1,1,1-三(二苯基膦)甲烷 | 28926-65-0

• 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: 1,1,1-三(二苯基膦)甲烷
• 中文别名: 1,1,1-三(二苯基膦基)甲烷；1,1,1-三(二苯基磷酰)甲烷
• 英文名称: Tris(diphenylphosphino)methan
• 英文别名: 1,1,1-tris(diphenylphosphino)methane；bis(diphenylphosphanyl)methyl-diphenylphosphane
• CAS: 28926-65-0
• 化学式: C₃₇H₃₁P₃
• mdl: MFCD00015527
• 分子量: 568.574
• InChiKey: KYDFRUPZLLIHQE-UHFFFAOYSA-N

物化性质

• 熔点：
  168-172°C
• 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)：
  9
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.027
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 储存条件：
  存于阴凉干燥处

SDS

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Section 1: Product Identification
Chemical Name: 1,1,1-Tris(diphenylphosphino)methane, 97%
CAS Registry Number: 28926-65-0
Formula: HC[P(C6H5)2]3
EINECS Number: none
Chemical Family: organophosphine ligand
Synonym: none

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title Compound 28926-65-0 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Irritating to the respiratory tract, skin and eyes. May be harmful if swallowed.
Primary Routes of Exposure: Ingestion, eyes, inhalation
Eye Contact: Causes moderate irritation of the eyes.
Skin Contact: Causes slight to mild irritation of the skin.
Inhalation: Irritating to the nose, mucous membranes and respiratory tract.
Ingestion: No specific information is available on the physiological effects of ingestion.
Acute Health Affects: Irritating to skin, eyes and respiratory tract.
Chronic Health Affects: No information available 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: not applicable
Autoignition Temperature: no data
Explosion Limits: no data
Extinguishing Medium: dry chemical, carbon dioxide, water, or foam.
Fire fighters should be equipped with a NIOSH approved positive pressure self-contained breathing apparatus
Special Fire Fighting Procedures:
and full protective clothing.
Hazardous Combustion and In a fire material may emit toxic organic fumes, carbon monoxide, carbon dioxide, and phosphorous pentoxide.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards.

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SECTION 6: Accidental Release Measures
Small spills can be mixed with vermiculite, sodium carbonate or other suitable non combustible adsorbent and
Spill and Leak Procedures:
swept up.

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SECTION 7: Handling and Storage
Store in a cool, dry, area away from heat. Material must be handled and stored under an inert atmosphere of
Handling and Storage:
nitrogen or argon.

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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. Consult with glove manufacturer to determine the proper type of glove.
Ventilation: Material may form a fine dust. If possible, 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: Material may form a fine dust. If possible, 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 xtl.
Molecular Weight: 568.58
Melting Point: 168-172°
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: none
Solubility in Water: insoluble

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

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

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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 federal, state, and local 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：

  1,1,1-三(二苯基膦)甲烷 在 KI 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 triiodo-μ3-{tris(diphenylphosphanyl)methane}-trigold(I)
  参考文献：
  名称：

  Stuetzer, Albert; Bissinger, Peter; Schmidbaur, Hubert, Chemische Berichte, 1992, vol. 125, # 2, p. 367 - 372

  摘要：

  DOI：
• 作为产物：
  描述：

  双二苯基膦甲烷 在 六甲基磷酰三胺 、 正丁基锂 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 1,1,1-三(二苯基膦)甲烷
  参考文献：
  名称：

  Schmidbaur, Hubert; Stuetzer, Albert; Herdtweck, Eberhardt, Chemische Berichte, 1991, vol. 124, # 5, p. 1095 - 1100

  摘要：

  DOI：
• 作为试剂：
  描述：

  溶剂黄146 、 苯胺 在 三(乙酰丙酮酸)钌(III) 、 1,1,1-三(二苯基膦)甲烷 、 氢气 、 双三氟甲烷磺酰亚胺 作用下， 以 甲苯 为溶剂， 160.0 ℃ 、6.0 MPa 条件下， 反应 18.0h， 以29%的产率得到N-乙酰苯胺
  参考文献：
  名称：

  使用羧酸和分子氢催化胺的 N-烷基化

  摘要：

  通过在分子氢存在下应用容易获得的羧酸，已经实现了胺的方便、实用和绿色的 N-烷基化。应用原位形成的钌/三磷配合物和有机酸作为助催化剂，可以以良好到极好的收率获得范围广泛的烷基化仲胺和叔胺。这种新方法还成功地应用于通过相应胺、羧酸和作为 C1 源的 CO2 的直接三组分偶联反应合成不对称取代的 N-甲基/烷基苯胺。

  DOI：

  10.1021/jacs.5b07994

文献信息

• Ferrocenyl‐Functionalized Tetranuclear Gold(I) and Gold(I)–Copper(I) Complexes Based on Tridentate Phosphanes
  作者：Thuy Minh Dau、Julia R. Shakirova、Antonio Doménech、Janne Jänis、Matti Haukka、Elena V. Grachova、Tapani A. Pakkanen、Sergey P. Tunik、Igor O. Koshevoy

  DOI：10.1002/ejic.201300615

  日期：2013.10

  Tetranuclear AuI–FeII dimetallic and AuI–CuI–FeII trimetallic complexes bearing ferrocenyl (Fc) groups have been assembled by using two triphosphane ligands, namely, (PPh2CH2)2PPh (dpmp) and (PPh2)3CH (tppm). The compositions and structural type of the clusters are dependent on the stereochemistry of the P donor ligands. The complexes [tppmAu3Cu(C2R)3]PF6 [R = Fc (1) and 4-C6H4-Fc (2)] adopt a trigonal

  通过使用两种三磷烷配体，即 (PPh2CH2)2PPh (dpmp) 和 (PPh2)3CH (tppm)，已经组装了带有二茂铁 (Fc) 基团的四核 AuI-FeII 双金属和 AuI-CuI-FeII 三金属配合物。簇的组成和结构类型取决于 P 供体配体的立体化学。配合物 [tppm (C2R)3]PF6 [R = Fc (1) 和 4-C6H4-Fc (2)] 采用配位金属核的三角锥 Au3Cu} 排列，而对于具有线性三膦的化合物 [ Au4(dpmp)2(C2R)2](PF6)2 [R = Fc (3) and 4- -Fc (4)]，发现了一个平面菱形Au4}框架。簇 1-4 通过 NMR 光谱和 ESI-MS 测量进行表征。1、3 和 4 的固态结构已通过 X 射线晶体学确定。研究了 1-4 的电化学性质，并揭示了归因于 Fc 功能的氧化还原过程。1、2 和 4
• Toward Luminescence Vapochromism of Tetranuclear Au^I–Cu^I Clusters
  作者：Julia R. Shakirova、Elena V. Grachova、Alexei S. Melnikov、Vladislav V. Gurzhiy、Sergey P. Tunik、Matti Haukka、Tapani A. Pakkanen、Igor O. Koshevoy

  DOI：10.1021/om301100v

  日期：2013.8.12

  gold–copper clusters bearing aliphatic and hydroxyaliphatic alkynyl ligands of general formula [HC(PPh2)3Au3Cu(C2R)3]+ (R = cyclohexyl (1), cyclopentyl (2), But (3), cyclohexanolyl (4), cyclopentanolyl (5), 2,6-dimethylheptanolyl (6), 2-methylbutanolyl (7), diphenylmethanolyl (8)) was synthesized via a self-assembly protocol, which involves treatment of the (AuC2R)n acetylides with the (PPh2)3CH ligand in the

  带有通式[HC（PPh 2）3 Au 3 Cu（C 2 R）3 ] +（R =环己基（1），环戊基（2），Bu t的脂族和羟基脂族炔基配体的三膦金-铜簇簇（3）通过自组装方法合成了环己基（4），环戊醇基（5），2,6-二甲基庚醇基（6），2-甲基丁醇基（7），二苯基甲醇基（8）），其中涉及对（ AuC 2 R）n（PPh 2）3 CH配体在Cu +离子和NEt 3存在的乙炔化合物。的Cl加成-或Br -阴离子复合物8所导致卤化物与铜原子配位以得到中性HC（PPH 2）3的Au 3 CuHal（C 2 COHPh 2）3个衍生物（哈尔=氯（9），溴（10））。通过NMR和ESI-MS光谱，和的结构的标题化合物进行表征1，4，7，和通过单晶X射线衍射分析确定了8个。已经研究了所有配合物的光物理行为，以揭示溶液中的中度至弱磷光以及固态时的强发射，最大量子产率为80％。无溶剂的X射线无定形样品暴露8
• Luminescent Silver–Copper “Hourglass” Hepta‐ and Decanuclear Alkynyl‐Phosphine Clusters
  作者：Ilya S. Kritchenkov、Anastasia Yu. Gitlina、Igor O. Koshevoy、Alexey S. Melnikov、Sergey P. Tunik

  DOI：10.1002/ejic.201800631

  日期：2018.9.16

  types of cluster skeletons – heptanuclear [Ag6Cu(C2R)3HC(PPh2)3}2(CF3SO3)3](CF3SO3) R = C6H4‐4‐X (X = CF3, 1A; OMe, 2A; NMe2, 3A; NC10H20O4, 4A); CPh2OH, 5A} and decanuclear [Ag6Cu4(C2C6H4‐4‐X)8HC(PPh2)3}2](CF3SO3)2 (X = CF3, 1B; H, 6B) species is governed by the electronic properties of the alkynyl ligands and the ratio of the starting components. All of the complexes, except 4A, were structurally

  在三（二苯基膦基）甲烷（tppm）存在下，在碱性条件下，Ag-Cu杂金属很容易从相应的三氟甲磺酸盐和炔烃中组装而来。两种簇状骨架的形成–七核[Ag 6 Cu（C 2 R）3 HC（PPh 2）3 } 2（CF 3 SO 3）3 ]（CF 3 SO 3）R = C 6 H 4 -4-X（X = CF 3，图1A ; OME，2A ; NME 2，图3A ; NC 10 ħ20 ø 4，4A）; 器CPh 2 OH，5A }和decanuclear将[Ag 6的Cu 4（C 2 ç 6 ħ 4 -4-X）8 HC（PPH 2）3 } 2 ]（CF 3 SO 3）2（X = CF 3，1B； H，6B）种类由炔基配体的电子性质和起始组分的比例决定。除4A外的所有复合体，通过单晶XRD分析进行了结构表征。固态光物理研究揭示了室温磷光（Φ EM = 0.3-42.5％，λ EM = 556-7
• A nickel(0) dimer/monomer system with facile and reversible carbon monoxide uptake: Ni2(CO)x(dppm)2 (x = 3, 4) and Ni(CO)3(.eta.1-dppm)
  作者：John A. Osborn、George G. Stanley、Peter H. Bird

  DOI：10.1021/ja00215a018

  日期：1988.3

  Ni(CO)/sub 2/(HC(PPh/sub 2/)/sub 3/) decomposes slowly at room temperature to produce the bis(diphenylphosphino)methane (dppm) bridged nickel(0) dimer Ni/sub 2/(CO)/sub 3/(dppm)/sub 2/ (4). Complex 4 crystallizes in the orthorhombic space group Pbcn with a = 14.015 (2) A, b = 18.784 (5) A, c = 22.743 (8) A, V = 5987 (4) A/sup 3/, and Z = 4. A total of 3913 reflections were collected using Mo K..cap

  Ni(CO)/sub 2/(HC(PPh/sub 2/)/sub 3/) 在室温下缓慢分解，生成双(二苯基膦)甲烷 (dppm) 桥接的镍 (0) 二聚体 Ni/sub 2/( CO)/sub 3/(dppm)/sub 2/ (4)。配合物 4 在正交空间群 Pbcn 中结晶，a = 14.015 (2) A, b = 18.784 (5) A, c = 22.743 (8) A, V = 5987 (4) A/sup 3/, and Z = 4 . 使用Mo K..cap alpha..辐射总共收集了3913次反射，并通过使用F/sub o//sup 2/ > 3 sigma(F/sub o/ )/sup 2/，导致最终的 R/sub 1/ = 0.062。忽略 Ni-Ni 键，4 的结构显示关于两个镍原子的近似四面体几何形状，其中两个桥连 dppm 配体、一个桥连羰基配体和两个末端羰基
• Neutral Gold(I) Metallosupramolecular Compounds: Synthesis and Characterization, Photophysical Properties, and Density Functional Theory Studies
  作者：Laura Rodríguez、Carlos Lodeiro、João Carlos Lima、Ramon Crehuet

  DOI：10.1021/ic800266m

  日期：2008.6.2

  calculations have been used to assign the lowest energy absorption bands to LMCT N(p, tertiary amine)-->Au transitions. Photophysical characterization of the complexes shows strong luminescence in the solid state. The formation of heterobimetallic species has been detected in solution in the presence of equimolar quantities of metal cations, and their structures have been identified by a combination of spectroscopic

  三吲哚InTREN配体（L）与不同的金膦片段的反应可根据所选的膦，构建具有不同几何形状的新的金（I）配合物。当金原子与三苯基膦配体连接时，获得金属树枝状结构，而当使用三膦时，则构建中性的金（I）金属隐链体。化合物的表征通过31P 1H}和1H NMR，IR，吸收和荧光光谱，电喷雾电离质谱（ESI-MS（+））和元素分析完成，并使用密度泛函理论对化合物的几何形状进行了优化（ B3LYP）。随时间变化的密度泛函理论（TD-DFT）计算已用于为LMCT N（p，叔胺）-> Au跃迁分配最低的能量吸收带。配合物的光物理表征显示出固态的强发光。在存在等摩尔量的金属阳离子的情况下，已在溶液中检测到了异双金属物种的形成，并且已通过结合光谱学方法和质谱法鉴定了它们的结构。