[3-(二苯基膦)丙基]二苯基氧化膦 | 85685-99-0

• 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: [3-(二苯基膦)丙基]二苯基氧化膦
• 中文别名: 1,3-双(二苯基膦)丙烷一氧化物；1,3-双(二苯基膦)氧化丙烷；1,3-二(二苯基膦基)丙烷单氧化
• 英文名称: (3-(diphenylphosphaneyl)propyl)diphenylphosphine oxide
• 英文别名: diphenylphosphino(diphenylphosphonyl)propane；1,3-bis(diphenylphosphino)propane monoxide；1,3-bis(diphenylphosphino)propane-monoxide；dpppO；1,3-Bis(diphenylphosphino)propane monooxide；3-diphenylphosphorylpropyl(diphenyl)phosphane
• CAS: 85685-99-0
• 化学式: C₂₇H₂₆OP₂
• 分子量: 428.45
• InChiKey: ZZDVOUAZWJNTRE-UHFFFAOYSA-N

物化性质

• 熔点：
  106-108 °C(lit.)
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• WGK Germany：
  3
• 海关编码：
  2931900090

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 1,3-Bis(diphenylphosphino)propane monooxide
CAS-No. : 85685-99-0
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
Caution - substance not yet tested completely.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : [3-(Diphenylphosphino)propyl]diphenylphosphine oxide
Formula : C27H26OP2
Molecular Weight : 428,44 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Oxides of phosphorus
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 106 - 108 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation
May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  [3-(二苯基膦)丙基]二苯基氧化膦 在 二异丁基氢化铝 、 硼烷 作用下， 以 环己烷 、 四氢呋喃 为溶剂， 反应 7.0h， 以84%的产率得到
  参考文献：
  名称：

  用DIBAL-H还原叔膦氧化物

  摘要：

  详细研究了用二异丁基氢化铝（DIBAL-H）还原叔膦氧化物（TPO）和硫化物。广泛的溶剂筛选表明，受阻脂族醚（例如MTBE）最适合在室温下进行此反应。许多TPO在环境温度下会经历相当大的降低，然后由于抑制作用而失速。31 P和13使用同位素标记的底物进行的13 C NMR研究以及竞争研究表明，这种抑制作用的来源是四异丁基二铝氧烷（TIBAO），随着反应的进行而积累。TIBAO有选择地协调TPO原料，防止进一步减少。已经发现了几种策略来绕开这种抑制作用并首次用这种极其廉价的还原剂获得完全转化。已经为这些关键目标制定了实用的减排方案。

  DOI：

  10.1021/jo7024064
• 作为产物：
  描述：

  1,3-bis(diphenylphosphoryl)propane 在 三氟甲磺酸酐 、 1-戊硫醇 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 以71%的产率得到[3-(二苯基膦)丙基]二苯基氧化膦
  参考文献：
  名称：

  Selective mono reduction of bis-phosphine oxides under mild conditions

  摘要：

  在非常温和的条件下，使用三氟磺酸酐和硫醇，可以将双膦氧化物选择性地还原为双膦单氧化物。

  DOI：

  10.1039/b807695b
• 作为试剂：
  描述：

  乙烯基正丁醚 、 1-((E)-2-溴乙烯基)-4-甲氧基苯 在 palladium diacetate 、 三乙胺 、 [3-(二苯基膦)丙基]二苯基氧化膦 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  富含电子的烯烃与乙烯基卤化物的区域选择性Heck乙烯基化：中性途径在运行吗？

  摘要：

  溴和氯苯乙烯对富电子烯烃的高度区域选择性乙烯基化是通过在分子溶剂中用单或二齿膦进行钯催化来实现的，不需要卤化物清除剂，离子液体或离子添加剂。半不稳定的1,3-双（二苯基膦基）丙烷一氧化碳（dpppO）作为配体的使用导致更具挑战性的2-取代乙烯基醚的反应更快，并降低了Pd的负载量。与相关的芳基化反应相反，证据表明乙烯基化可能通过中性的Heck机制进行。

  DOI：

  10.1021/jo802781m

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。
• 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。
• Complexes of platinum(II) and palladium(II) with hybrid phosphine-phosphine oxide ligands of type Ph2P(CH2)nP()Ph2 (n = 1, 2, 3, or 4)
  作者：Simon J. Higgins、Richard Taylor、Bernard L. Shaw

  DOI：10.1016/0022-328x(87)80408-4

  日期：1987.5

  [PtCl2(NCBut)2] or [PtCl2(cyclo-1,5-octadiene)] with Ph2P(CH2)n P(O)Ph2 (n = 1, dppmO; n = 2, dppeO; n = 3, dpppO; n = 4, dppbO) gives complexes of the type cis-[PtCl2Ph2P(CH2)nP(O)Ph2}2], independently of mole ratio. Treatment of cis-[PtCl2(dppmO)2] with LiBr or NaI gives [PtX2(dppmO)2] (X = Br, cis; X = I, cis/trans mixture) and on treatment with Hg(CCPh)2 in ethanol, trans-[Pt(CCPh)2(dppmO)2] is formed

  的治疗[氯铂酸2（NCBu吨）2 ]或[氯铂酸2（环-1,5-辛二烯）]的Ph 2 P（CH 2）Ñ P（O）PH 2（Ñ = 1，dppmO; Ñ = 2，dppeO; n = 3，dpppO; n = 4，dppbO）给出顺式-[PtCl 2 Ph 2 P（CH 2）n P（O）Ph 2 } 2 ]类型的络合物，与摩尔比无关。的治疗顺- [氯铂酸2（dppmO）2]与LiBr或NaI合成[ PtX 2（dppmO）2 ]（X = Br，顺式； X = I，顺式/反式混合物），然后在乙醇中用Hg（CCPh）2处理，反式-[Pt（C形成CPh）2（dppmO）2 ]。用[PtMe 2（环辛基-1,5-二烯）]处理这些配体仅产生顺式-[PtMe 2 Ph 2 P（CH 2）n P（= O）Ph 2 } 2 ]。通过处理[PtCl 2 Ph 2 P（CH2）n具有AgNO 3或TlPF