溴代(1,10-菲咯啉)(三苯基膦)铜(I) | 25753-84-8

• 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: 溴代(1,10-菲咯啉)(三苯基膦)铜(I)
• 中文别名: 溴（1,10-菲咯啉）（三苯基膦）铜（I）；溴（邻菲咯啉）（三苯基）铜；溴(邻菲咯啉)(三苯基)铜
• 英文名称: Cu(phen)(PPh₃)Br
• 英文别名: bromocopper;1,10-phenanthroline;triphenylphosphane
• CAS: 25753-84-8
• 化学式: C₃₀H₂₃BrCuN₂P
• 分子量: 585.95
• InChiKey: XKXXFZLAZILJJE-UHFFFAOYSA-M

物化性质

• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  7.07
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319
• 储存条件：
  存放于阴凉干燥处。

SDS

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Section 1: Product Identification
Chemical Name: Bromo(1,10-phenanthroline)(triphenylphosphine)copper (I), min. 97%
CAS Registry Number: 25753-84-8
Formula: CuBr(C12H8N2)P(C6H5)3
EINECS Number: none
Chemical Family: metal amine complex
Synonym: (1,10-phenanthroline)(triphenylphosphane)copper (I) bromide

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 25753-84-8 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Irritating to the respiratory tract, skin and eyes. May be harmful if swallowed.
Primary Routes of Exposure: Ingestion, inhalation, skin, eyes
Eye Contact: Causes irritation of the eyes.
Skin Contact: Causes irritation of the skin.
Inhalation: Dust is irritating to the nose, mucous membranes and respiratory tract.
Ingestion: No specific information is available on the physiological effects of ingestion. May be harmful if swallowed.
Acute Health Affects: Irritating to skin, eyes and respiratory tract. May be harmful if swallowed.
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: none
Autoignition Temperature: none
Explosion Limits: none
Extinguishing Medium: carbon dioxide, dry powder or foam
If involved in a fire, fire fighters should be equipped with a NIOSH approved positive pressure self-contained
Special Fire Fighting Procedures:
breathing apparatus and full protective clothing.
Hazardous Combustion and If involved in a fire, this material may emit toxic organic fumes and vapors of phosphorous pentoxide.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual 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: yellow powder
Molecular Weight: 595.94
Melting Point: no data
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: not determined
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: strong oxidizing agents
Decomposition Products: carbon monoxide, carbon dioxide, organic fumes, bromine, copper oxide and phosphorous oxide.

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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

反应信息

• 作为反应物：
  描述：

  溴代(1,10-菲咯啉)(三苯基膦)铜(I) 在 P(C₆H₅)3 、 water 、 CO₂ 、 carbon disulphide 作用下， 以 甲醇 为溶剂， 生成 (triphenylphosphine)2Cu(O-methyl-dithiocarbonate)
  参考文献：
  名称：

  CO2与四氢硼氢化铜（I）配合物在潮湿溶剂中的反应：[（phen）2Cu] [（HO）3B（O2CH）]和（phen）（Ph3P）Cu（O2COH）的合成和反应（phen = 1,10 -菲咯啉）

  摘要：

  二氧化碳在湿润的四氢呋喃中并在游离酚的存在下与四氢硼酸铜（I）配合物（phen）（Ph3P）Cu（BH4）（phen = 1,10-菲咯啉）（1）反应，得到离子衍生物[[ phen）2Cu] [（HO）3B（O2CH）]（3）。在苯的存在下，可以由1和甲酸水溶液制得相同的络合物3；由新的四氢硼酸铜（I）络合物，（phen）2Cu（BH4）（2）和甲酸水溶液制得；并在潮湿的四氢呋喃中加2与CO2混合。（phen）（Ph3P）Cu（BH4）（1）与CO2在潮湿甲醇中的反应生成重碳酸盐衍生物（phen）（Ph3P）Cu（O2COH）（4）。醇ROH在3上的作用导致形成离子型配合物[（phen）2Cu]（O2CH）（5），硼原子作为烷基硼酸酯（RO）3B被消除。配合物3与三苯基膦的醇溶液反应，得到已报道的共价甲酰衍生物，（phen）（Ph3P）Cu（O2CH）。3与PhCH2Br的反应生成苄基甲酸

  DOI：

  10.1016/s0020-1693(00)83696-8
• 作为产物：
  描述：

  {(1,10-phenanthroline)2Cu}(formate) 在 P(C₆H₅)3 作用下， 以 二氯甲烷 为溶剂， 生成 溴代(1,10-菲咯啉)(三苯基膦)铜(I)
  参考文献：
  名称：

  CO2与四氢硼氢化铜（I）配合物在潮湿溶剂中的反应：[（phen）2Cu] [（HO）3B（O2CH）]和（phen）（Ph3P）Cu（O2COH）的合成和反应（phen = 1,10 -菲咯啉）

  摘要：

  二氧化碳在湿润的四氢呋喃中并在游离酚的存在下与四氢硼酸铜（I）配合物（phen）（Ph3P）Cu（BH4）（phen = 1,10-菲咯啉）（1）反应，得到离子衍生物[[ phen）2Cu] [（HO）3B（O2CH）]（3）。在苯的存在下，可以由1和甲酸水溶液制得相同的络合物3；由新的四氢硼酸铜（I）络合物，（phen）2Cu（BH4）（2）和甲酸水溶液制得；并在潮湿的四氢呋喃中加2与CO2混合。（phen）（Ph3P）Cu（BH4）（1）与CO2在潮湿甲醇中的反应生成重碳酸盐衍生物（phen）（Ph3P）Cu（O2COH）（4）。醇ROH在3上的作用导致形成离子型配合物[（phen）2Cu]（O2CH）（5），硼原子作为烷基硼酸酯（RO）3B被消除。配合物3与三苯基膦的醇溶液反应，得到已报道的共价甲酰衍生物，（phen）（Ph3P）Cu（O2CH）。3与PhCH2Br的反应生成苄基甲酸

  DOI：

  10.1016/s0020-1693(00)83696-8
• 作为试剂：
  描述：

  2-(2,2-dibromo-vinyl)-naphthalene 在 溴代(1,10-菲咯啉)(三苯基膦)铜(I) 、 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 生成 1,4-di(naphthalen-2-yl)buta-1,3-diyne
  参考文献：
  名称：

  Copper-catalyzed coupling of imidazoles and pyrazoles with 1,1-dibromo-1-alkenes: a distinct approach for direct N-alkynylation of heteroarenes

  摘要：

  The direct N-alkynylation of heteroarenes, imidazoles, and pyrazoles with 1,1-dibromo-1-alkene has been carried out for the first time using [Cu(Phen)PPh3Br] (as a catalyst) and Cs2CO3 in DMSO at 80 degrees C. The products are formed in good to high yields (66-85%) within 3 h. No side products could be detected. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.117

文献信息

• Synthesis, structures, DNA-binding and anticancer activities of some copper(I)-phosphine complexes
  作者：Khlood H. Mashat、Bandar A. Babgi、Mostafa A. Hussien、Muhammad Nadeem Arshad、Magda H. Abdellattif

  DOI：10.1016/j.poly.2018.10.062

  日期：2019.1

  ligand appears to influence the copper(I)-phosphine anticancer activities against the different cancer cell lines. The data suggested that complexes 2a and 2d show potential anticancer activity against prostate and breast cancers. The four copper complexes were docked against four different proteins associated with prostate or breast cancers activities, highlighting some of the structural-DNA interactions

  摘要通过回流含至少四倍摩尔过量膦配体的CuBr2甲醇溶液，然后处理形成的CuBr（PR3）3配合物[ R ＝在DCM中具有1摩尔当量的1，10-菲咯啉的苯基（1a），4-氟苯基（1b），环己基（1c）或4-甲氧基苯基（1d）]}。三（4-甲氧基苯基）膦配体提供了[Cu（P [C6H4-4-OMe] 3）2（phen）] Br（2d）配合物，而其他膦则生成了通式为CuBr（PR3）（ phen）[R =苯基（2a），4-氟苯基（2b）或环己基（2c）]。通过元素分析，31P NMR光谱和质谱法对新的配合物进行了表征。进一步确认1b，2b，通过单晶X射线衍射确定2c和2d。对配合物2a–2d与ct-DNA的DNA结合研究显示结合常数值对应于结合的嵌入模式。配合物结合常数的显着变化表明膦配体有一定的贡献。从理论上评估了复合物的亲脂性，计算出的复合物2d的log P值为正且高，处于相对较易穿透膜
• Methods and systems for preparing fused heterocyclic compounds using copper(I) catalysts
  申请人：University of Massachusetts

  公开号：US07473786B1

  公开（公告）日：2009-01-06

  A copper(I)-catalyzed procedure for the synthesis of benzo[b]heterocycles. This protocol can be used to synthesize a variety of 2-arylbenzo[b]furans and indoles in good to excellent yields. This method can tolerate a variety of functional groups, does not require the use of expensive additives and is palladium-free.

  一种铜(I)催化的合成苯并[b]杂环化合物的方法。该方案可用于合成多种2-芳基苯并[b]呋喃和吲哚，收率良好至优秀。此方法能容忍多种官能团，无需使用昂贵添加剂，并且不含钯。
• Structural and Electrochemical Studies of Copper(I) Complexes with Diethoxyphosphoryl‐1,10‐phenanthrolines
  作者：Alexander Mitrofanov、Machima Manowong、Yoann Rousselin、Stéphane Brandès、Roger Guilard、Alla Bessmertnykh‐Lemeune、Ping Chen、Karl M. Kadish、Nataliya Goulioukina、Irina Beletskaya

  DOI：10.1002/ejic.201402161

  日期：2014.7

  Two series of copper(I) complexes with diethoxyphosphoryl-substituted 1,10-phenanthroline ligands were synthesized and characterized in the solid state and in solution. The first comprised mixed-ligand CuI complexes with phenanthroline and triphenylphosphine. The second series includes bis-chelates with two phenanthroline ligands. According to the X-ray data for the six complexes, the ditopic phenanthroline

  合成了两个系列的铜 (I) 配合物与二乙氧基磷酰基取代的 1,10-菲咯啉配体，并在固态和溶液中表征。第一种包括与菲咯啉和三苯基膦的混合配体 CuI 复合物。第二个系列包括具有两个菲咯啉配体的双螯合物。根据六种配合物的 X 射线数据，双位菲咯啉配体通过两个系列中的两个氮原子与铜 (I) 原子呈双齿配位。通过 1 H 和 31 P NMR 光谱、电化学和光谱电化学研究了涉及不同菲咯啉铜 (I) 物种的溶液平衡。这两个系列的这些不稳定配合物的溶液形态不同，取决于溶剂的性质和菲咯啉骨架上磷取代基的位置。配位溶剂可以取代金属中心内部配位球中的溴化物、三苯基膦，甚至菲咯啉配体。即使在 CH2Cl2 和 CHCl3 等非配位溶剂中，铜 (I) 与 α-取代的菲咯啉的配合物也很容易解离。在使用的溶液条件下观察到导致较少空间位阻物种的配体交换反应。菲咯啉螯合剂的配位模式在任何使用的溶液条件下都不会改变，并
• Isolation and characterization of copper(<scp>iii</scp>) trifluoromethyl complexes and reactivity studies of aerobic trifluoromethylation of arylboronic acids
  作者：Song-Lin Zhang、Wen-Feng Bie

  DOI：10.1039/c6ra10302b

  日期：——

  characterized using 1H, 19F, 31P NMR, elemental analyses and X-ray crystallography. Reactivity studies indicate that 2 is unreactive toward arylboronic acids. In contrast, 3 and 4 can react with various aryl and heteroaryl boronic acids to deliver trifluoromethylated arenes in good to quantitative yields under mild conditions. The presence of a fluoride additive in DMF under aerobic conditions is crucial to

  过渡金属三氟甲基配合物的分离，表征和反应性是三氟甲基化化学中的基础性和挑战性主题。我们在这里报告了两个新的配合物[（phen）Cu I（PPh 3）2 ] + [Cu III（CF 3）4 ] -（2）和（phen）Cu III（CF 3）3（3）的合成和分离）以及在室温下已知的络合物（bpy）Cu III（CF 3）3（4）。2和使用1 H，19 F，31 P NMR，元素分析和X射线晶体学对3进行了充分表征。反应性研究表明2对芳基硼酸没有反应性。相反，3和4可以与各种芳基和杂芳基硼酸反应，在温和的条件下以良好的定量收率递送三氟甲基化的芳烃。在有氧条件下，DMF中氟化物添加剂的存在对这些反应至关重要。这项研究提供了有关难捉摸的铜（III）的结构和反应性的基本信息。）三氟甲基络合物，已被提议作为许多三氟甲基化反应中的相关反应中间体。
• Methods of 1,3-enyne preparation using copper (I) catalysts
  申请人：University of Massachusetts

  公开号：US07473797B2

  公开（公告）日：2009-01-06

  A copper(I) bi-dentate ligand complex-catalyzed procedure for synthesis of 1,3-enynes. The methods and/or systems of this invention afford a variety of enynes, tolerate a variety of sensitive functional groups, and can be employed without resort to expensive palladium reagents.

  一种铜(I)双叉配体催化的合成1,3-炔烃的方法。本发明的方法和/或系统可以得到各种炔烃，容忍各种敏感的官能团，并且可以在不使用昂贵的钯试剂的情况下使用。