吡咯酮 | 1141-06-6

• 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 - 有机氧化合物
• 中文名称: 吡咯酮
• 中文别名: Α-吡啶偶姻
• 英文名称: 2-hydroxy-1,2-di-2-pyridylethanone
• 英文别名: 2-pyridoin；alpha-Pyridoin；2-hydroxy-1,2-dipyridin-2-ylethanone
• CAS: 1141-06-6
• 化学式: C₁₂H₁₀N₂O₂
• mdl: MFCD00010691
• 分子量: 214.224
• InChiKey: ZKBDAJDDDOIASC-UHFFFAOYSA-N

物化性质

• 熔点：
  156-160 °C(lit.)
• 沸点：
  354.35°C (rough estimate)
• 密度：
  1.2042 (rough estimate)
• 溶解度：
  DMSO（少量）、甲醇（少量）
• 稳定性/保质期：
  常温常压下稳定，避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  63.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2933399090
• 安全说明：
  S26,S37/39
• 储存条件：
  密封保存，应储存在阴凉干燥的仓库中。

SDS

Name:	alpha-Pyridoin 99% Material Safety Data Sheet
Synonym:
CAS:	1141-06-6

Section 1 - Chemical Product MSDS Name:alpha-Pyridoin 99% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1141-06-6	_-Pyridoin, 99%		214-526-5

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
The toxicological properties of this material have not been investigated. Use appropriate procedures to prevent opportunities for direct contact with the skin or eyes and to prevent inhalation.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids.
Skin:
Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Keep container closed when not in use.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate general or local exhaust ventilation to keep airborne concentrations below the permissible exposure limits. Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 1141-06-6: Personal Protective Equipment Eyes: Wear safety glasses and chemical goggles if splashing is possible.
Skin:
Wear appropriate protective gloves and clothing to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
Wear a NIOSH/MSHA or European Standard EN 149 approved full-facepiece airline respirator in the positive pressure mode with emergency escape provisions.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: red-brown
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: @ 760.00mm Hg
Freezing/Melting Point: 156.00 - 160.00 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C12H10N2O2
Molecular Weight: 214.22

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Not available.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1141-06-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
_-Pyridoin, 99% - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 1141-06-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1141-06-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1141-06-6 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  二(2-吡啶基)乙二酮	2,2'-Pyridil	492-73-9	C12H8N2O2	212.208

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	1,2-di-2-pyridylethanol	100142-26-5	C12H12N2O	200.24
  二(2-吡啶基)乙二酮	2,2'-Pyridil	492-73-9	C12H8N2O2	212.208
  1,2-二(2-吡啶基)乙二醇	1,2-di(2-pyridyl)-1,2-ethanediol	1141-05-5	C12H12N2O2	216.239

反应信息

• 作为反应物：
  描述：

  吡咯酮 在 lead(IV) acetate 、 盐酸 、 serpentine 、 钯 、 苯 作用下， 生成 吡啶-2-甲醛
  参考文献：
  名称：

  Mathes et al., Chemische Berichte, 1951, vol. 84, p. 452,456

  摘要：

  DOI：
• 作为产物：
  描述：

  吡啶-2-甲醛 在 TEA 、 N,N'-二甲基苯并咪唑鎓碘化物 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以70%的产率得到吡咯酮
  参考文献：
  名称：

  Catalytic Action of Azolium Salts. VI. Preparation of Benzoins and Acyloins by Condensation of Aldehydes Catalyzed by Azolium Salts.

  摘要：

  苯偶姻 4（在 1- 和 2-位置上带有芳基取代的 2-羟基乙酮）通过使用少量的唑盐 1 和 2 作为催化剂，由芳香醛 3 的自缩合反应高效制备得到。1,3-二甲基苯并咪唑碘盐（2）是制备乙偶姻 6（在 1- 和 2-位置上带有烷基取代的 2-羟基乙酮）的有效催化剂，通过脂肪醛 5 的自缩合反应实现。另一方面，使用 1,3-二甲基咪唑碘盐（1）催化己醛（5d）的缩合反应未能得到乙偶姻 6d，而是得到了醛醇型缩合产物 8d。

  DOI：

  10.1248/cpb.42.2633

文献信息

• New Route to Synthesis of Unexpected Pyridoin Derivatives: Their Structure Determination with Spectroscopic and X-Ray Methods
  作者：Alaaddin Cukurovali

  DOI：10.1080/00397910902906537

  日期：2009.11.18

  new 1,2,4-triazine-3-thione derivatives were obtained by a new route using a one-step process. The structure of the compounds was determined with infrared (IR), 1H NMR, and 13C NMR spectroscopic methods and elemental analysis. A representative x-ray crystallographic analysis of 3 was given, and its x-ray data are discussed in detail. This is a facile procedure and shorter than earlier methods.

  摘要 新的1,2,4-三嗪-3-硫酮衍生物通过一条新的路线一步法获得。化合物的结构通过红外(IR)、1H NMR和13C NMR光谱方法和元素分析确定。给出了 3 的代表性 X 射线晶体学分析，并详细讨论了其 X 射线数据。这是一个简单的过程并且比早期的方法更短。
• Chemoselective control of hydrogenation among aromatic carbonyl and benzyl alcohol derivatives using Pd/C(en) catalyst
  作者：Kazuyuki Hattori、Hironao Sajiki、Kosaku Hirota

  DOI：10.1016/s0040-4020(01)00421-5

  日期：2001.6

  of aromatic ketones and aldehydes quite smoothly give the corresponding methylene compounds via the formation of the intermediary benzyl alcohols in the presence of Pd/C as a catalyst. Therefore, it is extremely difficult to isolate the intermediary benzyl alcohol selectively. This paper describes a mild and chemoselective hydrogenation method of an aromatic carbonyl compound to benzyl alcohol using

  芳族酮和醛的氢解通过在Pd / C作为催化剂存在下形成中间体苄醇而非常顺利地得到相应的亚甲基化合物。因此，极其难于选择性地分离中间体苄醇。本文介绍了使用10％Pd / C（en）催化剂对芳族羰基化合物进行温和的化学选择性加氢制苯甲醇的方法，并将其应用于在苄基位置上存在苄醇官能团的情况下，在苄基位置进行化学选择性脱乙酰氧基化反应。分子。
• CaO-catalyzed Aerobic Oxidation of α-Hydroxy Ketones: Application to One-pot Synthesis of Quinoxaline Derivatives
  作者：Takayoshi Hara、Yukihiro Takami、Nobuyuki Ichikuni、Shogo Shimazu

  DOI：10.1246/cl.2012.488

  日期：2012.5.5

  The aerobic oxidation of α-hydroxy ketones into α-diketones catalyzed by CaO is compared with the same reaction catalyzed by other metal oxides. The catalytic activities of the various metal oxides were proportional to their surface basicities. The direct conversion of α-hydroxy ketones into quinoxalines via CaO-catalyzed aerobic oxidation followed by in situ reaction with 1,2-diaminoaromatics is also achieved. Various types of quinoxalines were synthesized in the presence of the CaO catalyst and molecular oxygen. It was also found that the CaO catalyst was reusable without any loss of its catalytic activity.

  通过比较CaO与其他金属氧化物催化α-羟基酮到α-二酮的好氧氧化反应，研究了CaO的催化活性。各种金属氧化物的催化活性与其表面碱性成正比。通过CaO催化的好氧氧化反应，直接将α-羟基酮转化为喹喉，并在原位与1,2-二氨基芳香化合物反应，也实现了这一转化。在CaO催化剂和分子氧的存在下，合成了各种类型的喹喔啉。还发现CaO催化剂可以重复使用，且没有任何催化活性的损失。
• Stetter Reaction in Room Temperature Ionic Liquids and Application to the Synthesis of Haloperidol
  作者：Siddam Anjaiah、Srivari Chandrasekhar、René Grée

  DOI：10.1002/adsc.200404123

  日期：2004.9

  Imidazolium-type room temperature ionic liquids (RTILs) have been used for the Stetter reaction, affording the desired 1,4-dicarbonyl compounds in good yields. Thiazolium salts and Et3N are efficient catalysts for this reaction performed in ionic liquid. The possibility to recycle and reuse the solvent has been demonstrated, although it was not possible to recycle the thiazolium catalyst. This method

  咪唑型室温离子液体（RTIL）已用于Stetter反应，以良好的收率提供了所需的1,4-二羰基化合物。噻唑鎓盐和Et 3 N是在离子液体中进行该反应的有效催化剂。已经证明了再循环和再利用溶剂的可能性，尽管不可能再循环噻唑鎓催化剂。该方法用于氟哌啶醇的全合成。
• Catalytic Action of Triarylstibanes: Oxidation of Benzoins into Benzyls Using Triarylstibanes Under an Aerobic Condition
  作者：Shuji Yasuike、Yoshihito Kishi、Shin-ichiro Kawara、Jyoji Kurita

  DOI：10.1248/cpb.53.425

  日期：——

  Benzoins are simply oxidized to benzils in excellent yields with a catalytic amount of triarylstibanes under an aerobic condition. This catalytic oxidation is heteroatom-specific in the antimony compound and no reaction take place with other group 15 reagents such as triphenylphosphane, -arsane and -bismuthane. The reaction should involve an oxidation-reduction cycle between stibane Sb(III) and stiborane

  在好氧条件下，将苯偶姻简单地以极高的收率氧化为苯甲酰，并催化量的三芳基芪酯。该催化氧化在锑化合物中是杂原子特有的，并且不与其他第15组试剂（如三苯基膦，-ar烷和-铋烷）发生反应。该反应应包括在空气中斯蒂巴烷Sb（III）和斯蒂硼烷Sb（V）之间的氧化还原循环。

表征谱图