二苄叉丙酮 | 538-58-9

• 物质功能分类: 有机原料 - 酮类化合物
• 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: 二苄叉丙酮
• 中文别名: 二亚苄叉丙酮DBA；1,5-二苯基戊-1,4-二烯-3-酮(反-反式结构)；二亚苄基丙酮；联甲基苯乙烯酮；1,5-二苯基戊-1,4-二烯-3-酮；二亚苄叉丙酮
• 英文名称: 1,5-diphenyl-1,4-pentadiene-3-one
• 英文别名: dibenzalacetone；dibenzylideneacetone；1,5-diphenylpenta-1,4-dien-3-one；distyryl ketone；dba；1,4-Pentadien-3-one, 1,5-diphenyl-
• CAS: 538-58-9
• 化学式: C₁₇H₁₄O
• 分子量: 234.298
• InChiKey: WMKGGPCROCCUDY-UHFFFAOYSA-N

物化性质

• 熔点：
  107-113 °C
• 沸点：
  336.62°C (rough estimate)
• 密度：
  1.0477 (rough estimate)
• 稳定性/保质期：
  按要求保存是不会发生分解或者反应的，远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 安全说明：
  S22,S24/25
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  建议将产品存储在0-6°C的环境下，并且需要密封保存。最好将其存放在通风、干燥的地方。

SDS

Name:	1,5-Diphenyl-3-pentadienone Material Safety Data Sheet
Synonym:	1,4-Pentadien-3-one, 1,5-diphenyl-; 1,5-Diphenyl-1,4-penadien-3-one; Dibenzalacetone; Dibenzylidene acetone; Distyryl ketone
CAS:	538-58-9

Section 1 - Chemical Product MSDS Name: 1,5-Diphenyl-3-pentadienone Material Safety Data Sheet
Synonym: 1,4-Pentadien-3-one, 1,5-diphenyl-; 1,5-Diphenyl-1,4-penadien-3-one; Dibenzalacetone; Dibenzylidene acetone; Distyryl ketone

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SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
538-58-9	1,5-Diphenyl-3-pentadienone	100	208-697-5

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

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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 immediately.
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:
If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid immediately.
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.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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SECTION 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

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SECTION 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. 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# 538-58-9: Personal Protective Equipment
Eyes:
Wear chemical splash goggles. 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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SECTION 9 - PHYSICAL AND CHEMICAL PROPERTIES
Physical State: Powder
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 111.00 - 113.00 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: C17H14O
Molecular Weight: 234.30

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SECTION 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 538-58-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1,5-Diphenyl-3-pentadienone - 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 Not regulated as a hazardous material. IMO Not regulated as a hazardous material. RID/ADR Not regulated as a hazardous material.

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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# 538-58-9: No information available. Canada CAS# 538-58-9 is listed on Canada's DSL List. CAS# 538-58-9 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 538-58-9 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 12/21/1998 Revision #2 Date: 3/18/2003 The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

二亚苄叉丙酮 用途

二亚苄叉丙酮可用作配体，用于制备钯催化剂，并广泛应用于催化加氢、偶联、羰基化、炔烃环三聚等方面。这类反应在合成天然产物、聚合物、功能材料、液晶材料及生物活性化合物和药物等领域均具有广泛的用途，例如钯催化的Negishi反应（卤代烃与有机锌）、Stille反应（卤代烃与有机锡）以及Suzuki反应（卤代烃与有机硼），还有Heck反应（卤代烃与烯烃）。

化学性质

二亚苄叉丙酮有三种异构体：反-反式为结晶固体，熔点110-111℃；顺-反式为淡黄色针状结晶，熔点60℃；顺-顺式为黄色油状液体，沸点130℃（2.7Pa）。该化合物溶于乙醇、丙酮和氯仿，但不溶于水。

用途

二亚苄叉丙酮还可用作防日光制品。

生产方法

由苯甲醛和丙酮反应得到。反应在乙醇水溶液中进行，反应温度为20-25℃，产率为78%。

反应信息

• 作为反应物：
  描述：

  二苄叉丙酮 在 氢氧化钾 、 乙醚 、 二氧化氮 、 苯 作用下， 生成 β-硝基苯乙烯
  参考文献：
  名称：

  Wieland; Bluemich, Justus Liebigs Annalen der Chemie, 1921, vol. 424, p. 84

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-dicinnamoyl-2,4-diphenyl-cyclobutane 生成 二苄叉丙酮
  参考文献：
  名称：

  Praetorius; Korn, Chemische Berichte, 1910, vol. 43, p. 2744

  摘要：

  DOI：
• 作为试剂：
  描述：

  3-氨基-9-乙基咔唑 、 1,3-dibenzyl-5-iodouracil 在 copper(I) trifluoromethanesulfonate benzene 1,10-菲罗啉 、 caesium carbonate 、 二苄叉丙酮 作用下， 以 xylene 为溶剂， 反应 24.0h， 以42%的产率得到1,3-Dibenzyl-5-(9-ethyl-9H-carbazol-3-ylamino)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Catalytic amination of 5-iodouracil derivatives

  摘要：

  Heterocyclic 5-amino uracil derivatives were prepared by catalytic amination of 1,3-dibenzyl-5-iodouracil using (CuOTf)(2). PhH, 1,10-phenanthroline, dibenzylidene acetone, and Cs2CO3 as base in xylenes at 95 degreesC. Imidazole and 2-amino thiazoline were problematic using the Cu catalyst, but were effectively coupled using Ni(COD)(2), dppf, and (NaOBu)-O-t in toluene at 100 degreesC. These are the first examples of catalytic amination with a uracil substrate. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02315-7

文献信息

• A novel and efficient stereo-controlled synthesis of hexahydroquinolinones via the diene-transmissive hetero-Diels–Alder reaction of cross-conjugated azatrienes with ketenes and electrophilic dienophiles
  作者：Satoru Kobayashi、Tomomi Semba、Taku Takahashi、Satoko Yoshida、Kotaro Dai、Takashi Otani、Takao Saito

  DOI：10.1016/j.tet.2008.10.090

  日期：2009.1

  factors and the electronic demand of the substituents. The second Diels–Alder reaction of the initial [4+2] cycloadducts with electron-deficient dienophiles (TCNE, N-phenylmaleimide) stereoselectively yielded hexahydroquinolinone derivatives. Similarly, a tandem intermolecular–intramolecular mode of the aza-DTHDA reactions produced tetracyclic nitrogen-containing heterocycles in a regio- and stereoselective

  具有N-芳基，N-烷基或N-二甲基氨基取代基的交叉共轭的氮杂三烯（二乙烯基lim或五-1,4-二烯-3-亚胺）的二烯可透过的杂狄尔斯-阿尔德（DTHDA）反应已经进行。检查。氮杂三烯与二苯乙烯酮在室温下的初始反应产生[2 + 2]环加合物的β-内酰胺，在加热后进行[1,3]-σ重排，生成正式的[4 + 2]环加合物。的反应Ñ -phenylazatriene用二甲基乙烯酮或二氯乙烯酮仅产生的[2 + 2] cycloadducts，而反应Ñ-（二甲基氨基）氮杂三烯与二氯乙烯烯不加热得到[4 + 2]环加合物。当[2 + 2]环加合物在β-内酰胺环的C-4具有两个不同的乙烯基取代基时，重排的区域选择性取决于空间因素和取代基的电子需求。最初的[4 + 2]环加合物与缺电子的亲二烯体（TCNE，N-苯基马来酰亚胺）的第二次Diels-Alder反应立体选择性地生成六氢喹啉酮衍生物。同样，氮杂-D
• Selective Reduction of α,β-Unsaturated Carbonyl Compounds with CO/H₂O Catalyzed by Selenium under Atmospheric Pressure
  作者：Shiwei Lu、Fengshou Tian

  DOI：10.1055/s-2004-830871

  日期：——

  Selective reduction of α,β-unsaturated carbonyl compounds with carbon monoxide and water in the presence of a catalytic amount of selenium proceeded efficiently to afford the corresponding saturated carbonyl compounds in high yields under atmospheric pressure without use of a base.

  在催化量的硒存在下，α,β-不饱和羰基化合物与一氧化碳和水的选择性还原反应高效进行，无需使用碱，在大气压下即可高产率地得到相应的饱和羰基化合物。
• Catalytic Transfer Hydrogenation Using Biomass as Hydrogen Source
  作者：Srimanta Manna、Andrey P. Antonchick

  DOI：10.1002/cssc.201801770

  日期：2019.7.5

  entities in a fundamentally important process, such as hydrogenation. Various carbohydrates, starch, and lignin were used for stereoselective hydrogenation. Employing a transition metal catalyst and a novel catalytic system, the reduction of alkynes, alkenes, and carbonyl groups with high yields was demonstrated. The regioselective hydrogenation to access different stereoisomers was established by simple

  我们开发了一种操作简单的方法，可在基本重要的过程（例如加氢）中直接使用生物质衍生的化学实体。各种碳水化合物，淀粉和木质素用于立体选择性氢化。利用过渡金属催化剂和新颖的催化体系，证明了炔烃，烯烃和羰基的高产率还原。通过简单改变反应条件来建立区域选择性氢化以得到不同的立体异构体。这项工作基于前所未有的催化系统，代表了生物质作为还原剂在化学反应中的直接应用。
• Polymer-Stabilized Palladium Nanoparticles for the Chemoselective Transfer Hydrogenation of α,β-Unsaturated Carbonyls: Single-Step Bottom-Up Approach
  作者：Sanjit K. Mahato、Rafique Ul Islam、Chiranjit Acharya、Michael J. Witcomb、Kaushik Mallick

  DOI：10.1002/cctc.201300985

  日期：2014.3.19

  Polypyrrole stabilised palladium nanoparticles show good catalytic efficiency for the chemoselective transfer hydrogenation of α,β‐unsaturated carbonyl compounds. The catalyst is very specific and selectively hydrogenates the olefins or acetylenes only, without affecting the carbonyl moiety, with an excellent yield of products for a wide range of substrates.

  聚吡咯稳定的钯纳米粒子对α，β-不饱和羰基化合物的化学选择性转移氢化显示出良好的催化效率。该催化剂是非常特殊的，并且仅选择性地氢化烯烃或乙炔，而不会影响羰基部分，对于广泛的底物具有优异的产物收率。
• Chemoselective transfer hydrogenation of α,β-unsaturated carbonyls catalyzed by a reusable supported Pd nanoparticles on biomass-derived carbon
  作者：Tao Song、Yanan Duan、Yong Yang

  DOI：10.1016/j.catcom.2018.11.017

  日期：2019.2

  We herein report highly chemoselective transfer hydrogenation of α,β-unsaturated carbonyl compounds to saturated carbonyls with formic acid as a hydrogen donor over a stable and recyclable heterogeneous Pd nanoparticles (NPs) on N,O-dual doped hierarchical porous biomass-derived carbon. The synergistic effect between Pd NPs and incorporated heteroatoms on carbon plays a critical role on promoting the

  我们在此报告了在N，O-双掺杂分层多孔生物质衍生碳上稳定且可回收的异质Pd纳米颗粒（NPs）上，以甲酸为氢供体，将α，β-不饱和羰基化合物高度化学选择性转移氢化为饱和羰基的方法。Pd NP和掺入的杂原子对碳的协同作用对提高反应效率起关键作用。一系列的α，β-芳族和脂族不饱和羰基化合物被选择性还原为相应的饱和羰基化合物，分离产率高达97％，并具有对各种官能团的良好耐受性。另外，催化剂可以连续重复使用至少6次，而不会显着降低反应效率。