1-(4-吡啶基)乙醇 | 23389-75-5

• 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: 1-(4-吡啶基)乙醇
• 中文别名: 1-(吡啶-4-基)乙醇
• 英文名称: 1-(4-Pyridyl)ethanol
• 英文别名: rac-1-(pyridin-4-yl)ethanol；1-(pyridin-4-yl)ethan-1-ol；1-(pyridin-4-yl)ethanol；(rac)-1-(pyridin-4-yl)ethan-1-ol；4-(1-hydroxyethyl)pyridine；1-pyridin-4-ylethanol
• CAS: 23389-75-5
• 化学式: C₇H₉NO
• mdl: MFCD00077867
• 分子量: 123.155
• InChiKey: HVOAMIOKNARIMR-UHFFFAOYSA-N

物化性质

• 熔点：
  51-55 °C
• 沸点：
  240℃
• 密度：
  1.082
• 闪点：
  99℃

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  T
• 安全说明：
  S22,S24/25
• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P280,P305+P351+P338,P304+P340,P405,P501
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
1-(Pyridin-4-yl)ethanol
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.
1-(Pyridin-4-yl)ethanol
Ingredient name:
CAS number: 23389-75-5

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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.

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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: C7H9NO
Molecular weight: 123.2

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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

制备方法与用途

用途 1-(4-吡啶基)乙醇用作研究用化合物。

反应信息

• 作为反应物：
  描述：

  1-(4-吡啶基)乙醇 在 甲基三氯硅烷 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到4-乙酰吡啶
  参考文献：
  名称：

  甲基三氯硅烷作为 Swern 氧化的有效活化剂

  摘要：

  摘要 已成功开发出实用且高效的 Swern 氧化替代版本。甲基三氯硅烷被用作二甲基亚砜的有效活化剂，它可以将多种伯醇和仲醇氧化成相应的羰基化合物，产率很高。图形概要

  DOI：

  10.1080/00397911.2014.912328
• 作为产物：
  描述：

  4-乙酰吡啶 在 C₂₆H₃₃ClN₅Ru⁽¹⁺⁾*BF₄^(1-) 、 potassium tert-butylate 作用下， 以 异丙醇 为溶剂， 反应 0.5h， 以98%的产率得到1-(4-吡啶基)乙醇
  参考文献：
  名称：

  1,2,3-三唑/三唑亚烷基侧基的异位Ru（II）-和Ir（III）-NHC配合物：对不饱和化合物转移加氢的立体电子影响

  摘要：

  咪唑-2-亚烷基（ImNHC）和1,2,3-三唑-5-亚烷基（tzNHC）已被确定为均相催化中卡宾配体的重要类别。考虑到氢化物转移反应的电子和空间分布，基于这些配体系统开发Ru（II）/ Ir（III）配合物，我们采用了以ImNHC和三唑-N或由CH桥接的中型tzNHC供体为特征的螯合配体2个在三唑主链上可能经过修饰的间隔子 通常，发现合成的Ru（II）配合物在还原酮和醛亚胺方面的性能明显优于类似的Ir（III）配合物。在Ru（II）配合物中，通式[（p -Cymene）（ImNHC–CH）的富电子配合物8/92 -tzNHC）的Ru II（CL）] BF 4具有两个不同的卡宾供体（ImNHC和tzNHC）被发现显着地在酮还原更好执行比ImNHC和三唑的组合类似络合物Ñ端供体（[（p - cymene）（ImNHC–CH 2 –tz–N）Ru II（Cl）] BF 4；4）解释了催化系统的

  DOI：

  10.1021/acs.organomet.9b00156

文献信息

• [EN] 2,4-DIAMINOQUINAZOLINES FOR SPINAL MUSCULAR ATROPHY<br/>[FR] 2,4-DIAMINOQUINAZOLINES UTILES POUR LE TRAITEMENT D'UNE ATROPHIE MUSCULAIRE SPINALE
  申请人：DECODE CHEMISTRY INC

  公开号：WO2005123724A1

  公开（公告）日：2005-12-29

  2,4-Diaminoquinazolines of formulae I-IV and VI (I, II, III, IV and VI) are useful for treating spinal muscular atrophy (SMA).

  2,4-二氨基喹唑啉的化学式I-IV和VI（I，II，III，IV和VI）可用于治疗脊髓性肌萎缩症（SMA）。
• Dynamic Kinetic Resolution of Alcohols by Enantioselective Silylation Enabled by Two Orthogonal Transition‐Metal Catalysts
  作者：Jan Seliger、Martin Oestreich

  DOI：10.1002/anie.202010484

  日期：2021.1.4

  A nonenzymatic dynamic kinetic resolution of acyclic and cyclic benzylic alcohols is reported. The approach merges rapid transition‐metal‐catalyzed alcohol racemization and enantioselective Cu‐H‐catalyzed dehydrogenative Si‐O coupling of alcohols and hydrosilanes. The catalytic processes are orthogonal, and the racemization catalyst does not promote any background reactions such as the racemization

  报道了无环和环状苯甲醇的非酶动态动力学拆分。该方法融合了快速过渡金属催化的醇外消旋化和对映选择性 Cu-H 催化的醇和氢硅烷的脱氢 Si-O 偶联。催化过程是正交的，并且外消旋催化剂不会促进任何背景反应，例如甲硅烷基醚的外消旋及其非选择性形成。常用的钌半夹心配合物并不合适，但双功能钌钳形配合物完美地实现了这一目的。由此，可以高产率和良好的对映选择水平实现外消旋醇混合物的对映选择性硅烷化。
• Ruthenium Complexes with PYA Pincer Ligands for Catalytic Transfer Hydrogenation of Challenging Substrates
  作者：Philipp Melle、Martin Albrecht

  DOI：10.2533/chimia.2019.299

  日期：——

  Here we highlight the potential of a series of ruthenium complexes with tridentate N,N,N pincer-type ligands featuring two pyridylidene amide (PYA) moieties in the ligand skeleton. They were successfully applied in transfer hydrogenation of ketones and C=C double bonds. Rational ligand design was key for increasing the catalytic performance in the reduction of challenging substrates such as potentially

  在这里，我们重点介绍了一系列具有三齿 N,N,N 钳型配体的钌配合物的潜力，该配体在配体骨架中具有两个吡啶基酰胺 (PYA) 部分。它们成功应用于酮和C=C双键的转移氢化。合理的配体设计是提高还原具有挑战性的底物（例如潜在螯合乙酰吡​​啶）的催化性能的关键。特定的反应曲线表明催化剂通过亚胺配位以及底物或产物的 N,O-二齿配位而中毒。提出了减轻这种抑制的方法。此外，这些PYA钳钌络合物实现了α，β-不饱和酮（例如亚苄基丙酮）的C=C相对于C=O键的选择性还原，而其他α，β-不饱和酮（例如反式查尔酮）主要经历氧化C= C键断裂。
• Modular Pincer-type Pyridylidene Amide Ruthenium(II) Complexes for Efficient Transfer Hydrogenation Catalysis
  作者：Philipp Melle、Yanisha Manoharan、Martin Albrecht

  DOI：10.1021/acs.inorgchem.8b01895

  日期：2018.9.17

  A set of bench-stable ruthenium complexes with new N,N,N-tridentate coordinating pincer-type pyridyl-bis(pyridylideneamide) ligands was synthesized in excellent yields, with the pyridylidene amide in meta or in para position (m-PYA and p-PYA, respectively). While complex [Ru(p-PYA)(MeCN)3]2+ is catalytically silent in transfer hydrogenation, its meta isomer [Ru(m-PYA)(MeCN)3]2+ shows considerable activity

  合成了一组具有新的N，N，N-三齿配位钳型吡啶基双（吡啶基亚酰胺）配体的长凳稳定钌络合物，吡啶基亚酰胺处于间位或对位（m- PYA和p -PYA）。而复杂的[Ru（p -PYA）（MeCN中）3 ] 2+是在转移氢化催化沉默，其元异构体的[Ru（米-PYA）（MeCN中）3 ] 2+示出了具有转换频率在50％的转化率相当大的活动TOF 50 = 100小时–1。光谱，电化学和晶体学分析表明，与两价的酸性p - PYA类似物相比，两价离子的m- PYA配体的供体性质明显强于化合价化。通过用亚胺（4-甲基吡啶），胺（乙二胺）和膦（PPh 3，dppm，dppe）交换辅助MeCN配体，可以实现进一步的催化剂优化。活性最高的催化剂由m -PYA钳形配体和PPh 3络合物[Ru（m- PYA）（PPh 3）（MeCN）2 ] 2+组成，TOF 50为430 h –1在有氧条件下，在没有氧气的情况下长达4000
• Manganese-catalyzed homogeneous hydrogenation of ketones and conjugate reduction of α,β-unsaturated carboxylic acid derivatives: A chemoselective, robust, and phosphine-free in situ-protocol
  作者：Thomas Vielhaber、Christoph Topf

  DOI：10.1016/j.apcata.2021.118280

  日期：2021.8

  glove-box-free catalytic protocol for the manganese-catalyzed hydrogenation of ketones and conjugated CCbonds of esters and nitriles. The respective catalyst is readily assembled in situ from the privileged [Mn(CO)5Br] precursor and cheap 2-picolylamine. The catalytic transformations were performed in the presence of t-BuOK whereby the corresponding hydrogenation products were obtained in good to excellent yields

  我们传达了一种用户友好且无需手套箱的催化协议，用于酮和酯和腈的共轭 C C键的锰催化氢化。相应的催化剂很容易由特权 [Mn(CO) 5 Br] 前体和廉价的 2-吡啶甲胺原位组装。催化转化在t- BuOK存在下进行，从而以良好至极好的收率获得相应的氢化产物。所描述的系统提供了对仲醇和饱和酯的快速和原子效率的访问，避免了使用氧敏感和昂贵的基于膦的配体。

表征谱图