4-吗啉二苯甲酮 | 24758-49-4

• 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 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-吗啉二苯甲酮
• 中文别名: 4-吗啉苯甲酮
• 英文名称: (4-morpholinophenyl)phenylmethanone
• 英文别名: 4-morpholinobenzophenone；N-(4-benzoylphenyl)morpholine；(4-morpholin-4-ylphenyl)-phenylmethanone
• CAS: 24758-49-4
• 化学式: C₁₇H₁₇NO₂
• mdl: MFCD00006167
• 分子量: 267.327
• InChiKey: CGCQHMFVCNWSOV-UHFFFAOYSA-N

物化性质

• 熔点：
  142-145 °C
• 沸点：
  410.51°C (rough estimate)
• 密度：
  1.0690 (rough estimate)
• 稳定性/保质期：

  在常温常压下稳定，应避免接触强氧化剂。

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.235
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2934999090
• 储存条件：
  将物品存放在密封容器中，并储存在阴凉、干燥的地方。

SDS

Name:	4-Morpholinobenzophenone 99% Material Safety Data Sheet
Synonym:
CAS:	24758-49-4

Section 1 - Chemical Product MSDS Name:4-Morpholinobenzophenone 99% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
24758-49-4	4-Morpholinobenzophenone	99	246-447-7

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate 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 or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 24758-49-4: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 138.00 - 141.00 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: C17H17NO2
Molecular Weight: 267.32

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 24758-49-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Morpholinobenzophenone - 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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 24758-49-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 24758-49-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 24758-49-4 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

反应信息

• 作为反应物：
  描述：

  4-吗啉二苯甲酮 在 乙二醇二甲醚 、 RuH₂(CO)(PPh₃)₃ 、 1,4-丁二醇 作用下， 以 乙二醇二甲醚 为溶剂， 反应 24.0h， 以68%的产率得到(4-morpholinophenyl)(phenyl)methanol
  参考文献：
  名称：

  氨基和酰胺基取代苯乙酮的钌催化转移氢化

  摘要：

  报道了富含电子的氨基取代苯乙酮的钌催化转移氢化。还原剂、配体、碱和溶剂的变化允许反应优化。一个关键发现是使用 1,4-丁二醇作为不可逆还原剂，这显着提高了转化率。探索了一系列氨基和酰胺基取代的芳基酮，它们都以良好的收率得到了相应的醇，这表明该方法具有更广泛的适用性。

  DOI：

  10.1002/ejoc.201301020
• 作为产物：
  描述：

  4-羟基-二苯甲酮 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， -15.0~62.0 ℃ 、1.33 MPa 条件下， 反应 20.17h， 生成 4-吗啉二苯甲酮
  参考文献：
  名称：

  High Pressure Organic Chemistry; XI.¹A New Convenient Synthesis of Aromatic Amines from Activated Phenols

  摘要：

  含有电子吸引取代基的芳基三氟甲磺酸酯在回流的乙腈中或在10千巴压力下与胺高效反应，生成多种芳香胺。

  DOI：

  10.1055/s-1990-27118

文献信息

• A General Palladium-Phosphine Complex To Explore Aryl Tosylates in the N-Arylation of Amines: Scope and Limitations
  作者：Pui Ying Choy、Kin Ho Chung、Qingjing Yang、Chau Ming So、Raymond Wai-Yin Sun、Fuk Yee Kwong

  DOI：10.1002/asia.201800575

  日期：2018.9.4

  heterocycles such as indole, carbazole, pyrrole, 10‐phenothiazine, and 10‐phenoxazine were shown to be feasible coupling partners under this catalytic system. The described reaction conditions tolerate a wide range of functional groups and allow an array of aromatic amines as well as unsymmetrical amine products to be easily accessed from the various phenolic derivatives. Interestingly, this catalyst

  提出了使用芳基和杂芳基甲苯磺酸盐对各种胺进行单选择性N-芳基化反应的范围和局限性。空气稳定且易于接近的Pd（OAc）2 / CM-phos CM-phos = 2- [2-（二环己基膦基）苯基] -1-甲基-1 H-吲哚}催化剂体系能够处理各种芳基甲苯磺酸酯底物以及胺亲核试剂，包括伯和仲环状/无环脂族胺和苯胺。在这种催化体系下，含NH的杂环如吲哚，咔唑，吡咯，10-吩噻嗪和10-吩恶嗪被证明是可行的偶联伙伴。所描述的反应条件容许宽范围的官能团，并允许从各种酚衍生物容易地获得一系列的芳族胺以及不对称胺产物。有趣的是，该催化剂体系甚至提供了在水介质中进行反应的机会。我们还报道了旋光性α-中心手性胺与芳基甲苯磺酸盐的分子间偶联，而没有削弱对映体的纯度。
• Well‐Defined Allylnickel Chloride/N‐Heterocyclic Carbene [(NHC)Ni(allyl)Cl] Complexes as Highly Active Precatalysts for CN and CS Cross‐Coupling Reactions
  作者：María José Iglesias、Auxiliadora Prieto、M. Carmen Nicasio

  DOI：10.1002/adsc.201000223

  日期：2010.10.9

  The room temperature Buchwald–Hartwig amination of heteroaromatic chlorides has been achieved using the sterically bulky allylnickel chloride/N-heterocyclic carbene [(IPr)Ni(allyl)Cl] complex as a well-defined precatalyst. Arylation of aromatic thiols, affording high yields of products under low catalyst loadings, has also been promoted with the same complex.

  室温下，杂芳基氯化物的布赫瓦尔德-哈特维格胺室温化反应已通过使用体积庞大的烯丙基氯化镍/ N-杂环卡宾[（IPr）Ni（烯丙基）Cl]络合物作为明确的预催化剂实现。相同的配合物也促进了芳族硫醇的丙烯酸化，在低催化剂负载下提供了高产率的产物。
• Nickel-catalyzed cross-coupling of aryltrimethylammonium triflates and amines
  作者：Xue-Qi Zhang、Zhong-Xia Wang

  DOI：10.1039/c3ob41989d

  日期：——

  Nickel-catalyzed cross-coupling of aryltrimethylammonium triflates and amines was carried out under mild conditions. The reaction has a broad scope of substrates and can be performed by a one-pot procedure from an aryldimethylamine.

  在温和条件下，通过镍催化实现了芳基三甲基铵三氟甲磺酸盐与胺的交叉偶联反应。该反应对底物具有广泛的适用性，并且可以从二甲基芳胺通过一步法实现。
• A Highly Versatile Catalyst System for the Cross-Coupling of Aryl Chlorides and Amines
  作者：Rylan J. Lundgren、Antonia Sappong-Kumankumah、Mark Stradiotto

  DOI：10.1002/chem.200902316

  日期：2010.2.8

  air‐stable P,N ligands enable the cross‐coupling of aryl and heteroaryl chlorides, including those bearing as substituents enolizable ketones, ethers, esters, carboxylic acids, phenols, alcohols, olefins, amides, and halogens, to a diverse range of amine and related substrates that includes primary alkyl‐ and arylamines, cyclic and acyclic secondary amines, NH imines, hydrazones, lithium amide, and ammonia

  2-（二-的合成叔- -butylphosphino）ñ，Ñ二甲基苯胺（L1，71％）和2-（二-1- adamantylphosphino） - ñ，Ñ二甲基苯胺（L2，74％），和它们的应用据报道在布赫瓦尔德-哈特维格胺的胺化反应。与[Pd（烯丙基）Cl] 2或[Pd（肉桂基）Cl] 2组合，这些结构简单且稳定的P，N配体可实现芳基和杂芳基氯化物的交叉偶联，包括带有可取代的酮，醚，酯，羧酸，酚，醇，烯烃，酰胺和卤素的取代基。胺和相关的基板的一个不同的范围，其包括初级烷基-和芳基胺，环状和非环状仲胺，N  ħ亚胺，腙，氨基锂，和氨。在许多情况下，反应可以在低催化剂负载量（0.5–0.02 mol％Pd）下进行，且具有出色的官能团耐受性和化学选择性。还报道了涉及1,4-溴氯苯和碘苯的交叉偶联反应的例子。在相似的条件下，使用Pd（OAc）2可获得较差的催化性能，PdCl 2，[PdCl 2（cod）]（cod
• Efficient C-N and C-S Bond Formation Using the Highly Active [Ni(allyl)Cl(IPr*^OMe)] Precatalyst
  作者：Anthony R. Martin、David J. Nelson、Sébastien Meiries、Alexandra M. Z. Slawin、Steven P. Nolan

  DOI：10.1002/ejoc.201402022

  日期：2014.5

  Two new [Ni(allyl)Cl(NHC)] complexes with the bulky yet flexible N-heterocyclic carbene (NHC) ligands IPr* N,N'-bis[2,6-bis(diphenylmethyl)-4-methylphenyl]imidazole-2-ylidene} and IPr*OMe N,N'-bis[2,6-bis(diphenylmethyl)-4-methoxyphenyl]imidazol-2-ylidene} are reported. These complexes were employed in the amination and sulfination of aryl halide species and were shown to perform well in these reactions

  两种新的 [Ni(allyl)Cl(NHC)] 配合物与庞大而灵活的 N-杂环卡宾 (NHC) 配体 IPr* N,N'-bis[2,6-bis(diphenylmethyl)-4-methylphenyl]imidazole -2-亚基}和IPr*OMe N,N'-双[2,6-双(二苯基甲基)-4-甲氧基苯基]咪唑-2-亚基}被报道。这些配合物用于芳基卤化物的胺化和亚磺化，并且在这些反应中表现良好，通常需要的催化剂少于以前最先进的镍配合物的一半。

表征谱图