N-乙酰丙酮吗啉 | 16695-54-8

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 中文名称: N-乙酰丙酮吗啉
• 中文别名: 4-吗啉-4-基-4-氧代-2-丁酮
• 英文名称: 1-(morpholin-4-yl)butane-1,3-dione
• 英文别名: 1-morpholinobutane-1,3-dione；N-acetoacetylmorpholine；4-(1,3-dioxobutyl)morpholine；Acetessigsaeure-morpholid；1-morpholin-4-ylbutane-1,3-dione
• CAS: 16695-54-8
• 化学式: C₈H₁₃NO₃
• mdl: MFCD00059774
• 分子量: 171.196
• InChiKey: RKPILPRSNWEZJV-UHFFFAOYSA-N

物化性质

• 熔点：
  68°C
• 沸点：
  140°C 2mm
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• 危险性防范说明：
  P264,P280,P305+P351+P338,P337+P313
• 危险性描述：
  H319
• 储存条件：
  室温且干燥

SDS

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Section I.Chemical Product and Company Identification
Chemical Name N-Acetoacetylmorpholine
Portland OR
Synonym N-(N-Morpholino)acetophenone
Chemical Formula C8H13NO3
CAS Number 16695-54-8

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Section II. Composition and Information on Ingredients
Chemical Name CAS Number Percent (%) TLV/PEL Toxicology Data
N-Acetoacetylmorpholine 16695-54-8 Min. 98.0 (T) Not available. Not available.

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Section III. Hazards Identification
Acute Health Effects No specific information is available in our data base regarding the toxic effects of this material for humans. However,
exposure to any chemical should be kept to a minimum. Skin and eye contact may result in irritation. May be harmful if
inhaled or ingested. Always follow safe industrial hygiene practices and wear proper protective equipment when handling
this compound.
CARCINOGENIC EFFECTS : Not available.
Chronic Health Effects
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
Toxicity to the reproductive system: Not available.
There is no known effect from chronic exposure to this product. Repeated or prolonged exposure to this compound is
not known to aggravate existing medical conditions.

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Section IV. First Aid Measures
Eye Contact Check for and remove any contact lenses. DO NOT use an eye ointment. Flush eyes with running water for a minimum
of 15 minutes, occasionally lifting the upper and lower eyelids. Seek medical attention. Treat symptomatically and
supportively.
Skin Contact
If the chemical gets spilled on a clothed portion of the body, remove the contaminated clothes as quickly as possible,
protecting your own hands and body. Place the victim under a deluge shower. If the chemical touches the victim's
exposed skin, such as the hands: Gently and thoroughly wash the contaminated skin with running water and non-abrasive
soap. Be particularly careful to clean folds, crevices, creases and groin. Cover the irritated skin with an emollient. Seek
medical attention. Treat symptomatically and supportively. Wash any contaminated clothing before reusing.
Inhalation If the victim is not breathing, perform artificial respiration. Loosen tight clothing such as a collar, tie, belt or waistband. If
breathing is difficult, oxygen can be administered. Seek medical attention. Treat symptomatically and supportively.
Ingestion Remove dentures if any. Have conscious person drink several glasses of water or milk. INDUCE VOMITING by sticking
finger in throat. Lower the head so that the vomit will not reenter the mouth and throat. NEVER give an unconscious
person anything to ingest. Seek medical attention. Treat symptomatically and supportively.

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Section V. Fire and Explosion Data
Not available.
Flammability Combustible. Auto-Ignition
Flammable Limits
Flash Points Not available.
Not available.
Combustion Products These products are toxic carbon oxides (CO, CO 2), nitrogen oxides (NO, NO2).
Fire Hazards
No specific information is available regarding the flammability of this compound in the presence of various materials.
Explosion Hazards Risks of explosion of the product in presence of mechanical impact: Not available.
Risks of explosion of the product in presence of static discharge: Not available.
No additional information is available regarding the risks of explosion.
Fire Fighting Media
SMALL FIRE: Use DRY chemicals, CO 2, water spray or foam.
and Instructions LARGE FIRE: Use water spray, fog or foam. DO NOT use water jet.
Continued on Next Page
N-Acetoacetylmorpholine

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Section VI. Accidental Release Measures
Spill Cleanup In case of a spill and/or a leak, always shut off any sources of ignition, ventilate the area, and exercise caution. Use a
Instructions shovel to put the material into a convenient waste disposal container. Finish cleaning the spill by rinsing any
contaminated surfaces with copious amounts of water.

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Section VII. Handling and Storage
Handling and Storage Keep away from heat and sources of ignition. Mechanical exhaust required. When not in use, tightly seal the container
and store in a dry, cool place. Avoid excessive heat and light. DO NOT breathe dust. In case of insufficient ventilation,
Information
wear suitable respiratory equipment. If you feel unwell, seek medical attention and show the label when possible. Treat
symptomatically and supportively. Avoid contact with skin and eyes.
Always store away from incompatible compounds such as oxidizing agents.

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Section VIII. Exposure Controls/Personal Protection
Engineering Controls Use process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below
recommended exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to
airborne contaminants below the exposure limit.
Personal Protection Splash goggles. Lab coat. Dust respirator. Boots. Gloves. A MSHA/NIOSH approved respirator should be used to
avoid inhalation of the product. Suggested protective clothing might not be sufficient; consult a specialist BEFORE
handling this product.
Exposure Limits Not available.

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Section IX. Physical and Chemical Properties
Solubility
Physical state @ 20°C Crystals. Not available.
Not available.
Specific Gravity
Molecular Weight 171.2 Partition Coefficient Not available.
Boiling Point Not available. Vapor Pressure Not available.
Melting Point 68°C (154.4°F) Vapor Density Not available.
Not available. Volatility Not available.
Refractive Index
Critical Temperature Not available. Odor Not available.
Viscosity Not available. Taste Not available.

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Section X. Stability and Reactivity Data
Stability

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This material is stable if stored under proper conditions. (See Section VII for instructions)
Conditions of Instability Avoid excessive heat and light.
Incompatibilities
Reactive with strong oxidizing agents.

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Section XI. Toxicological Information
RTECS Number Not available.
Ingestion. Inhalation.
Routes of Exposure
Toxicity Data Not available.
Chronic Toxic Effects CARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
Toxicity to the reproductive system: Not available.
There is no known effect from chronic exposure to this product. Repeated or prolonged exposure to this compound is not
known to aggravate existing medical conditions.
Acute Toxic Effects No specific information is available in our data base regarding the toxic effects of this material for humans. However,
exposure to any chemical should be kept to a minimum. Skin and eye contact may result in irritation. May be harmful if
inhaled or ingested. Always follow safe industrial hygiene practices and wear proper protective equipment when handling
this compound.
Continued on Next Page
N-Acetoacetylmorpholine

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Section XII. Ecological Information
Ecotoxicity Not available.
Environmental Fate Not available.

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Section XIII. Disposal Considerations
Recycle to process, if possible. Consult your local or regional authorities. You may be able to dissolve or mix material with
Waste Disposal
a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system. Observe all
federal, state, and local regulations when disposing of this substance.

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Section XIV. Transport Information
DOT Classification Not a DOT controlled material (United States).
PIN Number NONE
Proper Shipping Name
NONE
Packing Group (PG) NONE
DOT Pictograms

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Section XV. Other Regulatory Information and Pictograms
TSCA Chemical Inventory This product is NOT on the EPA Toxic Substances Control Act (TSCA) inventory. The following notices are required by 40
CFR 720.36 (C) for those products not on the inventory list:
(EPA)
(i) These products are supplied solely for use in research and development by or under the supervision of a technically
qualified individual as defined in 40 CFR 720.0 et sec.
(ii) The health risks of these products have not been fully determined. Any information that is or becomes available will be
supplied on an MSDS sheet.
WHMIS Classification Not available.
(Canada)
EINECS Number (EEC) Not available.
EEC Risk Statements Not available.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N-乙酰丙酮吗啉 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 氯仿 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  模拟单萜生物碱生物发生的逻辑以访问骨骼多样化的化学库

  摘要：

  我们开发了一种合成策略，可以模拟单萜吲哚生物碱生物合成的多样性产生能力。我们的一般方法超越了单一天然产物样子结构的多样化，并且能够生产高度多样化的小分子集合。反应序列开始于四环吲哚喹唑啶核的快速和高度模块化组装，可以化学选择性地加工成几个额外的骨架不同的结构框架。这种方法的通用性通过平行合成包含 847 种具有良好理化特性的化合物的两个代表性化学库来证明，以使其随后进行广泛的药理学评估。

  DOI：

  10.1021/jo401262v
• 作为产物：
  描述：

  4-(2-chloro-3-oxo-butyryl)-morpholine 在 4-甲苯硫酚 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以70%的产率得到N-乙酰丙酮吗啉
  参考文献：
  名称：

  在 K+/CH3CN 体系中使用苯硫醇对 α-卤代羰基化合物进行还原脱卤的简便方法

  摘要：

  图形摘要 摘要 苯硫醇作为各种 α-卤代羰基化合物脱卤的还原剂，在 K+/CH3CN 系统中进行了研究。该反应在温和的反应条件下以高产率提供还原的化合物，尤其是 α-氯代羰基化合物。此外，在超声波照射下进行的反应大大缩短了反应时间。

  DOI：

  10.1080/10426507.2016.1138309

文献信息

• Protecting Group Free Synthesis of Carboxyl-substituted Dihydropyrimidines Through Biginelli Reaction
  作者：Eugeniy N. Ostapchuk、Andrey S. Plaskon、Oleksandr O. Grygorenko、Andrey A. Tolmachev、Sergey V. Ryabukhin

  DOI：10.1002/jhet.1568

  日期：2013.11

  acetoacetic acid derivatives, and various carboxyl‐containing ureas was explored. It was found that the steric load of the urea substituents influenced strongly the reaction outcome; in particular, the method was efficient only in the case of unbranched mono‐substituted ureas bearing either aliphatic or aromatic groups. The method allows performing a one‐pot, protecting group free synthesis of dihydropyrimidines

  探索了氯三甲基硅烷促进的苯甲醛，乙酰乙酸衍生物和各种含羧基尿素的Biginelli型反应。发现脲取代基的空间负荷强烈影响反应结果。特别是，该方法仅在带有脂肪族或芳香族基团的直链单取代尿素中有效。该方法可以进行具有保护功能的二氢嘧啶的单锅，无保护基的合成。
• Fe(III) Complex Compounds For The Treatment And Prophylaxis Of Iron Deficiency Symptoms And Iron Deficiency Anemias
  申请人：Bark Thomas

  公开号：US20130109662A1

  公开（公告）日：2013-05-02

  The invention relates to iron(III) complex compounds and pharmaceutical compositions comprising them for the use as medicaments, in particular for the treatment and/or prophylaxis of iron deficiency symptoms and iron deficiency anemias.

  这项发明涉及铁（III）配合物和包括它们的药物组合物，用作药物，特别是用于治疗和/或预防缺铁症状和缺铁性贫血。
• <i>p</i>-Toluenesulfonic Acid Promoted Annulation of 2-Alkynylanilines with Activated Ketones: Efficient Synthesis of 4-Alkyl-2,3-Disubstituted Quinolines
  作者：Changlan Peng、Yong Wang、Lanying Liu、Honggen Wang、Jiaji Zhao、Qiang Zhu

  DOI：10.1002/ejoc.200901257

  日期：2010.2

  Reactions between readily available 2-alkynylanilines and activated ketones such as β-keto esters promoted by p-toluenesulfonic acid afford 4-alkyl-2,3-disubstituted quinolines in good to excellent yields. The generality of substituents at the other end of the triple bond of 2-alkynylanilines makes the method a valuable approach to diversified 4-alkylquin-olines, which are difficult to obtain by classical

  容易获得的 2-炔基苯胺和活化酮（如由对甲苯磺酸促进的 β-酮酯）之间的反应以良好至极好的收率提供 4-烷基-2,3-二取代喹啉。2-炔基苯胺三键另一端取代基的普遍性使该方法成为一种有价值的方法，可以通过经典方法如弗里德兰德反应难以获得多样化的4-烷基喹啉。喹啉二聚体可以使用 C-4 处的烷基或芳基接头有效地制备。
• A 4-Dimethylaminopyridine-Catalyzed Aminolysis of β-Ketoesters. Formation of β-Ketoamides
  作者：Janine Cossy、Annie Thellend

  DOI：10.1055/s-1989-27383

  日期：——

  Alkyl 3-oxoalkanoates (ß-ketoesters) react with amines in the presence of a catalytic amount of 4-dimethylaminopyridine (DMAP) under mild conditions to form 3-oxoalkanamides (ß-ketoamides) in good yields.

  烷基3-氧代烷酸酯(ß-酮酯)在温和条件下，以催化量的4-二甲氨基吡啶(DMAP)为催化剂，与胺反应生成3-氧代烷酰胺(ß-酮酰胺)，产率良好。
• [EN] PYRIMIDINONE DERIVATIVES AS THERAPEUTIC AGENTS AGAINST ACUTE AND CHRONIC INFLAMMATORY, ISCHAEMIC AND REMODELLING PROCESSES<br/>[FR] DERIVES DE PYRIMIDINONE UTILISES COMME AGENTS THERAPEUTIQUES CONTRE DES PROCESSUS INFLAMMATOIRES, ISCHEMIQUES ET DE REMODELAGE AIGUS ET CHRONIQUES
  申请人：BAYER HEALTHCARE AG

  公开号：WO2004024700A1

  公开（公告）日：2004-03-25

  The invention relates to novel heterocyclic derivatives, processes for their preparation, and their use in medicaments, especially for the treatment of chronic obstructive pulmonary diseases.

  这项发明涉及新颖的杂环衍生物，其制备方法以及它们在药物中的应用，特别是用于慢性阻塞性肺疾病的治疗。