4-Cyanophenylglyoxalhydrat | 19010-28-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Cyanophenylglyoxalhydrat
• 英文别名: 4-oxoacetyl-benzonitrile hydrate；4-dihydroxyacetyl-benzonitrile；4-(2,2-Dihydroxyacetyl)benzonitrile
• CAS: 19010-28-7
• 化学式: C₉H₇NO₃
• 分子量: 177.159
• InChiKey: KUWONPIVNVAGJT-UHFFFAOYSA-N

物化性质

• 熔点：
  76-79 °C (decomp)
• 沸点：
  376.8±32.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  81.3
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2926909090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Cyanophenylglyoxal 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-Cyanophenylglyoxal hydrate
CAS number: 19010-28-7

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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, refrigerated.
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: C9H5NO2.H2O
Molecular weight: 177.2

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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, nitrogen oxides.

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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-Cyanophenylglyoxalhydrat 在 caesium carbonate 、 对甲苯磺酰肼 作用下， 以 氯仿 为溶剂， 生成 4-(2-diazoacetyl)benzonitrile
  参考文献：
  名称：

  可见光驱动的 α-重氮酮作为脱氮合成子：通过多组分环化反应合成氟化 N-杂环

  摘要：

  我们在此公开了一种有效的光化学形式 [3+2+1] 环化策略，用于将重氮羰基化合物转化为各种氟化含氮杂环。这种转化的特征是氟代烷基自由基与 α-重氮酮反应，后者在可见光下用作罕见的脱氮合成子。此外，以中等至良好的产率构建了范围广泛的含有珍贵的 CF 3和全氟烷基化基团的 N-杂环。值得注意的是，这种光化学策略可能为通过重氮/氟/自由基化学合成复杂的有机氟化物提供了一条富有成效的途径。

  DOI：

  10.1021/acs.orglett.3c01145
• 作为产物：
  描述：

  对氰基苯乙酮 在 selenium(IV) oxide 、 水 作用下， 以 1,4-二氧六环 为溶剂， 生成 4-Cyanophenylglyoxalhydrat
  参考文献：
  名称：

  TOX/Cu(II)催化下的高效和对映选择性分子内坎尼扎罗反应

  摘要：

  基于新开发的拥挤 TOX 配体和活性乙二醛从乙二醛一水合物中逐渐释放的方案，芳基和烷基乙二醛与醇的不对称分子内 Cannizzaro 反应以前所未有的高水平对映选择性实现。初步结果表明，除了半缩醛中间体的动态动力学拆分之外，醇对映选择性加成到乙二醛的机制对立体选择性贡献最大。

  DOI：

  10.1021/ja409859x

文献信息

• FeCl₃or MeSO₃H-promoted multicomponent reactions for facile synthesis of structurally diverse furan analogues
  作者：Xiangqing Chang、Xiongfei Zhang、Zhiwei Chen

  DOI：10.1039/c8ob00942b

  日期：——

  An intriguing conversion of arylglyoxal, cyclic dicarbonyl compounds and phenols to diverse furan analogues under FeCl3 or MeSO3H catalysis is reported. Utilizing this synthetic protocol, a variety of furan analogues could be easily obtained in moderate to good yields with different substituted patterns by varying the reaction medium. Atom-economical characteristics and mild conditions of this method

  据报道，在FeCl 3或MeSO 3 H催化下，芳基乙二醛，环状二羰基化合物和酚转化为各种呋喃类似物的过程非常有趣。利用该合成方案，通过改变反应介质，可以容易地以中等至良好的产率获得具有不同取代模式的多种呋喃类似物。该方法的原子经济特性和温和条件符合现代绿色化学的概念。
• Chiral <i>N</i>,<i>N</i>′-dioxide–FeCl₃ complex-catalyzed asymmetric intramolecular Cannizzaro reaction
  作者：Wangbin Wu、Xiaohua Liu、Yuheng Zhang、Jie Ji、Tianyu Huang、Lili Lin、Xiaoming Feng

  DOI：10.1039/c5cc04213e

  日期：——

  An environmentally benign catalyst, the N,N′-dioxide–FeCl₃ complex, has been developed for the asymmetric intramolecular Cannizzaro reaction with high yields and enantioselectivities.

  一种对环境友好的催化剂，N,N'-二氧化物-FeCl3复合物，已经被开发用于高产率和对映选择性的不对称分子内Cannizzaro反应。
• Three-component reaction of azulene, aryl glyoxal and 1,3-dicarbonyl compound for the synthesis of various azulene derivatives
  作者：Jing Gong、Anatoly A. Peshkov、Jiafeng Yu、Sagadat Amandykova、Aidana Gimnkhan、Jianjun Huang、Stepan Kashtanov、Olga P. Pereshivko、Vsevolod A. Peshkov

  DOI：10.1039/d0ra00356e

  日期：——

  A three-component reaction of an azulene, an aryl glyoxal and a 1,3-dicarbonyl compound has been elaborated to access a series of azulene derivatives. Some of these azulene-containing adducts were further subjected to post-MCR transformations to assemble azulene–heterocycle conjugates.

  已经阐述了薁、芳基乙二醛和 1,3-二羰基化合物的三组分反应以获得一系列薁衍生物。其中一些含薁的加合物进一步经过 MCR 后转化以组装薁 - 杂环共轭物。
• New β-carboline fluorophores with superior sensitivity and endoplasmic reticulum specificity for tracking ER changes
  作者：Wenteng Chen、Jiaan Shao、Yujie Huang、En Chen、Mingzhu Huang、Feng Han、Xingguang Liang、Yongping Yu

  DOI：10.1039/c9cc03370j

  日期：——

  Endoplasmic reticulum-specific carboline-fluors were efficiently and rationally developed via a Pictet–Spengler involved one-pot multicomponent reaction.

  内质网特异性的吲哚-荧光素经过Pictet-Spengler参与的一锅多组分反应被高效且理性地开发。
• Synthesis of 2,2-Difluoro-3-hydroxy-1,4-diketones via an HFIP-Catalyzed Mukaiyama Aldol Reaction of Glyoxal Monohydrates with Difluoroenoxysilanes
  作者：Jianguo Yang、Saimei Liu、Peng Hong、Jinshan Li、Zhiming Wang、Jun Ren

  DOI：10.1021/acs.joc.1c02504

  日期：2022.1.21

  A novel efficient HFIP-catalyzed synthesis of structurally diverse 2,2-difluoro-3-hydroxy-1,4-diketone derivatives from readily available glyoxal monohydrates and difluoroenoxysilanes is described. This convenient protocol is induced by the distinctive fluorine effect of the reactants and the fluoroalcohol catalyst, which represents the first application of fluoroalcohol catalysis in a Mukaiyama aldol

  描述了一种新型高效的 HFIP 催化合成结构多样的 2,2-二氟-3-羟基-1,4-二酮衍生物的方法，该衍生物来自现成的乙二醛一水合物和二氟烯氧基硅烷。这种方便的协议是由反应物和氟代醇催化剂的独特氟效应引起的，这代表了氟代醇催化在 Mukaiyama 醛醇反应中的首次应用。