2,6-二溴-4-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)吡啶 | 1192037-24-3

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸酯
• 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: 2,6-二溴-4-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)吡啶
• 中文别名: 2,6-二溴吡啶-4-硼酸酯
• 英文名称: 2,6-dibromo-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• CAS: 1192037-24-3
• 化学式: C₁₁H₁₄BBr₂NO₂
• 分子量: 362.857
• InChiKey: GGABMANFVFZXDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2,6-Dibromopyridine-4-boronic acid pinacol ester
Synonyms: 2,6-Dibromo-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

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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: 2,6-Dibromopyridine-4-boronic acid pinacol ester
CAS number: 1192037-24-3

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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, under −20◦C.
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: C11H14BBr2NO2
Molecular weight: 362.9

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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, hydrogen bromide.

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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：

  2,6-二溴-4-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 Oxone 、 potassium fluoride 、 copper(l) iodide 、 水 、 sodium hydride 、 二异丙胺 、 三对苯甲基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 生成 2,6-bis(2-pyridylethynyl)-4-methoxymethoxypyridine
  参考文献：
  名称：

  Rate enhancement of hexose sugar oxidation on an ethynylpyridine-functionalized Pt/Al2O3 catalyst with induced chirality

  摘要：

  在功能化的乙炔吡啶（EPy）-铂/铝氧化物催化剂上，实现了对六碳糖选择性氧化反应的速率提升。EPy配体与六碳糖反应物之间的宿主- guest相互作用生成了一种在催化剂表面引发手性复杂的复合物。

  DOI：

  10.1039/c3cc43482f
• 作为产物：
  描述：

  2,6-二溴吡啶 、 频那醇硼烷 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 甲基环己烷 为溶剂， 反应 3.0h， 以90%的产率得到2,6-二溴-4-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)吡啶
  参考文献：
  名称：

  钳型配体中的稳定化亚镓：PGaIP-Ir配合物的合成，结构和反应性

  摘要：

  利用双（膦基）吡啶作为Ir-Ga I键的有效骨架，成功地合成了具有钳型亚镓配体的铱配合物。钳型结构对亚镓部分的稳定作用使Ir能够进行各种反应，同时又保持了亚镓配体的完整性，从而导致了PGa I P-Ir配合物的独特结构和反应性。

  DOI：

  10.1002/anie.201904968

文献信息

• Microwave-assisted, Ir-catalyzed aromatic C–H borylation
  作者：Li Zeqing、Liang Zhibin、Wang Yuqiang、Yu Pei

  DOI：10.1007/s11164-012-0725-4

  日期：2013.4

  One-step conversions of 1,3-disubstituted benzenes to aryl boronates and 2,6-disubstituted pyridines to heteroaryl boronates are described. Microwave heating was used for all reactions. [(COD)Ir(μ-OMe)]2 and 4,4′-di-tert-butyl-2,2′-bipyridine were used as catalysts, in methyl tert-butyl ether. Acceleration of the rate of reaction was remarkable compared with that of same reaction under conventional heating conditions.

  一步法将1,3-二取代苯转化为芳基硼酸盐，以及将2,6-二取代吡啶转化为杂芳基硼酸盐的反应被描述。所有反应均采用微波加热。使用[(COD)Ir(μ-OMe)]2和4,4′-二叔丁基-2,2′-联吡啶作为催化剂，溶剂为甲基叔丁基醚。与传统加热条件下的相同反应相比，反应速率的加速效果显著。
• Radiosynthesis and evaluation of 4-(6-[¹⁸F]Fluoro-4-(5-isopropoxy-1<i>H</i>-indazol-3-yl)pyridin-2-yl)morpholine as a novel radiotracer candidate targeting leucine-rich repeat kinase 2
  作者：Wakana Mori、Tomoteru Yamasaki、Yasushi Hattori、Yiding Zhang、Katsushi Kumata、Masayuki Fujinaga、Masayuki Hanyu、Nobuki Nengaki、Hong Zhang、Ming-Rong Zhang

  DOI：10.1039/c9md00590k

  日期：——

  with fluorine-18 (18F), to develop a positron emission tomography (PET) tracer for in vivo visualization of LRRK2 in the brain. FIPM showed high in vitro binding affinity for LRRK2 (IC50 = 8.0 nM). [18F]FIPM was prepared in 5% radiochemical yield (n = 5), by inserting 18F into a pyridine ring, followed by removal of the protecting group. After HPLC separation and formulation, [18F]FIPM was acquired

  增加大脑中富含亮氨酸的重复激酶2（LRRK2）活性的突变与帕金森氏病有关。在这里，我们合成了新型化合物4-（6-氟-4-（5-异丙氧基-1 H-吲唑-3-基）吡啶-2-基）吗啉（FIPM），并用氟18（18 F ），以开发正电子发射断层扫描（PET）示踪剂，以在体内可视化LRRK2在大脑中。FIPM对LRRK2表现出很高的体外结合亲和力（IC 50 = 8.0 nM）。通过将18 F插入吡啶环，然后除去保护基，可以以5％的放射化学收率（n = 5）制备[ 18 F] FIPM 。HPLC分离和配制后，[获得18 F] FIPM，其放射化学纯度> 97％，在放射合成结束时的摩尔活性为103-300 GBqμmol - 1。小鼠的生物分布和小动物PET研究表明[ 18 F] FIPM的体内特异性结合率低。尽管[ 18 F] FIPM作为LRRK2的体内PET示踪剂显示出有限的潜力，但我们建议将
• Access to C(sp³) borylated and silylated cyclic molecules: hydrogenation of corresponding arenes and heteroarenes
  作者：Arzoo Chhabra、Sabrina Reich、Timothy M. Shannon、Robert E. Maleczka、Milton R. Smith

  DOI：10.1039/d4ra00491d

  日期：2024.3.26

  Readily available and bench stable catalyst. Tolerates a variety of functional groups including orthogonal functionality. Circumvents the limitations of sp³ C–H borylation.
• Rate enhancement of hexose sugar oxidation on an ethynylpyridine-functionalized Pt/Al2O3 catalyst with induced chirality
  作者：Minoru Waki、Satoshi Muratsugu、Mizuki Tada

  DOI：10.1039/c3cc43482f

  日期：——

  Rate enhancement of the selective oxidation of hexoses was achieved on an ethynylpyridine (EPy)-functionalized Pt/Al2O3 catalyst. Host–guest interaction between the EPy ligand and a hexose sugar reactant produced a complex with induced chirality on the catalyst surface.

  在功能化的乙炔吡啶（EPy）-铂/铝氧化物催化剂上，实现了对六碳糖选择性氧化反应的速率提升。EPy配体与六碳糖反应物之间的宿主- guest相互作用生成了一种在催化剂表面引发手性复杂的复合物。
• Stabilized Gallylene in a Pincer‐Type Ligand: Synthesis, Structure, and Reactivity of PGa ^I P‐Ir Complexes
  作者：Narumasa Saito、Jun Takaya、Nobuharu Iwasawa

  DOI：10.1002/anie.201904968

  日期：2019.7.15

  Iridium complexes having a pincer‐type gallylene ligand were successfully synthesized utilizing bis(phosphino)terpyridine as an efficient scaffold for the Ir−GaI bond. The stabilization of the gallylene moiety by the pincer‐type structure enabled various reactions at Ir with keeping the gallylene ligand intact, leading to unique structures and reactivities of PGaIP−Ir complexes.

  利用双（膦基）吡啶作为Ir-Ga I键的有效骨架，成功地合成了具有钳型亚镓配体的铱配合物。钳型结构对亚镓部分的稳定作用使Ir能够进行各种反应，同时又保持了亚镓配体的完整性，从而导致了PGa I P-Ir配合物的独特结构和反应性。