2,6-二氯-3-吡啶硼酸 | 148493-34-9

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 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: 2,6-二氯-3-吡啶硼酸
• 中文别名: 2,6-二氯吡啶-3-硼酸
• 英文名称: (2,6-dichloropyridin-3-yl)boronic acid
• 英文别名: 2,6-dichloro-3-pyridinylboronic acid；2,6-Dichloropyridine-3-boronic acid
• CAS: 148493-34-9
• 化学式: C₅H₄BCl₂NO₂
• mdl: MFCD03094989
• 分子量: 191.809
• InChiKey: XBBLBQZAVMHEER-UHFFFAOYSA-N

物化性质

• 熔点：
  150°C(lit.)
• 沸点：
  373.7±52.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)
• 稳定性/保质期：

  避氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37
• 危险类别码：
  R36/37/38,R22
• 海关编码：
  2933399090
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  保存方法：密封、阴凉、通风干燥处。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2,6-Dichloropyridine-3-boronic acid
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.
2,6-Dichloropyridine-3-boronic acid
Ingredient name:
CAS number: 148493-34-9

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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, 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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C5H4BCl2NO2
Molecular weight: 191.8

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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 chloride.

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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

2,6-二氯-3-吡啶硼酸是一种有机中间体，可通过在-78℃下将2,6-二氯吡啶与硼酸三异丙酯反应一步制备得到。

应用

有文献报道，2,6-二氯-3-吡啶硼酸可用于制备新型双卤代乙酰化杂环菊酯。

制备

在-78℃下，将4毫升二异丙胺溶解于60毫升四氢呋喃（THF）中，并滴加1.55M正丁基锂/正己烷溶液20毫升。搅拌30分钟后，在相同温度下滴加2,6-二氯吡啶（2.0克）和10毫升THF的混合物，继续搅拌1小时。随后，再向其中滴加硼酸三异丙酯（6.8毫升）与10毫升THF的混合物，并在室温下搅拌20小时。

反应混合物用水稀释后用盐酸中和，然后使用乙酸乙酯萃取。有机层用蒸馏水洗涤并用硫酸镁干燥，最后在减压下浓缩，得到2,6-二氯-3-吡啶硼酸（2.6克）。

反应信息

• 作为反应物：
  描述：

  2,6-二氯-3-吡啶硼酸 在 N-硝基琥珀酰亚胺 、 tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate 作用下， 以 乙腈 为溶剂， 反应 19.0h， 以65%的产率得到2,6-二氯-3-硝基吡啶
  参考文献：
  名称：

  N-硝基杂环：用于芳基和杂芳基硼酸的催化Ipso硝化的稳定型有机试剂。

  摘要：

  光催化与通过不含金属的协议来访问各种芳族和杂芳族硝基化合物本位基于非金属使用被开发容易得到的硼酸衍生物的-nitration，长凳稳定的，并可回收硝化试剂。这些方法操作简便，温和，区域选择性，并且具有出色的官能团相容性，可提供高达99％的收率的所需产品。

  DOI：

  10.1021/acs.orglett.0c00671
• 作为产物：
  描述：

  2,6-二氯吡啶 在 正丁基锂 、 二异丙胺 、 硼酸三异丙酯 、 氢溴酸 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 4.0h， 以73%的产率得到2,6-二氯-3-吡啶硼酸
  参考文献：
  名称：

  铃木交叉偶联反应制备（二甲氧基和二卤吡啶基）硼酸和高度官能化的杂芳基吡啶

  摘要：

  我们报道了（2,6-二甲氧基-3-吡啶基）硼酸（2）、（2,3-二甲氧基-4-吡啶基）硼酸（4）、（2,6-二氟-3-吡啶基）的合成硼酸 (6)、(2,6-二氯-3-吡啶基) 硼酸 (8) 和 (2,3-二氯-4-吡啶基) 硼酸 (10) 通过在相应的双取代吡啶上进行定向邻位金属化反应前体，然后与硼酸三异丙酯 (TPB) 或硼酸三甲酯反应。已经评估了吡啶基硼酸与杂芳基卤化物在 Suzuki-Miyaura 交叉偶联反应中的反应性。从而以中等至高产率获得了新的高度官能化的杂芳基吡啶衍生物。8 和 3-氨基-2-氯吡啶反应生成稀有的 5H-吡咯并[2,3-b:4,5-b']二吡啶（即 1, 5-二氮杂咔唑）环系统通过顺序交叉偶联和分子内环化反应。报道了吡啶基硼酸 2、4、8 和 10 的 X 射线晶体结构。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim

  DOI：

  10.1002/ejoc.200701156

文献信息

• [EN] 9H-PYRROLO-DIPYRIDINE DERIVATIVES<br/>[FR] DÉRIVÉS DE 9H-PYRROLO-DIPYRIDINE
  申请人：UCB BIOPHARMA SPRL

  公开号：WO2016124508A1

  公开（公告）日：2016-08-11

  The invention relates to 9H-pyrrolo-dipyridine derivatives of formula I, processes for preparing them, pharmaceutical compositions containing them and their use as radiopharmaceuticals in particular as imaging agents for the detection of Tau aggregates.

  这项发明涉及到式I的9H-吡咯-二吡啶衍生物，以及制备它们的方法、含有它们的药物组合物以及它们作为放射性药物的用途，特别是作为检测Tau聚集体的成像剂。
• TRICYCLIC CRBN LIGANDS AND USES THEREOF
  申请人：Kymera Therapeutics, Inc.

  公开号：US20200010468A1

  公开（公告）日：2020-01-09

  The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of CRBN, and the treatment of CRBN-mediated disorders.

  本发明提供了化合物、其组合物以及使用这些化合物抑制CRBN和治疗CRBN介导的疾病的方法。
• Development of a safe and scalable route towards a tau PET tracer precursor
  作者：Bjoern Bartels、Philipp Cueni、Dieter Muri、Matthias Koerner

  DOI：10.1016/j.bmc.2017.10.007

  日期：2018.2

  A scalable 5-step synthesis of the diazacarbazole derivative 1 used as tau PET tracer precursor is reported. Key features of this synthesis include a Buchwald-Hartwig amination, a Pd catalyzed CH activation and a Suzuki-Miyaura cross-coupling.

  据报道用作tau PET示踪剂前体的重氮咔唑衍生物1的可扩展的5步合成。该合成的关键特征包括布赫瓦尔德-哈特维格胺胺化，钯催化的C H活化和铃木-宫浦交叉偶联。
• TETRACYCLIC HETEROCYCLE COMPOUNDS AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES
  申请人：MERCK SHARP & DOHME CORP.

  公开号：US20140213571A1

  公开（公告）日：2014-07-31

  The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5B polymerase inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5B polymerase activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.

  本发明涉及公式（I）的化合物，这些化合物可用作丙型肝炎病毒（HCV）NS5B聚合酶抑制剂，以及这些化合物的合成，以及将这些化合物用于抑制HCV NS5B聚合酶活性，用于治疗或预防HCV感染，以及用于在基于细胞的系统中抑制HCV病毒复制和/或病毒产生。
• Ligand-Regulated Palladium-Catalyzed Regiodivergent Hydroarylation of the Distal Double Bond of Allenamides with Aryl Boronic Acid
  作者：Xin Du、Huan Zhao、Xinling Li、Lizhi Zhang、Yunhui Dong、Ping Wang、Daopeng Zhang、Qing Liu、Hui Liu

  DOI：10.1021/acs.joc.1c01303

  日期：2021.10.1

  inducing excellent E selectivity and anti-Markovnikov selectivity. (2) A switch of regioselectivity to 1,2-Markovnikov hydroarylation was obtained using bidentate phosphine ligand (dppf or Xantphos). The formed coordination Intermediate II led to the N-tether away from the Intermediate II and at the trans position of aryl, resulting in excellent E selectivity and Markovnikov selectivity. Meanwhile, tentative

  在钯 (II) 催化剂存在下，实现了烯酰胺远端双键与芳基硼酸的配体调节区域发散加氢芳基化，提供了各种具有优异 E 选择性和马尔科夫尼科夫/反马尔科夫尼科夫选择性的官能化烯酰胺。提出了两种可能的配位中间体负责区域发散的氢化芳基化：（1）配位中间体 I，提议通过 MeCN、远端双键、苯基与钯的配位形成，导致芳基远离中间体 I，诱导优异的 E 选择性和抗马尔科夫尼科夫选择性。(2) 区域选择性转换为 1,2- Markovnikov使用双齿膦配体（dppf 或 Xantphos）获得氢芳基化。形成的配位中间体 II导致 N-tether 远离中间体 II并位于芳基的反式位置，从而导致优异的 E 选择性和马尔可夫尼科夫选择性。同时，对机理的初步研究证明，这种加氢芳基化的氢源更可能是硼酸。芳基硼酸和钯催化剂之间的金属转移是这种转变的第一步。