4-甲基苯丙酮 | 2096-86-8

• 物质功能分类: 香精与香料 - 合成香料 - 酮类香料
• 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-甲基苯丙酮
• 中文别名: 4-甲基苯基乙酮；对甲基苯丙-2-酮；4-甲基苯丙-2-酮；4-甲基苯基丙酮；4'-甲基苯基丙酮；对甲基苯基丙酮
• 英文名称: p-Tolylaceton
• 英文别名: 1-(p-tolyl)propan-2-one；1-(4-methylphenyl)propan-2-one；4-methylphenylacetone
• CAS: 2096-86-8
• 化学式: C₁₀H₁₂O
• mdl: MFCD00017250
• 分子量: 148.205
• InChiKey: NOXKUHSBIXPZBJ-UHFFFAOYSA-N

物化性质

• 沸点：
  132 °C
• 密度：
  0.96
• 稳定性/保质期：
  - 避免与氧化物接触，因为它可能会发生危险分解，产生一氧化碳和二氧化碳。 - 这种物质存在于主流烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  2914399090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H312,H315,H319
• 储存条件：
  储存时应避免与氧化剂接触，将其密封保存在密封的容器中，并放置于阴凉、干燥处。

SDS

Name:	4-Methylphenylacetone 98% Material Safety Data Sheet
Synonym:	None Known
CAS:	2096-86-8

Section 1 - Chemical Product MSDS Name:4-Methylphenylacetone 98% Material Safety Data Sheet
Synonym:None Known

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2096-86-8	4-Methylphenylacetone	98%	unlisted

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

---

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. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
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.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

---

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. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. Avoid breathing dust, vapor, mist, or gas. 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 dry area. Keep refrigerated. (Store below 4C/39F.)

---

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# 2096-86-8: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear light yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
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: C10H12O
Molecular Weight: 148.21

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
None reported.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2096-86-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Methylphenylacetone - Not listed by ACGIH, IARC, or NTP.

---

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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 2096-86-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2096-86-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2096-86-8 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

制备

1. 丙酞氯的合成工艺

   将250kg丙酸和185kg三氯化磷分别投入500L搪玻璃反应锅，慢慢升温进行反应。在50℃下搅拌保温6小时后静置3小时，分去下层亚磷酸，即得297kg丙酞氯，收率为95%。所得丙酞氯无需进一步提纯即可用于下一步生产。

2. 4-甲基苯丙酮的合成

   将225kg无水三氯化铝和160kg甲苯投入500L搪玻璃反应锅中，在夹套冷却下，于搅拌下缓缓滴加120kg丙酞氯。保持内温不超过30℃，滴加完毕后室温搅拌1小时，再缓缓升温至82℃保温2小时，然后冷却。将反应液滴入装有冰水混合物的2000L搪玻璃反应锅中低温水解，静止分层后取上层油状物，用清水及饱和纯碱溶液洗至中性，干燥后常压脱除甲苯。最后收集96-100℃/930Pa馏份，得到含量大于98%的4-甲基苯丙酮，收率为88%。

应用

4-甲基苯丙酮是生产药物脑脉宁的重要中间体，其合成机理属于傅一克酰化反应。但由于原料甲苯和乙苯在苯环上的取代基不同，导致邻、间、对位酞化产物的比例差异，因此生产工艺中溶剂、反应时间和温度的选择各不相同。

反应信息

• 作为反应物：
  描述：

  4-甲基苯丙酮 在 Thermobifida fusca phenylacetone monooxygenase 作用下， 以 aq. phosphate buffer 、 乙醇 、 水 为溶剂， 生成 乙酸对甲基苄酯
  参考文献：
  名称：

  自然保持自然：用于合成香精醛和风味醛的两种新型化学酶一锅法级联反应

  摘要：

  人们非常需要基于绿色化学 12 项原则生产高价值化学品的新型合成策略。在本文中，我们提出了两种新型化学酶一锅法级联反应的概念验证，可用于生产有价值的香料和风味醛。我们使用可再生的苯基槐烯作为起始材料，例如丁香中的丁香酚或来自埃斯特拉贡的雌芪。对于第一种策略，进行 Pd 催化的烯丙基双键异构化和随后的酶介导的（芳香族双加氧酶，ADO）烯烃裂解以获得所需的醛。在第二条途径中，通过无铜 Wacker 氧化方案将双键氧化成相应的酮，然后进行酶促 Baeyer-Villiger 氧化（来自福氏嗜睡双歧杆菌的苯丙酮单加氧酶）、酯酶介导的（来自荧光假单胞菌的酯酶，PfeI）水解和随后的伯醇氧化（来自恶臭假单胞菌的醇脱氢酶， AlkJ） 添加到相应的醛类产物中。对八种不同的苯丙烯衍生物进行这些反应序列，允许在 4 个反应步骤后以高达 55% 的产率合成七种醛（每步为 86%）。

  DOI：

  10.1039/d3gc04191c
• 作为产物：
  描述：

  4-丙基甲苯 在 二氯乙酸 、 bis(dimethylglyoximatodifluoroboryl)cobalt(II) 、 3,6‐di‐tert‐butyl‐9‐(4‐fluoro‐2,6‐dimethylphenyl)‐10‐phenylacridin‐10‐ium tetrafluoroborate 、 lithium nitrate 、 水 作用下， 以 乙腈 为溶剂， 反应 44.0h， 以64%的产率得到4-甲基苯丙酮
  参考文献：
  名称：

  由双重有机光氧化还原和钴催化实现的均苄基氧化

  摘要：

  在更活化的苄基 C(sp3)-H 键存在的情况下激活脂肪族 C(sp3)-H 键通常是一项非常重要的任务，即使不是不可能的任务。在本文中，我们表明，可以使用双有机光氧化还原/钴催化，利用苄基 C(sp3)-H 键的反应性来实现高苄基位置的反应性。通过两部分催化系统，烷基芳烃进行脱氢，然后进行反马尔科夫尼科夫瓦克型氧化，生成苄基酮产品。这种正式的均苄氧化是在不使用导向基团的情况下以高原子经济性完成的；实现传统上需要多次化学转化的有价值的反应性。

  DOI：

  10.1021/jacs.0c04422

文献信息

• INDANYLOXYDIHYDROBENZOFURANYLACETIC ACIDS
  申请人：ECKHARDT Matthias

  公开号：US20140163025A1

  公开（公告）日：2014-06-12

  The present invention relates to compounds of general formula I, wherein the groups (Het)Ar and R 1 are defined as in claim 1 , which have valuable pharmacological properties, in particular bind to the GPR40 receptor and modulate its activity. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2.

  本发明涉及一般式I的化合物， 其中基团(Het)Ar和R1如权利要求1所定义， 具有有价值的药理特性，特别是结合GPR40受体并调节其活性。这些化合物适用于治疗和预防可以受到该受体影响的疾病，如代谢性疾病，特别是2型糖尿病。
• NAPHTHALENE-BASED INHIBITORS OF ANTI-APOPTOTIC PROTEINS
  申请人：Pellecchia Maurizio

  公开号：US20090105319A1

  公开（公告）日：2009-04-23

  Methods of using apogossypol and its derivatives for treating inflammation is disclosed. Also, there is described a group of compounds having structure A, or a pharmaceutically acceptable salt, hydrate, N-oxide, or solvate thereof are provided: wherein each R is independently selected from the group consisting of H, C(O)X, C(O)NHX, NH(CO)X, SO 2 NHX, and NHSO 2 X, wherein X is selected from the group consisting of an alkyl, a substituted alkyl, an aryl, a substituted aryl, an alkylaryl, and a heterocycle. Compounds of group A may be used for treating various diseases or disorders, such as cancer.

  使用阿波戈司宝及其衍生物治疗炎症的方法被披露。此外，还描述了一组具有结构A的化合物，或其药学上可接受的盐、水合物、N-氧化物或溶剂化合物： 其中每个R独立地选自H、C(O)X、C(O)NHX、NH(CO)X、SO2NHX和NHSO2X组成的组，其中X选自烷基、取代烷基、芳基、取代芳基、烷基芳基和杂环的组。A组化合物可用于治疗各种疾病或疾病，如癌症。
• Dihydropyrrolones as bacterial quorum sensing inhibitors
  作者：Basmah Almohaywi、Tsz Tin Yu、George Iskander、Daniel S.H. Chan、Kitty K.K. Ho、Scott Rice、David StC. Black、Renate Griffith、Naresh Kumar

  DOI：10.1016/j.bmcl.2019.03.004

  日期：2019.5

  through quorum sensing (QS), which is an intercellular communication system mediated by the binding of signaling molecules to QS receptors such as LasR. In this study, a range of dihydropyrrolone (DHP) analogues were synthesized via the lactone-lactam conversion of lactone intermediates. The synthesized compounds were tested for their ability to inhibit QS, biofilm formation and bacterial growth of

  细菌通过群体感应（QS）调节其致病性和生物膜形成，群体感应是一种细胞间通讯系统，通过信号分子与QS受体（例如LasR）的结合而介导。在这项研究中，通过内酯中间体的内酯-内酰胺转化合成了一系列二氢吡咯烷酮（DHP）类似物。测试了合成的化合物抑制铜绿假单胞菌的QS，生物膜形成和细菌生长的能力。这些化合物也停靠在LasR晶体结构中，以合理化所观察到的结构-活性关系。在这项研究中鉴定出的最具活性的化合物是化合物9i，在31.25 µM时QS抑制率为63.1％，在250 µM时生物膜减少了60％，对细菌细胞的生长只有中等毒性。
• Reaction Pathway and Rate-Determining Step of the Schmidt Rearrangement/Fragmentation: A Kinetic Study
  作者：Ryo Akimoto、Takehiro Tokugawa、Yutaro Yamamoto、Hiroshi Yamataka

  DOI：10.1021/jo300419c

  日期：2012.4.20

  pre-equilibrium in the formation of iminodiazonium (ID) ion and that the N2 liberation from the ID ion is rate-determining. Under high azide concentration conditions, where the effective reactant is the ID ion, the reaction gave a linear Hammett plot with a ρ value of −0.50. The observed substituent effects on the rate and the product selectivity imply that path bifurcation on the way from the rate-determining

  三甲基叠氮化硅在90％（v / v）的TFA水溶液中将3-苯基-2-丁酮与取代的3-苯基-2-丁酮进行Schmidt重排，生成了两种类型的产物：碎片和重排，其比例取决于取代基：碎片越多，电子越多-供体取代基。通过固氮法进行的速率测量表明存在诱导期，并且拟一级反应速率常数显示出相对于叠氮化物浓度的饱和动力学。结果表明，反应通过预平衡进行，形成亚氨基重氮（ID）离子，并且N 2从ID离子的释放是决定速率的。在高叠氮化物浓度的条件下，其中有效反应物是ID离子，该反应给出了ρ值为-0.50的线性Hammett图。如先前的分子动力学模拟所示，观察到的取代基对速率和产物选择性的影响暗示着从速率确定TS到产物态的路径发生分支，类似于贝克曼重排/片段化反应。
• Iron powder and tin/tin chloride as new reducing agents of Meerwein arylation reaction with unexpected recycling to anilines
  作者：Ahmed B. Abdelwahab、Eslam R. El-Sawy、Gilbert Kirsch

  DOI：10.1080/00397911.2019.1704786

  日期：2020.2.16

  of NaNO2/HCl was trapped by alkyl aryl radical to form oximes in the E configuration form. The presence of tin/tin chloride mixture in the reaction of the aryl diazonium salts with methyl vinyl ketone produced Michael products along with β-aryl methyl ketones. The predicted α-aryl methyl ketones from the reaction of isopropenyl acetate with the diazotized anilines were obtained using iron or tin/tin

  摘要 开发了使用铁粉或锡/氯化锡混合物进行Meerwein芳基化反应的简单快速路线。在铁粉存在下，不同的芳基重氮盐与甲基乙烯基酮、丙烯酸酯和乙酸异丙烯酯反应。在甲基乙烯基酮的情况下，肟的生产被检测为丙烯酸酯的主要产物或与β-芳基甲基酮的混合物。由过量的 NaNO2/HCl 原位生成的 HNO2 被烷基芳基捕获，形成 E 构型形式的肟。在芳基重氮盐与甲基乙烯基酮的反应中锡/氯化锡混合物的存在产生迈克尔产物以及β-芳基甲基酮。使用铁或锡/锡氯化物混合物从乙酸异丙烯酯与重氮化苯胺的反应中获得预测的α-芳基甲基酮。图形概要

表征谱图