双(1-金刚烷基)膦酰氯 | 126683-99-6

• 物质功能分类: 有机原料 - 有机膦化合物
• 分子结构分类: 有机化合物 - 有机磷化合物
• 中文名称: 双(1-金刚烷基)膦酰氯
• 中文别名: 二-1-金刚烷基氯化膦
• 英文名称: di-1-adamantylphosphinic chloride
• 英文别名: 1-[1-adamantyl(chloro)phosphoryl]adamantane
• CAS: 126683-99-6
• 化学式: C₂₀H₃₀ClOP
• 分子量: 352.884
• InChiKey: RTFVOXURDFZPKR-UHFFFAOYSA-N

物化性质

• 熔点：
  214°C
• 沸点：
  498.0±12.0 °C(Predicted)
• 密度：
  1.23
• 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)：
  5.5
• 重原子数：
  23
• 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

• 海关编码：
  2903890090
• 储存条件：
  存放于阴凉干燥处

SDS

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Section 1: Product Identification
Chemical Name: Di-1-adamantylphosphinic chloride, 98%
CAS Registry Number: 126683-99-6
Formula: (C10H15)2POCl
EINECS Number: none
Chemical Family: organophosphine ligand
Synonym: Di-1-adamantylchlorophosphane

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 126683-99-6 100% 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: Dust causes moderate to severe irritation of the eyes.
Skin Contact: Causes moderate to severe irritation of the skin. May cause redness, itching and pain.
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.
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.
Fire fighters should be equipped with a NIOSH approved positive pressure self-contained breathing apparatus
Special Fire Fighting Procedures:
and full protective clothing.
Hazardous Combustion and If involved in a fire this material may emit toxic organic fumes.
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 powdered sodium carbonate or ground limestone and swept up.

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SECTION 7: Handling and Storage
Handling and Storage: Store the material in a cool, dry place in a tightly sealed container. Handle under a dry atmosphere.

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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 xtl.
Molecular Weight: 352.88
Melting Point: 214°
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: moisture sensitive
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: none
Incompatibility: oxidizing agents and halogens
Decomposition Products: carbon monoxide, carbon dioxide, hydrogen chloride, organic fumes and phosphorus pentoxide.

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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 federal, state, and local 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：

  双(1-金刚烷基)膦酰氯 在 三氟化锑 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以80.8%的产率得到Di-1-adamantylphosphinsaeurefluorid
  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 、 三氯化磷 、 水 作用下， 以99%的产率得到双(1-金刚烷基)膦酰氯
  参考文献：
  名称：

  钯催化交叉偶联反应中的芳基-二金刚烷膦配体：合成，结构分析和应用

  摘要：

  合成了大体积的二金刚烷基芳基膦配体，并将其用于空间要求的邻位取代的芳基氯化物的Buchwald-Hartwig偶联反应中。在甲苯磺酰also和芳基卤化物的偶联中，配体还显示出增强的催化活性。

  DOI：

  10.1002/ejoc.201901834

文献信息

• 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。
• Production of novel phosphane ligands and use in catalytical reactions
  申请人：——

  公开号：US20040068131A1

  公开（公告）日：2004-04-08

  The invention relates to novel phosphane ligands of formula (Ia) and (Ib): (adamantyl)nP(alkyl)m(1a); (adamantyl)o(Alkyl)qP (alkylen′)P(adamantyl)r(alkyl)s (1b), wherein adamantyl represents an adamantyl radical (IIa, IIb) bonded to the phosphorous atom in position 1 or 2. The invention also relates to the production and use of the above-mentioned ligands in the presence of transitional metal compounds of the 8th. Subgroup of PSE for catalytic reactions, particularly for the refining of halogen aromatics for producing aryl olefins, dienes, diarylene, benzoic acid and acrylic acid derivatives, aryl alkanes and also amines.

  该发明涉及公式(Ia)和(Ib)的新型膦配体：(脱氢胆固醇)nP(烷基)m(1a)；(脱氢胆固醇)o(烷基)qP(烷基)P(脱氢胆固醇)r(烷基)s(1b)，其中脱氢胆固醇代表与磷原子在1或2位置结合的脱氢胆固醇基团(IIa, IIb)。该发明还涉及在第8周期元素周期表的过渡金属化合物存在下制备和使用上述配体，特别用于催化反应，尤其用于精炼卤代芳烃以生产芳基烯烃、二烯烃、二芳基烯、苯甲酸和丙烯酸衍生物、芳基烷烃以及胺类。
• Catalyst system
  申请人：Lucite International UK Limited

  公开号：US09802185B2

  公开（公告）日：2017-10-31

  The present invention provides a catalyst system capable of catalyzing the carbonylation of an ethylenically unsaturated compound, which system is obtainable by combining: a) a metal of Group VIB or Group VIIIB or a compound thereof, b) a bidentate phosphine, arsine or stibine ligand, and c) an acid, wherein the ligand is present in at least a 2:1 molar excess compared to the metal or the metal in the metal compound, and that the acid is present in at least a 2:1 molar excess compared to the ligand, a process for the carbonylation of an ethylenically unsaturated compound, a reaction medium, and use of the system.

  本发明提供了一种催化剂体系，能够催化烯烃不饱和化合物的羰基化反应，该体系可通过组合以下成分获得：a) 第VIB族或第VIIIB族的金属或其化合物，b) 双齿膦、砷或锑配体，以及c) 酸。其中，与金属或金属化合物相比，配体的存在量至少是2:1的摩尔过量，而酸的存在量至少是与配体相比的2:1的摩尔过量。还提供了一种烯烃不饱和化合物羰基化的方法、反应介质以及该体系的用途。
• A Bulky Three-Hindered Quadrant Bisphosphine Ligand: Synthesis and Application in Rhodium-Catalyzed Asymmetric Hydrogenation of Functionalized Alkenes
  作者：Yuuki Sawatsugawa、Ken Tamura、Natsuhiro Sano、Tsuneo Imamoto

  DOI：10.1021/acs.orglett.9b02702

  日期：2019.11.15

  quadrant bisphosphine ligand, di-1-adamantylphosphino(tert-butylmethylphosphino)methane, named BulkyP*, has been synthesized via a convergent short pathway with chromatography-free procedures. The ligand is a crystalline solid and can be readily handled in air. Its rhodium(I) complex exhibits very high enantioselectivities and catalytic activities in the asymmetric hydrogenation of functionalized alkenes

  庞大的三阻碍象限双膦配体，二-1-金刚烷基膦基（叔丁基甲基膦基）甲烷，称为BulkyP *，是通过收敛的短路径和无色谱方法合成的。配体是结晶固体，可以很容易地在空气中处理。它的铑（I）配合物在官能化烯烃的不对称氢化中表现出很高的对映选择性和催化活性。
• Reductive Elimination to Form C(sp³)–N Bonds from Palladium(II) Primary Alkyl Complexes
  作者：D. Matthew Peacock、Quan Jiang、Thomas R. Cundari、John F. Hartwig

  DOI：10.1021/acs.organomet.8b00617

  日期：2018.10.8

  Reductive eliminations to form alkyl–nitrogen bonds are rare, and examples of this reaction from isolated complexes containing simple, unstabilized primary alkyl groups have not been observed. We report the synthesis of stable neopentylpalladium(II) anilido and methyleneamido complexes that undergo reductive elimination to form the C(sp3)–N bonds in N-neopentyl anilines and N-neopentyl imines, respectively

  还原消除形成烷基-氮键的现象很少见，而且还没有观察到由含有简单的，不稳定的伯烷基的孤立配合物引起的反应实例。我们报告了合成的稳定的新戊基钯（II）苯胺和亚氨基酰胺配合物，经过还原消除形成N-新戊基苯胺和N中的C（sp 3）-N键-新戊基亚胺。这些配合物的合成和分离是通过P，O辅助配体对钯的弱螯合实现的。DFT计算表明，新戊基钯（II）络合物通过协同作用机理进行还原消除，该协同作用机理类似于烷基配体向氧的迁移，或者在供体最初解离之后或与Pd-O键的延长相一致，具体取决于身份反应的和辅助的配体。