1,8-二(二苯基膦)辛烷 | 41625-30-3

• 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 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,8-二(二苯基膦)辛烷
• 中文别名: 1,8-二(二苯基膦基)辛烷
• 英文名称: 1,8-bis(diphenylphosphino)octane
• 英文别名: dppo；8-diphenylphosphanyloctyl(diphenyl)phosphane
• CAS: 41625-30-3
• 化学式: C₃₂H₃₆P₂
• 分子量: 482.585
• InChiKey: BABUPOVYOOZOAE-UHFFFAOYSA-N

物化性质

• 熔点：
  103-105℃
• 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)：
  8.4
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902909090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存放于阴凉干燥处

SDS

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Section 1: Product Identification
Chemical Name: 1,8-Bis(diphenylphosphino)octane, 99%
CAS Registry Number: 41625-30-3
Formula: C32H36P2
EINECS Number: none
Chemical Family: organophosphine ligand
Synonym: 1,8-Bis(diphenylphosphano)octane

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 41625-30-3 100% 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, skin, eyes
Eye Contact: Causes irritation of the eyes.
Skin Contact: Causes 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: 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 toxic organic fumes and vapors of phosphorus 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: white powder
Molecular Weight: 482.58
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 and halogens
Decomposition Products: carbon monoxide, carbon dioxide, phosphorous oxides 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): 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：

  1,8-二(二苯基膦)辛烷 以 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Van Calcar, Pamela M.; Olmstead, Marilyn M.; Balch, Alan L., Inorganic Chemistry, 1997, vol. 36, # 23, p. 5231 - 5238

  摘要：

  DOI：
• 作为产物：
  描述：

  1,8-二溴辛烷 、 potassium diphenylphosphine 以 四氢呋喃 为溶剂， 反应 3.0h， 以53%的产率得到1,8-二(二苯基膦)辛烷
  参考文献：
  名称：

  通过双膦配体控制金纳米团簇

  摘要：

  我们报告了由六个双齿二膦配体协调的新 Au22 纳米簇的合成和结构测定：1,8-双（二​​苯基膦）辛烷（简称 L(8)）。单晶 X 射线晶体学和电喷雾电离质谱表明该簇组件是中性的，可以制定为 Au22(L(8))6。Au22 核心由由四个 L(8) 配体夹在一起的两个 Au11 单元组成，而另外两个配体以双齿方式与每个 Au11 单元协调。两个 Au11 单元界面处的八个金原子没有被任何配体配位。由于四个剪切配体的夹持力和强电子相互作用，在两个 Au11 簇的界面处观察到四个短金-金距离 (2.64-2.65 Å)。

  DOI：

  10.1021/ja411061e
• 作为试剂：
  描述：

  溴苯 、 2-((S)-(2-methoxyethoxy)(phenyl)methyl)naphthalene 在 碘 、 magnesium 、 bis(acetylacetonate)nickel(II) 、 1,8-二(二苯基膦)辛烷 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 50.0h， 以86%的产率得到2-benzhydrylnaphthalene
  参考文献：
  名称：

  立体定向交叉偶联反应合成对映体富集的三芳基甲烷

  摘要：

  与反转偶联：手性二芳基甲醇衍生物与芳基格氏试剂进行立体定向的镍催化交叉偶联反应（参见方案）。该反应随着构型的转化和高对映体特异性而进行。该方法已应用于基于三芳基甲烷的抗癌化合物的不对称合成。

  DOI：

  10.1002/anie.201202527

文献信息

• En Route to a Practical Primary Alcohol Deoxygenation
  作者：Xi-Jie Dai、Chao-Jun Li

  DOI：10.1021/jacs.6b02344

  日期：2016.4.27

  efficient mainly with activated alcohols, which dictates harsh reaction conditions and thus limits its synthetic utility. Later, a significant advancement has been made on aliphatic primary alcohol deoxygenation by employing a ruthenium complex, with good functional group tolerance and exclusive selectivity under practical reaction conditions. Its synthetic utility is further illustrated by excellent

  醇脱氧领域的一个长期科学挑战是在存在其他官能团（如广泛存在于生物分子中的游离羟基和胺）的情况下，具有高选择性和高效率的直接催化 sp(3) CO 去官能化。以前，选择性问题只能通过使用化学计量试剂的经典多步脱氧策略来解决。在此，我们提出了一种基于脱氢/沃尔夫-基什纳 (WK) 还原的催化后过渡金属催化氧化还原设计，以同时解决步骤经济性和选择性方面的挑战。我们假设的早期发展侧重于主要使用活化醇有效的铱催化过程，这决定了苛刻的反应条件，从而限制了其合成效用。之后，采用钌配合物在脂肪族伯醇脱氧方面取得了重大进展，在实际反应条件下具有良好的官能团耐受性和专属选择性。在简单和复杂的分子设置中，其卓越的效率以及完全的化学和区域选择性进一步说明了其合成效用。实验支持还包括机械讨论。总体而言，我们目前的方法成功地解决了相关领域中的上述挑战，为脂肪族伯醇的直接 sp(3) CO 去官能化提供了一种实用的基于
• Decarboxylative Phosphine Synthesis: Insights into the Catalytic, Autocatalytic, and Inhibitory Roles of Additives and Intermediates
  作者：Shengfei Jin、Graham C. Haug、Vu T. Nguyen、Carsten Flores-Hansen、Hadi D. Arman、Oleg V. Larionov

  DOI：10.1021/acscatal.9b03366

  日期：2019.11.1

  used ligands, catalysts, and reagents. Current synthetic approaches to phosphines are dominated by nucleophilic displacement reactions with organometallic reagents. Here, we report a radical-based approach to phosphines that proceeds by a cross-electrophile coupling of chlorophosphines and redox-active esters. The reaction allows for the synthesis of a broad range of substituted phosphines that were not

  膦是最广泛使用的配体，催化剂和试剂。当前的膦的合成方法主要是与有机金属试剂的亲核取代反应。在这里，我们报告了基于膦的自由基方法，该方法通过氯膦与氧化还原活性酯的交叉亲电偶联而进行。该反应允许合成广泛范围的取代膦，这些取代膦是用本方法不易达到的。我们的实验和DFT计算研究也阐明了添加剂和中间体的催化，自催化和抑制作用，以及光催化和锌介导的氧化还原模式的机理细节，这些机理可能对其他跨亲电偶合的机理解释有影响。反应。
• Gold(I) complexes of unidentate and bidentate phosphorus-, arsenic-, antimony-, and sulphur-donor ligands
  作者：Charles A. McAuliffe、R. V. (Dick) Parish、P. David Randall

  DOI：10.1039/dt9790001730

  日期：——

  Complexes of gold(I) with a variety of unidentate and potentially chelating P-, As-, Sb-, and S-donor ligands have been characterised by analysis, 1H n.m.r., i.r., and u.v.–visible spectroscopy, and electrical conductivity. In the majority of cases, the gold atom is two co-ordinate, [AuX(L)] or [XAu(L′–L′)AuX](L = unidentate ligand, L′–L′= bidentate ligand, X = Cl, Br, or SCN), but a few examples of

  通过分析，1 H nmr，ir和uv可见光谱和电导率表征了金（I）与各种未知的和潜在螯合的P-，As-，Sb-和S-供体配体的配合物。在大多数情况下，金原子是两个坐标，[AuX（L）]或[XAu（L'–L'）AuX]（L =相同的配体，L'–L'=齿状的配体，X = Cl，Br或SCN），但发现了一些可能的三配位实例，[AuXL 2 ]或[AuX（L'–L'）]。对于双齿配体，主链的刚性似乎是促进螯合的关键因素。阳离子络合物[AuL 2 ] +的形成容易程度取决于溶剂的极性。
• High-frequency (245 GHz) and X-band EPR study of stable dicopper radical complexes
  作者：Anne-Laure Barra、Louis-Claude Brunel、Frank Baumann、Manuela Schwach、Michael Moscherosch、Wolfgang Kaim

  DOI：10.1039/a903419f

  日期：——

  Stable, readily accessible and in part even structurally established paramagnetic complex cations [Cu2(µ-η4-BL)L2]+˙, BL = bridging ligand, L = Ph2P(CH2)nPPh2 or 2 PPh3, were studied by high-frequency (245 GHz) and X-band EPR spectroscopy. The dicopper(I)/anion radical ligand formulation as opposed to a mixed-valent dimetal description is supported by the high-frequency EPR results which show g components between 2.0220 and 1.9968. The largest (rhombic) g anisotropy Δg was found for the system with BL = azodi-tert-butyl formate and L = Ph2P(CH2)6PPh2, and the smallest (axial) Δg splittings for 1,2,4,5-tetrazine-bridged species. There is a clear relation between Δg as obtained from the high-field measurements and the 63,65Cu hyperfine coupling as measured from solution spectra in the X band.

  通过高频（ 245 GHz）和 X 波段 EPR 光谱。高频 EPR 结果支持了二铜 (I)/阴离子自由基配体配方，而不是混合价二金属描述，该结果显示 g 分量在 2.0220 和 1.9968 之间。 BL = 偶氮二叔丁基甲酸和 L = Ph2P(CH2)6PPh2 的系统发现最大（菱形）g 各向异性 Δg，最小（轴向）Δg 分裂为 1,2,4,5-四嗪-桥接物种。从高场测量获得的 Δg 与从 X 波段溶液光谱测量的 63,65Cu 超精细耦合之间存在明显的关系。
• Synthesis of α,ω-bis(diphenylphosphino)alkane and α,ω-bis(diphenylphosphino)(poly)ether ligands and complexes of rhodium(I)
  作者：D.Harry M.W. Thewissen、Klaas Timmer、Jan G. Noltes、Jan W. Marsman、Richard M. Laine

  DOI：10.1016/s0020-1693(00)86576-7

  日期：1985.2

  α,ω-Bis(diphenylphosphino)alkane and α,ω-bis(diphenylphosphino)(poly)ether ligands can be prepared in very high yields via reaction of the appropriate dihalide with two equivalents of LiPPh2. For the [Rh(COD)(P P)][ClO4] complexes of these ligands, the P P ligands with five or less atoms in the alkane or ether bridge form monomeric complexes via η2-coordination. In general the ligands with eight or

  通过使适当的二卤化物与两当量的LiPPh2反应，可以非常高的产率制备α，ω-双（二苯基膦基）烷烃和α，ω-双（二苯基膦基）（聚）醚配体。对于这些配体的[Rh（COD）（PP）] [ClO4]配合物，在烷烃或醚桥中具有五个或更少原子的PP配体通过η2-配位形成单体配合物。通常，在桥中具有八个或更多个原子的配体给出双核或多核物质。此外，长链二膦基聚醚通过η2-配位在某种程度上形成单体形式。