3-吡啶硼酸新戊二醇酯 | 845885-86-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 3-吡啶硼酸新戊二醇酯
• 中文别名: 5-二甲基-1；2-二氧杂戊硼烷-2-基)吡啶；吡啶-3-硼酸酯；3-(5,5-二甲基-1,3,2-二氧硼烷-2-基)吡啶
• 英文名称: 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl) pyridine
• 英文别名: 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridine；5,5-dimethyl-2-(3-pyridyl)-1,3,2-dioxaborinane；pyridin-3-ylboronic acid neopentylglycol ester；3-pyridineboronic acid neopentylglycol ester；3-pyridylboronic neopentyl glycol ester；pyridine-3-boronic acid neopentyl glycol ester
• CAS: 845885-86-1
• 化学式: C₁₀H₁₄BNO₂
• mdl: MFCD03425979
• 分子量: 191.038
• InChiKey: QMEKTOQBDDVVBE-UHFFFAOYSA-N

物化性质

• 熔点：
  92-96 °C (lit.)
• 沸点：
  309.8±15.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 安全说明：
  S26,S36
• 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：
  2-8℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Pyridine-3-boronic acid, neopentyl glycol ester
Synonyms: 3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine

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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
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: Pyridine-3-boronic acid, neopentyl glycol ester
CAS number: 845885-86-1

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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, refrigerated.

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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
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H14BNO2
Molecular weight: 191.0

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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, nitrogen oxides.

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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-吡啶硼酸新戊二醇酯 在 sodium periodate 、 碘苯 作用下， 以 水 、 乙腈 为溶剂， 反应 8.0h， 以59%的产率得到3-羟基吡啶
  参考文献：
  名称：

  有机高价碘（III）催化芳基和烷基硼酸/酯的ipso-羟基化

  摘要：

  的有机高价碘（III）催化的高效方法为本位多样化官能芳基-和烷基硼酸/酯的羟基化使用的NaIO已经开发4作为共氧化剂。该方案也适用于N-杂环硼酸和酯。进一步的机理研究表明，在存在高价碘的羟基化反应中，有机硼酸（一种需要电子的部分）起着亲核试剂的作用。总之，这是有机超价碘（III）催化有机硼化合物羟基化的一般路线的第一个字母。

  DOI：

  10.1016/j.tetlet.2015.01.118
• 作为产物：
  描述：

  在 bis(1,5-cyclooctadiene)nickel (0) 、 C₁₅H₂₄N₂*H⁽¹⁺⁾*BF₄^(1-) 、 间氯过氧苯甲酸 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 3-吡啶硼酸新戊二醇酯
  参考文献：
  名称：

  镍催化芳基亚砜的硼化反应

  摘要：

  镍/ N-杂环卡宾(NHC)催化系统已被开发用于芳基亚砜与B 2 (neop) 2 (neop=新戊基甘醇酸)的硼基化。具有不同电子和空间性质的各种芳基亚砜以良好的收率转化为相应的芳基硼酸酯。不对称二芳基亚砜的区域选择性硼基化也是可行的，导致空间阻碍较少的芳基取代基的硼基化。竞争实验表明缺电子芳基部分优先反应。 Ni催化的电子偏压不对称二芳基亚砜硼化反应的选择性起源在于催化循环的氧化加成步骤，因为甲氧基苯基4-(三氟甲基)苯基亚砜与Ni(0)配合物的氧化加成选择性地发生给出结构特征复杂的反式-[Ni(ICy) 2 (4-CF 3 -C 6 H 4 ){(SO)-4-MeO-C 6 H 4 }] 4 。对于络合物5 ，异构体反式-[Ni(ICy) 2 (C 6 H 5 )(OSC 6 H 5 )] 5 - I的结构特征在于其中苯基亚磺酰基配体通过氧原子与镍结合。 在溶液中，配合物trans -[Ni(ICy)

  DOI：

  10.1002/chem.202100342

文献信息

• Chan-Lam cross-coupling reaction based on the Cu 2 S/TMEDA system
  作者：Kateřina Janíková、Lukáš Jedinák、Tereza Volná、Petr Cankař

  DOI：10.1016/j.tet.2017.12.042

  日期：2018.2

  several pinacol or neopentylglycol boronates indicated further potential of the catalyst. The reaction conditions tolerate the hydroxyl and bromo functional groups. The catalytic system also enables to synthesize the mono-N-substituted anilines from primary aliphatic amines. However, the two model compounds for the secondary and aromatic amines, piperidine and aniline, do not react. Two sterically demanding

  基于Chan-Lam交叉偶联反应，开发了一种基于使用稳定铜（I）源的现成Cu 2 S / TMEDA系统的催化剂。用1 H-苯并[ d ]咪唑-2（3 H）-1，1 H-苯并[ d ]咪唑和1 H-咪唑以及缺电子，富电子和在室温下，在大气氧的存在下，对空间需求量高的硼酸，以中等至极好的收率得到交叉偶联的产物。另外，1 H-苯并[ d]的偶联反应]咪唑与几种频哪醇或新戊二醇硼酸酯表明该催化剂的进一步潜力。反应条件容许羟基和溴官能团。该催化体系还能够由伯脂族胺合成单-N-取代的苯胺。但是，仲胺和芳族胺的两种模型化合物哌啶和苯胺不会反应。两个空间要求的产品与受限Ç N键的旋转，通过将合成的Ñ 1的-arylation ħ -苯并[ d ]咪唑-2（3 H ^） -酮与ö-甲苯磺酸，能够确认由Chan-Lam交叉偶联反应制得的阻转异构体。此外，已经报道了一锅Chan-Lam和Suzuki-Miyaura反应的例子。
• Biological Evaluation and X-ray Co-crystal Structures of Cyclohexylpyrrolidine Ligands for Trypanothione Reductase, an Enzyme from the Redox Metabolism of Trypanosoma
  作者：Raoul De Gasparo、Elke Brodbeck-Persch、Steve Bryson、Nina B. Hentzen、Marcel Kaiser、Emil F. Pai、R. Luise Krauth-Siegel、François Diederich

  DOI：10.1002/cmdc.201800067

  日期：2018.5.8

  were freely soluble and showed competitive inhibition constants (Ki) against Trypanosoma (T.) brucei TR and T. cruzi TR and in vitro activities (half‐maximal inhibitory concentration, IC50) against these parasites in the low micromolar range, with high selectivity against human glutathione reductase. X‐ray co‐crystal structures confirmed the binding of the ligands to the hydrophobic wall of the “mepacrine

  人类非洲锥虫病，南美锥虫病和各种形式的利什曼病是热带疾病，是由锥虫病家族的寄生虫引起的。这些原生动物具有独特的氧化还原代谢，该代谢基于锥虫硫烷和锥虫硫醇还原酶（TR），使TR成为有前途的药物靶标。我们通过基于结构的设计报告了TR的环己基吡咯烷抑制剂的性能和效能的优化。最好的抑制剂是可自由溶解的，并显示出对锥虫（T.）brucei TR和T. cruzi TR的竞争抑制常数（K i）和体外活性（半数最大抑制浓度，IC 50）在低微摩尔范围内对这些寄生虫具有抗人谷胱甘肽还原酶的高选择性。X射线共晶结构证实了配体与“ mepacrine结合位点”的疏水壁的结合，并且具有面向大活性位点表面的新的可提供溶解度的载体。
• One-pot conversion of 1,1-dibromoalkenes into internal alkynes by sequential Suzuki–Miyaura and dehydrobromination reactions
  作者：Giorgio Chelucci、Francesca Capitta、Salvatore Baldino、Gerard A. Pinna

  DOI：10.1016/j.tetlet.2007.07.050

  日期：2007.9

  1-dibromoalkenes is reported. The method is hinged upon the Suzuki–Miyaura cross-coupling of 2-aryl- or 2-heteroaryl-1,1-dibromoalkenes with aryl or heteroaryl boronic acids or borate esters followed by dehydrobromination of the intermediate coupled products. Yields up to 89% were obtained.

  报道了一种由1，1-二溴烯烃一锅法合成内部炔烃的方案。该方法取决于2-芳基或2-杂芳基-1,1-二溴烯烃与芳基或杂芳基硼酸或硼酸酯的Suzuki-Miyaura交叉偶联，然后进行中间偶联产物的脱氢溴化反应。获得了高达89％的产率。
• Rhodium-catalyzed cross-coupling of aryl carbamates with arylboron reagents
  作者：Keisuke Nakamura、Kosuke Yasui、Mamoru Tobisu、Naoto Chatani

  DOI：10.1016/j.tet.2015.02.088

  日期：2015.7

  A new method has been developed for the rhodium-catalyzed cross-coupling of aryl carbamates with organoboron reagents. The use of an NHC ligand bearing a 2-adamantyl group, i.e., I(2-Ad), is essential to the success of the reaction. The reaction involves the rhodium-mediated activation of the relatively inert C(aryl)-O bond of aryl carbamates.

  已经开发出一种新方法，用于铑催化的氨基甲酸芳基酯与有机硼试剂的交叉偶联。使用带有2-金刚烷基，即I（2-Ad）的NHC配体对于反应成功是必不可少的。该反应涉及铑介导的氨基甲酸芳基酯的相对惰性的C（芳基）-O键的活化。
• Copper‐Catalyzed Oxidative Arylation of Heteroarenes under Mild Conditions Using Dioxygen as the Sole Oxidant
  作者：Fanzhi Yang、Zhaoqing Xu、Zhe Wang、Zhengkun Yu、Rui Wang

  DOI：10.1002/chem.201100136

  日期：2011.5.27

  Dioxy‐gently does it! A new copper‐catalyzed oxidative cross‐coupling reaction between heteroarenes and arylboronic esters has been developed. Uniformly high yields are obtained by using dioxygen as the sole oxidant under mild conditions (see scheme).

  强力地做到这一点！杂芳烃和芳基硼酸酯之间的铜催化氧化交叉偶联反应得到了发展。通过在温和的条件下使用双氧作为唯一的氧化剂，可获得一致的高收率（参见方案）。