双(三环己基膦)钯 - CAS号 33309-88-5

物化性质

熔点：

87-92°C

计算性质

辛醇/水分配系数(LogP)：

12.93
重原子数：

39
可旋转键数：

6
环数：

6.0
sp3杂化的碳原子比例：

1.0
拓扑面积：

0
氢给体数：

0
氢受体数：

0

安全信息

安全说明：

S24/25
危险类别码：

R36/37/38
WGK Germany：

2
海关编码：

29310099
危险品标志：

Xi,T
危险性防范说明：

P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
危险性描述：

H315,H319,H335
储存条件：

保持贮藏器密封，并将其存放在阴凉、干燥的地方。确保工作间有足够的通风或排气装置。

SDS

SDS：c60dd52ab43b745e6a36d29e0ad777ff

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Name:	Bis(tricyclohexylphosphine)palladium(0) Material Safety Data Sheet
Synonym:
CAS:	33309-88-5

Section 1 - Chemical Product MSDS Name:Bis(tricyclohexylphosphine)palladium(0) Material Safety Data Sheet
Synonym:

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
33309-88-5	Bis(tricyclohexylphosphine)palladium(0		unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Air sensitive.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

Section 4 - FIRST AID MEASURES
Eyes: 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.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
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.
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:
Vacuum or sweep up material and place into a suitable disposal container.

Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Store under an inert atmosphere.

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 33309-88-5: Personal Protective Equipment Eyes: Not available.
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: Crystals
Color: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Insoluble.
Specific Gravity/Density:
Molecular Formula: C36H66P2Pd
Molecular Weight: 667.28

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials, exposure to air.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of phosphorus, carbon dioxide.
Hazardous Polymerization: Has not been reported

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 33309-88-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Bis(tricyclohexylphosphine)palladium(0) - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
No information available.

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 33309-88-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 33309-88-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 33309-88-5 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

用途：作为催化剂，用于Suzuki、Kumada、Negishi和Buchwald等多种偶联反应中。

反应信息

作为反应物：

描述：

双(三环己基膦)钯以四氢呋喃、氘代四氢呋喃、甲苯为溶剂， 20.0~100.0 ℃ 、101.33 kPa 条件下，反应 5.0h，生成 trans-(PCy3)2Pd(Cl)(η(1)-CF=CF2)

参考文献：

名称：

氟化烯烃和芳烃通过氟化钯关键中间体的钯催化无碱 Suzuki-Miyaura 偶联反应

摘要：

开发了一种通过氟化烯烃和芳烃的 C-F 活化与有机硼酸酯形成 C-C 键的新策略。在这种 Pd 催化的 Suzuki-Miyaura 型交叉偶联反应中，既不需要用于增强有机硼试剂反应性的碱，也不需要用于促进 C-F 键活化的路易斯酸。氟钯中间体在该反应中发挥了重要作用。此外，Ni(NHC)催化剂通过氟芳烃的C-F键活化对C-C偶联是有效的。

DOI：

10.1002/ejoc.201201405
作为产物：

描述：

trans-chlorohydridobis(tricyclohexylphosphine)palladium(II) 以四氢呋喃、苯为溶剂，生成双(三环己基膦)钯

参考文献：

名称：

Seligson, Allen L.; Cowan, Robert L.; Trogler, William C., Inorganic Chemistry, 1991, vol. 30, # 18, p. 3371 - 3381

摘要：

DOI：
作为试剂：

描述：

3-溴-4-甲氧基-5-甲基苯甲醛在双(三环己基膦)钯、 cesium pivalate 作用下，以甲苯为溶剂，反应 16.0h，以91%的产率得到2,3-二氢苯并呋喃-5-甲醛

参考文献：

名称：

由1,4-钯位移实现的两个C（sp3）-H键之间的氧化还原-中性偶联，用于合成杂环。

摘要：

通过从三取代的芳基溴化物进行的1,4-Pd转移，可以使两个C（sp3）-H键形成一个C（sp3）-C（sp3）键进行分子内偶联。与大多数C（sp3）-C（sp3）交叉脱氢偶联相反，该反应在氧化还原中性条件下进行，其中C-Br键充当内部氧化剂。此外，它允许两个中等酸性的伯或仲CH键之间的偶联，其在一侧与氧或氮原子相邻，而在另一侧为苄基或与羰基相邻。从易于获得的邻溴苯酚和苯胺前体中获得了各种有价值的稠合杂环。第二个CH键裂解成功地被羰基插入取代，以生成其他类型的C（sp3）-C（sp3）键。

DOI：

10.1002/anie.201908460

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文献信息

Investigation of the Mechanism of C(sp3)−H Bond Cleavage in Pd(0)-Catalyzed Intramolecular Alkane Arylation Adjacent to Amides and Sulfonamides

作者：Sophie Rousseaux、Serge I. Gorelsky、Benjamin K. W. Chung、Keith Fagnou

DOI：10.1021/ja103081n

日期：2010.8.11

reactivity of C(sp(3))-H bonds adjacent to a nitrogen atom can be tuned to allow intramolecular alkane arylation under Pd(0) catalysis. Diminishing the Lewis basicity of the nitrogen lone pair is crucial for this catalytic activity. A range of N-methylamides and sulfonamides react exclusively at primary C(sp(3))-H bonds to afford the products of alkane arylation in good yields. The isolation of a Pd(II) reaction

可以调整与氮原子相邻的 C(sp(3))-H 键的反应性，以允许在 Pd(0) 催化下进行分子内烷烃芳基化。降低氮孤对的路易斯碱度对于这种催化活性至关重要。一系列 N-甲基酰胺和磺酰胺仅在初级 C(sp(3))-H 键上反应，以高产率提供烷烃芳基化产物。Pd(II) 反应中间体的分离使得能够评估反应机理，重点是碱在 C(sp(3))-H 键断裂步骤中的作用。这些化学计量研究的结果，连同动力学同位素效应实验，为协调的金属化-去质子化 (CMD) 过渡态提供了罕见的实验支持，此前已在烷烃 C(sp(3))-H 芳基化中提出了这种过渡态。而且，DFT 计算揭示了新戊酸盐添加剂作为磷化氢从 Pd(II) 中间体解离的促进剂的额外作用，使 CMD 过渡态成为可能。最后，进行了动力学研究，揭示了反应速率表达及其与新戊酸盐浓度的关系。
Single component cationic palladium proinitiators for the latent polymerization of cycloolefins

申请人：Bell Andrew

公开号：US20050187398A1

公开（公告）日：2005-08-25

Palladium compound compositions are provided in accordance with Formulae [((R) 3 E) a Pd(Q)(LB) b ] p [WCA] r , where ((R) 3 E) is a Group 15 electron donor ligand, Q is an anionic ligand, LB is a Lewis base, WCA is a weakly coordinating anion, a is 1, 2 or 3, b is 0, 1 or 2, the sum of a and b is 1, 2 or 3 and each of p and r is an integer such that the molecular charge is zero, or [(E(R) 3 )(E(R) 2 R*)Pd(LB)] p [WCA] r where E(R) 2 R* represents a Group 15 neutral electron donor ligand and where R* is an anionic hydrocarbyl containing moiety, bonded to the Pd and having a β hydrogen with respect to the Pd center. Such compound composition exhibits latent polymerization activity in the presence of polycyclic olefins.

钯化合物组成按照以下公式提供：[((R)3E)aPd(Q)(LB)b]p[WCA]r，其中((R)3E)是第15族电子供体配体，Q是阴离子配体，LB是路易斯碱，WCA是弱配位阴离子，a为1、2或3，b为0、1或2，a和b的总和为1、2或3，p和r各自为整数，使得分子电荷为零，或[(E(R)3)(E(R)2R*)Pd(LB)]p[WCA]r，其中E(R)2R*代表第15族中性电子供体配体，R*是与Pd键合的含有阴离子烃基的部分，并且相对于Pd中心具有β氢。这种化合物组成在多环烯烃存在时表现出潜在的聚合活性。
Preparation and Structure of a New Dipalladium Complex with Bridging Diphenylgermyl Ligands. Diverse Reactivities of Pd(PCy3)2 and Pt(PCy3)2 toward Ph2GeH2

作者：Makoto Tanabe、Naoko Ishikawa、Kohtaro Osakada

DOI：10.1021/om050981u

日期：2006.1.1

Pd centers via a Ge−H−Pd three-center−two-electron bond and a Ge−Pd σ bond. The reaction of Ph2GeH2 with [Pt(PCy3)2] produces the (germyl)hydridoplatinum complexes cis-[Pt(H)(GeHPh2)(PCy3)2] (cis-3) and trans-[Pt(H)(GeHPh2)(PCy3)2] (trans-3) as the kinetic and thermodynamic products, respectively.

的双核的钯络合物具有桥接diphenylgermyl配体，[的Pd（PCY 3）} 2（μ-HGePh 2）2 ]（1）中，由pH的反应而得到的2的GeH 2与[钯（PCY 3）2 ]。X射线晶体学结果和1的NMR光谱表明，Ge配体通过Ge-H-Pd三中心双电子键和Ge-Pdσ键与两个Pd中心配位。Ph 2 GeH 2与[Pt（PCy 3）2 ]的反应产生（锗烷基）氢化铂络合物顺式-[Pt（H）（GeHPh 2））（PCy 3）2 ]（顺-3）和反-[Pt（H）（GeHPh 2）（PCy 3）2 ]（反-3）分别作为动力学和热力学产物。
Mechanistic Studies of a Pd-Catalyzed Direct Arylation En Route to Beclabuvir: Dual Role of a Tetramethylammonium Cation and an Unusual Turnover-Limiting Step

作者：Chao Hang、Antonio Ramirez、Collin Chan、Yi Hsiao、Albert J. DelMonte、Eric M. Simmons

DOI：10.1021/acscatal.0c05533

日期：2021.3.5

arylpalladium acetate complex that undergoes C–H bond cleavage, and this equilibrium favors the former species. As a consequence, the Br/OAc exchange process becomes increasingly disfavored as the catalytic reaction progresses because of the liberation of bromide ions, but with TMAOAc as the base, the reaction can be efficiently driven forward by sequestration of bromide as the poorly soluble tetramethylammonium

报道了在向HCV NS5B抑制剂belclabuvir途中含吲哚的芳基溴化物分子内直接芳基化的机理研究。化学计量，动力学和计算研究的结合揭示了乙酸四甲基铵（TMAOAc）碱独特功效的起源，并揭示了四甲基铵阳离子的出乎意料的双重作用，以及这种分子内直接芳基化的不寻常的营业额限制步骤反应。芳基溴化钯的氧化加成配合物与经历了C–H键裂解的关键乙酸芳基钯的配合物处于平衡状态，这种平衡有利于前者。结果，由于溴离子的释放，随着催化反应的进行，Br / OAc交换过程变得越来越不利。但是以TMAOAc为碱，可通过螯合难溶的四甲基铵盐溴化物来有效地推进反应。通过可协同的金属化-去质子化过程进行的可逆的C–H键裂解事件，然后是限制营业额的还原消除反应，从而释放出环化产物。从这些研究中获得的知识使这种化学方法能够成功地在50 kg规模上执行，并且更广泛地讲，这项工作强调了化学计量的卤化物副产物可能对过渡金属催
Synthesis, Structure, Theoretical Studies, and Ligand Exchange Reactions of Monomeric, T-Shaped Arylpalladium(II) Halide Complexes with an Additional, Weak Agostic Interaction

作者：James P. Stambuli、Christopher D. Incarvito、Michael Bühl、John F. Hartwig

DOI：10.1021/ja037928m

日期：2004.2.1

The oxidative addition of phenyl bromide and iodide to Pd(Q-phos)2 was faster than oxidative addition to Pd(1-AdPtBu2)2 or Pd(PtBu3)2. Several of the arylpalladium complexes were characterized by X-ray diffraction. All of the arylpalladium(II) complexes are T-shaped monomers. The phenyl ligand, which has the largest trans influence, is located trans to the open coordination site. The complexes appear

已经制备了一系列含有单个膦配体的单体芳基钯 (II) 配合物 LPd(Ph)X（L = 1-AdPtBu2、PtBu3 或 Ph5FcPtBu2（Q-phos）；X = Br、I、OTf）。在 1 当量膦存在下，将芳基溴或芳基碘氧化加成到体积庞大的三烷基膦的双连接钯 (0) 配合物或 Pd(dba)2（dba = 二亚苄基丙酮），生成相应的芳基钯 (II) 配合物收益良好。相比之下，苯氯氧化加成到双连接钯 (0) 配合物不会产生芳基钯 (II) 配合物。苯基三氟甲磺酸酯氧化加成到 PdL2（L = 1-AdPtBu2、PtBu3 或 Q-phos）也没有形成芳基钯 (II) 配合物。三氟甲磺酸银与 (1-AdPtBu2)Pd(Ph)Br 反应以良好的收率提供相应的芳基钯 (II) 三氟甲磺酸盐。苯基溴化物和碘化物氧化加成到 Pd(Q-phos)2 比氧化加成到 Pd(1-AdPtBu2)2

双(三环己基膦)钯 | 33309-88-5

物质功能分类

分子结构分类

物化性质

计算性质

安全信息

SDS

制备方法与用途

反应信息

文献信息

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