1,2-双(二苯基膦)乙烷一氧化物 | 984-43-0

• 物质功能分类: 有机原料 - 有机膦化合物
• 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: 1,2-双(二苯基膦)乙烷一氧化物
• 中文别名: [2-(二苯基膦)乙基]二苯基氧化膦；1,2-二(二苯基膦基)乙烷单氧化物
• 英文名称: 1,2-bis(diphenylphosphanyl)ethane monoxide
• 英文别名: 1,2-bis(diphenylphosphino)ethane monooxide；1,2-bis(diphenylphosphino)ethane monoxide；[2-(Diphenylphosphanyl)ethyl](diphenyl)phosphane oxide；2-diphenylphosphorylethyl(diphenyl)phosphane
• CAS: 984-43-0
• 化学式: C₂₆H₂₄OP₂
• 分子量: 414.423
• InChiKey: JCAUAUKUBUBNSB-UHFFFAOYSA-N

物化性质

• 熔点：
  195-199 °C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 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
• WGK Germany：
  3
• 海关编码：
  2902909090

SDS

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Section 1: Product Identification
Chemical Name: 1,2-Bis(diphenylphosphino)ethane monooxide, min. 97%
CAS Registry Number: 984-43-0
Formula: (C6H5)2PCH2CH2P(O)(C6H5)2
EINECS Number: none
Chemical Family: organophosphine ligand
Synonym: [2-(Diphenylphosphino)ethyl]diphenylphosphine oxide; [2-(Diphenyl-phosphinoyl)-ethyl]-diphenyl-phosphane

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 984-43-0 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Irritating to skin, eyes and respiratory tract. May be harmful if swallowed.
Primary Routes of Exposure: Inhalation, skin, eyes.
Eye Contact: Causes moderate irritation of the eyes.
Skin Contact: Causes irritation of the skin. May cause redness, itching and pain.
Inhalation: Irritating to the nose, mucous membranes and respiratory tract.
Ingestion: No specific information is available on the physiological effects of ingestion. May be harmful if swallowed.
Acute Health Affects: Irritating to skin, eyes and respiratory tract.
Chronic Health Affects: No information on long-term chronic effects.
NTP: No
IARC: No
OSHA: No

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SECTION 4: First Aid Measures
Immediately flush the eyes with copious amounts of water for at least 10-15 minutes. A victim may need
Eye Exposure:
assistance in keeping their eye lids open. Get immediate medical attention.
Wash the affected area with water. Remove contaminated clothes if necessary. Seek medical assistance if
Skin Exposure:
irritation persists.
Remove the victim to fresh air. Closely monitor the victim for signs of respiratory problems, such as difficulty
Inhalation:
in breathing, coughing, wheezing, or pain. In such cases seek immediate medical assistance.
Seek medical attention immediately. Keep the victim calm. Give the victim water (only if conscious). Induce
Ingestion:
vomiting only if directed by medical personnel.

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SECTION 5: Fire Fighting Measures
Flash Point: no data
Autoignition Temperature: no data
Explosion Limits: no data
Extinguishing Medium: carbon dioxide, dry powder or foam
If this product is involved in a fire, fire fighters should be equipped with a NIOSH approved positive pressure
Special Fire Fighting Procedures:
self-contained breathing apparatus and full protective clothing.
Hazardous Combustion and If involved in a fire this material may emit toxic organic fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards.

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SECTION 6: Accidental Release Measures
Spill and Leak Procedures: Small spills can be mixed with vermiculite or sodium carbonate and swept up.

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SECTION 7: Handling and Storage
Handling and Storage: Store the material in a cool, dry place in a tightly sealed container.

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SECTION 8: Exposure Controls and Personal Protection
Eye Protection: Always wear approved safety glasses when handling a chemical substance in the laboratory.
Skin Protection: Wear protective clothing and gloves.
Ventilation: Handle the material in an efficient fume hood.
If ventilation is not available a respirator should be worn. The use of respirators requires a Respirator
Respirator:
Protection Program to be in compliance with 29 CFR 1910.134.
Ventilation: Handle the material in an efficient fume hood.
Additional Protection: No additional protection required.

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SECTION 9: Physical and Chemical Properties
Color and Form: white powder
Molecular Weight: 414.42
Melting Point: no data
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: not determined
Solubility in Water: no data

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SECTION 10: Stability and Reactivity
Stability: air and moisture stable
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: none
Incompatibility: strong oxidizing agents and halogens
Decomposition Products: carbon monoxide, carbon dioxide, phosphorous pentoxide, and organic fumes.

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SECTION 11: Toxicological Information
RTECS Data: No information available in the RTECS files.
Carcinogenic Effects: no data
Mutagenic Effects: no data
Tetratogenic Effects: no data

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SECTION 12: Ecological Information
Ecological Information: No information available

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SECTION 13: Disposal Considerations
Disposal: Dispose of according to local, state and federal regulations.

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SECTION 14: Transportation
Shipping Name (CFR): Non-hazardous
Hazard Class (CFR): NA
Additional Hazard Class (CFR): NA
Packaging Group (CFR): NA
UN ID Number (CFR): NA
Shipping Name (IATA): Non-hazardous
Hazard Class (IATA): NA
Additional Hazard Class (IATA): NA
Packaging Group (IATA): NA
UN ID Number (IATA): NA

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SECTION 15: Regulatory Information
TSCA: Not listed in the TSCA inventory.
SARA (Title 313): Title compound not listed.
Second Ingredient: none

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1,2-双(二苯基膦)乙烷一氧化物 在 双(对硝基苯基)磷酸酯 、 1,3-diphenyldisiloxane 作用下， 以 乙酸乙酯 为溶剂， 反应 70.0h， 以96%的产率得到1,2-双(二苯基膦)乙烷
  参考文献：
  名称：

  1,3-二苯基二硅氧烷化学选择性还原氧化膦

  摘要：

  将氧化膦还原为相应的膦是制备这些有价值的试剂的最直接的方法。然而，由于P=O键的强度和/或较差的原子经济性，现有的还原氧化膦的方法存在化学选择性不足的问题。在此，我们报告了迄今为止用于这种​​转化的最强大的化学选择性还原剂的发现，1,3-二苯基二硅氧烷（DPDS）。无添加剂的DPDS选择性还原仲膦氧化物和叔膦氧化物，即使存在醛、硝基、酯、α,β-不饱和羰基、偶氮羧酸酯和氰基官能团，也能保持构型。阿累尼乌斯分析表明， DPDS还原的活化势垒明显低于任何先前计算的硅烷还原系统。催化布朗斯台德酸的加入进一步降低了活化能垒，并首次在室温下实现了硅烷介导的无环氧化膦还原。

  DOI：

  10.1002/chem.201703875
• 作为产物：
  描述：

  diphenylphosphine oxide 在 potassium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 1,2-双(二苯基膦)乙烷一氧化物
  参考文献：
  名称：

  2-苯氧乙基二苯基氧化膦在亲核加成中相当于二苯基乙烯基氧化膦

  摘要：

  摘要 基于容易获得的 2-苯氧基乙基二苯基氧化膦，在 KOH 存在下，在 DMSO 中添加不同的 PH-和 NH-亲核试剂的反应中，作为二苯基乙烯基氧化膦的当量，开发了一种合成 β-官能化乙基二苯基氧化膦的简便方法。通式 Ph 2 P(O)CH 2 CH 2 OR的不稳定氧化膦在 aq.KOH/DMSO 和固体 KOH 中的转化，其中 R = Ph、H 或 Ph 2 P(O)CH = CH 2 /DMSO 系统是在没有亲核试剂的情况下进行的。

  DOI：

  10.1080/10426507.2021.1939346
• 作为试剂：
  描述：

  1-庚烯 、 一氧化碳 在 水 、 1,2-双(二苯基膦)乙烷一氧化物 、 palladium dichloride 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-甲基庚酸 、 辛酸
  参考文献：
  名称：

  Complexes of PdCl2 with phosphoryl- and thiophosphoryl-substituted phosphines as catalysts for the hydrocarboxylation of olefins

  摘要：

  The influence of the ligands Ph2P(CH2)mP(X)Ph2 (L), Where m = 1, 2 and X = O, S, on the rate and regional selectivity of the hydrocarboxylation of alpha-olefins has been investigated, catalyzed by PdCl2, in a series of organic solvents. A high regional selectivity of the process (> 80%) for products with normal structure has been achieved by using L with m = 2, X = O. The influence of the ligand used and of triphenylphosphine on the properties of the catalytic system in the given reaction has been compared.

  DOI：

  10.1007/bf00863571

文献信息

• HYDROGENATION OF ESTERS OR CARBONYL GROUPS WITH PHOSPHINO-OXIDE BASED RUTHENIUM COMPLEXES
  申请人：Saudan Lionel

  公开号：US20110190523A1

  公开（公告）日：2011-08-04

  The present invention relates to the field of catalytic hydrogenation and, more particularly, to the use of specific ruthenium catalysts or pre-catalysts in hydrogenation processes for the reduction of ketones, aldehydes, esters or lactones into their corresponding alcohols or diols respectively. The preferred catalysts are ruthenium complexes comprising a ligand of the type (N—N) type and a ligand of the type (P—PO).

  本发明涉及催化加氢领域，更具体地涉及在加氢过程中使用特定的钌催化剂或前驱体，用于将酮、醛、酯或内酯还原为相应的醇或二醇。首选催化剂是包含(N—N)型配体和(P—PO)型配体的钌配合物。
• The Trityl‐Cation Mediated Phosphine Oxides Reduction
  作者：Claire Laye、Jonathan Lusseau、Frédéric Robert、Yannick Landais

  DOI：10.1002/adsc.202100189

  日期：2021.6.21

  Reduction of phosphine oxides into the corresponding phosphines using PhSiH3 as a reducing agent and Ph3C+[B(C6F5)4]− as an initiator is described. The process is highly efficient, reducing a broad range of secondary and tertiary alkyl and arylphosphines, bearing various functional groups in generally good yields. The reaction is believed to proceed through the generation of a silyl cation, which reaction

  描述了使用PhSiH 3作为还原剂和Ph 3 C + [B(C 6 F 5 ) 4 ] -作为引发剂将氧化膦还原成相应的膦。该方法效率很高，可以减少各种带有各种官能团的仲和叔烷基和芳基膦，收率通常很高。据信，该反应通过生成甲硅烷基阳离子进行，该阳离子与氧化膦反应提供鏻盐，进一步被硅烷还原以提供所需的膦和硅氧烷。
• Ruthenium(II) carbonyl complexes of P,P and P,O donor diphosphine ligands, Ph₂P(CH₂)_<i>n</i>PPh₂ and Ph₂P(CH₂)_<i>n</i>P(O)Ph₂, <i>n</i> = 2, 3 and their activities in catalytic transfer hydrogenation reactions
  作者：Biswajit Deb、Dipak Kumar Dutta

  DOI：10.1080/00958972.2018.1449947

  日期：2018.4.18

  Abstract The polymeric precursor [RuCl2(CO)2]n reacts with the ligands, P∩P (a, b) and P∩O (c, d), in 1:1 M ratio to generate six-coordinate complexes [RuCl2(CO)2(ƞ2-P∩P)] (1a, 1b) and [RuCl2(CO)2(ƞ2-P∩O)] (1c, 1d), where P∩P: Ph2P(CH2)nPPh2, n = 2(a), 3(b); P∩O: Ph2P(CH2)nP(O)Ph2, n = 2(c), 3(d). The complexes are characterized by elemental analyses, mass spectrometry, thermal studies, IR, and NMR

  摘要 聚合物前体 [RuCl2(CO)2]n 与配体 P∩P (a, b) 和 P∩O (c, d) 以 1:1 M 的比例反应生成六配位配合物 [RuCl2( CO)2(ƞ2-P∩P)] (1a, 1b) 和 [RuCl2(CO)2(ƞ2-P∩O)] (1c, 1d)，其中 P∩P：Ph2P(CH2)nPPh2，n = 2(a)、3(b)；P∩O: Ph2P(CH2)nP(O)Ph2, n = 2(c), 3(d)。这些配合物的特征在于元素分析、质谱、热研究、IR 和 NMR 光谱。1a-1d 在苯乙酮及其衍生物向相应醇的催化转移氢化中具有活性，转换频率 (TOF) 为 75-290 h-1。与由 RuCl3 本身催化相比，该配合物显示出更高的氢化产物产率。在 1a-1d 中，双齿膦的 Ru(II) 配合物 (1a, 1b) 显示出比其一氧化物类似物 (1c, 1d) 更高的效率。然而，
• ³¹ P NMR spectroscopic analysis on photooxidation of 1,n‐bis(diphenylphosphino)alkanes with the aid of DFT calculations
  作者：Shinro Yasui、Shoko Yamazaki

  DOI：10.1002/poc.4021

  日期：2020.4

  Ph2P(═O)(CH2)nP(═O)Ph2. The oxidation of the diphosphine to the diphosphine monoxide took place according to first‐order kinetics with respect to the concentration of the diphosphine, the first‐order rate constant, kobs, being larger with increasing number of the methylene units in the spacer. The observation in kinetics is interpreted based on the conformation of the diphosphine radical cation intermediate initially

  的氯仿d二膦，1的溶液，N-双（二苯基膦基）烷烃（PH 2 P（CH 2）Ñ PPH 2 ; Ñ = 1-6），用光从光分解空气中的氙气灯。通过31 P NMR光谱跟踪反应进程。观察到的光谱变化表明，二膦首先被氧化为一氧化二膦，Ph 2 P（= O）（CH 2）n PPh 2，进一步被氧化成二氧化二膦，Ph 2 P（= O）（CH 2）n P（═O）Ph 2。根据有关二膦浓度的一级动力学，一级速率常数k obs，将二膦氧化为一氧化二膦。，随着间隔物中亚甲基单元数目的增加而变大。基于从光激发的二膦到氧的电子转移最初产生的二膦自由基阳离子中间体的构象来解释动力学的观察结果。密度泛函理论（DFT）计算预测，二膦自由基阳离子呈“折叠”构型，其中两个磷原子彼此紧密排列。二膦自由基阳离子的“折叠”构象异构体是由这两个磷原子的静电相互作用产生的。该构象异构体解释了观察到的k obs对二膦中间隔基长度的依赖性。
• Diastereoselective Rhodium Catalyzed [4 + 2] Cycloisomerization of Allenes
  作者：Jun Li、Scott R. Gilbertson

  DOI：10.1021/acs.orglett.1c00554

  日期：2021.4.16

  A diastereoselective [4 + 2] cycloisomerization of asymmetric allenyl dienes is reported. The asymmetric dienyl allenes are synthesized using the method reported by Ma. These substrates readily undergo diastereoselective intramolecular rhodium catalyzed [4 + 2] cycloisomerization analogous to thermal intramolecular Diels–Alder reactions. Overall, 29 examples are presented with tethers possessing nitrogen

  报道了不对称烯基二烯的非对映选择性[4 + 2]环异构化。使用Ma报道的方法合成不对称二烯基丙二烯。这些底物很容易经历非对映选择性分子内铑催化的[4 + 2]环异构化，类似于热分子内Diels–Alder反应。总体而言，给出了29个具有氮，氧和碳的束缚绳的例子。在大多数示例中，非对映异构体的选择性范围为99：1至90:10。