3-(N,N-二甲氨基)苯硼酸频那醇酯 | 325142-87-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 3-(N,N-二甲氨基)苯硼酸频那醇酯
• 英文名称: N,N-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
• CAS: 325142-87-8
• 化学式: C₁₄H₂₂BNO₂
• mdl: MFCD06795669
• 分子量: 247.145
• InChiKey: BIJRPONWUBCGES-UHFFFAOYSA-N

物化性质

• 沸点：
  356.1±25.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

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

---

Section 1. Identification of the substance
Product Name: 3-(N,N-Dimethylamino)phenylboronic acid, pinacol ester
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H317: May cause an allergic skin reaction
P280: Wear protective gloves/protective clothing/eye protection/face protection

---

Section 3. Composition/information on ingredients.
Ingredient name: 3-(N,N-Dimethylamino)phenylboronic acid, pinacol ester
CAS number: 325142-87-8

---

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.

---

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.

---

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.

---

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.

---

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.

---

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: C14H22BNO2
Molecular weight: 247.1

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-(N,N-二甲氨基)苯硼酸频那醇酯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 C₁₅H₂₄BNO₃
  参考文献：
  名称：

  Oxa-Matteson 反应实现的可编程醚合成

  摘要：

  Matteson 型反应越来越受到人们对通过迭代合成策略构建复杂有机分子的兴趣。然而，目前的策略几乎完全基于纯碳链的认证。在这里，我们报告了 oxa-Matteson 反应的发展，该反应能够将氧和类胡萝卜素连续插入到不同的烷基硼酸盐和芳基硼酸盐中。它为广泛的硼取代醚提供了独特的入口。该方法的实用性在各种功能性醚的制备、乙酰辅酶A-羧化酶抑制剂的不对称合成和聚醚的可编程构建中得到了证明。

  DOI：

  10.1021/jacs.2c03621
• 作为产物：
  描述：

  3-羟基-N,N-二甲基苯胺 在 2-吡啶甲酸 、 potassium phosphate 、 copper(l) iodide 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 1,3-dimesityl-4,5-dimethyl-1H-imidazol-2-ylidene 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 39.0h， 生成 3-(N,N-二甲氨基)苯硼酸频那醇酯
  参考文献：
  名称：

  芳基 2-吡啶基醚通过碳氧键断裂的铑催化硼酸化：导向基团的硼酸化去除

  摘要：

  芳基 2-吡啶基醚与二硼试剂的铑催化反应导致通过活化 C(芳基)-O 键形成芳基硼酸衍生物。1,2-二取代芳烃的直接合成是通过由 2-吡啶氧基引导的催化邻位 CH 键官能化，然后用硼基取代该基团来实现的。几个对照实验表明，在底物的 2 位存在 sp(2) 氮原子和使用基于硼的试剂对于芳基相对惰性的 C(芳基)-O 键的活化至关重要。 2-吡啶基醚。

  DOI：

  10.1021/ja511622e

文献信息

• Steric and Chelate Directing Effects in Aromatic Borylation
  作者：Jian-Yang Cho、Carl N. Iverson、Milton R. Smith

  DOI：10.1021/ja0013069

  日期：2000.12.1

  Jian-Yang Cho, Carl N. Iverson, and Milton R. Smith, III*Department of Chemistry, Michigan State UniVersityEast Lansing, Michigan 48824ReceiVed April 14, 2000ReVised Manuscript ReceiVed October 18, 2000Hydrocarbon activation has attracted considerable attentionbecause hydrocarbon feedstocks are ubiquitous.

  Jan-Yang Cho, Carl N. Iverson, and Milton R. Smith, III*Department of Chemistry, Michigan State University East Lansing, Michigan 48824ReceiVed April 14, 2000Receive Manuscript Received 2000 年 10 月 18 日 碳氢化合物活化已引起相当多的关注，因为碳氢化合物的原料无处不在。
• Palladium‐Catalyzed Decarbonylative Borylation of Carboxylic Acids: Tuning Reaction Selectivity by Computation
  作者：Chengwei Liu、Chong‐Lei Ji、Xin Hong、Michal Szostak

  DOI：10.1002/anie.201810145

  日期：2018.12.17

  demonstrated in the selective borylation of a variety of aromatics (>50 examples). This strategy was used in the late‐stage derivatization of pharmaceuticals and natural products. Computations reveal the mechanistic details of the unprecedented C−O bond activation of carboxylic acids. By circumventing the challenging decarboxylation, this strategy provides a general synthetic platform to access arylpalladium

  据报道羧酸的脱羰基硼酸酯化。在催化剂控制的条件下，对羧酸进行原位可及的空间受阻的酰基衍生物进行试剂脱羰后，会立即生成亲电子碳。该方法的范围和潜在影响在各种芳烃的选择性硼化中得到证明（> 50个实例）。该策略用于药物和天然产品的后期衍生化。计算揭示了前所未有的羧酸氧键活化机理。通过规避具有挑战性的脱羧反应，该策略提供了一个通用的合成平台，可用于从芳基钯物质中获得由丰富的羧酸形成的各种键。
• Synthesis of fluorenes and their related compounds from biaryls and Meldrum's acid derivatives
  作者：Zhiyan Jiang、Kohei Sekine、Yoichiro Kuninobu

  DOI：10.1039/d1cc06212c

  日期：——

  A new synthetic method for preparing fluorenes from amino group-containing biaryls and Meldrum's acid derivatives was developed. The reaction proceeded without a catalyst and loss of functional groups. The corresponding six- and seven-membered cyclic products were obtained using biaryl ether and ortho-terphenyl as substrates, respectively.

  开发了一种由含氨基联芳基和麦氏酸衍生物制备芴的新合成方法。该反应在没有催化剂和官能团损失的情况下进行。分别以联芳基醚和邻三联苯为底物得到相应的六元和七元环状产物。
• METHOD FOR SYNTHESIZING BORONATE ESTER COMPOUND, SODIUM SALT OF BORONATE ESTER COMPOUND, AND METHOD FOR SYNTHESIZING THE SAME
  申请人：KOBELCO ECO-SOLUTIONS CO., LTD.

  公开号：US20210070782A1

  公开（公告）日：2021-03-11

  An object is to establish a technology with which a boronate ester compound can be easily and efficiently synthesized at a low cost with a small number of steps without the need for a complex chemical method and reagents that need to be carefully handled. A further object is to establish a sodium salt of a boronate ester compound that is a novel compound and a technology for synthesizing the sodium salt of a boronate ester compound. Provided are a sodium salt of a boronate ester compound and a method for synthesizing a boronate ester compound or a sodium salt of a boronate ester compound that includes reacting, in a reaction solvent, an organic chloride with a dispersion product obtained by dispersing sodium in a dispersion solvent to obtain an organic sodium compound, and reacting the obtained organic sodium compound with a borate ester compound to obtain a boronate ester compound or a sodium salt of a boronate ester compound.

  本发明的目的是建立一种技术，通过该技术，硼酸酯化合物可以在低成本、少量步骤、无需复杂化学方法和需要小心处理的试剂的情况下轻松高效地合成。另一个目的是建立一种硼酸酯盐的钠盐，这是一种新型化合物，以及合成硼酸酯盐的钠盐的技术。提供了一种硼酸酯盐的钠盐和一种合成硼酸酯化合物或硼酸酯盐的钠盐的方法，包括在反应溶剂中，将有机氯化物与在分散溶剂中分散钠得到的分散产物反应，以获得有机钠化合物，然后将获得的有机钠化合物与硼酸酯化合物反应，从而获得硼酸酯化合物或硼酸酯盐的钠盐。
• Recyclable Pd2dba3/XPhos/PEG-2000 System for Efficient Boryl­ation of Aryl Chlorides: Practical Access to Aryl Boronates
  作者：Mingzhong Cai、Bin Huang、Chengkai Luo、Caifeng Xu

  DOI：10.1055/s-0037-1610787

  日期：2022.3

  Pd2dba3/XPhos in poly(ethylene glycol) (PEG-2000) is shown to be a highly stable and efficient catalyst for the borylation of aryl chlorides with bis(pinacolato)diboron. The borylation reaction proceeds smoothly at 110 °C, delivering a wide variety of aryl boronates in good to excellent yields with high functional group tolerance. The crude products were easily isolated via simple extraction of the reaction mixture with cyclohexane. Moreover, both expensive Pd2dba3 and XPhos in PEG-2000 system could be readily recycled and reused more than six times without loss of catalytic efficiency.

  摘要：Pd2dba3/XPhos在聚乙二醇（PEG-2000）中被证明是一种高度稳定和高效的催化剂，用于芳基氯化物与双(对甲苯硼)二硼烷的硼化反应。硼化反应在110°C下顺利进行，以高功能团耐受性以良好至优良的产率提供各种芳基硼酸酯。通过简单的环己烷提取反应混合物，可以轻松分离粗品。此外，昂贵的Pd2dba3和XPhos在PEG-2000系统中可轻松回收和重复使用超过六次，而不会损失催化效率。