1-(4-硝基苯基)-2-苯基-1,2-乙二酮 | 22711-24-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1-(4-硝基苯基)-2-苯基-1,2-乙二酮
• 英文名称: 4-nitrobenzil
• 英文别名: 1-(4-nitrophenyl)-2-phenylethane-1,2-dione
• CAS: 22711-24-6
• 化学式: C₁₄H₉NO₄
• 分子量: 255.23
• InChiKey: GPDKREBNFFEDHW-UHFFFAOYSA-N

物化性质

• 熔点：
  141 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2914700090

SDS

Name:	1-(4-Nitrophenyl)-2-phenylethane-1 2-dione 95+% Material Safety Data Sheet
Synonym:	4-Nitrobenzi
CAS:	22711-24-6

Section 1 - Chemical Product MSDS Name:1-(4-Nitrophenyl)-2-phenylethane-1 2-dione 95+% Material Safety Data Sheet
Synonym:4-Nitrobenzi

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
22711-24-6	1-(4-Nitrophenyl)-2-phenylethane-1,2-d	95+%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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:
Treat symptomatically and supportively.

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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.
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:
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# 22711-24-6: 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: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 130 - 132 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: C14H9NO4
Molecular Weight: 255

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 22711-24-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(4-Nitrophenyl)-2-phenylethane-1,2-dione - 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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 22711-24-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 22711-24-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 22711-24-6 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：

  1-(4-硝基苯基)-2-苯基-1,2-乙二酮 在 盐酸 、 tin 作用下， 生成 2-(4-氨基苯基)-1-苯乙酮
  参考文献：
  名称：

  Golubew, Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1874, vol. 6, p. 114

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(4-硝基苯基)乙酰氯 在 三氯化铝 、 selenium(IV) oxide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.76h， 生成 1-(4-硝基苯基)-2-苯基-1,2-乙二酮
  参考文献：
  名称：

  Synthesis of novel substituted diaryl-1,4-diazepines

  摘要：

  DOI：

  10.1007/s10593-006-0178-z

文献信息

• Visible-Light-Induced Photocatalytic Oxidative Decarboxylation of Cinnamic Acids to 1,2-Diketones
  作者：Shiv Chand、Anand Kumar Pandey、Rahul Singh、Krishna Nand Singh

  DOI：10.1021/acs.joc.1c00322

  日期：2021.5.7

  A concerted metallophotoredox catalysis has been realized for the efficient decarboxylative functionalization of α,β-unsaturated carboxylic acids with aryl iodides in the presence of perylene bisimide dye to afford 1,2-diketones.

  已经实现了协同的金属光氧化还原催化，以在of双酰亚胺染料的存在下用芳基碘将α，β-不饱和羧酸有效地脱羧官能化，得到1,2-二酮。
• A Bifunctional Iron Nanocomposite Catalyst for Efficient Oxidation of Alkenes to Ketones and 1,2-Diketones
  作者：Tao Song、Zhiming Ma、Peng Ren、Youzhu Yuan、Jianliang Xiao、Yong Yang

  DOI：10.1021/acscatal.9b05197

  日期：2020.4.17

  sites of Fe–Nx and Fe phosphate, as oxidation and Lewis acid sites, were simultaneously integrated into a hierarchical N,P-dual doped porous carbon. As a bifunctional catalyst, it exhibited high efficiency for direct oxidative cleavage of alkenes into ketones or their oxidation into 1,2-diketones with a broad substrate scope and high functional group tolerance using TBHP as the oxidant in water under

  我们在此报告了一种双功能铁纳米复合催化剂的制备，其中两个Fe–N x催化活性位点磷酸铁和铁的氧化位和路易斯酸位同时被整合到一个分层的N，P-双掺杂多孔碳中。作为一种双功能催化剂，它具有良好的催化作用，可在较温和的反应条件下使用TBHP作为氧化剂，将烯烃直接氧化裂解为酮或将其氧化为1,2-二酮，具有广泛的底物范围，并具有较高的官能团耐受性。此外，可以很容易地将其回收以进行后续回收，而不会造成明显的活性损失。机理研究表明，烯烃的直接氧化是通过形成环氧化物作为中间体，然后进行酸催化的Meinwald重排而产生的，该酮的碳原子短了一个或亲核开环，从而以级联方式生成1,2-二酮。
• One-pot cascade synthesis of α-diketones from aldehydes and ketones in water by using a bifunctional iron nanocomposite catalyst
  作者：Tao Song、Xin Zhou、Xiaoxue Wang、Jianliang Xiao、Yong Yang

  DOI：10.1039/d0gc03739g

  日期：——

  A new methodology for the synthesis of α-diketones was reported via a one-pot cascade process from aldehydes and ketones catalyzed by a bifunctional iron nanocomposite using H2O2 as a green oxidant in water. The one-pot strategy showed excellent catalytic stability, comprehensive suitability of substrates and important practical utility for directly synthesizing biologically active and medicinally

  据报道，通过双锅铁纳米复合物在水中使用H 2 O 2作为绿色氧化剂，通过醛和酮的一锅级联过程，合成了一种合成α-二酮的新方法。一锅法显示出优异的催化稳定性，底物的全面适用性和重要的实际实用性，可通过间歇过程直接合成具有生物活性和医学价值的N-杂环。
• Vanadium-Catalyzed Oxidative C(CO)–C(CO) Bond Cleavage for C–N Bond Formation: One-Pot Domino Transformation of 1,2-Diketones and Amidines into Imides and Amides
  作者：Chander Singh Digwal、Upasana Yadav、P. V. Sri Ramya、Sravani Sana、Baijayantimala Swain、Ahmed Kamal

  DOI：10.1021/acs.joc.7b00950

  日期：2017.7.21

  identified that enables their transformation into imides and amides. The reaction proceeds by dual acylation of amidines via oxidative C(CO)–C(CO) bond cleavage of 1,2-diketones to afford N,N′-diaroyl-N-arylbenzamidine intermediates. In the reaction, these intermediates are easily hydrolyzed into imides and amides through vanadium catalysis. This method provides a practical, simple, and mild synthetic

  1,2-二酮与am的新型钒催化的一锅多米诺反应已被鉴定，该反应可使它们转化为酰亚胺和酰胺。反应通过1，2-二酮的C（CO）-C（CO）键的氧化裂解使dual进行双酰化，从而得到N，N'-二酰基-N-芳基苯甲m中间体。在反应中，这些中间体容易通过钒催化水解成酰亚胺和酰胺。该方法提供了一种实用，简单且温和的合成方法，可以高产率获得各种酰亚胺和酰胺。而且，具有长链烷基的酰亚胺和酰胺键的一步构建是该方案的吸引人的特征。
• Rate Enhancement in CAN-Promoted Pd(PPh₃)₂Cl₂-Catalyzed Oxidative Cyclization: Synthesis of 2-Ketofuran-4-carboxylate Esters
  作者：Sureeporn Ruengsangtongkul、Nattawadee Chaisan、Charnsak Thongsornkleeb、Jumreang Tummatorn、Somsak Ruchirawat

  DOI：10.1021/acs.orglett.9b00053

  日期：2019.4.19

  Stoichiometric ceric ammonium nitrate (CAN) and a catalytic amount of Pd(PPh3)2Cl2 (5 mol %) can rapidly produce multisubstituted 2-ketofuran-4-carboxylate esters from 2-propargylic 1,3-ketoesters via oxidative O-cyclization reaction. Pd(PPh3)2Cl2 was found to be the crucial catalyst as its inclusion greatly enhanced the rate of the reaction and cleanly afforded the products within minutes. Over 30

  化学计量的硝酸铈铵（CAN）和Pd（PPH催化量3）2氯2（5摩尔％）可以迅速产生通过氧化多取代2- ketofuran -4-羧酸酯由2-丙炔-1,3-酮酯ø -环化反应。发现Pd（PPh 3）2 Cl 2是关键催化剂，因为它的加入大大提高了反应速度，并在数分钟内干净地得到了产物。超过30种底物已成功转化为所需化合物，且收率大多为中度到良好。