chloro(2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl)[2-(2-aminoethylphenyl)]palladium(II) | 1028206-58-7

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: chloro(2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl)[2-(2-aminoethylphenyl)]palladium(II)
• 英文别名: Sphos；(SPhos)PdCl(C6H4CH2CH2NH2)；(Cy2PC6H4C6H3(OMe)2)PdCl(C6H4CH2CH2NH2)；chloro(2-dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl)[2-(2-aminoethylphenyl)]palladium(II), methyl-t-butylether adduct；Dicyclohexyl-[2-(2,6-dimethoxyphenyl)phenyl]phosphane;palladium(2+);2-phenylethanamine;chloride；dicyclohexyl-[2-(2,6-dimethoxyphenyl)phenyl]phosphane;palladium(2+);2-phenylethanamine;chloride
• CAS: 1028206-58-7
• 化学式: C₃₄H₄₅ClNO₂PPd
• 分子量: 672.584
• InChiKey: RUWSWVWKRCXWAA-UHFFFAOYSA-M

物化性质

• 熔点：
  176℃

计算性质

• 辛醇/水分配系数(LogP)：
  8.82
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

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Section 1: Product Identification
Chloro(2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl)[2-(2-aminoethylphenyl)]palladium(II)
Chemical Name:
methyl-t-butylether adduct, min. 98% [SPhos Palladacycle]
CAS Registry Number: 1028206-58-7
Formula: C34H45ClNO2PPd
EINECS Number: none
Chemical Family: organometallic complex
Chloro(2-dicyclohexylphosphano-2',6'-dimethoxy-1,1'-biphenyl)[2-(2-aminoethylphenyl)]palladium(II)
Synonym:
dichloromethane adduct, min. 98%

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 1028206-58-7 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Irritating to skin, eyes and respiratory tract.
Primary Routes of Exposure: Inhalation, skin, eyes
Eye Contact: Causes slight to mild 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 information available on the physiological effects of ingestion. May be harmful if swallowed.
Acute Health Affects: Irritating to skin, eyes and respiratory tract.
Chronic Health Affects: No information 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: no data
Autoignition Temperature: no data
Explosion Limits: no data
Extinguishing Medium: carbon dioxide, dry powder or foam
If this product is involved in a fire, fire fighters should be equipped with a NIOSH approved positive pressure
Special Fire Fighting Procedures:
self-contained breathing apparatus and full protective clothing.
Hazardous Combustion and If involved in a fire this material may emit irritating fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unususal fire or explosion hazards.

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SECTION 6: Accidental Release Measures
Spill and Leak Procedures: Small spills can be mixed with vermiculite or sodium carbonate and swept up.

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SECTION 7: Handling and Storage
Handling and Storage: Store in a tightly sealed container. Keep in a cool, dry, well ventilated place.

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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.
Ventilation: 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: 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 powder
Molecular Weight: 672.57
Melting Point: no data
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 monoxide, palladium chloride, nitrigen oxides, phosphorus oxides and organic fumes.

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

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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 local, state and federal 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

制备方法与用途

该化合物为二环己基膦基取代的1,1-联苯衍生物（2-二环己基膦-2,6-二甲氧基-1,1-联苯），可用作医药中间体。

反应信息

• 作为反应物：
  描述：

  chloro(2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl)[2-(2-aminoethylphenyl)]palladium(II) 在 NaOCH₂C(CH₃)3 or LiN(Si(CH₃)3)2 作用下， 以 1,4-二氧六环 为溶剂， 生成 (Cy₂PC₆H₄C₆H₃(OMe)2)Pd
  参考文献：
  名称：

  一类新的易于活化的钯预催化剂，用于简单的 C−N 交叉偶联反应和芳基氯化物的低温氧化加成

  摘要：

  描述了一类新的带有联芳基膦配体的单组分 Pd 预催化剂。这些预催化剂对空气和热稳定，在室温或低于室温的正常反应条件下很容易活化，并确保形成氧化加成所需的高活性单连接 Pd(0) 络合物。探索了在 CN 交叉偶联反应中使用这些预催化剂作为 LPd(0) 的方便来源。本研究中展示的反应性在钯化学中是前所未有的。

  DOI：

  10.1021/ja801137k
• 作为产物：
  描述：

  2-phenylethan-1-aminium trifluoromethanesulfonate 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.5h， 生成 chloro(2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl)[2-(2-aminoethylphenyl)]palladium(II)
  参考文献：
  名称：

  NH 2键合的环钯缩合的1-苯丙氨酸与碱辅助的分子内C–N偶联反应成吲哚-2-羧酸

  摘要：

  对苯丙氨酸衍生的palladacycles的去质子化分子内胺化反应进行了研究，以突出在碳氮键形成之前碳酸盐辅助的NH活化的简便性。一个主要的抗衡离子效应导致了不同的途径，其中SPhos-Pd与碘，三氟甲磺酸根或三氟乙酸根阴离子的络合物是获得（S）-2-二氢吲哚羧酸衍生物的关键中间体。

  DOI：

  10.1021/acs.organomet.0c00030
• 作为试剂：
  描述：

  5-溴-2-甲基-2H-吲唑 、 5-氯-1H-吡唑并[3,4-c]吡啶 在 potassium phosphate 、 chloro(2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl)[2-(2-aminoethylphenyl)]palladium(II) 、 bis[(tetrabutylammoniumiodide)copper(I) iodide] 、 (1R,2R)-(-)-N,N'-二甲基-1,2-环己二胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 22.0h， 生成 1-(2-methyl-2H-indazol-5-yl)-1H-pyrazolo[3,4-c]pyridin-5-amine
  参考文献：
  名称：

  [EN] ERK INHIBITORS
  [FR] INHIBITEURS D'ERK

  摘要：

  本发明提供了一种化合物(I)或其药学上可接受的盐、酯和前药，这些化合物是ERK2抑制剂。该发明还提供了一种包括至少一种化合物(I)和药学上可接受的载体的有效量的药物组合物。该发明还提供了一种包括至少一种化合物(I)的有效量和至少一种其他药学活性成分的有效量（例如，化疗药物等）以及药学上可接受的载体的药物组合物。

  公开号：

  WO2016100050A1

文献信息

• A New Method for High-Yield Cyclopalladation of Primary and Secondary Amines. Atom-Efficient Open-to-Air Inexpensive Synthesis of Buchwald-Type Precatalysts
  作者：José Vicente、Isabel Saura-Llamas、María-José Oliva-Madrid、José-Antonio García-López、Delia Bautista

  DOI：10.1021/om200464s

  日期：2011.9.12

  A new method for high-yield cyclopalladation of primary and secondary amines involving the corresponding ammonium triflates, instead of the amines generally employed, is reported. The method is applied for the synthesis of Buchwald-type precatalysts [Pd(C,N-C6H4CH2CH(R′)NHR-2)X(phosphine)] that can be easily prepared by reaction of Pd(OAc)2, 1 equiv of the ammonium triflate [PhCH2CH(R′)NH2R]OTf, and

  据报道，涉及相应的三氟甲磺酸铵的伯胺和仲胺的高产环palpalladation的新方法，而不是通常使用的胺。该方法适用于布奇瓦尔德型预催化剂的合成[Pd（C，N -C 6 H 4 CH 2 CH（R'）NHR-2）X（膦）]，可以通过Pd（OAc）反应容易地制备）2，1当量的三氟甲磺酸铵[PhCH 2 CH（R'）NH 2 R] OTf和过量的NaX，然后处理所得的络合物[Pd 2（C，N -C 6 H 4 CH 2CH（R'）NHR-2）2（μ-X）2 ]与适当的膦。与Buchwald报道的合成方法相比，该新方法具有多个优点。