二苯甲酮肟 | 574-66-3

• 物质功能分类: 化学试剂 - 有机试剂 - 肟
• 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: 二苯甲酮肟
• 中文别名: 二苯酮肟；苯甲酮肟
• 英文名称: Benzophenone oxime
• 英文别名: diphenylmethanone oxime；N-benzhydrylidenehydroxylamine
• CAS: 574-66-3
• 化学式: C₁₃H₁₁NO
• mdl: MFCD00051461
• 分子量: 197.236
• InChiKey: DNYZBFWKVMKMRM-UHFFFAOYSA-N

物化性质

• 熔点：
  140-144 °C
• 沸点：
  334.34°C (rough estimate)
• 密度：
  1.0957 (rough estimate)
• 稳定性/保质期：
  稳定性和反应性： 要避免的物料：氧化物、空气、水分、潮湿、热、光。 要分解的产品：一氧化碳和二氧化碳、氧化氮。

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 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：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• TSCA：
  Yes
• 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：
  2928000090
• 危险品运输编号：
  HAZARD
• RTECS号：
  DJ1810000
• 包装等级：
  III
• 危险类别：
  4.1,6.1
• 危险性防范说明：
  P240,P210,P241,P280,P370+P378,P501,P261,P270,P271,P264,P337+P313,P305+P351+P338,P361+P364,P332+P313,P301+P310+P330,P302+P352+P312,P304+P340+P311,P403+P233,P405
• 危险性描述：
  H228,H301+H311+H331,H315,H319
• 储存条件：
  贮存： 将密器密封后，放入密封的主容器中，并存放在阴凉、干燥的地方。

SDS

Name:	Benzophenone Oxime 98% Material Safety Data Sheet
Synonym:	Diphenylketone Oxime
CAS:	574-66-3

Section 1 - Chemical Product MSDS Name:Benzophenone Oxime 98% Material Safety Data Sheet
Synonym:Diphenylketone Oxime

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
574-66-3	Benzophenone Oxime	98%	209-373-6

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or 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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam. Use agent most appropriate to extinguish fire.

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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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 574-66-3: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: Crystalline powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 141-143 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Insoluble.
Specific Gravity/Density:
Molecular Formula: C6H5CNOH(C6H5)
Molecular Weight: 197.0831

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 574-66-3: DJ1810000 LD50/LC50:
Not available.
Carcinogenicity:
Benzophenone Oxime - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 574-66-3: No information available.
Canada
CAS# 574-66-3 is listed on Canada's NDSL List.
CAS# 574-66-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 574-66-3 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

类别：有毒物品

• 毒性分级：中毒
• 急性毒性：未名-小鼠 LD50: 560 毫克/公斤
• 可燃性危险特性：可燃；燃烧产生有毒氮氧化物烟雾
• 储运特性：通风、低温、干燥
• 灭火剂：干粉、泡沫、沙土、二氧化碳、雾状水

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  二苯甲酮亚胺	Benzophenone imine	1013-88-3	C13H11N	181.237
  ——	Benzophenon-(O-benzyl-oxim)	3362-43-4	C20H17NO	287.361
  ——	c-phenyl-N-(t-butyl)-c-phenylnitrone	58796-23-9	C17H19NO	253.344

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	benzophenone oxime methyl ether	3376-34-9	C14H13NO	211.263
  ——	N-(benzhydrylideneamino)oxy-1,1-diphenylmethanimine	7463-88-9	C26H20N2O	376.458
  二苯甲酮-(O-乙基肟)	benzophenon-(O-ethyl oxime )	58133-21-4	C15H15NO	225.29
  二苯甲酮亚胺	Benzophenone imine	1013-88-3	C13H11N	181.237
  ——	Benzophenonoxim-O-methylthiomethylaether	25056-49-9	C15H15NOS	257.356
  ——	benzophenone O-allyloxime	163224-06-4	C16H15NO	237.301
  ——	Benzophenonoxim-O-isopropylether	61582-66-9	C16H17NO	239.317
  ——	benzophenone-O-prop-2-ynyl oxime	——	C16H13NO	235.285
  ——	1,1-diphenyl-N-[(E)-prop-1-enoxy]methanimine	1453804-71-1	C16H15NO	237.301
  ——	diphenylmethanone, O-(2-chloroethyl)oxime	——	C15H14ClNO	259.735

反应信息

• 作为反应物：
  描述：

  二苯甲酮肟 在 吡啶 作用下， 生成 二苯甲酮吖嗪
  参考文献：
  名称：

  肟酯在苯和吡啶中的光化学芳基化：联芳基化合物的简单合成

  摘要：

  在苯和吡啶中照射二苯甲酮O-芳烃羰基肟，分别以高收率得到相应的芳基苯和芳基吡啶。

  DOI：

  10.1016/s0040-4039(01)91195-5
• 作为产物：
  描述：

  二苯甲酮对家苯磺酰腙 在 sodium hydroxide 作用下， 以 硝基甲烷 、 二甲基亚砜 为溶剂， 反应 16.0h， 以50%的产率得到二苯甲酮肟
  参考文献：
  名称：

  Base and solvent mediated decomposition of tosylhydrazones: highly selective synthesis of N-alkyl substituted hydrazones, dialkylidenehydrazines, and oximes

  摘要：

  Base and solvent mediated decomposition of tosylhydrazones was studied. It was found that reaction of tosylhydrazones in CH3NO2 in the presence of 1 equiv of K2CO3 in 90 degrees C gave N-alkylated products in 52-96% yield. However, when the same reaction was carried out in mixed solvent of CH3NO2 and dioxane in the presence of 3 equiv of NaOH at 110 degrees C, dialkylidenehydrazines were obtained in moderate to high yield. If the reaction was carried out in mixed solvent of CH3NO2 and DMSO in the presence of 10 equiv of NaOH at 110 degrees C, CH3NO2 can act as the precursor of hydroxylamine and corresponding oximes were formed in up to 92% yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.055
• 作为试剂：
  描述：

  4-甲基二苯甲酮 在 二苯甲酮肟 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 1-acetoxyfluorene
  参考文献：
  名称：

  Photochemistry of diaryl ketones: a new photocyclization reaction

  摘要：

  DOI：

  10.1021/jo00161a030

文献信息

• Aren- und cyclopentadienyl-halbsandwichkomplexe des rutheniums mit oximaten, carboxylaten, iminen und azavinylidenen als liganden
  作者：H. Werner、T. Daniel、W. Knaup、O. Nürnberg

  DOI：10.1016/0022-328x(93)83372-3

  日期：1993.12

  The reaction of [C6H6Ru(PiPr3)Cl2] (1) with NaONCRR′ in the presence of KPF6 leads to the formation of the oximatoruthenium(II) complexes [C6H6Ru(η2-ONCRR′)(PiPr3)]PF6 (2–5) in 70–90% yield. Compound 5 (R  Me, R′  tBu) reacts with HNCPh2 via ligand exchange to give [C6H6Ru(NCPh2)(Pi Pr3)]PF6 (8). The azavinylidene complex 8 has also been prepared from the acetatoruthenium derivative [C6H6Ru(η2-O2

  在KPF 6存在下，[C 6 H 6 Ru（P i Pr 3）Cl 2 ]（1）与NaONCRR'的反应导致形成氧亚氨基钌（II）络合物[C 6 H 6 Ru（ η 2 -ONCRR'）（P我镨3）] PF 6（2 - 5）在70-90％的产率。化合物5（RMe中，R'吨卜）与HNCPh发生反应2通过配体交换，得到[C 6 H ^ 6的Ru（NCPh 2）（Pi Pr 3）] PF 6（8）。所述azavinylidene复杂8也被从acetatoruthenium衍生物制备[C 6 H ^ 6的Ru（η 2 -O 2 CCH 3）（P我镨3）] PF 6（6），其可以或者从可以得到1，CH 3 CO 2 Na和KPF 6或从治疗的5用过量的CH 3 CO 2 H的hexamethylbenzeneruthenium化合物的合成[C6我6的Ru（NCR' 2）PR 3 ]）PF
• Iron-Catalyzed Synthesis of 2<i>H</i>-Imidazoles from Oxime Acetates and Vinyl Azides under Redox-Neutral Conditions
  作者：Zhongzhi Zhu、Xiaodong Tang、Jianxiao Li、Xianwei Li、Wanqing Wu、Guohua Deng、Huanfeng Jiang

  DOI：10.1021/acs.orglett.7b00203

  日期：2017.3.17

  A novel and versatile method for the synthesis of 2H-imidazoles via iron-catalyzed [3 + 2] annulation from readily available oxime acetates with vinyl azides has been developed. This denitrogenative process involved N–O/N–N bond cleavages and two C–N bond formations to furnish 2,4-substituted 2H-imidazoles. This protocol was performed under mild reaction conditions and needed no additives or ligands

  已开发出一种新颖且通用的方法，该方法通过铁催化的[3 + 2]环合反应从易于获得的肟肟与叠氮化乙烯中合成2 H-咪唑。该脱氮过程涉及N–O / N–N键断裂和两个C–N键形成，以提供2,4-取代的2 H-咪唑。该方案在温和的反应条件下进行，不需要添加剂或配体。此外，这是绿色反应，涉及乙酸肟肟作为内部氧化剂，乙酸和氮作为副产物。
• Deoximation of Oxime<i>O</i>-Acetates, Oximes, and Oxime Ethers by Nonacarbonyldiiron or Pentacarbonyliron. An Electronic Effect for the N–O Bond Cleavage
  作者：Makoto Nitta、Ichiro Sasaki、Hiroyuki Miyano、Tomoshige Kobayashi

  DOI：10.1246/bcsj.57.3357

  日期：1984.11

  The reaction of [Fe2(CO)9] or [Fe(CO)5] with oxime O-acetates, oximes, and oxime ethers under photoirradiation or thermal conditions undergoes deoximation to give the corresponding ketones. The oxime O-acetate was found to be the most reactive class of these compounds. A proposed mechanism involves an initial complexation of the [Fe(CO)4] species to the nitrogen atom of the oxime group, and the subsequent

  [Fe2(CO)9] 或 [Fe(CO)5] 与肟 O-乙酸酯、肟和肟醚在光辐射或热条件下的反应进行脱肟反应得到相应的酮。发现肟 O-乙酸酯是这些化合物中反应性最强的一类。提出的机制涉及 [Fe(CO)4] 物质与肟基团的氮原子的初始络合，以及随后的 N-O 键断裂以产生亚氨基络合物。然后，酰亚胺复合物可以通过质子介质中的亚胺中间体塌缩成相应的酮。
• SO₂ F₂ -Activated Efficient Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams
  作者：Guofu Zhang、Yiyong Zhao、Lidi Xuan、Chengrong Ding

  DOI：10.1002/ejoc.201900844

  日期：2019.8.15

  A novel protocol for the efficient activation of the Beckmann rearrangement utilizing the readily available sulfuryl fluoride (SO2F2 gas) is reported. The substrate scope of this methodology has been demonstrated by 37 examples with good to nearly quantitative isolated yields in a short time. A tentative mechanism was proposed involving formation and elimination of sulfonyl ester.

  报道了一种利用容易获得的硫酰氟（SO 2 F 2气体）有效激活贝克曼重排的新方案。该方法的底物范围已通过37个实例证明，并在短时间内获得了良好至近乎定量的分离产率。提出了一种尝试性的机制，涉及形成和消除磺酰基酯。
• On the mixed oxides-supported niobium catalyst towards benzylamine oxidation
  作者：Álisson Silva Granato、Gustavo S. Gonçalves de Carvalho、Carla G. Fonseca、Javier Adrio、Alexandre A. Leitão、Giovanni Wilson Amarante

  DOI：10.1016/j.cattod.2020.08.011

  日期：2021.12

  synthesized and applied towards oxidation reactions of benzylamine derivatives. Under the optimized reaction conditions, the selectivity to oxime enhanced, leading to the main product with up to 72 %. Moreover, even α-substituted benzylamines were well tolerated and led to oximes in good isolated yields. It is important to mention; four equivalents of the harmless and inexpensive hydrogen peroxide were employed

  合成了一系列负载混合氧化物的铌基催化剂并应用于苄胺衍生物的氧化反应。在优化的反应条件下，对肟的选择性提高，主产物可达72%。此外，即使是α-取代的苄胺也具有良好的耐受性，并以良好的分离产率产生肟。值得一提的是；使用四当量的无害且廉价的过氧化氢作为氧化剂。机制假设表明，反应进行选择性苄胺氧化成亚硝基中间体，随后形成相应的肟互变异构体，由 NbO x产生的不稳定水介导负载型催化剂。这包括第一个混合氧化物负载的铌基催化剂，用于将苄胺选择性氧化为肟。

表征谱图