di-μ-chlorobis(2'-amino-1,1'-biphenyl-2-yl-C,N)dipalladium(II) | 847616-85-7

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: di-μ-chlorobis(2'-amino-1,1'-biphenyl-2-yl-C,N)dipalladium(II)
• 英文别名: di-μ-chlorobis(2-amino-1,1-biphenyl-2-yl-C,N)dipalladium(ll)；chloropalladium(1+);2-phenylaniline
• CAS: 847616-85-7
• 化学式: C₂₄H₂₀Cl₂N₂Pd₂
• 分子量: 620.182
• InChiKey: RPAYRDJYFJKAML-UHFFFAOYSA-L

物化性质

• 熔点：
  207°C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.53
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P264,P280,P337+P313,P305+P351+P338,P302+P352,P332+P313,P362
• 危险性描述：
  H315,H319

SDS

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Section 1: Product Identification
Chemical Name: Chloro(2'-amino-1,1'-biphenyl-2-yl)palladium(II) dimer, min. 98%
CAS Registry Number: 847616-85-7
Formula: C24H20Cl2N2Pd2
EINECS Number: none
Chemical Family: organometallic complex
Synonym: none

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 847616-85-7 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Irritating to skin, eyes and respiratory tract. May be harmful if swallowed.
Primary Routes of Exposure: Ingestion, inhalation
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 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
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: pale grey pwdr.
Molecular Weight: 620.17
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 active metals
Decomposition Products: carbon monoxide, carbon dioxide, palladium oxide, 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): Not reportable under SARA 313
Second Ingredient: none

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  di-μ-chlorobis(2'-amino-1,1'-biphenyl-2-yl-C,N)dipalladium(II) 在 四丁基氟化铵 、 silver(I) acetate 、 palladium dichloride 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 15.0h， 生成 6-甲基菲啶
  参考文献：
  名称：

  钯催化的伯芳基联胺-2-胺的伯胺定向区域选择性单和双炔基化

  摘要：

  通过使用（溴乙炔基）三异丙基硅烷作为烷基化试剂，开发了钯催化的伯芳基-2-胺的伯胺定向的C（sp 2）–H烷基化伯胺的第一个例子。该协议具有广泛的底物范围，出色的区域选择性和克级合成。值得注意的是，这种简单方法的多功能性通过受控的单和双炔基化进一步得到证明。

  DOI：

  10.1039/c7cc09308j
• 作为产物：
  描述：

  2-氨基联苯 、 palladium dichloride 以 甲醇 为溶剂， 反应 24.0h， 以68%的产率得到di-μ-chlorobis(2'-amino-1,1'-biphenyl-2-yl-C,N)dipalladium(II)
  参考文献：
  名称：

  钯催化的伯芳基联胺-2-胺的伯胺定向区域选择性单和双炔基化

  摘要：

  通过使用（溴乙炔基）三异丙基硅烷作为烷基化试剂，开发了钯催化的伯芳基-2-胺的伯胺定向的C（sp 2）–H烷基化伯胺的第一个例子。该协议具有广泛的底物范围，出色的区域选择性和克级合成。值得注意的是，这种简单方法的多功能性通过受控的单和双炔基化进一步得到证明。

  DOI：

  10.1039/c7cc09308j
• 作为试剂：
  描述：

  对溴甲苯 、 4,5-dimethyl-9-phenyl-9H-fluoren-9-ol 在 di-μ-chlorobis(2'-amino-1,1'-biphenyl-2-yl-C,N)dipalladium(II) 、 C₆₀H₅₄NO₅P 、 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以99%的产率得到
  参考文献：
  名称：

  对映选择性碳-碳键裂解制联芳基阻转异构体

  摘要：

  对映选择性碳-碳和碳-杂原子键形成的新合成策略的开发是现代有机化学的支柱之一。尽管在中心手性结构上已经取得了重大进展，但是轴向手性的催化不对称结构仍在开发中。而且，通过碳-碳和碳-杂原子键裂解构建的轴向手性分子受到极大限制。在这里，我们报告通过钯催化的9-芳基-9 H的化学选择性碳-碳裂解不对称合成联芳基阻转异构体-芴-9-醇。该反应证明了广泛的底物范围并且以高收率和对映选择性产生了阻转异构体。基质中联芳基骨架的两个邻位取代基之间的空间排斥所产生的扭转应变极大地加速了开环反应性。高对映体控制取决于新的基于TADDOL的亚磷酰胺作为配体的发展。这些发现为通过不对称碳-碳裂解的新型合成方法的开发建立了一个新平台。

  DOI：

  10.1016/j.chempr.2019.04.008

文献信息

• 碳水化合物单膦、它们的制备方法和用途
  申请人：东莞市均成高新材料有限公司

  公开号：CN111018923A

  公开（公告）日：2020-04-17

  本发明提供具有通式Ia、Ib、IIa或IIb的碳水化合物单膦，包括磷原子构型不同的Ia和Ib的混合物或者磷原子构型不同的IIa和IIb的混合物，和它们的制备方法；本发明描述了碳水化合物单膦的硼烷加合物、氧化物、硫化物或硒化物；此外，本发明还提供了碳水化合物单膦配位的钯络合物；碳水化合物单膦与钯盐或络合物组成的催化体系、或碳水化合物单膦配位的钯络合物在催化有机反应中的用途亦是本发明的一部分，特别是在催化（拟）卤代芳烃去形成新的C‑C、或C‑N键的偶联反应中的用途。
• Pd-Catalyzed α-Arylation of α,α-Difluoroketones with Aryl Bromides and Chlorides. A Route to Difluoromethylarenes
  作者：Shaozhong Ge、Wojciech Chaładaj、John F. Hartwig

  DOI：10.1021/ja501117v

  日期：2014.3.19

  α-difluoroketones with aryl and heteroaryl bromides and chlorides catalyzed by an air- and moisture-stable palladacyclic complex containing P(t-Bu)Cy2 as ligand. The combination of this Pd-catalyzed arylation and base-induced cleavage of the acyl–aryl C–C bond within the α-aryl-α,α-difluoroketone constitutes a one-pot, two-step procedure to synthesize difluoromethylarenes from aryl halides. A broad range

  我们报告了 Pd 催化的 α,α-二氟酮与芳基和杂芳基溴化物和氯化物的 α-芳基化反应，该反应由含有 P(t-Bu)Cy2 作为配体的空气和水分稳定的钯环络合物催化。这种 Pd 催化的芳基化和碱诱导的 α-芳基-α,α-二氟酮内酰基-芳基 C-C 键断裂的组合构成了从芳基卤化物合成二氟甲基芳烃的一锅两步法。广泛的电子变化芳基和杂芳基溴化物和氯化物经历了这两种转化，以高产率提供了 α-芳基-α,α-二氟酮、二氟甲基芳烃和二氟甲基杂芳烃。
• Pd-Catalyzed α-Arylation of Trimethylsilyl Enolates of α,α-Difluoroacetamides
  作者：Shaozhong Ge、Sophie I. Arlow、Michael G. Mormino、John F. Hartwig

  DOI：10.1021/ja508590k

  日期：2014.10.15

  ilyl)acetamides with aryl and heteroaryl bromides catalyzed by an air- and moisture-stable palladacyclic complex containing P(t-Bu)2Cy as ligand. A broad range of electronically varied aryl and heteroaryl bromides underwent this transformation to afford α-aryl-α,α-difluoroacetamides in high yields. Due to the electrophilicity of the fluorinated amide, this palladium-catalyzed cross-coupling reaction

  我们报道了由含有 P(t-Bu)2Cy 作为配体的空气和湿气稳定的钯环配合物催化的 α,α-二氟-α-(三甲基硅基)乙酰胺与芳基和杂芳基溴的芳基化和杂芳基化。多种电子变化的芳基和杂芳基溴化物经历了这种转化，以高产率提供 α-芳基-α,α-二氟乙酰胺。由于氟化酰胺的亲电性，这种钯催化的交叉偶联反应提供了一个通用平台来生成一系列 α,α-二氟羰基化合物，例如 α-芳基-α,α-二氟酮、-乙醛、-在温和条件下，可以制备乙酸酯、乙酸和二氟烷基衍生物，例如2-芳基-2,2-二氟乙醇和乙胺。
• Dialkylterphenyl Phosphine‐Based Palladium Precatalysts for Efficient Aryl Amination of <i>N</i> ‐Nucleophiles
  作者：Raquel J. Rama、Celia Maya、M. Carmen Nicasio

  DOI：10.1002/chem.201903279

  日期：2020.1.22

  in aryl amination reactions. Cationic complexes bearing the phosphines PiPr2 ArXyl2 and PCyp2 ArXyl2 were the most active of the series. These precatalysts have demonstrated a high versatility and efficiency in the coupling of a variety of nitrogen nucleophiles, including secondary amines, alkyl amines, anilines, and indoles, with electronically deactivated and ortho-substituted aryl chlorides at low

  由二烷基三联苯膦，PR2 Ar'（R = Me，Et，iPr，Cyp（环戊基），Ar'= ArDipp2，ArXyl2f，Dipp（2,6-C6H3-（2,6-C6H3 -（CHMe 2）2）2），Xyl ＝二甲苯基）已经制备并在结构上表征。获得具有较小体积的三联苯膦（即Me和Et取代基）的中性Palladacycles，而最大的膦则提供了阳离子Palladacycles，其中膦采用了双齿半键k1-P，η1-Carene配位模式。在芳基胺化反应中评价了配体结构对这些Pd预催化剂催化性能的影响。带有膦基PiPr2 ArXyl2和PCyp2 ArXyl2的阳离子配合物是该系列中活性最高的。
• Phosphine-Ligated Palladium Sulfonate Palladacycles
  申请人：Massachusetts Institute of Technology

  公开号：US20130331566A1

  公开（公告）日：2013-12-12

  Described are palladium precatalysts, and methods of making and using them. The palladium precatalysts show improved stability and improved reactivity in comparison to previously-described palladium precatalysts.

  描述了钯前催化剂及其制备和使用方法。与先前描述的钯前催化剂相比，这些钯前催化剂表现出更高的稳定性和更高的反应性。