抑制剂。本研究证明了这种基于底物的快速鉴定和优化弱片段方法的独特特征和优点，并提供了框架用于开发针对许多不同蛋白酶的完全非肽抑制剂。
• Preparation of preparing substituted indanones
  申请人：Basell Polypropylen GmbH

  公开号：US06492539B1

  公开（公告）日：2002-12-10

  a process for the preparation of indanones of the formula II from, indanones of the formula I or of indanones of the formula IIa from indanones of the formula Ia comprises reacting an indanone of the formula I or Ia with a coupling component.

  从公式I的茚酮或公式Ia的茚酮与偶联组分反应，制备公式II的茚酮或从公式Ia的茚酮制备公式IIa的茚酮的方法。
• General Method for the Suzuki–Miyaura Cross-Coupling of Primary Amide-Derived Electrophiles Enabled by [Pd(NHC)(cin)Cl] at Room Temperature
  作者：Peng Lei、Guangrong Meng、Yun Ling、Jie An、Steven P. Nolan、Michal Szostak

  DOI：10.1021/acs.orglett.7b03191

  日期：2017.12.15

  temperature Suzuki–Miyaura cross-coupling of commonly encountered primary benzamides is reported. A combination of site-selective N,N-di-Boc-activation (tert-butoxycarbonyl activation) of the amide nitrogen with practical air- and moisture-stable, well-defined, and highly reactive [Pd(NHC)(cin)Cl] (NHC = N-heterocyclic carbene; cin = cinnamyl) provides a highly effective route to biaryl ketones from primary

  据报道，室温下，通常遇到的主要苯甲酰胺的Suzuki-Miyaura交叉偶联是一种通用的，高度选择性的方法。酰胺氮的位点选择性N，N -di-Boc活化（叔丁氧基羰基活化）与稳定的空气和水分稳定的，定义明确的和高反应性的[Pd（NHC）（cin）Cl ]（NHC = N-杂环卡宾； cin =肉桂基）提供了一种从伯酰胺高收率制备联芳基酮的高效途径。酰胺酰基交叉偶联首次获得了> 1000的TON。

表征谱图