4-甲基苯基乙二醛水合物 | 16208-14-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-甲基苯基乙二醛水合物
• 英文名称: 2,2-dihydroxy-1-(p-tolyl)ethanone
• 英文别名: 2,2-dihydroxy-1-(p-tolyl)ethan-1-one；2,2-Dihydroxy-1-(4-methylphenyl)ethanone
• CAS: 16208-14-3
• 化学式: C₉H₁₀O₃
• mdl: MFCD19982289
• 分子量: 166.177
• InChiKey: XYZCEPPNDUWKPE-UHFFFAOYSA-N

物化性质

• 沸点：
  289.1±25.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2915900090
• 安全说明：
  S26,S36/37/39
• 储存条件：
  室温且干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Methylphenylglyoxal hydrate
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 4-Methylphenylglyoxal hydrate
CAS number: 16208-14-3

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C9H8O2.H2O
Molecular weight: 166.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-甲基苯基乙二醛水合物 生成 4-甲基苯甲酰甲醛水合物
  参考文献：
  名称：

  铜催化的对映选择性杂Diels-Danishefsky's Diene与乙二醛的Alder反应

  摘要：

  Danishefsky的二烯与乙二醛的高度对映选择性杂Diels-Alder反应是通过容易获得的手性铜催化剂开发的。这种有效的转化提供了对具有高对映选择性的大量生物活性二氢吡喃酮的简便且可扩展的获取途径。而且，该反应的底物范围可以通过该催化体系扩展至靛红。更重要的是，在中间体的明确结构的基础上提出了该反应所涉及的机理。

  DOI：

  10.1021/acs.joc.5b02780
• 作为产物：
  描述：

  4-甲基苯甲酰甲醛水合物 在 水 作用下， 反应 0.25h， 以82%的产率得到4-甲基苯基乙二醛水合物
  参考文献：
  名称：

  选择性Cu(I)催化氧化α-羟基酮合成α-酮醛

  摘要：

  通过以氧气为氧化剂，Cu( I )催化α-羟基酮选择性氧化，建立了一种合成α-酮醛的有效方法。制备了多种 α-酮醛，分离产率高达 87%。该反应的潜在利用通过克级反应和合成应用进行了评估。

  DOI：

  10.1039/d2cc00773h

文献信息

• Mechanochemical Aza-Vinylogous Povarov Reactions for the Synthesis of Highly Functionalized 1,2,3,4-Tetrahydroquinolines and 1,2,3,4-Tetrahydro-1,5-Naphthyridines
  作者：José Clerigué、M. Teresa Ramos、J. Carlos Menéndez

  DOI：10.3390/molecules26051330

  日期：——

  performed on a vibratory ball mill operating at 20 Hz and using zirconium oxide balls and milling jar, and afforded 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydro- 1,5-naphthyridines functionalized at C-2, C-4 and also at C-6, in the latter case. This protocol generally afforded the target compounds in good to excellent yields and diastereoselectivities. A comparison of representative examples

  在机械化学条件下，以连续的三组分方式进行芳族胺，α-酮醛或α-甲酸酯与α，β-不饱和二甲基hydr的氮杂-Povarov反应。经过广泛的优化工作，反应在振动球磨机上以20 Hz的频率进行操作，并使用氧化锆球和研磨罐进行操作，得到1,2,3,4-四氢喹啉和1,2,3,4-四氢-1 1，5-萘啶在C-2，C-4以及在C-6处官能化，在后一种情况下。该方案通常以良好的产率和优异的非对映选择性提供了目标化合物。
• Efficient Synthesis of Functionalized Dihydro-1<i>H</i>-indol-4(5<i>H</i>)-ones via One-Pot Three-Component Reaction under Catalyst-Free Conditions
  作者：Hui-Yan Wang、Da-Qing Shi

  DOI：10.1021/co4000198

  日期：2013.5.13

  A facile and efficient one-pot procedure for the preparation of functionalized dihydro-1H-indol-4(5H)-ones by a catalyst-free, three-component reaction of 1,3-dicarbonyl compounds, arylglyoxal monohydrate and enaminones under mild conditions in excellent yield is reported. This synthesis was confirmed to follow the group-assisted-purification (GAP) chemistry process, which can avoid traditional purifications

  一种简便有效的一锅法，用于在温和条件下通过无催化剂的1,3-二羰基化合物，芳基乙二醛一水合物和烯胺酮的三组分反应制备官能化的二氢-1H-吲哚-4（5H）-酮据报道，其收率极高。证实该合成遵循组辅助纯化（GAP）化学过程，该过程可避免传统的纯化，色谱法和重结晶。
• Synthesis and X-ray Characterization of Alkali Metal 2-Acyl-1,1,3,3-tetracyanopropenides
  作者：Sergey V. Karpov、Arthur A. Grigor’ev、Yakov S. Kayukov、Irina V. Karpova、Oleg E. Nasakin、Victor A. Tafeenko

  DOI：10.1021/acs.joc.6b01040

  日期：2016.8.5

  A novel route for synthesis of 2-acyl-1,1,3,3-tetracyanopropenides (ATCN) salts in high yields and excellent purities starting from readily available methyl ketones, malononitrile, bromine, and alkali metal acetates is reported. The starting aryl(heteroaryl) methyl ketones were oxidized to the corresponding α-ketoaldehydes by new a DMSO–NaBr–H2SO4 oxidation system in yields up to 90% within a short

  从容易获得的甲基酮，丙二腈，溴和碱金属乙酸盐开始，报道了一种以高收率和优良纯度合成2-酰基-1,1,1,3,3-四氰基丙烯盐（ATCN）盐的新颖途径。新型DMSO–NaBr–H 2 SO 4将起始的芳基（杂芳基）甲基酮氧化为相应的α-酮醛在8-10分钟的短时间内，氧化系统的收率高达90％。根据“绿色化学”的原则5，ATCN的后续制备过程可在水性介质中完成，无需使用任何有毒溶剂。通过X射线衍射分析表征2-苯甲酰基-1,1,3,3-四氰基丙烯腈中的锂，钠，钾，和铯。这些盐显示出合成五元和六元杂环的良好潜力，并且可以在配位和超分子化学中用作潜在有用的配体。
• Catalytic asymmetric Meerwein–Ponndorf–Verley reduction of glyoxylates induced by a chiral N,N′-dioxide/Y(OTf)₃complex
  作者：Wangbin Wu、Sijia Zou、Lili Lin、Jie Ji、Yuheng Zhang、Baiwei Ma、Xiaohua Liu、Xiaoming Feng

  DOI：10.1039/c7cc00273d

  日期：——

  An asymmetric Meerwein-Ponndorf-Verley (MPV) reduction of glyoxylates was for the first time accomplished via an N,N'-dioxide/Y(OTf)3 complex with aluminium alkoxide and molecular sieves (MSs) as crucial additives. A variety of optically active α-hydroxyesters were obtained with excellent results. A possible reaction mechanism was proposed based on the experiments.

  乙醛酸酯的不对称Meerwein-Ponndorf-Verley（MPV）还原是首次通过N，N'-dioxide / Y（OTf）3配合物与烷氧基铝和分子筛（MSs）作为关键添加剂实现的。获得了多种旋光性α-羟基酯，具有优异的结果。根据实验提出了可能的反应机理。
• Naphthol synthesis: annulation of nitrones with alkynes via rhodium(<scp>iii</scp>)-catalyzed C–H activation
  作者：Qiang Wang、Youwei Xu、Xifa Yang、Yunyun Li、Xingwei Li

  DOI：10.1039/c7cc05000c

  日期：——

  An efficient and redox-neutral naphthol synthesis has been realized via rhodium(III) catalyzed C-H activation of alpha-carbonyl nitrones and annulation with alkynes, where the nitrone group functioned as a traceless directing group.

  通过铑（III）催化的α-羰基硝酮的CH活化和炔烃的环化反应，已经实现了一种高效且氧化还原中性的萘酚合成，其中硝酮基团起着无痕导向基团的作用。