di-1-adamantylphosphine oxide | 131266-79-0

• 分子结构分类: 有机化合物 - 有机磷化合物 - 有机膦及其衍生物
• 英文名称: di-1-adamantylphosphine oxide
• 英文别名: di-1-adamantylphosphinoxid；diadamantylphosphine oxide；1-(1-adamantylphosphonoyl)adamantane
• CAS: 131266-79-0
• 化学式: C₂₀H₃₁OP
• 分子量: 318.439
• InChiKey: KSPQHGMECVEYEN-UHFFFAOYSA-N

物化性质

• 熔点：
  255-258 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  436.8±28.0 °C(Predicted)
• 稳定性/保质期：

  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  8.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 储存条件：
  存于阴凉干燥处。

SDS

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Section 1: Product Identification
Chemical Name: Di-1-adamantylphosphine oxide, min. 90%
CAS Registry Number: 131266-79-0
Formula: (C10H15)2P(O)H
EINECS Number: none
Chemical Family: organophosphine ligand
Synonym: Di-1-adamantylphosphane oxide

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 131266-79-0 100% 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, skin, eyes
Eye Contact: Causes irritation to eyes
Skin Contact: Causes irritation to 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: none
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 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: 318.43
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: oxidizing agents, halogens
Decomposition Products: carbon monoxide, carbon dioxide, phosphorus pentoxide, 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

反应信息

• 作为反应物：
  描述：

  di-1-adamantylphosphine oxide 在 三氯化磷 作用下， 反应 24.0h， 以27.9%的产率得到双(1-金刚烷基)氯化磷
  参考文献：
  名称：

  Goerlich, Jens R.; Fischer, Axel; Jones, Peter G., Zeitschrift fur Naturforschung, B: Chemical Sciences, 1994, vol. 49, # 6, p. 801 - 811

  摘要：

  DOI：
• 作为产物：
  描述：

  金刚烷 在 aluminum (III) chloride 、 亚磷酸 作用下， 以 四氢呋喃 为溶剂， 以90 %的产率得到di-1-adamantylphosphine oxide
  参考文献：
  名称：

  一种有机氧膦类化合物的合成方法

  摘要：

  本发明公开了一种有机氧膦类化合物的合成方法，属于有机合成领域。通过如下方法实现：在无水无氧氛围中，以不同种类烷烃或芳烃为原料，在路易斯酸的催化作用下与亚磷酸反应生成有机氧膦类化合物。与现有技术相比，本发明反应条件温和，操作简单，产率高，原料简单易得，适合工业化生产。

  公开号：

  CN115850332A
• 作为试剂：
  描述：

  1-溴-2-甲基萘 、 (pyridin-2-yl)magnesium bromide 在 tris-(dibenzylideneacetone)dipalladium(0) 、 di-1-adamantylphosphine oxide 作用下， 以 四氢呋喃 为溶剂， 反应 20.08h， 以61%的产率得到2-(2-methylnaphthalen-1-yl)pyridine
  参考文献：
  名称：

  带有2-吡啶基格氏试剂的Kumada–Corriu交叉偶联

  摘要：

  SPO迎接挑战：由空气和湿气稳定的次生氧化膦（SPO）（1-Ad）2 P（O）H衍生的钯配合物可实现具有挑战性的缺乏电子的2-吡啶基格氏试剂与范围足够（请参阅方案）。

  DOI：

  10.1002/chem.201000032

文献信息

• The reaction of secondary phosphines and di-1-adamantylphosphine oxide with trifluoroacetic anhydride and hexafluoroacetone
  作者：Jens R. Goerlich、Volker Plack、Reinhard Schmutzler

  DOI：10.1016/0022-1139(95)03288-6

  日期：1996.1

  reacted readily with trifluoroacetic anhydride (TFAA) to give the trifluoroacetylphosphines 7 and 8. (1-Ad)2P(:O)H (6) could not be converted into the corresponding trifluoroacetylphosphine oxide 10 by treatment with TFAA. Compound 10 was observed by 19F and 31P NMR spectroscopy in the reaction of (1-Ad)2PC(:O)CF3(7) with (H2N)2C(:O) · H2O2. Two pathways were observed for the reaction of 1 with excess

  仲膦（1-Ad）2 PH（1）（1-Ad =金刚烷基）和Trt（Ph）PH （2）（Trt =三苯甲基）与三氟乙酸酐（TFAA）容易反应生成三氟乙酰基膦7和8。（1-Ad）2 P（：O）H （6）无法通过TFAA处理转化为相应的三氟乙酰基膦氧化物10。在（1-Ad）2 PC（：O）CF 3 （7）与（H 2 N）2 C（：O）·H 2的反应中，通过19 F和31 P NMR光谱观察到化合物10。O 2。从一级HFA加合物（1-Ad）2 PC（CF 3）2 OH （13）开始，观察到1与过量六氟丙酮（HFA）反应的两个途径。13的氧化导致叔膦氧化物14，其也可从（1-Ad）2 P（：O）H （6）和HFA获得。13的异构化得到（1-Ad）2 POCH（CF 3）2（15），其用过量的HFA氧化提供了磷烷16。水解16生成次膦酸酯17。如对于Ph 2 PH （3）已知的，Ph（C 6 F 5）PH
• N-(PHOSPHINOALKYL)-N-(THIOALKYL)AMINE DERIVATIVE, METHOD FOR PRODUCING SAME, AND METAL COMPLEX THEREOF
  申请人：TAKASAGO INTERNATIONAL CORPORATION

  公开号：US20170233418A1

  公开（公告）日：2017-08-17

  The purpose of the present invention is to provide: a ligand that is useful in a catalytic organic synthetic reaction; a method for producing said ligand; and a metal complex that is useful as a catalyst in an organic synthetic reaction. The present invention provides a compound represented by general formula (1 A ), a method for producing said compound, and a metal complex including said compound as a ligand. (In the formula, H, N, P, S, L, R 1 , R 2 , R 3 , Q 1 , and Q 2 have the meaning as defined in the Description.)

  本发明的目的是提供：在催化有机合成反应中有用的配体；制备所述配体的方法；以及在有机合成反应中作为催化剂有用的金属配合物。本发明提供了由通式（1A）表示的化合物，制备所述化合物的方法，以及包括所述化合物作为配体的金属配合物。（在该式中，H、N、P、S、L、R1、R2、R3、Q1和Q2的含义如描述中所定义。）
• Novel catalysts useful for catalyzing the coupling of arylhalides with arylboronic acids
  申请人：Ionkin Sergey Alex

  公开号：US20060281923A1

  公开（公告）日：2006-12-14

  The present invention relates to a new method of cross-coupling aryl moieties comprising reacting an arylhalide with an arylboronic acid in the presence of a palladium compound and a compound comprising a di-alkylphosphine moiety.

  本发明涉及一种新的芳基偶联方法，包括在钯化合物和含有二烷基膦基团的化合物存在下，将芳基卤化物与芳基硼酸反应。
• General and Selective Copper-Catalyzed Reduction of Tertiary and Secondary Phosphine Oxides: Convenient Synthesis of Phosphines
  作者：Yuehui Li、Shoubhik Das、Shaolin Zhou、Kathrin Junge、Matthias Beller

  DOI：10.1021/ja301764m

  日期：2012.6.13

  Novel catalytic reductions of tertiary and secondary phosphine oxides to phosphines have been developed. Using tetramethyldisiloxane (TMDS) as a mild reducing agent in the presence of copper complexes, PO bonds are selectively reduced in the presence of other reducible functional groups (FGs) such as ketones, esters, and olefins. Based on this transformation, an efficient one pot reduction/phosphination

  已经开发了将叔和仲氧化膦新型催化还原为膦的方法。在铜配合物的存在下使用四甲基二硅氧烷 (TMDS) 作为温和的还原剂，PO 键在其他可还原的官能团 (FG) 的存在下被选择性还原，例如酮、酯和烯烃。基于这种转化，有效的一锅还原/膦化多米诺序列允许以良好的产率合成各种官能化的芳族和脂肪族膦。
• METHOD FOR PRODUCING FLUOROVINYL ETHER COMPOUND
  申请人：DAIKIN INDUSTRIES, LTD.

  公开号：US20210284593A1

  公开（公告）日：2021-09-16

  An object of the present invention is to provide, for example, a novel method for synthesizing a fluorovinyl ether compound from a fluorine-containing vinyl compound. This problem is solved by a method for producing a compound represented by formula (1): wherein R a1 is a hydrogen atom, a halogeno group, an alkyl group, a fluoroalkyl group, or an aromatic group optionally having one or more substituents, Rf is a fluoro group or a perfluoroalkyl group, R a2 is a hydrogen atom, a halogeno group, an alkyl group, a fluoroalkyl group, or an aromatic group optionally having one or more substituents, or (i) R a1 and R a2 , (ii) R a1 and Rf, or (iii) Rf and R a2 may be linked to each other, R b1 is R S , R b2 is a hydrogen atom or R S , R b3 is a hydrogen atom or R S , or two or three of R b1 , R b2 , and R b3 , taken together with the adjacent carbon atom, may form a ring optionally having one or more substituents, and R S , in each occurrence, is the same or different and represents a hydrocarbon group optionally having one or more substituents, the method comprising step A of reacting a compound represented by formula (2): wherein R x is a leaving group, and other symbols are as defined above, with a compound represented by formula ( 3 ): wherein the symbols in the formula are as defined above, in the presence of a transition metal catalyst.

  本发明的一个目标是提供一种从含氟乙烯化合物合成氟乙烯醚化合物的新方法。这个问题通过以下方法解决：生产一个由以下式表示的化合物的方法(1)：其中Ra1是氢原子、卤素基团、烷基基团、氟烷基基团或可能具有一个或多个取代基的芳香基团，Rf是氟基团或全氟烷基基团，Ra2是氢原子、卤素基团、烷基基团、氟烷基基团或可能具有一个或多个取代基的芳香基团，或(i) Ra1和Ra2、(ii) Ra1和Rf或(iii) Rf和Ra2可能连接在一起，Rb1是RS，Rb2是氢原子或RS，Rb3是氢原子或RS，或者Rb1、Rb2和Rb3中的两个或三个，与相邻的碳原子一起，可以形成一个可能具有一个或多个取代基的环，RS在每次出现时相同或不同，表示一个可能具有一个或多个取代基的碳氢基团，该方法包括以下步骤：步骤A，将由以下式表示的化合物(2)：其中Rxis是一个离去基团，和上述其他符号的定义相同，与由以下式表示的化合物(3)：其中式中的符号与上述定义相同，在过渡金属催化剂存在下反应。