三(4-三氟甲苯基)膦 | 13406-29-6

• 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: 三(4-三氟甲苯基)膦
• 中文别名: 三(对三氟甲苯基)膦；三（4-三氟甲苯基）膦
• 英文名称: P(p-CF3C6H4)3
• 英文别名: tris(para-trifluoromethyl)phenyl phosphine；tris(p-trifluoromethylphenyl)phosphine；tris(4-trifluoromethylphenyl)phosphine；tris[4-(trifluoromethyl)phenyl]phosphane
• CAS: 13406-29-6
• 化学式: C₂₁H₁₂F₉P
• mdl: MFCD00058883
• 分子量: 466.286
• InChiKey: PXYCJKZSCDFXLR-UHFFFAOYSA-N

物化性质

• 熔点：
  70-75 °C
• 沸点：
  382.8±42.0 °C(Predicted)
• 溶解度：
  氯仿（微溶）、甲醇（微溶）
• 稳定性/保质期：
  常温常压下稳定，应避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  9

安全信息

• TSCA：
  No
• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2903999090
• 危险品运输编号：
  NONH for all modes of transport
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P261,P273,P305+P351+P338
• 危险性描述：
  H315,H319,H335,H413
• 储存条件：
  常温密闭保存，阴凉通风干燥。

SDS

Name:	Tris(4-trifluoromethylphenyl)phosphine Material Safety Data Sheet
Synonym:	None Known
CAS:	13406-29-6

Section 1 - Chemical Product MSDS Name:Tris(4-trifluoromethylphenyl)phosphine Material Safety Data Sheet
Synonym:None Known

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13406-29-6	Tris(4-trifluoromethylphenyl)phosphine		unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
No information found.

---

Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
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:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
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:
Treat symptomatically and supportively.

---

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 water spray, dry chemical, carbon dioxide, or chemical foam.

---

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.

---

Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

---

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# 13406-29-6: Personal Protective Equipment Eyes: 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:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: fine - light yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 72 - 75 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: C21H12F9P
Molecular Weight: 466.29

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of phosphorus, carbon dioxide, hydrogen fluoride gas, phosphoric acid.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 13406-29-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Tris(4-trifluoromethylphenyl)phosphine - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 13406-29-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 13406-29-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13406-29-6 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

作用

三(4-三氟甲苯基)膦是一种有机磷配体或催化剂，在多种有机反应中发挥重要作用。

制备

制备三(4-三氟甲苯基)膦时，首先需要准备苄膦和三氟甲基苯基溴化镁两种原料。将这两种原料加入干燥的有机溶剂（常用的包括乙醚、四氢呋喃等）中，并在室温下进行反应，通常需要搅拌数小时至数天。反应结束后，通过过滤沉淀物并蒸馏溶剂的方法分离和纯化产物。最终可以通过结晶或柱层析方法获得纯净的三(4-三氟甲苯基)膦。

反应信息

• 作为反应物：
  描述：

  三(4-三氟甲苯基)膦 在 三溴化磷 、 溴化铁(III) 作用下， 以 四氯化碳 为溶剂， 反应 10.0h， 以91%的产率得到bis(4-trifluoromethylphenyl)phosphonium bromide
  参考文献：
  名称：

  一种二芳基磷溴化合物的制备方法

  摘要：

  本发明公开了一种二芳基磷溴化合物的制备方法，属于有机合成领域。该方法以三芳基磷为起始原料，溴化铁为催化剂，与三溴化磷反应后经蒸馏得到芳基磷溴化合物。本发明与现有技术相比反应收率高，后处理简单，更适合工业化生产。制得的芳基磷溴化合物可用于合成金属催化剂的配体，应用于有机光电材料及医药等领域。

  公开号：

  CN107936056B
• 作为产物：
  描述：

  4-三氟甲基苯基溴化镁 在 三氯化磷 作用下， 生成 三(4-三氟甲苯基)膦
  参考文献：
  名称：

  Zhmurova,I.N.; Kirsanov,A.V., Journal of general chemistry of the USSR, 1966, vol. 36, p. 1265 - 1269

  摘要：

  DOI：
• 作为试剂：
  描述：

  2'-溴苯乙酮 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium fluoride 、 copper(l) iodide 、 三乙胺 、 三氟乙酸 、 双三氟甲烷磺酰亚胺银盐 、 三(4-三氟甲苯基)膦 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 20.0h， 生成 1-(4-methoxybenzyl)-1-methyl-3-phenyl-1H-isochromene
  参考文献：
  名称：

  开发π-路易斯酸性金属催化环化/自由基加成序列的流动光化学工艺：原位生成的2-苯并吡喃鎓作为光氧化还原催化剂和反应中间体

  摘要：

   抽象的 开发了一种用于 π-Lewis 酸性金属催化环化/自由基加成序列的流动光化学反应系统，该系统利用原位生成的 2-苯并吡喃鎓中间体作为光氧化还原催化剂和亲电子底物。通过π-Lewis酸性金属催化剂AgNTf 2对邻羰基炔基苯衍生物进行分子内环化，并随后用三氟乙酸进行原脱金属，在流动反应体系中生成了关键的2-苯并吡喃鎓中间体。 2-苯并吡喃鎓中间体在流动光反应器中与苄基三甲基硅烷衍生物作为供体分子进行进一步的光反应，在大多数情况下比间歇反应系统以更高的产率提供 1 H-异色烯衍生物。 贝尔斯坦 J. 组织。化学。 2024, 20, 1973–1980。 doi:10.3762/bjoc.20.173

  DOI：

  10.3762/bjoc.20.173

文献信息

• Ir(III)-Catalyzed Direct C–H Functionalization of Arylphosphine Oxides: A Strategy for MOP-Type Ligands Synthesis
  作者：Zhong Liu、Ji-Qiang Wu、Shang-Dong Yang

  DOI：10.1021/acs.orglett.7b02710

  日期：2017.10.6

  efficiently applied to Ir(III)-catalyzed direct C–H functionalization of arylphosphine oxides. Involving C–H activation, carbene insertion, and tautomerism, this reaction proceeds under mild conditions, thus proving an approach to the synthesis of MOP-type ligand precursor in a single step. The utility of this transformation has been further demonstrated in ligand synthesis as well as in the construction

  重氮化合物作为偶联伙伴可有效地应用于Ir（III）催化的芳基膦氧化物的直接C–H官能化。涉及C–H活化，卡宾插入和互变异构，该反应在温和条件下进行，因此证明了一步合成MOP型配体前体的方法。这种转化的效用已在配体合成以及磷脂骨架的构建中得到了进一步证明。
• N-(PHOSPHINOALKYL)-N-(THIOALKYL)AMINE DERIVATIVE, METHOD FOR PRODUCING SAME, AND METAL COMPLEX THEREOF
  申请人：TAKASAGO INTERNATIONAL CORPORATION

  公开号：US20170233418A1

  公开（公告）日：2017-08-17

  The purpose of the present invention is to provide: a ligand that is useful in a catalytic organic synthetic reaction; a method for producing said ligand; and a metal complex that is useful as a catalyst in an organic synthetic reaction. The present invention provides a compound represented by general formula (1 A ), a method for producing said compound, and a metal complex including said compound as a ligand. (In the formula, H, N, P, S, L, R 1 , R 2 , R 3 , Q 1 , and Q 2 have the meaning as defined in the Description.)

  本发明的目的是提供：在催化有机合成反应中有用的配体；制备所述配体的方法；以及在有机合成反应中作为催化剂有用的金属配合物。本发明提供了由通式（1A）表示的化合物，制备所述化合物的方法，以及包括所述化合物作为配体的金属配合物。（在该式中，H、N、P、S、L、R1、R2、R3、Q1和Q2的含义如描述中所定义。）
• Coulombic inter-ligand repulsion effects on the Pt(ii) coordination chemistry of oligocationic, ammonium-functionalized triarylphosphines
  作者：Dennis J. M. Snelders、Maxime A. Siegler、Lars S. von Chrzanowski、Anthony L. Spek、Gerard van Koten、Robertus J. M. Klein Gebbink

  DOI：10.1039/c0dt01105c

  日期：——

  triarylphosphines (L) is described. Complexes of the type PtX2(L)2 (X = Cl, I) have been isolated and characterized. For the hexa-meta-ammoniomethyl-substituted ligands [1]6+ and [2]6+, two ligands always occupy a trans-configuration with respect to each other in complexes of the type PtX2(L)2, while for the tri-para-ammoniomethyl-substituted ligand [7]3+, the trans/cis ratio is dependent on the ionic

  描述了低阳离子铵甲基和中性氨基甲基取代的三芳基膦（L）的Pt（II）配位化学。已分离出PtX 2（L）2（X = Cl，I）类型的复合物。对于六-间-氨基甲基取代的配体[ 1 ] 6+和[ 2 ] 6+，两个配体在PtX 2（L）2类型的复合物中始终相对于彼此占据反式构型，而对于三对-氨甲基取代的配体[ 7 ] 3+，反式/顺式比取决于溶液的离子强度。对于中性氨基甲基取代的配体未观察到此行为。在反式-[PtI 2（1）2 ] I 12的晶体结构中，膦配体[ 1 ] 6+的几何参数与基准配体PPh 3的类似配合物中所发现的几何参数非常相似，即反式- PtI 2（PPh 3）2，表明该复合物中不存在明显的空间充血增加。取而代之的是，这类膦配体的配位化学是由排斥库仑间配体相互作用决定的。
• Synthesis and Structure–Activity Relationship Study of Antimicrobial Auranofin against ESKAPE Pathogens
  作者：Bin Wu、Xiaojian Yang、Mingdi Yan

  DOI：10.1021/acs.jmedchem.9b00550

  日期：2019.9.12

  including multidrug resistant strains. It is, however, inactive toward Gram-negative bacteria, for which we are in dire need of new therapies. In this work, 40 auranofin analogues were synthesized by varying the structures of the thiol and phosphine ligands, and their activities were tested against ESKAPE pathogens. The study identified compounds that exhibited bacterial inhibition (MIC) and killing

  FDA批准的关节炎药物金诺芬（Auranofin）最近已被重新用作潜在的抗菌药物。它对许多革兰氏阳性细菌（包括耐多药菌株）表现良好。但是，它对革兰氏阴性细菌没有活性，因此我们急需新疗法。在这项工作中，通过改变硫醇和膦配体的结构合成了40种金诺芬类似物，并测试了它们对ESKAPE病原体的活性。该研究鉴定出的化合物具有比金诺芬高65倍的细菌抑制（MIC）和杀灭（MBC）活性，从而使它们对革兰氏阴性病原体有效。硫醇和膦结构都影响类似物的活性。三甲基膦和三乙基膦配体分别对革兰氏阴性菌和革兰氏阳性菌具有最高的活性。我们的SAR研究表明，巯基配体也非常重要，其结构可以调节AuI复合物对革兰氏阴性细菌和革兰氏阳性细菌的活性。而且，这些类似物具有的哺乳动物细胞毒性与金诺芬相似或更低。
• Construction of pincer-type symmetrical ruthenium(<scp>ii</scp>) complexes bearing pyridyl-2,6-pyrazolyl arms: catalytic behavior in transfer hydrogenation of ketones
  作者：Zhu Zhu、Jie Zhang、Haiyan Fu、Maolin Yuan、Xueli Zheng、Hua Chen、Ruixiang Li

  DOI：10.1039/c4ra07524b

  日期：——

  Convenient synthesis of four new distorted octahedral ruthenium(II) complexes (1, 2, 3, 4) having general molecular formula [RuCl2LPAr3] (L = pyridine-based tridentate ligands not containing N–H bonds) is described. Their composition and structure were determined by elemental analysis and NMR spectra, and complexes 2 and 4 were also identified by X-ray single-crystal diffraction. All ruthenium(II)

  方便合成的四个新的扭曲的八面体的钌（II）配合物（1，2，3，4），其具有一般分子式将[RuCl 2大号PAR 3 ]（大号=不含有N-H键的基于吡啶的三齿配体）进行说明。通过元素分析和NMR谱确定了它们的组成和结构，还通过X射线单晶衍射鉴定了配合物2和4。所有钌（II）配合物在酮的转移加氢中均表现出良好的催化活性。其中，复杂4对于高底物与催化剂的摩尔比（2000：1），获得了最高的最终TOF值51 600 h -1。

表征谱图