1,1'-bis[(5-methyl-2-furanyl)phosphino]ferrocene | 756824-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 1,1'-bis[(5-methyl-2-furanyl)phosphino]ferrocene
• 英文别名: 1,1'-Bis[bis(5-methyl-2-furanyl)phosphino]ferrocene；cyclopenta-2,4-dien-1-yl-bis(5-methylfuran-2-yl)phosphane;iron(2+)
• CAS: 756824-22-3
• 化学式: C₃₀H₂₈FeO₄P₂
• 分子量: 570.344
• InChiKey: LBQFGHNIRDZESS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.93
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  6

SDS

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Section 1: Product Identification
Chemical Name: 1,1'-Bis[bis(5-methyl-2-furanyl)phosphino]ferrocene, 98% HiersoPHOS-3
CAS Registry Number: 756824-22-3
Formula: C30H28FeO4P2
EINECS Number: none
Chemical Family: metal phosphine complex
Synonym: Bis(5-methylfuran-2-yl)ferrocenylphosphine; HiersoPHOS-3

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 756824-22-3 100% 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: Ingestion, inhalation, 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: not applicable
Autoignition Temperature: none
Explosion Limits: none
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 area.

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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: orange xtl.
Molecular Weight: 570.33
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, carbon dioxide, phosphorus oxides, organic fumes and metal oxides.

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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：

  dichloro( 1,5-cyclooctadiene)platinum(ll) 、 1,1'-bis[(5-methyl-2-furanyl)phosphino]ferrocene 以 二氯甲烷 为溶剂， 反应 10.0h， 以82%的产率得到(dmfpf)PtCl₂
  参考文献：
  名称：

  用于腈和氰醇水合的高活性铂催化剂：通过高通量技术进行催化剂设计和配体筛选

  摘要：

  腈水合为化学和制药行业的研究人员提供了必不可少的酰胺。然而，禁止使用这种古老的反应是 (1) 缺乏能够在环境温度下以高转换数有效水合腈类的双相催化剂，以及 (2) 水合氰醇的未解决挑战。在此，我们报告了通过精确地将富电子和缺电子配体相互反式排列，从而增强羟基的亲核性和腈基的亲电性来设计新型“供体-受体”型铂催化剂。利用高通量、自动化的工作流程并评估双齿配体库，我们发现了市售的廉价 DPPF [1,1' -ferrocenendiyl-bis(diphenylphosphine)] 提供优异的反应性。相应的“供体-受体”型催化剂2a很容易由(DPPF)PtCl2、PMe2OH和AgOTf制备。2a 的增强活性允许各种腈和氰醇在 40 °C 下以优异的转化率进行水合。对配体结构的合理重新评估导致发现了改性催化剂 2c，它含有更多富电子的 1,1'-双[双（5-甲基-2-呋喃基）膦基]二茂铁配体

  DOI：

  10.1021/jacs.8b11667
• 作为产物：
  描述：

  [(bis(5-methyl-2-furyl)phosphino)cyclopentadienyl]lithium 、 iron(II) chloride 、 1,2-bis(diphenylphosphino)-4-tert-butylcyclopentadienyl lithium 以 四氢呋喃 为溶剂， 以3%的产率得到1,2-bis(diphenylphosphino)-1'-[bis(5-methyl-2-furyl)phosphino]-4-tert-butylferrocene
  参考文献：
  名称：

  不对称杂原子环官能化的二茂铁基1,2-二膦的一般路线：新型三和四取代的二茂铁基化合物的选择性合成和表征

  摘要：

  几个单取代的环戊二烯基阴离子（A- Li）和[1,2-双（二苯基膦基）-4-叔丁基环戊二烯基]锂（B - Li）与FeCl 2反应，得到一类新型的多齿二茂铁基膦（A -Fe- B）。拟议的合成方法代表了一种独特的方法，可生产非均相的1,1'，2-取代的二茂铁（A -Fe- B），其带有不同于同环1和2取代基的异环1'-取代基。两步反应的选择性有利于形成所需的不对称产物（A -Fe- B），而不是同时形成对称的二取代和四取代的二茂铁（A -Fe- A和B -Fe- B）。因此，该方法允许访问大量不对称的多齿金属配体，尤其是当人们认为功能化的Cp盐在数量和多样性方面不断扩展时。在此，重点放在金属配体的1 H，13 C和31 P NMR表征上。有几个例子显示出有趣的构象特性和罕见的“贯穿空间”磷核自旋耦合。

  DOI：

  10.1021/om050882g
• 作为试剂：
  描述：

  乙酸肉桂酯 、 二乙胺 在 bis(η3-allyl-μ-chloropalladium(II)) 1,1'-bis[(5-methyl-2-furanyl)phosphino]ferrocene 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 N-[(E)-3-phenyl-2-propenyl]diethylamine 、 (1-phenyl-2-propenyl)diethylamine
  参考文献：
  名称：

  使用具有弱σ-偶氮性的大体积膦和钯作为通用的高活性催化体系： 二茂铁基双（二呋喃基膦）/ Pd的催化剂负载量为10 -1 –10 -4 mol％时的烯丙基化和芳基化偶联反应

  摘要：

  碳-碳（SP 2 -SP 2和SP 1 -SP 2）和碳-氮（亲核烯丙基化）耦合过程由含有催化体系促进[的PdCl（η 3 -C 3 H ^ 5）] 2与新的二茂铁基双（二呋喃基膦）1，1'-双[二（5-甲基-2-呋喃基）膦基]二茂铁，Fc [P（Fu Me）2 ] 2。从芳基溴化物或乙酸烯丙酯开始，这种通用的催化剂体系可以在低钯载量下使用（10 -1 –10 -4 摩尔％）在一些Heck，Suzuki，Sonogashira和烯丙基胺化反应中以优异的产率得到交叉偶联的产物。在烯丙基取代反应中获得了显着的高活性，这为该特定反应具有弱的σ-强度的大尺寸膦的发展提供了重要的动力。

  DOI：

  10.1016/j.tet.2005.06.065

文献信息

• 催化剂及其制备方法和酰胺化合物的制备方法
  申请人：南方科技大学

  公开号：CN110642895B

  公开（公告）日：2022-09-30

  本发明涉及一种催化剂及其制备方法、腈基水化为酰胺的制备方法。一种催化剂，用于催化腈基水化为酰胺，所述催化剂的结构通式为：其中，多个R1分别独立地选自芳香族基团、杂芳香族基团及非芳香族环系基团中的一种；多个R2分别独立地选自直链烷基及烷烃芳香族基团中的一种；X选自Cl及Br中的一种；及L选自OTf、BF4、PF6及SbF6中的一种。上述催化剂能够催化腈基水化为酰胺，且即使在较低的温度下(20℃～80℃)即可催化腈基水化为酰胺；另外，与目前常用的催化腈基水化为酰胺的催化剂相比，上述催化剂可以明显降低催化剂当量，催化剂当量仅为0.01mol％～0.5mol％就可以使得腈基达到较高的转化率；同时，上述催化剂的适用范围更广，可以催化多种腈基化合物水解与酰胺化合物。
• Synthesis, characterization and electrochemistry of [Pd(PP)MeCl] compounds with 1,1′-bis(phosphino)ferrocene ligands
  作者：Michelle E. Hendricks、Xiaoyu Xu、Thomas R. Boller、Evan M. Samples、Adam R. Johnson、Chip Nataro

  DOI：10.1016/j.poly.2021.115104

  日期：2021.5
• Enlarging the family of ferrocenylphosphine dinuclear rhodium complexes: synthesis and X-ray structure of a novel “A-frame”-type trimetallic Rh/Fe/Rh complex
  作者：Aziz Fihri、Jean-Cyrille Hierso、Vladimir V Ivanov、Bertrand Rebière、Régine Amardeil、Roland Broussier、Philippe Meunier

  DOI：10.1016/j.ica.2004.01.012

  日期：2004.7

  The symmetrically substituted ligand 1,1'-bis[di(5-methyl-2-furyl)phosphino]ferrocene (1) has been obtained from the bromo-phosphine BrP(Fu(Me))(2) and the dilithioferrocene/TMEDA adduct. The quantitative addition of this ferrocene derivative to the tetracarbonyl dimer [(CO)(4)Rh-2mu-(S'Bu)(2)}] leads, through decarbonylation, to the dinuclear rhodium complex [(CO)(2)Rh-2 mu-(S'Bu)(2)} mu-P,P-Fc[P(Fu(Me))(2)](2)}] (2) in high yield. A X-ray structure [orthorhombic, space group P2(1)2(1)2(1); a = 11.2982(2) Angstrom, b = 13.3165(3) Angstrom, c = 27.2687(7) Angstrom] and the solution multinuclear NMR characterization are reported, which show that the rare "quasi-closed bridging" A-frame structure of the complex is rather similar to the one reported for [(CO)(2)Rh-2mu-(S'Bu)(2)}mu-P,P-dppf}] in solid state. However, in solution the furyl-containing ferrocenylphosphine complex presents a greater fluxionality, together with an electronic environment at phosphorus very different from the dppf analogue (delta(p) = -10 and 27 ppm, respectively). (C) 2004 Elsevier B.V. All rights reserved.