二苯基膦酸酐 | 5849-36-5

• 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: 二苯基膦酸酐
• 英文名称: diphenylphosphinic anhydride
• 英文别名: Diphenylphosphinsaeure-anhydrid；bis(diphenylphosphinic) anhydride；Diphenylphosphin-anhydrid；[diphenylphosphoryloxy(phenyl)phosphoryl]benzene
• CAS: 5849-36-5
• 化学式: C₂₄H₂₀O₃P₂
• 分子量: 418.369
• InChiKey: XTAYANNRWHXQOL-UHFFFAOYSA-N

物化性质

• 熔点：
  146 °C
• 沸点：
  230 °C(Press: 2 Torr)
• 密度：
  1.28±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 储存条件：
  请将药品存放在避光、阴凉干燥的地方，并密封保存。

SDS

Diphenylphosphinic Anhydride
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: Diphenylphosphinic Anhydride

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: Diphenylphosphinic Anhydride
Percent: >98.0%(T)
CAS Number: 5849-36-5
Chemical Formula: C24H20O3P2

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Diphenylphosphinic Anhydride

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Section 4. FIRST AID MEASURES
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store under inert gas.
Protect from moisture.
Store away from incompatible materials such as oxidizing agents.
Moisture-sensitive
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Install a closed system or local exhaust as possible so that workers should not be
Engineering controls:
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Protective gloves.
Hand protection:
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Diphenylphosphinic Anhydride

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Form: Crystal- Powder
Colour: White - Almost white
Odour: No data available
pH: No data available
Melting point/freezing point:146°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents] No data available

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Phosphorus oxides
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
No data available
Fish:
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobility in soil
Log Pow: No data available
No data available
Soil adsorption (Koc):
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
Diphenylphosphinic Anhydride

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Section 14. TRANSPORT INFORMATION
UN-No: Not listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  二苯基膦酸酐 在 sodium fluoride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 copper(ll) bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以85%的产率得到diphenylphosphinic fluoride
  参考文献：
  名称：

  Copper-promoted oxidative-fluorination of arylphosphine under mild conditions

  摘要：

  一种通过氢氧化膦氧化物与氟化钠之间的氧化偶联合成磷氟化物的高效方法被报道。

  DOI：

  10.1039/c4cc04830j
• 作为产物：
  描述：

  二苯基次膦酰氯 在 吡啶 、 水 作用下， 以 氯仿 为溶剂， 生成 二苯基膦酸酐
  参考文献：
  名称：

  通过31P NMR光谱法测定橄榄油中的水分含量。

  摘要：

  开发了一种使用31P NMR光谱法测定橄榄油中水分的方法。该方法基于用标记剂2-氯-4,4,5,5-四甲基-1,3,2-二氧杂膦烷和二苯基次膦酰氯代替水分子的氢原子。两种试剂均能成功测定橄榄油中的水分。然而，只有第二种试剂在温和的条件下提供了干净而即时的反应，而没有与第一种试剂所观察到的副反应。进行了研究比较，以评估当前的NMR分析方法与完善的Karl Fischer滴定方法之间的一致性。

  DOI：

  10.1021/jf073227n
• 作为试剂：
  描述：

  2-蒈烯 在 二苯基膦酸酐 、 双氧水 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以80%的产率得到α-3,4-Epoxycarane
  参考文献：
  名称：

  烯烃环氧化的新范例：有机磷亲电试剂活化过氧化氢

  摘要：

  二苯次膦酸酐和某些其他有机磷亲电试剂在缓冲的四氢呋喃水溶液中通过过氧化氢介导烯烃向环氧化物的高产率转化。

  DOI：

  10.1016/0040-4039(94)88260-6

文献信息

• Biomimetic building-up of the carbamic moiety: the intermediacy of carboxyphosphate analogues in the synthesis of N-aryl carbamate esters from arylamines and organic carbonates promoted by phosphorus acids
  作者：Michele Aresta、Chlara Berloco、Eugenio Quaranta

  DOI：10.1016/0040-4020(95)00424-7

  日期：1995.7

  The reaction of aromatic amines with dimethyl carbonate (DMC) or diphenyl carbonate (DPC) in the presence of organo-phosphorus acids [Ph2P(O)OH (1); (PhO)2P(O)OH (2); (BuO)2P(O)OH/(BuO)P(O)(OH)2 equimolar mixture (3)] affords carbamate esters, ArNHC(O)OR (R = Me, Ph) with high selectivity. The catalytic role played by the P-acid has been investigated and rationalized in terms of a reaction mechanism

  在有机磷酸[Ph 2 P（O）OH（1）;的存在下，芳族胺与碳酸二甲酯（DMC）或碳酸二苯酯（DPC）的反应。（PhO）2 P（O）OH（2）; （BuO）2 P（O）OH /（BuO）P（O）（OH）2等摩尔混合物（3）]产生具有高选择性的氨基甲酸酯ArNHC（O）OR（R = Me，Ph）。对P-酸所起的催化作用已进行了研究，并根据涉及中间形成碳-次膦酸（磷）酸酐X 2的反应机理进行了合理化研究。P（O）OC（O）OR（X = Ph，PhO; R = Me，Ph）。所提出的机制与通过氨基甲酰磷酸合成酶（CPS）酶在生物系统中形成氨基甲酸酯阴离子的机制具有相似的趣味。
• Enantiodivergent Kinetic Resolution of 1,1′‐Biaryl‐2,2′‐Diols and Amino Alcohols by Dipeptide‐Phosphonium Salt Catalysis Inspired by the Atherton–Todd Reaction
  作者：Siqiang Fang、Jian‐Ping Tan、Jianke Pan、Hongkui Zhang、Yuan Chen、Xiaoyu Ren、Tianli Wang

  DOI：10.1002/anie.202102352

  日期：2021.6.25

  halide catalyst differentiates between the in-situ-generated P-species in the A-T process, mainly involving phosphoryl chloride and phosphoric anhydride, thus leading to highly enantiodivergent O-phosphorylation reactions. Furthermore hydrogen bonding interactions between the catalysts and phosphorus molecules were crucial in asymmetric induction.

  公开了一种高度对映发散的有机催化方法，通过受二肽-鏻盐催化的 Atherton-Todd (AT) 反应启发的动力学拆分合成阻转异构联芳基化合物。这种灵活的方法通过微调具有优异选择性因子的双功能鏻，产生R - 和S - 对映异构体（s) 分别高达 1057 和 525。轴向手性有机磷化合物的合成说明了新合成的 O-磷酸化联芳二醇的潜力。机理研究表明，双功能卤化鏻催化剂区分了 AT 过程中原位生成的 P 物种，主要涉及磷酰氯和磷酸酐，从而导致高度对映发散的 O-磷酸化反应。此外，催化剂和磷分子之间的氢键相互作用在不对称诱导中至关重要。
• Enantioselective Ring-Opening/Oxidative Phosphorylation and P-Transfer Reaction of Cyclic Diaryliodoniums
  作者：Longhui Duan、Kun Zhao、Zhonggui Wang、Feng-Lian Zhang、Zhenhua Gu

  DOI：10.1021/acscatal.9b03454

  日期：2019.11.1

  A Cu-catalyzed enantioselective ring-opening/oxidative phosphorylation reaction of cyclic diaryliodonium salts and diarylphosphine oxides in the presence of TEMPO was reported. 18O-Labeled experiments showed that the reaction proceeded via oxidation, followed by C–O bond formation. Furthermore, atropisomeric phosphine oxides were prepared via a t-BuLi-mediated P-transfer reaction. Computational studies

  据报道，在TEMPO存在下，环二芳基碘鎓盐和二芳基膦氧化物的Cu催化对映选择性开环/氧化磷酸化反应。18 O-Labeled实验表明，反应通过氧化进行，然后形成C-O键。此外，通过t -BuLi介导的P-转移反应制备了阻转异构的氧化膦。计算研究表明，氧化膦的转移是通过协调的C–P键形成和P–O键解离过程实现的。
• Indazole or indole derivatives, and use thereof in human medicine and more particularly in oncology
  申请人：Aventis Pharma S.A.

  公开号：US20040162276A1

  公开（公告）日：2004-08-19

  The present invention relates to novel compounds derived from indazoles or indoles of formula (1) or formula (2), to methods for treating tumors or cancerous cells with compounds of formula (1) or formula (2) and to pharmacaetutical compositions comprising a pharmaceutically acceptable carrier and a compound of formula (1) or formula (2). 1

  本发明涉及从式（1）或式（2）的吲唑或吲哚衍生的新化合物，以及使用式（1）或式（2）的化合物治疗肿瘤或癌细胞的方法，还涉及包含药学上可接受的载体和式（1）或式（2）化合物的药物组合物。
• Oxidation of Diphosphine Dioxides, Disulfides and Phosphinothioite and Photolysis of Diphosphine Disulfides. Formation of Phosphinic and Phosphinothioic Anhydrides
  作者：Tateki Emoto、Renji Okazaki、Naoki Inamoto

  DOI：10.1246/bcsj.46.898

  日期：1973.3

  yields of V increased with reaction temperature and with reaction time, indicating a homolytic fission of the P(S)–P(S) bond. Reaction of tetraphenyldiphosphine disulfide with sulfur in refluxing o-dichlorobenzene gave bis(diphenylphosphinothioyl) sulfide. Photolysis of II with a low pressure mercury lamp gave phosphinic acid and sulfur under oxygen, and gave phosphine sulfide and O-methyl phosphinothioate

  四苯基二氧化膦与等摩尔量的过苯甲酸 (III) 氧化得到二苯基次膦酸酐，收率良好。类似地，二硫化二膦 (II) 与 III 的 1.5-2.0 摩尔倍，得到相应的硫代膦酸酐 (V)，以及相应的次膦酸和硫。II 在回流的二甲苯或邻二氯苯中在空气中得到 V。V 的产率随着反应温度和反应时间的增加而增加，表明 P(S)-P(S) 键的均裂。二硫化四苯基二膦与硫在回流的邻二氯苯中反应得到双(二苯基硫代膦)硫化物。在氧气下用低压汞灯光解 II 得到次膦酸和硫，并在甲醇中得到硫化膦和 O-甲基硫代膦酸酯。