4,4-二甲基菲尼酮 | 2654-58-2

• 物质功能分类: 有机原料 - 酮类化合物
• 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: 4,4-二甲基菲尼酮
• 中文别名: 4,4-二甲基-1-苯基-3-吡唑酮；菲尼酮D；4,4-二甲基-1-苯基-3-吡唑烷酮
• 英文名称: 4,4-dimethyl-1-phenylpyrazolidin-3-one
• 英文别名: Dimezone
• CAS: 2654-58-2
• 化学式: C₁₁H₁₄N₂O
• mdl: MFCD00044325
• 分子量: 190.245
• InChiKey: SJSJAWHHGDPBOC-UHFFFAOYSA-N

物化性质

• 熔点：
  167-172 °C(lit.)
• 沸点：
  325.75°C (rough estimate)
• 密度：
  1.0815 (rough estimate)
• 闪点：
  195 °C
• 稳定性/保质期：

  遵循规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  6.1
• 危险品标志：
  T
• 安全说明：
  S24,S26,S28A,S36/37,S37/39,S45
• 危险类别码：
  R36/37/38,R25,R43
• WGK Germany：
  2
• RTECS号：
  UQ8710000
• 海关编码：
  2933990090
• 包装等级：
  II
• 危险类别：
  6.1
• 危险品运输编号：
  UN 2811 6.1/PG 2
• 储存条件：
  存于阴凉干燥处。

SDS

Name:	4 4-Dimethyl-1-phenyl-3-pyrazolidone 99% Material Safety Data Sheet
Synonym:	3-pyrazolidinone, 4,4-dimethyl-1-phenyl
CAS:	2654-58-2

Section 1 - Chemical Product MSDS Name:4 4-Dimethyl-1-phenyl-3-pyrazolidone 99% Material Safety Data Sheet
Synonym:3-pyrazolidinone, 4,4-dimethyl-1-phenyl

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2654-58-2	3-pyrazolidinone, 4,4-dimethyl-1-pheny	99	220-181-1

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Dust may cause mechanical irritation. No information reported.
Skin:
May cause skin irritation. No information reported.
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.
Skin:
Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists.
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.
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 if cough or other symptoms appear.
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.
Extinguishing Media:
For small fires, use water spray, dry chemical, carbon dioxide or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Avoid generating dusty conditions.

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Section 7 - HANDLING and STORAGE
Handling:
Wash hands before eating. Use with adequate ventilation. Avoid contact with skin and eyes. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 2654-58-2: 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:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white to off-white to pink
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 167.00 - 169.00 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: soluble
Specific Gravity/Density:
Molecular Formula: C11H14N2O
Molecular Weight: 190.24

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Strong oxidants.
Incompatibilities with Other Materials:
None reported.
Hazardous Decomposition Products:
No data available.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2654-58-2: UQ8710000 LD50/LC50:
CAS# 2654-58-2: Oral, rat: LD50 = 30 mg/kg.
Carcinogenicity:
3-pyrazolidinone, 4,4-dimethyl-1-phenyl- - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 2654-58-2: No information available.
Canada
CAS# 2654-58-2 is listed on Canada's DSL List.
CAS# 2654-58-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2654-58-2 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4,4-二甲基菲尼酮 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 氘代甲醇 、 二环己胺 作用下， 反应 0.5h， 生成 4,4-dimethyl-1-phenylpyrazolidin-3-one
  参考文献：
  名称：

  通过 1-苯基吡唑烷酮与 α,α-二氟亚甲基炔烃的级联反应选择性合成 3-(α-氟乙烯基) 吲哚和 3-酰基吲哚

  摘要：

  本文介绍了通过1-苯基吡唑烷酮与 α,α-二氟亚甲基炔烃的偶联选择性合成 3-(α-氟乙烯基) 吲哚和 3-酰基吲哚。从机制上讲，3-(α-氟乙烯基)吲哚的形成是由一个级联过程引起的，包括Rh(III)催化的邻-C-H键断裂、区域选择性三键插入、吡唑烷酮开环、吲哚成环和HF消除。有趣的是，当该反应在 CH 3 OH/H 2 O 中而不是 CH 3 中进行时CN，原位形成的 3-(α-氟乙烯基)吲哚很容易经过水合过程得到 3-酰基吲哚衍生物。该协议具有选择性可控、同时形成杂环支架和单氟烯基部分、原子经济性、底物多样性、良好的官能团耐受性和氧化还原中性反应条件等特点。针对两种人类癌细胞系的选定产品的抗癌筛选证明了它们作为药物开发先导化合物的潜力。

  DOI：

  10.1002/adsc.202100441
• 作为产物：
  描述：

  3-羟基-2,2-二甲基-2'-苯基丙酰肼 在 PPA 作用下， 生成 4,4-二甲基菲尼酮
  参考文献：
  名称：

  Process for preparing 3-pyrazolidones

  摘要：

  公开号：

  US02843598A1
• 作为试剂：
  描述：

  甲醇 、 2-methyl-2-(3-phenylprop-2-yn-1-yl)cyclopentane-1,3-dione 、 在 4,4-二甲基菲尼酮 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 sodium acetate 作用下， 反应 0.5h， 生成
  参考文献：
  名称：

  Ru（II）通过CH / CC键裂解催化可调级联反应。

  摘要：

  已经开发了通过C–H / C–C键活化从吡唑烷酮，2-炔酮和烷基醇轻松合成各种3-（烷氧基烷基）-1 H-吲哚的方法。在适当的反应条件下，反应可以顺利进行，初步的机理研究表明，NaOAc对于C–C键的活化至关重要。本方法的优点代表氧化还原中性过程，并表现出优异的化学和区域选择性。

  DOI：

  10.1021/acs.joc.0c01614

文献信息

• Enantioselective Enolate Protonation in Sulfa–Michael Addition to α-Substituted <i>N</i>-Acryloyloxazolidin-2-ones with Bifunctional Organocatalyst
  作者：Nirmal K. Rana、Vinod K. Singh

  DOI：10.1021/ol202808n

  日期：2011.12.16

  Organocatalytic conjugate addition of thiols to α-substituted N-acryloyloxazolidin-2-ones followed by asymmetric protonation has been studied in the presence of cinchona alkaloid derived thioureas. Both of the enantiomers are accessible with the same level of enantioselectivity using pseudoenantiomeric quinine/quinidine derived catalysts. The addition/protonation products have been converted to useful biologically

  在金鸡纳生物碱衍生的硫脲的存在下，已经研究了硫醇向α-取代的N-丙烯酰基恶唑烷丁二酮的有机催化共轭加成反应，然后进行不对称质子化。使用假对映异构体奎宁/奎尼丁衍生的催化剂，两种对映体都可以以相同水平的对映体选择性获得。加成/质子化产物已转化为有用的生物活性分子。
• Ruthenium-Catalyzed Redox-Neutral C–H Activation via N–N Cleavage: Synthesis of N-Substituted Indoles
  作者：Zhenxing Zhang、Hao Jiang、Yong Huang

  DOI：10.1021/ol502998n

  日期：2014.11.21

  The first Ru-catalyzed redox-neutral C–H activation reaction via N–N bond cleavage is reported. Pyrazolidin-3-one is demonstrated as an internally oxidative directing group that enables C–H annulation reactions with a broad scope of alkynes, including previously incompetent terminal alkynes. Pharmacologically privileged 3-(1H-indol-1-yl)propanamides were synthesized in high yields.

  据报道，第一个通过N–N键断裂的Ru催化的氧化还原中性C–H活化反应。吡唑烷丁-3-酮被证明是一种内部氧化性导向基团，可与广泛范围的炔烃（包括以前不称职的末端炔烃）进行CH环合反应。以高收率合成了具有药理学优势的3-（1 H-吲哚-1-基）丙酰胺。
• 一种吡唑烷酮并苯并1,3-氧氮杂卓类化合物的合成方法
  申请人：河南师范大学

  公开号：CN113185536B

  公开（公告）日：2022-06-17

  本发明公开了一种吡唑烷酮并苯并1,3‑氧氮杂卓类化合物的合成方法，属于有机合成技术领域。以1‑芳基吡唑烷酮1和重氮萘酮类化合物2为原料，在催化剂、氧化剂和添加剂存在下，有机溶剂中升温反应得到吡唑烷酮并苯并1,3‑氧氮杂卓类化合物3。该方法通过1‑芳基吡唑烷酮类化合物和重氮萘酮类化合物之间发生串联反应，高效地、区域选择性地合成了吡唑烷酮并苯并1,3‑氧氮杂卓类化合物，具有原料简单易得、操作简便、条件温和、选择性好及底物适用范围广等优点。
• Rhodium-catalyzed redox-neutral coupling of phenidones with alkynes
  作者：Zhoulong Fan、Heng Lu、Wei Li、Kaijun Geng、Ao Zhang

  DOI：10.1039/c7ob01271c

  日期：——

  A switchable synthesis of N-substituted indole derivatives from phenidones via rhodium-catalyzed redox-neutral C–H activation has been achieved. In this protocol, we firstly disclosed that the reactivity of Rh(III) catalysis could be enhanced through employing palladium acetate as an additive. Some representative features include external oxidant-free, applicable to terminal alkynes, short reaction

  通过铑催化的氧化还原中性CH活化，可从苯二酮中可合成N取代的吲哚衍生物。在该协议中，我们首先公开了通过使用乙酸钯作为添加剂可以增强Rh（III）催化的反应性。一些代表性功能包括：无外部氧化剂，适用于末端炔烃，反应时间短，操作简便。有效合成抗癌PARP-1抑制剂的经济合成进一步证明了该方法的实用性。
• Construction of Pyridazine Analogues <i>via</i> Rhodium-mediated C-H Activation
  作者：Chao Yang、Feifei Song、Jiean Chen、Yong Huang

  DOI：10.1002/adsc.201700905

  日期：2017.10.25

  Herein a rhodium (III)‐mediated catalysis was demonstrated for approaching the structurally divergent N,N‐bicyclic pyridazine analogues. The pyrazolidinone moiety was used to direct the ortho C−H activation and this led to a general synthesis of benzopyridazine analogues with satisfactory yields. The crucial effect of the base was illustrated in the sequential dehydration process. For mechanistic insight

  在本文中，铑（III）介导的催化被证明可以接近结构上不同的N，N-双环哒嗪类似物。吡唑烷酮部分用于指导邻域C H活化，这导致了苯并哒嗪类似物的普遍合成，并获得了令人满意的收率。在连续脱水过程中说明了碱的关键作用。为了获得机械学见解，进行了控制实验以说明催化环。进行了革兰氏合成和一些实际的转化，以供进一步应用。

表征谱图