4-(三氟甲基)苯硼酸频哪醇酯 | 214360-65-3

• 物质功能分类: 化学试剂 - 有机试剂 - 磺酸/亚磺酸
• 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: 4-(三氟甲基)苯硼酸频哪醇酯
• 中文别名: 4,4,5,5-四甲基-2-(4-(三氟甲基)苯基)-1,3,2-二噁硼烷；4-三氟甲基苯硼酸频呐醇酯
• 英文名称: 4-trifluoromethylphenylboronic acid pinacol ester
• 英文别名: 4,4,5,5-Tetramethyl-2-[4-(trifluoromethyl)phenyl]-1,3,2-dioxaborolane；2-(4-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；4,4,5,5-Tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane
• CAS: 214360-65-3
• 化学式: C₁₃H₁₆BF₃O₂
• 分子量: 272.075
• InChiKey: GCQADNWXVSTJQW-UHFFFAOYSA-N

物化性质

• 熔点：
  68-69 °C
• 沸点：
  291.4±40.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  19
• 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：
  P264,P270,P273,P301+P312,P330
• 危险性描述：
  H302,H413
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Trifluoromethylphenylboronic acid, pinacol ester
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H413: May cause long lasting harmful effects to aquatic life

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Section 3. Composition/information on ingredients.
Ingredient name: 4-Trifluoromethylphenylboronic acid, pinacol ester
CAS number: 214360-65-3

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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.
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.

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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: C13H16BF3O2
Molecular weight: 272.1

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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, 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：

  4-(三氟甲基)苯硼酸频哪醇酯 在 potassium methanolate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以81%的产率得到三氟甲苯
  参考文献：
  名称：

  一种绿色的有机硼试剂碳硼键裂解氢化的新 方法

  摘要：

  本发明涉及一种绿色、高效的有机硼试剂碳硼键裂解氢化的新方法。该方法以廉价易得的无机碱为催化剂，常见的有机醇作为反应溶剂和氢源，置于空气环境下即可方便的催化有机硼酸或硼酸酯发生碳硼键裂解氢化反应，反应底物普适性广、官能团兼容性优秀。系统的实现非金属催化各类硼酸和硼酸酯发生碳硼键断裂反应，也克服传统方法需要使用大大过量无机碱、环境危害性大的有机氟酸或复杂的金属催化剂来进行脱硼氢化的局限，为实验室制备和工业生产有机硼试剂的脱硼氢化反应提供了一种全新的策略。

  公开号：

  CN107188773B
• 作为产物：
  描述：

  4-硝基三氟甲苯 在 SPhos Pd G2 、 caesium carbonate 、 间氯过氧苯甲酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 99.0h， 生成 4-(三氟甲基)苯硼酸频哪醇酯
  参考文献：
  名称：

  钯催化的二芳基亚砜与双硼的双硼化反应

  摘要：

  作为合成中硼化的现代策略特别主题的一部分发布 抽象的 二芳基亚砜的C–S键与双（频哪醇）二硼（B 2 pin 2）的硼化反应是通过膦连接的钯催化剂和LiN（SiMe 3）2为基础进行的。二芳基亚砜的两个芳基环都转化为硼化产物。 二芳基亚砜的C–S键与双（频哪醇）二硼（B 2 pin 2）的硼化反应是通过膦连接的钯催化剂和LiN（SiMe 3）2为基础进行的。二芳基亚砜的两个芳基环都转化为硼化产物。

  DOI：

  10.1055/s-0036-1588848

文献信息

• Catalytic Transfer Hydrogenation of Arenes and Heteroarenes
  作者：Coralie Gelis、Arne Heusler、Zackaria Nairoukh、Frank Glorius

  DOI：10.1002/chem.202002777

  日期：2020.11.6

  Transfer hydrogenation reactions are of great interest to reduce diverse molecules under mild reaction conditions. To date, this type of reaction has only been successfully applied to alkenes, alkynes and polarized unsaturated compounds such as ketones, imines, pyridines, etc. The reduction of benzene derivatives by transfer hydrogenation has never been described, which is likely due to the high energy

  转移氢化反应对于在温和的反应条件下还原各种分子非常重要。迄今为止，这种类型的反应仅成功地用于烯烃，炔烃和极化的不饱和化合物，例如酮，亚胺，吡啶等。从未描述过通过转移氢化还原苯衍生物的方法，这很可能是由于高使这些化合物脱芳香化所需的能量屏障。在此背景下，我们开发了一种催化转移氢化反应，用于还原苯衍生物和杂芳烃，从而在不需要压缩氢气的情况下，在室温下形成带有各种官能团的复杂三维支架。
• Conversion of Aromatic Amino into Trifluoromethyl Groups through a Sandmeyer­-Type Transformation
  作者：Jianbo Wang、Xi Wang、Yan Xu、Yujing Zhou、Yan Zhang

  DOI：10.1055/s-0033-1338659

  日期：——

  strategy for aromatic trifluoromethylation by converting amino into trifluoromethyl groups via a Sandmeyer-type reaction is reported. The transformation involves diazotization of the aromatic amines with tert-butyl nitrite and hydrochloric acid to form aryldiazonium chlorides, followed by trifluoromethylation with trifluoromethylsilver at low temperature. Various readily available aromatic amines are

  摘要 报道了通过Sandmeyer型反应将氨基转化为三氟甲基的芳香族三氟甲基化的新策略。该转化包括用亚硝酸叔丁酯和盐酸将芳族胺重氮化以形成芳基重氮氯化物，然后在低温下用三氟甲基银进行三氟甲基化。各种容易获得的芳族胺在温和条件下均能平稳转化。 报道了通过Sandmeyer型反应将氨基转化为三氟甲基的芳香族三氟甲基化的新策略。该转化包括用亚硝酸叔丁酯和盐酸将芳族胺重氮化以形成芳基重氮氯化物，然后在低温下用三氟甲基银进行三氟甲基化。各种容易获得的芳族胺在温和条件下均能平稳转化。
• Additive- and Photocatalyst-Free Borylation of Arylazo Sulfones under Visible Light
  作者：Yuliang Xu、Xinying Yang、Hao Fang

  DOI：10.1021/acs.joc.8b01662

  日期：2018.10.19

  developed a photocatalyst-free and additive-free, visible light induced borylation reaction using arylazo sulfones as starting material. This protocol shows some advantages such as mild conditions, simple equipment, and wide substrate scope, which gives a complementary protocol for the preparation of arylboronates.

  我们开发了一种以芳基偶氮砜为起始原料的无光催化剂和无添加剂的可见光诱导的硼酸酯化反应。该方案显示出一些优点，例如温和的条件，简单的设备和广泛的底物范围，为制备芳基硼酸酯提供了补充方案。
• Suzuki–Miyaura coupling of unstrained ketones <i>via</i> chelation-assisted C–C bond cleavage
  作者：Cheng Jiang、Zhao-Jing Zheng、Tian-Yang Yu、Hao Wei

  DOI：10.1039/c8ob02075b

  日期：——

  Herein, we report that unstrained ketones can be efficiently employed as electrophiles in Suzuki–Miyaura reactions via catalytic activation of unstrained C–C bonds assist by an N-containing directing group. A wide range of aromatic ketones directly coupled with boronic ester with excellent functional group tolerance. This strategy provides an alternative and versatile approach to constructing biaryls

  在本文中，我们报道，未催化反应的酮可通过含氮的导向基团催化未反应的C-C键的催化活化而有效地用作Suzuki-Miyaura反应中的亲电子试剂。多种芳族酮直接与硼酸酯偶联，具有出色的官能团耐受性。该策略提供了从未应变的酮构建联芳基的另一种通用方法。
• Efficient Synthesis of Aryl Boronates via Zinc-Catalyzed Cross-Coupling of Alkoxy Diboron Reagents with Aryl Halides at Room Temperature
  作者：Shubhankar Kumar Bose、Todd B. Marder

  DOI：10.1021/ol502120q

  日期：2014.9.5

  A zinc(II)/NHC system catalyzes the borylation of aryl halides with diboron (4) reagents in the presence of KOMe at rt. This transformation can be applied to a broad range of substrates with high functional group compatibility. Radical scavenger experiments do not support a radical-mediated process.

  锌（II）/ NHC系统在室温下在KOMe存在下催化芳基卤化物与二硼（4）试剂的硼酸酯化反应。这种转变可应用于具有高官能团相容性的各种基材。自由基清除剂实验不支持自由基介导的过程。