菲尼酮 S | 13047-13-7

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 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: 菲尼酮 S
• 中文别名: 菲尼酮S；4-甲基-4-羟甲基-1-苯基-3-吡唑烷酮；4-羟甲基-4-甲基-1-苯基-3-吡唑烷酮
• 英文名称: 4-methyl-4-hydroxymethyl-1-phenyl-3-pyrazolidinone
• 英文别名: 4-(hydroxymethyl)-4-methyl-1-phenylpyrazolidin-3-one；4-Methyl-4-(hydroxymethyl)-1-phenyl-3-pyrazolidone；4-methyl-4-hydroxymethyl-1-phenyl-3-pyrazolidone；4-hydroxymethyl-4-methyl-1-phenyl-pyrazolidin-3-one；4-hydroxymethyl-4-methyl-1-phenyl-3-pyrazolidinone；1-phenyl-4-methyl-4-hydroxymethyl-3-pyrazolidone
• CAS: 13047-13-7
• 化学式: C₁₁H₁₄N₂O₂
• mdl: MFCD00055653
• 分子量: 206.244
• InChiKey: DSVIHYOAKPVFEH-UHFFFAOYSA-N

物化性质

• 熔点：
  122-126 °C
• 沸点：
  345.1°C (rough estimate)
• 密度：
  1.1427 (rough estimate)
• 闪点：
  113 °C
• LogP：
  0.18
• 稳定性/保质期：
  常温常压下稳定，避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  3

ADMET

毒理性

• 副作用

高铁血红蛋白血症 - 血液中高铁血红蛋白含量增加；该化合物被归类为继发性毒性效应。

Methemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xn
• 危险类别码：
  R22,R43
• RTECS号：
  UQ8727500
• 海关编码：
  2933990090
• 安全说明：
  S24,S26,S36,S37
• 包装等级：
  III
• 危险类别：
  9
• 危险性防范说明：
  P501,P273,P260,P270,P264,P280,P391,P314,P337+P313,P305+P351+P338,P301+P312+P330
• 危险品运输编号：
  3077
• 危险性描述：
  H302,H319,H372,H410
• 储存条件：
  常温下应存于密闭容器中，避免光照，并置于通风、干燥处。

SDS

Name:	4-Hydroxymethyl-4-Methyl-1-Phenyl-3-Pyrazolidone 98% Material Safety Data Sheet
Synonym:	None known
CAS:	13047-13-7

Section 1 - Chemical Product MSDS Name:4-Hydroxymethyl-4-Methyl-1-Phenyl-3-Pyrazolidone 98% Material Safety Data Sheet
Synonym:None known

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13047-13-7	4-Hydroxymethyl-4-Methyl-1-Phenyl-3-Py	98	235-920-3

Hazard Symbols: XN
Risk Phrases: 22 43

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed. May cause sensitization by skin contact.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May cause skin sensitization, an allergic reaction, which becomes evident upon re-exposure to this material.
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.

---

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:
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:
Never give anything by mouth to an unconscious person. Get medical aid. 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. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

---

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.

---

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. Avoid generating dusty conditions. Provide ventilation.

---

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.

---

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# 13047-13-7: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: yellow
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 121.00 - 126.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: > 110 deg C (> 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: 7.1 g/l (20 c)
Specific Gravity/Density:
Molecular Formula: C11H14N2O2
Molecular Weight: 206.20

---

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

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 13047-13-7: UQ8727500 LD50/LC50:
CAS# 13047-13-7: Oral, mouse: LD50 = 283 mg/kg; Oral, rat: LD50 = 566 mg/kg.
Carcinogenicity:
4-Hydroxymethyl-4-Methyl-1-Phenyl-3-Pyrazolidone - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

---

Section 12 - ECOLOGICAL INFORMATION

---

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

---

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.

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 22 Harmful if swallowed.
R 43 May cause sensitization by skin contact.
Safety Phrases:
S 22 Do not breathe dust.
S 24 Avoid contact with skin.
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# 13047-13-7: 2
Canada
CAS# 13047-13-7 is listed on Canada's DSL List.
CAS# 13047-13-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13047-13-7 is listed on the TSCA inventory.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N-cyclopentyl-O-benzoylhydroxylamine 、 菲尼酮 S 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 cesium acetate 、 三甲基乙酸 作用下， 以 甲苯 为溶剂， 以97%的产率得到1-[2-(cyclopentylamino)phenyl]-4-(hydroxymethyl)-4-methyl-3-pyrazolidinone
  参考文献：
  名称：

  RhIII 催化的肼导向 C(sp2)-H 与 N-烷基-O-苯甲酰基-羟胺对苯酮进行胺化

  摘要：

  使用 N-烷基-O-苯甲酰基-羟胺作为胺化剂，并以环肼部分作为导向基团，在温和条件下开发了 RhIII 催化的苯乙酮邻位 C-H 胺化，产率高达 97%，并且观察到官能团耐受性。该策略为合成 5-脂氧合酶抑制剂菲尼酮的氨基类似物提供了另一种途径，并且该产品对于进一步的官能团转化很有价值。

  DOI：

  10.1002/ejoc.201402999
• 作为产物：
  描述：

  4-Methyl-4-(hydroxymethyl)-1-phenyl-3-pyrazolidone radical 、 维生素 C 以 水 为溶剂， 生成 菲尼酮 S
  参考文献：
  名称：

  氢醌和抗坏血酸与 1-苯基-3-吡唑烷酮自由基的电子转移反应动力学

  摘要：

  已在 pH 6.5 至 9.5 的水溶液中检查了 1-苯基-3-吡唑烷酮自由基氧化四种氢醌和抗坏血酸的动力学。对于氢醌，除非溶液中存在亚硫酸盐，否则动力学是显着的自催化。自催化显然是由于通过醌产物与未反应的氢醌的再比例反应形成的大量半醌的积累。如果以足够的浓度存在，亚硫酸盐会通过清除醌来消除自催化，并且每个反应物的动力学都是一级的。动力学结果表明电子从氢醌转移到自由基形成半醌是限速的。在抗坏血酸的情况下，没有观察到自催化，并且动力学在氧化剂和还原剂中是一级的。对 pH 的动力学依赖性允许解析完全电离和单质子化还原剂氧化的双分子速率常数。这些速率常数与热力学驱动力的相关性与 Marcus 理论一致。

  DOI：

  10.1021/ja00187a045

文献信息

• 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。
• Sensitizing dye and silver halide photographic material
  申请人：——

  公开号：US20020106593A1

  公开（公告）日：2002-08-08

  Spectral sensitizing dyes represented by the following formulas ( 1 ) to ( 4 ) are disclosed; silver halide photographic materials and thermally developable photosensitive materials containing the dyes are also disclosed. 1

  以下公式（1）至（4）所代表的光谱敏化染料被揭示；同时也揭示了含有这些染料的银盐感光材料和热敏感材料。
• Processes for preparing substituted
  申请人：Eastman Kodak Company

  公开号：US04835285A1

  公开（公告）日：1989-05-30

  A process for preparing a substituted 4-hydroxymethyl-1-phenyl-3-pyrazolidinone of the formula ##STR1## wherein R.sup.1 is alkyl and R.sup.2 is selected from the group consisting of halogen, alkoxy, nitro, alkyl, and aryl, comprising reacting a cyclic sulfite of the formula ##STR2## wherein R.sup.1 is as described above and X is halide, with an aromatic hydrazine of the formula ##STR3## wherein R.sup.2 is as described above, in the presence of a basic catalyst and a solvent.

  一种制备式为##STR1##的取代4-羟甲基-1-苯基-3-吡唑啉酮的方法，其中R.sup.1是烷基，R.sup.2选自卤素，烷氧基，硝基，烷基和芳基，包括在碱性催化剂和溶剂的存在下，将式为##STR2##的环状亚磺酸酯与式为##STR3##的芳香族肼反应，其中R.sup.1如上所述，X为卤素。
• Organic/inorganic developer composition
  申请人：Eastman Kodak Company

  公开号：US06083673A1

  公开（公告）日：2000-07-04

  The present invention concerns an organic/inorganic developer composition comprising a regeneratable iron chelate, novel codevelopers of the phenidone type including one or more solubilizing groups that are not directly attached to the phenyl nucleus or to the pyrazolidino nucleus and optionally ascorbic acid. These compositions are particularly useful for the black-and-white development of films or photographic papers, in particular for the fast development of radiographic products.

  本发明涉及一种有机/无机显影剂组合物，包括可再生铁螯合物、新型苯哌酮类共显剂，其中包括一个或多个不直接连接到苯基或吡唑啉基上的增溶基团，以及可选的抗坏血酸。这些组合物特别适用于胶片或照相纸的黑白显影，特别是用于放射影像产品的快速显影。
• 3-pyrazolidone compounds and photographic developer solutions containing
  申请人：Eastman Kodak Company

  公开号：US05942379A1

  公开（公告）日：1999-08-24

  The present concerns compounds of the 3-pryazolidone type comprising solubilizing groups which are not directly attached to the phenyl ring or to the pyrazolidino ring. These compounds can be used as co-developing agents in the development of black and white photographic products.

  本发明涉及一种3-吡唑酮类化合物，包括不直接连接到苯环或吡唑烷环的增溶基团。这些化合物可用作共同显影剂，用于黑白照相产品的显影中。