4-(羟甲基)苯甲腈 | 874-89-5

• 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-(羟甲基)苯甲腈
• 中文别名: 4-氰基苯甲醇；4-(羟基甲基)苯腈；4-氰基苄醇；4-羟甲基苯腈
• 英文名称: 4-Cyanobenzyl alcohol
• 英文别名: 4-(hydroxymethyl)-benzonitril,4-cyanobenzylalcohol；4-(hydroxymethyl)benzonitrile
• CAS: 874-89-5
• 化学式: C₈H₇NO
• mdl: MFCD00870633
• 分子量: 133.15
• InChiKey: XAASLEJRGFPHEV-UHFFFAOYSA-N

物化性质

• 熔点：
  39-43 °C(lit.)
• 沸点：
  203 °C(Press: 53 Torr)
• 密度：
  1.16±0.1 g/cm3(Predicted)
• 闪点：
  >230 °F
• 稳定性/保质期：

  在常温常压下，该物质呈稳定状态，并以白色粉末的形式存在。

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  44
• 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：
  Xn
• 危险类别码：
  R20/21/22
• 危险品运输编号：
  UN 3439
• 海关编码：
  2926909090
• 安全说明：
  S26,S36
• WGK Germany：
  3
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302+H312+H332,H315,H319,H335
• 储存条件：
  常温下应存放在避光、通风干燥的地方。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(Hydroxymethyl)benzonitrile
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H312: Harmful in contact with skin
H315: Causes skin irritation
H319: Causes serious eye irritation
Harmful if inhaled
H332:
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 4-(Hydroxymethyl)benzonitrile
CAS number: 874-89-5

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H7NO
Molecular weight: 133.1

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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
UN Number: UN3439 Class: 6.1 Packing group: III
Proper shipping name: NITRILES, TOXIC, SOLID, N.O.S. (4-(Hydroxymethyl)benzonitrile)

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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-(羟甲基)苯甲腈 在 ((CH₃C₆H₄CH(CH₃)2)RuI(C₆H₄NC₃H₂NCH₃)) 、 potassium hydroxide 作用下， 以 间二甲苯 为溶剂， 反应 12.0h， 生成 4-羟甲基苯甲酸
  参考文献：
  名称：

  在超低 Ru 负载下通过醇和氢氧化物的催化无受体脱氢偶联合成羧酸

  摘要：

  醇和水/氢氧化物的无受体脱氢偶联 (ADC) 是一种新兴且优雅的生产羧酸的方法。因此，迫切需要为这种有吸引力的转化开发活性和实用的催化剂/催化体系。在此，我们通过[Ru-1] 的配体调谐设计并制造了一系列环金属化N-杂环卡宾-Ru (NHC-Ru) 配合物，我们之前工作中的高级复合体。令人欣慰的是，在露天环境中，以超低的 Ru 负载量（62.5 ppm）有效地实现了羧酸的克级合成。此外，对不同的辅助 NHC 配体和其他参数对该催化过程的影响进行了深入研究，同时进行了进一步的系统研究，为[Ru-1] - [Ru-7]的活性趋势提供了理论依据。最后，定量绿色指标的确定表明，目前的工作表现出优于代表性文献报告的优势。希望这项研究可以为从事金属催化 ADC 反应的研究人员提供有价值的输入。

  DOI：

  10.1016/j.apcata.2021.118443
• 作为产物：
  描述：

  对氰基苯甲酸 在 (4-Me)Triaz(NHPⁱPr₂)₂Mn(CO)₂Br 、 水 、 silica gel 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 6.0h， 生成 4-(羟甲基)苯甲腈
  参考文献：
  名称：

  均相锰催化剂对羧酸的选择性加氢硼化

  摘要：

  将羧酸催化还原成相应的醇是具有挑战性的任务，对于生产各种增值化学品而言，这一任务非常重要。在此，已开发出锰催化的羧酸的化学选择性氢硼化反应，其在25°C时具有较高的周转数（> 99 000）和周转频率（> 2000 h –1）。该方法显示了具有高化学选择性的电子和空间分化底物的耐受性。重要的是，可以有效地还原脂族长链脂肪酸，包括生物质衍生的化合物。机理研究表明，该反应是通过插入和键易位类型机制，通过活性锰氢化物物种的形成而发生的。

  DOI：

  10.1021/acs.joc.8b03108
• 作为试剂：
  描述：

  4-氰基苯甲醛 、 硼氢化钠 、 水 在 氮 、 乙酸乙酯 、 氯化钠 、 Sodium sulfate-III 、 4-(羟甲基)苯甲腈 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以(9.44 g; 93%) was obtained as a white solid的产率得到4-(羟甲基)苯甲腈
  参考文献：
  名称：

  Heteroarylakanoic acids as intergrin receptor antagonists

  摘要：

  本发明涉及一类由式（I）表示的化合物或其药学上可接受的盐、包含式（I）化合物的制药组合物以及选择性拮抗&agr;&ngr;&bgr;3和/或&agr;&ngr;&bgr;5整合素而不显著拮抗IIb/IIIa整合素的方法。

  公开号：

  US20040092497A1

文献信息

• Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups
  作者：Gabriella Amberchan、Rachel A. Snelling、Enrique Moya、Madison Landi、Kyle Lutz、Roxanne Gatihi、Bakthan Singaram

  DOI：10.1021/acs.joc.0c03062

  日期：2021.5.7

  from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce

  由氢化二异丁基铝（DIBAL）和硼烷二甲基硫醚（BMS）合成的二元氢化物二异丁基硼氢化铝[（i Bu）2 AlBH 4 ]在还原各种有机官能团方面显示出巨大潜力。这种独特的二元氢化物（i Bu）2 AlBH 4易于合成，通用且易于使用。醛，酮，酯和环氧化物以基本定量的收率非常快地还原为相应的醇。该二元氢化物可以在25°C下以有效方式将叔酰胺迅速还原为相应的胺。此外，腈以基本上定量的产率转化为相应的胺。这些反应在环境条件下发生，并在一个小时或更短的时间内完成。还原产物可通过简单的酸碱萃取而分离，无需使用柱色谱法。进一步的研究表明（i Bu）2 AlBH 4如一系列竞争反应所示，它具有成为选择性氢化物供体的潜力。讨论了（i Bu）2 AlBH 4，DIBAL和BMS之间的异同。
• Clean and selective oxidation of aromatic alcohols using silica-supported Jones’ reagent in a pressure-driven flow reactor
  作者：Charlotte Wiles、Paul Watts、Stephen J. Haswell

  DOI：10.1016/j.tetlet.2006.05.157

  日期：2006.7

  By exploiting the high surface to volume ratio obtained within continuous flow reactors, we are able to oxidise selectively an array of primary alcohols to either the aldehyde or carboxylic acid, depending on the flow rates employed, demonstrating a degree of reaction control unattainable in traditional stirred reactors.

  通过利用连续流动反应器中获得的高表面积体积比，我们能够根据所使用的流速将一系列伯醇选择性地氧化为醛或羧酸，证明了在传统搅拌条件下无法实现的反应控制程度反应堆。
• Air-Stable, Nitrile-Ligated (Cyclopentadienone)iron Dicarbonyl Compounds as Transfer Reduction and Oxidation Catalysts
  作者：Taylor N. Plank、Jessica L. Drake、Daniel K. Kim、Timothy W. Funk

  DOI：10.1002/adsc.201100896

  日期：2012.3

  A series of air‐stable, nitrile‐ligated (cyclopentadienone)iron dicarbonyl compounds was synthesized and their activities as catalysts in the transfer reduction of acetophenone were explored. While all were active catalysts, the acetonitrile adduct was chosen for further study and was found to be active in the transfer reduction of aldehydes and ketones and in the Oppenauer‐type oxidation of secondary

  合成了一系列稳定的，腈键合的（环戊二烯酮）铁二羰基铁化合物，并探讨了它们在催化还原苯乙酮中的催化活性。尽管所有这些都是活性催化剂，但乙腈加合物被选择用于进一步研究，并且发现其在醛和酮的转移还原以及仲醇的Oppenauer型氧化中具有活性。乙腈催化剂显示出与类似的对空气敏感的氢化铁类似的活性，但与氢化铁不同，它在使用氢气的羰基还原反应中没有反应性。
• Anaerobic Nitroxide-Catalyzed Oxidation of Alcohols Using the NO⁺/NO· Redox Pair
  作者：Martin Holan、Ullrich Jahn

  DOI：10.1021/ol403016p

  日期：2014.1.3

  A new method for alcohol oxidation using TEMPO or AZADO in conjunction with BF3·OEt2 or LiBF4 as precatalysts and tert-butyl nitrite as a stoichiometric oxidant has been developed. The system is based on a NO+/NO· pair for nitroxide reoxidation under anaerobic conditions. This allows the simple, high-yielding conversion of various achiral and chiral alcohols to carbonyl compounds without epimerization

  开发了一种新的醇氧化方法，该方法使用TEMPO或AZADO结合BF 3 ·OEt 2或LiBF 4作为预催化剂，并使用亚硝酸叔丁酯作为化学计量的氧化剂。该系统基于NO + / NO·对，用于厌氧条件下的氮氧化物再氧化。这允许各种非手性和手性醇简单，高产率地转化为羰基化合物，而没有差向异构化，并且不形成非挥发性副产物。
• The oxidation of alcohols with O-iodoxybenzoic acid (IBX) in aqueous nanomicelles at room temperature
  作者：Aming Xie、Xiangxiang Zhou、Liandong Feng、Xinyu Hu、Wei Dong

  DOI：10.1016/j.tet.2014.03.047

  日期：2014.5

  GMPGS-2000, a nonionic amphiphile composed of Guerbet alcohol (2-octyldodecan-1-ol), MPEG-2000 and succinic acid, has been prepared as an effective nanomicelle forming species for the oxidation of alcohols with 2-iodoxybenzoic acid (IBX) in water at room temperature.

  GMPGS-2000是由Guerbet醇（2-辛基十二烷基-1-醇），MPEG-2000和琥珀酸组成的非离子两亲物，已被制备为有效的形成纳米胶束的物质，用于用2-碘氧基苯甲酸（IBX）氧化醇在室温下的水中。