3,5-二氯吡啶 N-氧化物 | 15177-57-8

• 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: 3,5-二氯吡啶 N-氧化物
• 中文别名: 3,5-二氯吡啶N-氧化物；3,5-二氯吡啶1-氧化物；3,5-二氯吡啶-1-氧化物
• 英文名称: 3,5-dicholoropyridine N-oxide
• 英文别名: 3,5-dichloropyridine N-oxide；3,5-dichloropyridine 1-oxide；3,5-dichloro-1-oxidopyridin-1-ium
• CAS: 15177-57-8
• 化学式: C₅H₃Cl₂NO
• mdl: MFCD00955620
• 分子量: 163.991
• InChiKey: RODXBOIDZPQDBH-UHFFFAOYSA-N

物化性质

• 熔点：
  110-113 °C(lit.)
• 沸点：
  344.2±22.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.5
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26
• 危险类别码：
  R36/37/38
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将产品存放在阴凉干燥处并保持密封。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3,5-Dichloropyridine 1-oxide
Synonyms: 3,5-Dichloropyridine N-oxide

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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: 3,5-Dichloropyridine 1-oxide
CAS number: 15177-57-8

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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.

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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: C5H3Cl2NO
Molecular weight: 164.0

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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, 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

反应信息

• 作为反应物：
  描述：

  3,5-二氯吡啶 N-氧化物 在 频哪醇 、 {MoO2Cl2(dmf)2} 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以95%的产率得到3,5-二氯吡啶
  参考文献：
  名称：

  频哪醇为还原剂的钼催化杂芳族N-氧化物和氢氧化物的脱氧

  摘要：

  的吡啶甲钼催化脱氧Ñ -oxides和Ñ -hydroxybenzotriazoles，以及其它唑Ñ -oxides，使用频哪醇作为环保氧代受体已经研制成功。唯一的副产品是丙酮和水，使该工艺成为废物生成方面既定规程的便捷替代方案。该反应是高度化学选择性的，并且可以容忍各种官能团。该过程通常非常干净，在大多数情况下，经过简单的萃取即可分离出纯净的脱氧产物。

  DOI：

  10.1002/adsc.201700071
• 作为产物：
  描述：

  3,5-二氯吡啶 在 双氧水 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以70%的产率得到3,5-二氯吡啶 N-氧化物
  参考文献：
  名称：

  异构的三氘和四氘吡啶的合成及光谱性质

  摘要：

  描述了六个可能的异构的三氘吡啶和三个可能的异构的四氘吡啶的合成。这些氘代吡啶通过它们的质量和NMR谱来表征。

  DOI：

  10.1002/jhet.5570440637
• 作为试剂：
  描述：

  苯丙炔酸乙酯 、 丙腈 在 3,5-二氯吡啶 N-氧化物 、 1,3-双(2,6-二-异丙基苯基)咪唑-2-亚基金(I)氯化物 、 双三氟甲烷磺酰亚胺银盐 作用下， 反应 3.0h， 以83%的产率得到6,7-dihydro-2-methylbenzo[d]oxazole-4(5H)-one
  参考文献：
  名称：

  金催化的酸辅助区域选择性环化反应合成多取代的恶唑

  摘要：

  多取代的恶唑衍生物是通过在腈存在下，α-炔基酰胺和炔酸的区域选择性金催化反应获得的。中间体获得的金卡宾是通过吡啶N-氧化物进行炔烃氧化而生成的。酸性条件确保这些中间体中的两个羰基氧原子中只有一个以优良的收率选择性地环化成产物。

  DOI：

  10.1002/ejoc.201900699

文献信息

• Strategic Approach on <i>N</i> -Oxides in Gold Catalysis - A Case Study
  作者：Jasmin Schießl、Philipp M. Stein、Judith Stirn、Kirsten Emler、Matthias Rudolph、Frank Rominger、A. Stephen K. Hashmi

  DOI：10.1002/adsc.201801007

  日期：2019.2.19

  An extensive kinetic study of selected key reactions of (oxidative) gold catalysis concentrates on the decrease of the catalytic activity due to inhibition of the gold(I) catalyst caused by pyridine derivatives that are obtained as by‐products if N‐oxides are applied as oxygen donors. The choice of the examined pyridine derivatives and their corresponding N‐oxides has been made regardless of their

  对（氧化）金催化的选定关键反应的广泛动力学研究集中在催化活性的降低，这是由于吡啶衍生物引起的金（I）催化剂的抑制，如果使用N氧化物作为副产物获得的吡啶衍生物氧气供体。不管它们的市售性如何，都已对受检吡啶衍生物及其相应的N-氧化物进行了选择。特别注意的是迄今为止在大多数反应筛选中都被忽略的实际益处。用GC和1监测测试反应1 H NMR光谱。所接收的反应常数提供了关于杂环的电子结构与催化活性之间的相关性的信息。根据收集的动力学数据，有可能开发出一套基本的三种N氧化物，这些氧化物必须在进一步的氧化金（I）催化反应中加以考虑。
• Gold‐Catalyzed Oxidative Aminocyclizations of Propargyl Alcohols and Propargyl Amines to Form Two Distinct Azacyclic Products: Carbene Formation versus a 3,3‐Sigmatropic Shift of an Initial Intermediate
  作者：Amit Vijay Sasane、Antony Sekar Kulandai Raj、Tzu‐Hsuan Chao、Mu‐Jeng Chen、Rai‐Shung Liu

  DOI：10.1002/chem.202003840

  日期：2020.12.15

  Gold‐catalyzed oxidations of propargyl alcohols with nitrones by using a P(tBu)2(o‐biphenyl)Au+ catalyst, afforded bicyclic annulation products from the Mannich reactions of gold enolates. The same reactions of propargyl amines with nitrones by using the same gold catalyst gave distinct oxoarylation products. Our DFT calculations indicate that oxidation of propargyl alcohols with nitrones by using electron‐rich

  通过使用P（t Bu）2（邻联苯）Au +催化剂在金催化下用炔烃氧化炔丙醇，从烯醇金的曼尼希反应中得到双环环化产物。通过使用相同的金催化剂，炔丙基胺与硝酮的相同反应产生不同的羰基化产物。我们的DFT计算表明，通过使用富电子的金催化剂将炔丙醇与硝酮氧化仅会生成金卡宾，这些碳卡宾可以生成烯醇盐类金的烯醇盐或羰基化中间体，而烯醇盐类的阻挡层小于羰基化物种。
• [EN] AZABIPHENYLAMINOBENZOIC ACID DERIVATIVES AS DHODH INHIBITORS<br/>[FR] DÉRIVÉS D'ACIDE AZABIPHÉNYLAMINOBENZOÏQUE COMME INHIBITEURS DE LA DHODH
  申请人：ALMIRALL LAB

  公开号：WO2009021696A1

  公开（公告）日：2009-02-19

  New azabiphenylaminobenzoic acid derivatives having the chemcial structure of formula (I) are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of the dehydroorotate dihydrogenase (DHODH).

  揭示了具有化学结构式(I)的新的阿扎比苯胺基苯甲酸衍生物；以及它们的制备过程、包含它们的药物组合物以及它们在治疗中作为脱氢乳酸脱氢酶（DHODH）抑制剂的用途。
• Gold-Catalyzed Oxidative Cycloadditions to Activate a Quinoline Framework
  作者：Deepak B. Huple、Satish Ghorpade、Rai-Shung Liu

  DOI：10.1002/chem.201302533

  日期：2013.9.23

  gold! Gold‐catalyzed reactions of 3,5‐ and 3,6‐dienynes with 8‐alkylquinoline oxides results in an oxidative cycloaddition with high stereospecificity (see scheme; EWG = electron‐withdrawing group); this process involves a catalytic activation of a quinoline framework. The reaction mechanism involves the intermediacy of α‐carbonyl pyridinium ylides (I) in a concerted [3+2]‐cycloaddition with a tethered

  追求黄金！3,5-和3,6-二烯与8-烷基喹啉氧化物的金催化反应导致具有高立体特异性的氧化环加成反应（见方案； EWG =吸电子基团）；该过程涉及喹啉骨架的催化活化。该反应机理涉及α-羰基吡啶鎓烷基化物（I）与链状烯烃的协同[3 + 2] -环加成反应的中间过程。
• [EN] ANIONS AND DERIVED SALTS WITH HIGH DISSOCIATION IN NON-PROTOGENIC SOLVENTS<br/>[FR] ANIONS ET SELS DÉRIVÉS PRÉSENTANT UNE DISSOCIATION ÉLEVÉE DANS DES SOLVANTS NON PROTOGÈNES
  申请人：JONSSON ERLENDUR

  公开号：WO2013072470A1

  公开（公告）日：2013-05-23

  Salts with formula X-M+ wherein M+ is Li, Na, K, an ammonium, a phosphonium, an imidazolium, a pyridinium, or a pyrazolium and X- is an anion formed from covalent linking of two negative moieties to a positive onium-type core are provided. Also provided are electrolytes and batteries produced from these salts.

  提供了具有化学式X-M+的盐，其中M+为Li、Na、K、铵、磷铵、咪唑铵、吡啶铵或吡唑铵，而X-是由两个负基团共价连接到正的铵型核心形成的阴离子。还提供了由这些盐制备的电解质和电池。