3-氯-5-(三氟甲基)苯硼酸频哪醇酯 | 942069-65-0

• 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-氯-5-(三氟甲基)苯硼酸频哪醇酯
• 中文别名: 3-氯-5-(三氟甲基)苯硼酸频哪酯
• 英文名称: 2-(3-chloro-5-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 2-[3-chloro-5-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 942069-65-0
• 化学式: C₁₃H₁₅BClF₃O₂
• 分子量: 306.52
• InChiKey: DSRHHGXMHRASQY-UHFFFAOYSA-N

物化性质

• 沸点：
  321.0±42.0 °C(Predicted)
• 密度：
  1.23g/ml

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 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
Product Name: 3-Chloro-5-(trifluoromethyl)phenylboronic acid, pinacol ester
Synonyms: 2-(3-Chloro-5-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 3-Chloro-5-(trifluoromethyl)phenylboronic acid, pinacol ester
CAS number: 942069-65-0

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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.
Store in closed vessels.
Storage:

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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
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C13H15BClF3O2
Molecular weight: 306.5

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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 chloride, 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
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：

  3-氯-5-(三氟甲基)苯硼酸频哪醇酯 在 oxone 、 水 作用下， 以 丙酮 为溶剂， 反应 0.12h， 生成 3-氯-5-三氟甲基苯酚
  参考文献：
  名称：

  实用的一锅CH活化/硼氢化/氧化：数克规模的制备3-溴-5-甲基苯酚

  摘要：

  提出了一种实用的一锅法CH活化/硼化/氧化顺序，用于生成3,5-二取代的苯酚。具体地，在不分离中间体的情况下，由3-溴甲苯以数克规模并且以高收率制备3-溴-5-甲基苯酚。该过程在温和的条件下进行，可以在一天之内完成。 苯酚-CH活化-硼化-氧化-硼酸酯

  DOI：

  10.1055/s-0030-1258443
• 作为产物：
  描述：

  间氯三氟甲苯 、 频那醇硼烷 在 1,2-双(二甲基瞵)乙烷 作用下， 生成 3-氯-5-(三氟甲基)苯硼酸频哪醇酯
  参考文献：
  名称：

  实用的一锅CH活化/硼氢化/氧化：数克规模的制备3-溴-5-甲基苯酚

  摘要：

  提出了一种实用的一锅法CH活化/硼化/氧化顺序，用于生成3,5-二取代的苯酚。具体地，在不分离中间体的情况下，由3-溴甲苯以数克规模并且以高收率制备3-溴-5-甲基苯酚。该过程在温和的条件下进行，可以在一天之内完成。 苯酚-CH活化-硼化-氧化-硼酸酯

  DOI：

  10.1055/s-0030-1258443

文献信息

• Regioselective Conversion of Arenes to<i>N</i>-aryl-1,2,3-triazoles Using CH Borylation
  作者：Rajavel Srinivasan、Anthony G. Coyne、Chris Abell

  DOI：10.1002/chem.201403021

  日期：2014.9.8

  A one‐pot protocol for the synthesis of N‐aryl 1,2,3‐triazoles from arenes by an iridium‐catalyzed CH borylation/copper catalyzed azidation/click sequence is described. 1 mol % of Cu(OTf)2 was found to efficiently catalyze both the azidation and the click reaction. The applicability of this method is demonstrated by the late‐stage chemoselective installation of 1,2,3‐triazole moiety into unactivated

  的单釜协议用于合成Ñ -芳基的1,2,3-三唑从芳烃通过铱催化的Ç  ħ硼化/铜催化的叠氮化/击序列进行说明。发现1mol％的Cu（OTf）2有效地催化了叠氮化和点击反应。1,2,3-三唑部分在化学上重要的未活化分子的后期化学选择性安装证明了该方法的适用性。
• Iridium-Catalyzed Borylation of Primary Benzylic C–H Bonds without a Directing Group: Scope, Mechanism, and Origins of Selectivity
  作者：Matthew A. Larsen、Conner V. Wilson、John F. Hartwig

  DOI：10.1021/jacs.5b04899

  日期：2015.7.8

  Primary benzylic boronate esters are useful intermediates in organic synthesis, but these reagents cannot be prepared by hydroboration. The benzylic C-H borylation of methylarenes would be a method to form these products, but such reactions without neat methylarene or a directing group are unknown. We report an approach to divert the borylation of methylarenes from aromatic positions to benzylic positions

  主要的苄基硼酸酯是有机合成中有用的中间体，但这些试剂不能通过硼氢化反应制备。甲基芳烃的苄基 CH 硼酸化将是形成这些产物的一种方法，但这种没有纯甲基芳烃或导向基团的反应是未知的。我们报告了一种以甲硅烷基硼烷为试剂和含有缺电子菲咯啉作为配体的新型铱催化剂将甲基芳烃的硼酸化从芳族位置转移到苄位位置的方法。该系统相对于相应的芳基硼酸酯选择性地形成苄基硼酸酯。由菲咯啉连接的 Ir 二硼基单甲硅烷基复合物被分离并确定为催化剂的静止状态。机理研究表明，这种复合物在动力学上有能力成为催化过程中的中间体。各种 Ir 配合物催化的苄基和芳基 CH 硼化的动力学研究表明，芳基 CH 硼化速率随着 Ir 催化剂金属中心电子密度的降低而降低，但苄基 CH 硼化速率对Ir 催化剂金属中心的电子密度。动力学和计算研究表明，这两种硼酸化反应对金属中心的电子密度程度的反应不同，因为它们发生在不同的转换限制步骤中。已知芳基
• Merging Iridium-Catalyzed C–H Borylations with Palladium-Catalyzed Cross-Couplings Using Triorganoindium Reagents
  作者：Chathurika R. K. Jayasundara、José M. Gil-Negrete、Jose R. Montero Bastidas、Arzoo Chhabra、M. Montserrat Martínez、José Pérez Sestelo、Milton R. Smith、Robert E. Maleczka

  DOI：10.1021/acs.joc.1c01978

  日期：2022.1.7

  borylated arenes furnished with alkyl, alkenyl, alkynyl, aryl, and heteroaryl functional groups is developed by merging Ir-catalyzed C–H borylations (CHB) with a chemoselective palladium-catalyzed cross-coupling of triorganoindium reagents (Sarandeses–Sestelo coupling) with aryl halides bearing a boronic ester substituent. Using triorganoindium cross-coupling reactions to introduce unsaturated moieties

  通过将 Ir 催化的 C-H 硼化 (CHB) 与化学选择性钯催化的三有机铟试剂的交叉偶联相结合，开发了一种制备具有烷基、烯基、炔基、芳基和杂芳基官能团的硼化芳烃的通用且有效的方法。 Sarandeses-Sestelo 偶联）与带有硼酸酯取代基的芳基卤化物。使用三有机铟交叉偶联反应引入不饱和部分可以合成通过直接应用 CHB 方法难以获得的硼化芳烃。顺序双催化程序也可以在一个容器中进行。
• A One-Pot, Single-Solvent Process for Tandem, Catalyzed C-H Borylation-Suzuki-Miyaura Cross-Coupling Sequences
  作者：Patrick Steel、Todd Marder、Peter Harrisson、James Morris

  DOI：10.1055/s-0028-1087374

  日期：——

  Methyl tert-butyl ether is a suitable solvent for iridium-catalyzed C-H borylation followed, in the same pot, by palladium-catalyzed Suzuki-Miyaura cross-coupling sequences, giving high yields of biaryls.

  甲基叔丁基醚是铱催化的C-H硼化反应的合适溶剂，随后在同一锅中进行钯催化的铃木-宫浦交叉偶联反应，能得到高产率的二芳烃。
• Process for the synthesis of phenols from arenes
  申请人：Board of Trustees of Michigan State University

  公开号：US20040030197A1

  公开（公告）日：2004-02-12

  A process to synthesize substituted phenols such as those of the general formula RR′R″Ar(OH) wherein R, R′, and R″ are each independently hydrogen or any group which does not interfere in the process for synthesizing the substituted phenol including, but not limited to, halo, alkyl, alkoxy, carboxylic ester, amine, amide; and Ar is any variety of aryl or hetroaryl by means of oxidation of substituted arylboronic esters is described. In particular, a metal-catalyzed C—H activation/borylation reaction is described, which when followed by direct oxidation in a single or separate reaction vessel affords phenols without the need for any intermediate manipulations. More particularly, a process wherein Ir-catalyzed borylation of arenes using pinacolborane (HBPin) followed by oxidation of the intermediate arylboronic ester by OXONE is described.

  描述了一种合成取代酚的过程，如通式RR′R″Ar(OH)中的那些，其中R、R′和R″分别独立地是氢或不干扰合成取代酚过程的任何基团，包括但不限于卤素、烷基、烷氧基、羧酸酯、胺、酰胺；Ar是芳基或杂芳基的任何种类，通过氧化取代芳基硼酸酯来实现。具体地，描述了一种金属催化的C—H活化/硼化反应，随后在单个或分离的反应容器中直接氧化，从而获得酚，无需任何中间操作。更具体地，描述了一种通过Ir催化的芳烃硼化反应，使用二醇硼烷（HBPin）后，通过OXONE氧化中间芳基硼酸酯的过程。