4-氰基苯甲酮 | 1503-49-7

• 物质功能分类: 化学试剂 - 有机试剂 - 芳香酮
• 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-氰基苯甲酮
• 中文别名: 4-氰基苯并苯基酮；4-苯甲酰苯甲腈
• 英文名称: p-cyanobenzophenone
• 英文别名: 4-benzoylbenzonitrile；4-cyanobenzophenone；(4-cyanophenyl)(phenyl)methanone；4-cyanophenyl phenyl ketone
• CAS: 1503-49-7
• 化学式: C₁₄H₉NO
• mdl: MFCD00016382
• 分子量: 207.232
• InChiKey: YSZWJJANSNFQMM-UHFFFAOYSA-N

物化性质

• 熔点：
  110-114 °C(lit.)
• 沸点：
  346.25°C (rough estimate)
• 密度：
  1.1259 (rough estimate)
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，没有已知的危险反应。应避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  6.1
• 危险品标志：
  Xn
• 安全说明：
  S26,S36
• 危险类别码：
  R20/21/22
• WGK Germany：
  3
• 海关编码：
  2926909090
• 危险品运输编号：
  3439
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H312,H315,H319,H332,H335
• 储存条件：
  请将贮藏器密封保存在阴凉干燥处，并确保工作环境有良好的通风或排气设施。

SDS

Name:	4-Cyanobenzophenone Material Safety Data Sheet
Synonym:
CAS:	1503-49-7

Section 1 - Chemical Product MSDS Name:4-Cyanobenzophenone Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1503-49-7	4-Cyanobenzophenone		216-126-6

Hazard Symbols: XN
Risk Phrases: 20/21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. May cause respiratory tract irritation.
Chronic:
Not available.

---

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:
Get medical aid. Wash mouth out with 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:

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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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1503-49-7: Personal Protective Equipment Eyes: Not available.
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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 109 - 112 deg C
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: C14H9NO
Molecular Weight: 207.23

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong bases, strong reducing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1503-49-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Cyanobenzophenone - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
Safety Phrases:
S 36/37 Wear suitable protective clothing and
gloves.
WGK (Water Danger/Protection)
CAS# 1503-49-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1503-49-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1503-49-7 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-氰基苯甲酮 在 (1,1'-双(二苯基膦)二茂铁)二氯化镍 、 乙醇 、 potassium tert-butylate 、 双(三甲基硅烷基)氨基钾 、 potassium 2-methylbutan-2-olate 作用下， 以 甲苯 为溶剂， 反应 20.0h， 生成 三苯乙烯
  参考文献：
  名称：

  乙醇作为还原剂的镍催化腈还原氰化反应

  摘要：

  已经开发出镍催化的芳香腈的还原性脱氰，其中易得且丰富的乙醇用作氢化物供体。在该催化方案中，芳环上的各种官能团如烷氧基，氨基，亚氨基和酰胺是相容的。杂芳基，苄基和烯基腈也可耐受。机理研究表明，在该还原性脱氰反应中，乙醇通过消除β-氢化物有效地提供了氢化物。

  DOI：

  10.1039/d0cc07743g
• 作为产物：
  描述：

  4-甲基二苯甲酮 在 氢溴酸 、 双氧水 、 氨 、 碘 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 19.0h， 以83%的产率得到4-氰基苯甲酮
  参考文献：
  名称：

  使用无机无金属试剂将甲基芳烃一锅法转化为芳香腈

  摘要：

  通过用水溶液处理，各种甲基芳烃以良好到中等的产率转化为相应的芳香腈。HBr 和水溶液。H2O2，然后与分子碘和水溶液反应。氨在一锅程序中。本反应是一种有用的、实用的、无过渡金属和无有机试剂的方法，用于从甲基芳烃制备芳香腈。

  DOI：

  10.1002/ejoc.201402270

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。
• Ionic liquid-mediated benzoyl transfer-coupling in the Suzuki and Sonogashira reactions and aryl transfer-coupling by decarbonylative Heck reaction, using N-Benzoyl-saccharin (NBSac) as reagent
  作者：Shruti S. Malunavar、Suraj M. Sutar、Pavankumar Prabhala、Rajesh G. Kalkhambkar、Kenneth K. Laali

  DOI：10.1016/j.tetlet.2020.151987

  日期：2020.6

  of N-benzoyl-saccharin (NBSac) as reagent for selective benzoyl transfer-coupling in the Suzuki reaction in BMIM-IL/[PAIM][NTf2] as solvent/base, and in the Sonogashira reaction employing guanidinium-IL (GIL) as solvent, are demonstrated. Decarbonylative aryl transfer-coupling occurs in the Heck reaction employing GIL as solvent. The reactions are catalyzed by Pd(OAc)2 or NiCl2(dppp), are performed

  在BMIM-IL / [PAIM] [NTf 2 ]作为溶剂/碱的Suzuki反应中以及在使用胍基-IL的Sonogashira反应中，N-苯甲酰糖精（NBSac）作为选择性苯甲酰转移偶联试剂的功效GIL）作为溶剂进行了演示。在使用GIL作为溶剂的Heck反应中发生脱羰基芳基转移偶联。该反应由Pd（OAc）2或NiCl 2（dppp）催化，在温和条件下以高收率进行，并且具有回收/再利用IL溶剂的潜力。总之，这些方法提供了对二芳基酮，酮-乙炔和二芳基-乙烯的各种文库的便捷访问。
• Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers
  作者：Tristan Delcaillau、Philip Boehm、Bill Morandi

  DOI：10.1021/jacs.1c00529

  日期：2021.3.17

  We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications

  我们描述了芳基腈和芳基硫醚之间的新官能团复分解。催化系统镍/dcype 对于实现这种完全可逆的转化，以良好的收率至关重要。此外，不含氰化物和硫醇的反应显示出高官能团耐受性和商业分子后期衍生化的高效率。最后，合成应用证明了它在多步合成中的多功能性和实用性。
• Nickel-Catalyzed Diaryl Ketone Synthesis by N–C Cleavage: Direct Negishi Cross-Coupling of Primary Amides by Site-Selective <i>N</i>,<i>N</i>-Di-Boc Activation
  作者：Shicheng Shi、Michal Szostak

  DOI：10.1021/acs.orglett.6b02952

  日期：2016.11.18

  the first amide cross-coupling by direct metal insertion of simple and readily available primary amides. The overall strategy by N,N-di-Boc activation/metal insertion is suitable for a broad range of coupling protocols via acylmetals. Mechanistic experiments suggest high reactivity of N,N-di-Boc activated 1° amides in direct amide C–N cross-couplings.

  首次报道了通过位点选择性N，N -di-Boc活化和镍催化的组合实现的伯酰胺的一般Negishi酰化反应。稳定的，廉价的镍催化剂促进了反应的进行。该反应显示出优异的官能团相容性，可通过选择性N-C裂解获得官能化的二芳基酮。最值得注意的是，该方案代表了通过直接金属插入简单易得的伯酰胺而进行的第一个酰胺交叉偶联。N，N -di-Boc活化/金属插入的整体策略适用于广泛的通过酰基金属的偶联方案。力学实验表明N，N具有高反应活性-di-Boc在酰胺直接C–N交叉偶联中活化了1°酰胺。
• Cobalt-Catalyzed Electrophilic Cyanation of Arylzinc Halides with<i>N</i>-Cyano-<i>N</i>-phenyl-<i>p</i>-methylbenzenesulfonamide (NCTS)
  作者：Yingxiao Cai、Xin Qian、Alice Rérat、Audrey Auffrant、Corinne Gosmini

  DOI：10.1002/adsc.201500245

  日期：2015.11.16

  The cobalt-catalyzed cross-coupling of organozinc bromides with N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) is described. The same cobalt catalyst, cobalt(II) bromide, was used for both the synthesis of the organozinc species and the cross-coupling reaction. However in this case, a catalytic amount of zinc dust is necessary in the second step to release the low-valent cobalt. Under these mild

  描述了有机锌溴化物与N-氰基-N-苯基-对甲基苯磺酰胺（NCTS）的钴催化交叉偶联。相同的钴催化剂溴化钴（II）用于有机锌物质的合成和交叉偶联反应。然而，在这种情况下，在第二步骤中需要催化量的锌粉以释放低价钴。在这些温和的条件下，获得了中等至极好的不同苄腈的收率。

表征谱图