6-氯-5-甲基吡啶-3-硼酸 | 1003043-40-0

• 物质功能分类: 医药中间体 - 杂环化合物 - 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: 6-氯-5-甲基吡啶-3-硼酸
• 中文别名: 2-氯-3-甲基吡啶-5-硼酸
• 英文名称: (6-chloro-5-methylpyridin-3-yl)boronic acid
• 英文别名: 2-Chloro-3-methylpyridine-5-boronic acid
• CAS: 1003043-40-0
• 化学式: C₆H₇BClNO₂
• mdl: MFCD03411564
• 分子量: 171.391
• InChiKey: WWOOKOBRTKSRLV-UHFFFAOYSA-N

物化性质

• 熔点：
  180-183°C
• 沸点：
  358.7±52.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 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：
  Xn
• 安全说明：
  S26,S36/37/39
• 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：
  P280,P305+P351+P338
• 危险性描述：
  H302

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-Chloro-3-methylpyridine-5-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-Chloro-3-methylpyridine-5-boronic acid
Ingredient name:
CAS number: 1003043-40-0

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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, 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: C6H7BClNO2
Molecular weight: 171.4

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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

6-氯-5-甲基吡啶-3-硼酸是一种常用的有机合成中间体和医药中间体，广泛应用于实验室研发及化工生产过程。

反应信息

• 作为反应物：
  描述：

  6-氯-5-甲基吡啶-3-硼酸 在 双氧水 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以93%的产率得到2-溴-5-羟基-3-甲基吡啶
  参考文献：
  名称：

  First Identification of Boronic Species as Novel Potential Inhibitors of the Staphylococcus aureus NorA Efflux Pump

  摘要：

  Overexpression of efflux pumps is an important mechanism of bacterial resistance that results in the extrusion of antimicrobial agents outside the bacterial cell. Inhibition of such pumps appears to be a promising strategy that could restore the potency of existing antibiotics. The NorA efflux pump of Staphylococcus aureus confers resistance to a wide range of unrelated substrates, such as hydrophilic fluoroquinolones, leading to a multidrug-resistance phenotype. In this work, approximately 150 heterocyclic boronic species were evaluated for their activity against susceptible and resistant strains of S. aureus. Twenty-four hit compounds, although inactive when tested alone, were found to potentiate ciprofloxacin activity by a 4-fold increase at concentrations ranging from 0.5 to 8 μg/mL against S. aureus 1199B, which overexpresses NorA. Boron-free analogues showed no biological activity, thus revealing that the boron atom is crucial for biological activity. This work describes the first reported efflux pump inhibitory activity of boronic acid derivatives.

  DOI：

  10.1021/jm401808n

文献信息

• [EN] INDANE AND INDOLINE DERIVATIVES AND THE USE THEREOF AS SOLUBLE GUANYLATE CYCLASE ACTIVATORS<br/>[FR] DÉRIVÉS D'INDANE ET D'INDOLINE ET LEUR UTILISATION EN TANT QU'ACTIVATEURS DE LA GUANYLATE CYCLASE SOLUBLE
  申请人：NOVARTIS AG

  公开号：WO2016001875A1

  公开（公告）日：2016-01-07

  The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof; a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

  本发明提供了化合物(I)或其药学上可接受的盐；制造本发明化合物的方法及其治疗用途。本发明还提供了药理活性剂的组合和制药组合物。
• FUSED HETEROCYCLIC COMPOUNDS AS ION CHANNEL MODULATORS
  申请人：Corkey Britton

  公开号：US20110021521A1

  公开（公告）日：2011-01-27

  The present invention relates to compounds that are sodium channel inhibitors and to their use in the treatment of various disease states, including cardiovascular diseases and diabetes. In particular embodiments, the structure of the compounds is given by Formula I: wherein W 1 , W 2 , W 3 , R 1 , Q, X 1 , X 2 and X 3 are as described herein, to methods for the preparation and use of the compounds and to pharmaceutical compositions containing the same.

  本发明涉及一类钠通道抑制剂化合物，以及它们在治疗各种疾病状态中的应用，包括心血管疾病和糖尿病。具体实施例中，该化合物的结构由下式给出：其中W1、W2、W3、R1、Q、X1、X2和X3如本文所述，以及制备和使用该化合物的方法，以及含有该化合物的药物组合物。
• 硼烷衍生物及其制备方法、电致发光器件
  申请人：广东聚华印刷显示技术有限公司

  公开号：CN111484513B

  公开（公告）日：2022-09-09

  本发明涉及一种硼烷衍生物及其制备方法、电致发光器件，其中，所述硼烷衍生物具有如下通式(I)的结构：式(I)中，R的结构为Ar1—Ar2；其中，Ar1为取代或未取代的缺电子芳香杂环基团，Ar2为取代或未取代的富电子芳香环基团，且Ar2与通式(I)中的乙烯基相连。该硼烷衍生物具有良好的溶解性和成膜性，通过热交联的方式形成于不溶于常规溶剂的交联型聚合物薄膜，且成膜后不易被下一层功能层的溶剂溶解，从而可以避免界面混溶和界面侵蚀的问题。因此，该硼烷衍生物特别适合使用溶液法加工制作大面积、低成本电致发光器件。
• Br vs. TsO Chemoselective Suzuki–Miyaura Cross‐Coupling Reaction on Nicotinaldehyde Moiety for the Preparation of 2,3,5‐Trisubstituted Pyridines
  作者：Damien Hédou、Anne Sophie Voisin‐Chiret

  DOI：10.1002/ejoc.202000417

  日期：2020.6.30

  Br vs. TsO chemoselective pallado‐catalyzed Suzuki–Miyaura reaction on nicotinaldehyde moiety allows the preparation of 2,3,5‐trisubstituted pyridines.

  Br对TsO的烟醛醛部分进行化学选择性的Pallado催化的Suzuki-Miyaura反应可以制备2,3,5-三取代的吡啶。
• Rhodium-Catalyzed Asymmetric Conjugate Pyridylation with Pyridylboronic Acids
  作者：Bihai Ye、Jian Yao、Changhui Wu、Huilong Zhu、Weijun Yao、Lili Jin、Xiaowei Dou

  DOI：10.1021/acscatal.1c05732

  日期：2022.2.18

  asymmetric arylation reaction has been extensively studied for chiral Csp2–Csp3 bond formation, the asymmetric pyridylation reaction remains a great challenge. In this study, the rhodium-catalyzed asymmetric conjugate pyridylation of α,β-unsaturated carbonyl compounds with pyridylboronic acids is reported. The bifunctional chiral amide-diene ligand, which dramatically accelerated the reaction via possible

  尽管不对称芳基化反应已被广泛研究用于手性 Csp 2 -Csp 3键的形成，但不对称吡啶基化反应仍然是一个巨大的挑战。在这项研究中，报道了铑催化的 α,β-不饱和羰基化合物与吡啶基硼酸的不对称共轭吡啶化反应。双功能手性酰胺-二烯配体通过可能的氢键活化显着加速反应，醇溶剂在铑催化下显着抑制吡啶基硼酸的竞争性原去硼化反应，共同促进反应，从而能够生产吡啶化产物的高产率（高达 99%）和良好的对映选择性（高达 >99% ee）。