(1-萘)三氟硼酸钾 | 166328-07-0

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟硼酸钾系列
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (1-萘)三氟硼酸钾
• 中文别名: 三氟钾(萘-1-基)硼酸盐；1-萘三氟硼酸钾
• 英文名称: potassium trifluoro(naphth-1-yl)borate
• 英文别名: potassium 1-naphthyltrifluoroborate；potassium trifluoro(1-naphthyl)borate；potassium naphthalen-1-yltrifluoroborate；potassium (1-naphthalene)trifluoroborate；potassium;trifluoro(naphthalen-1-yl)boranuide
• CAS: 166328-07-0
• 化学式: C₁₀H₇BF₃*K
• 分子量: 234.07
• InChiKey: SBEPDIKXYGSGJL-UHFFFAOYSA-N

物化性质

• 熔点：
  89-91℃

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存于室温、干燥且密封的环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Potassium (1-naphthalene)trifluoroborate
Product Name:
Synonyms:

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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.
Potassium (1-naphthalene)trifluoroborate
Ingredient name:
CAS number: 166328-07-0

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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.

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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: C10H7BF3K
Molecular weight: 234.1

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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

制备方法与用途

简介

(1-萘)三氟硼酸钾是一种芳基三氟硼酸钾的衍生物。芳基三氟硼酸钾不仅稳定性高，结晶性好，而且其反应性能与相应的芳基硼酸最为接近，是极具工业生产应用前景的芳基硼酸衍生物。

应用

芳基硼酸作为安全、高效的芳基化试剂，在医药、农药、液晶和OLED光电材料等相关精细化学品的科研和开发中已被广泛应用。然而，由于芳基硼酸容易脱水形成酸酐，并且对酸、碱和氧化剂不够稳定，尤其是在空气中的氧化或脱硼质解等问题，导致其实际使用中普遍存在储存时间短和计量困难的问题。一些杂环芳基硼酸甚至在室温下也会逐渐分解，需要在-30℃以下的低温条件下储存，使其失去在工业生产中的应用价值。

为解决这一问题，研究人员将芳基硼酸转化为芳基硼酸酯或盐的衍生物以提高其稳定性。

制备

(1-萘)三氟硼酸钾的制备过程如下：

1. 0.41摩尔的1-萘硼酸与0.82摩尔的二氟氢化钾混合，经500rpm高速搅拌10分钟后得到均匀物料。
2. 将上述物料通过双螺杆挤出机进料口连续加入，并设定挤出时间为5分钟。
3. 挤出后的物料直接接收于盛有等重量水的接收器中，进行搅拌分散，形成浆状物。
4. 过滤得到滤液和滤饼。将滤饼用水清洗后，在热风下干燥得最终产品(1-萘)三氟硼酸钾。

反应信息

• 作为反应物：
  描述：

  (1-萘)三氟硼酸钾 在 ammonium hydroxide 、 copper(ll) sulfate pentahydrate 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 以83%的产率得到1-萘胺
  参考文献：
  名称：

  氨水在铜催化下芳基三氟硼酸钾的胺化反应

  摘要：

  描述了使用催化量的CuSO 4 ·5H 2 O将含有不同官能度的芳基三氟硼酸钾转化为相应的芳基胺。该方法在好氧条件下使用水作为溶剂，以高收率得到产物。

  DOI：

  10.1016/j.tetlet.2012.06.011
• 作为产物：
  描述：

  1-萘硼酸 在 二氟化氢钾 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以81%的产率得到(1-萘)三氟硼酸钾
  参考文献：
  名称：

  氨水在铜催化下芳基三氟硼酸钾的胺化反应

  摘要：

  描述了使用催化量的CuSO 4 ·5H 2 O将含有不同官能度的芳基三氟硼酸钾转化为相应的芳基胺。该方法在好氧条件下使用水作为溶剂，以高收率得到产物。

  DOI：

  10.1016/j.tetlet.2012.06.011

文献信息

• Hydrogen‐Bond‐Donor Solvents Enable Catalyst‐Free (Radio)‐Halogenation and Deuteration of Organoborons
  作者：Yi Yang、Xinyan Gao、Xiaojun Zeng、Junbin Han、Bo Xu

  DOI：10.1002/chem.202003919

  日期：2021.1.18

  A hydrogen bond donor solvent assisted (radio)halogenation and deuteration of organoborons has been developed. The reactions exhibited high functional group tolerance and needed only an ambient atmosphere. Most importantly, compared to literature methods, our conditions are more consistent with the principals of green chemistry (e.g., metal‐free, strong oxidant‐free, more straightforward conditions)

  已经开发了氢键供体溶剂辅助的有机硼的（放射性）卤化和氘代。该反应表现出高的官能团耐受性并且仅需要环境气氛。最重要的是，与文献方法相比，我们的条件与绿色化学原理更加一致（例如，无金属，无强氧化剂，更简单的条件）。
• Preparation of Organotrifluoroborate Salts: Precipitation-Driven Equilibrium under Non-Etching Conditions
  作者：Alastair J. J. Lennox、Guy C. Lloyd-Jones

  DOI：10.1002/anie.201203930

  日期：2012.9.10

  Simple, rapid, and scaleable: In contrast to current procedures using corrosive HF/MF or MHF2 reagents (M=e.g. K), a wide range of trifluoroborates can be rapidly, simply, and safely prepared from MF (M=K, Cs), RCO2H, and a boronic acid/ester in regular glassware (see figure; left versus right). The use of L‐(+)‐tartaric acid as an alkali‐metal sponge is key and allows isolation of RBF3M by a simple

  简便，快速，且可扩展：使用腐蚀性的HF / MF或MHF相反当前程序2种试剂（M =例如K），大范围的三氟硼酸的可迅速，简单地和安全地从MF（M = K，Cs的制备），RCO 2 H，和在常规的玻璃器皿一硼酸/硼酸酯（参见图;左与右）。的使用大号- （+） -酒石酸作为碱金属海绵是键，并且允许的RBF隔离3 M分别简单搅拌/过滤器/蒸发顺序。
• Sterically Hindered Benzophenones via Rhodium-Catalyzed Oxidative Arylation of Aldehydes
  作者：Olivier Chuzel、Alexander Roesch、Jean-Pierre Genet、Sylvain Darses

  DOI：10.1021/jo801460w

  日期：2008.10.3

  Efficient cross-coupling, allowing a straightforward access to congested benzophenones, between aromatic aldehydes and potassium aryltrifluoroborates, is described in the presence of a rhodium/tri-tert-butylphosphane catalyst system and acetone as cosolvent. The use of the stable phosphonium salts of tri-tert-butylphosphane prevented the use of highly oxidizable tri-tert-butylphosphane and allowed

  在铑/三叔丁基膦烷催化剂体系和丙酮作为助溶剂的存在下，描述了有效的交叉偶联，使芳族醛和芳基三氟硼酸钾之间可以直接进入拥挤的二苯甲酮。三叔丁基膦的稳定phospho盐的使用阻止了高度可氧化的三叔丁基膦的使用，并允许用铑小心地控制化学计量。
• Halodeboronation of organotrifluoroborates using tetrabutylammonium tribromide or cesium triiodide
  作者：Min-Liang Yao、George W. Kabalka、David W. Blevins、Marepally Srinivasa Reddy、Li Yong

  DOI：10.1016/j.tet.2012.03.016

  日期：2012.5

  Halodeboronation of organotrifluoroborates using commercially available tetrabutylammonium tribromide (TBATB) or cesium triiodide in aqueous medium is reported. The mild, transition metal-free method has proven to be tolerant of a wide range of functional groups. High regio- and chemoselectivity are observed. Two synthetic routes to (Z)-dibromoalkenes from alkynes, through stereodefined (Z)-2-brom

  报道了在水介质中使用市售的三溴化四丁基铵（TBATB）或三碘化铯对有机三氟硼酸盐进行卤代硼烷化。事实证明，这种温和的不含过渡金属的方法可耐受多种官能团。观察到高的区域选择性和化学选择性。两个合成路线（ż）从炔-dibromoalkenes，通过stereodefined（ż）-2- bromoalkenyltrifluoroborates和（Ž）-1,2-双（硼烷基）alkenyltrifluoroborates，已经使用TBATB介导bromodeboronation作为关键步骤开发的。
• Pd-Catalyzed C-3 functionalization of indolizines via C–H bond cleavage
  作者：Baoli Zhao

  DOI：10.1039/c2ob25643f

  日期：——

  New transition metal-catalyzed methods for the arylation of indolizines by the direct cleavage of C–H bonds have been developed. A wide range of aryltrifluoroborate salts react with indolizines in the presence of Pd(OAc)2 catalyst and AgOAc oxidant to give the arylated indolizines in high yields. Both electron-donating and electron-withdrawing groups perform smoothly while bromide and chlorine substituents are tolerated. In addition, the indolizines display similar reactivities in the Pd-catalyzed reaction with 3-phenylpropiolic acid to afford the corresponding C-3 alkynylated indolizines. These methods allow the direct functionalization of indolizines in one step.

  开发了新的过渡金属催化方法，通过直接断裂C-H键实现吲哚并环己烯的芳基化。一系列芳基三氟硼酸盐在Pd(OAc)2催化剂和AgOAc氧化剂的存在下与吲哚并环己烯反应，高效地得到芳基化的吲哚并环己烯。供电子和吸电子基团均表现良好，而溴和氯取代基也可耐受。此外，吲哚并环己烯在Pd催化反应中与3-苯基丙炔酸显示出相似的反应活性，从而获得相应的C-3炔基化吲哚并环己烯。这些方法使得吲哚并环己烯能够在一步中直接进行官能团化。