(2R,4R)-(+)-2,4-双(二苯基磷)戊烷 | 96183-46-9

• 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: (2R,4R)-(+)-2,4-双(二苯基磷)戊烷
• 中文别名: 4,5-二甲基-3-异丙基苯胺
• 英文名称: (R,R)-bdpp
• 英文别名: (2R,4R)-(+)-2,4-bis(diphenylphosphino)pentane；(R,R)-Skewphos；((2R,4R)-(-)-2,4-bis(diphenylphosphine)pentane)；(2r,4r)-BDPP；(R)-BDPP；[(2R,4R)-4-diphenylphosphanylpentan-2-yl]-diphenylphosphane
• CAS: 96183-46-9
• 化学式: C₂₉H₃₀P₂
• 分子量: 440.505
• InChiKey: CTYPJIUQROQJBG-JWQCQUIFSA-N

物化性质

• 熔点：
  78°C
• 比旋光度：
  +124° (c 4.0, CHCl3)
• 沸点：
  543.8±33.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• TSCA：
  No
• 海关编码：
  2902909090
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 危险性防范说明：
  P261,P264,P270,P271,P273,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332,H413
• 储存条件：
  储存条件：2-8°C，需保存在惰性气体中。

SDS

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Section 1: Product Identification
Chemical Name: (2R,4R)-(+)-2,4-Bis(diphenylphosphino)pentane, 99% (R,R-BDPP)
CAS Registry Number: 96183-46-9
Formula: (C6H5)2PCH(CH3)CH2CH(CH3)P(C6H5)2
EINECS Number: none
Chemical Family: organophosphine ligand
Synonym: (R,R)-BDPP

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title Compound 96183-46-9 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Irritating to skin, eyes and respiratory tract. May be harmful if swallowed.
Primary Routes of Exposure: Ingestion, inhalation
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 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 the effects of long-term exposure.
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
If this material 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.
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
Store in a tightly sealed container. Keep away from heat and direct sunlight. Handle and store under an inert
Handling and Storage:
atmosphere of nitrogen or argon. Prolonged exposure to air may result in the degradation of the product.

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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: Material may form a fine dust. If possible, 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: Material may form a fine dust. If possible, 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: 440.49
Melting Point: 78°
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 sensitive solid
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: prolonged contact with air.
Incompatibility: oxidizing agents, halogens and oxygen.
Decomposition Products: carbon dioxide, carbon monoxide, phosphorus oxide, and organic fumes

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SECTION 11: Toxicological Information
RTECS Data: No information available in the RTECS files.
Carcinogenic Effects: No data available
Mutagenic Effects: No data available
Tetratogenic Effects: No data available

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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：

  (2R,4R)-(+)-2,4-双(二苯基磷)戊烷 在 三氧化硫 作用下， 反应 96.0h， 以100%的产率得到
  参考文献：
  名称：

  Lecomte, L.; Sinou, D., Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 53, # 1-4, p. 239 - 251

  摘要：

  DOI：
• 作为产物：
  描述：

  (2S,4S)-(+)-戊二醇 在 lithium 作用下， 以 吡啶 为溶剂， 反应 3.0h， 生成 (2R,4R)-(+)-2,4-双(二苯基磷)戊烷
  参考文献：
  名称：

  一种简便的2,4-双（二苯基膦基）戊烷（BDPP）对映体的制备方法及其在不对称加氢中的应用

  摘要：

  乙酰丙酮的不对称异质氢化用于制备2，4-双（二苯基膦基）戊烷（BDPP）的两种对映异构体（2 R，4 R和2 S，4 S）。在迄今为止制备的手性膦中，BDPP在其铑（I）配合物不仅可用于还原Z -α-酰胺基丙烯酸而且还可以用于还原α-上，均起着有效的均相不对称氢化催化剂的作用，因此看来是独特的。乙基苯乙烯，苯乙酮和苯乙酮苄基亚胺。类似的次膦酸酯配体BDPOP产生选择性较低的催化剂。

  DOI：

  10.1016/0022-328x(85)87004-2
• 作为试剂：
  描述：

  (4-methoxy-2-vinylphenyl)(methyl)phenylsilane 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 (2R,4R)-(+)-2,4-双(二苯基磷)戊烷 作用下， 以 二氯甲烷 为溶剂， 以8%的产率得到
  参考文献：
  名称：

  通过铑催化对映选择性分子内氢化硅烷化催化动力学拆分单氢硅烷

  摘要：

  开发了催化动力学拆分策略来获得手性硅立体硅烷。通过采用Rh催化的分子内氢化硅烷化反应，可以在一次操作中高效地制备二氢苯并硅杂环基有机硅烷和含有邻乙烯基的一氢硅烷，并且具有良好至优异的选择性因子。

  DOI：

  10.1002/anie.202404732

文献信息

• [EN] MONOCARBONYL RUTHENIUM AND OSMIUM CATALYSTS<br/>[FR] CATALYSEURS MONOCARBONYLE DE RUTHÉNIUM ET D'OSMIUM
  申请人：UNIVERSITA' DEGLI STUDI DI UDINE

  公开号：WO2017134618A1

  公开（公告）日：2017-08-10

  The invention relates to monocarbonyl complexes of ruthenium and osmium with bi- and tridentate nitrogen and phosphine ligands. The invention relates to methods for preparing these complexes and the use of these complexes, isolated or prepared in situ, as catalysts for reduction reactions of ketones and aldehydes both via transfer hydrogenation or hydrogenation with hydrogen.

  这项发明涉及具有双齿和三齿氮磷配体的钌和锇的单羰基配合物。该发明涉及制备这些配合物的方法以及将这些配合物（无论是分离的还是原位制备的）用作酮和醛的还原反应的催化剂，可以通过氢转移加氢或氢气加氢进行。
• Novel olefination process to itaconate and succinate derivatives
  申请人：——

  公开号：US20020058832A1

  公开（公告）日：2002-05-16

  An efficient and selective process, capable of scale-up, to make itaconate derivatives of formula (IV), and/or succinate derivatives of formula (V) and/or (VI) by asymmetric hydrogenation of the itaconate derivatives. 1

  一种高效且选择性的工艺，可扩大规模，通过对顺丁烯二酸衍生物进行不对称加氢，制备化学式（IV）的顺丁烯二酸衍生物，以及/或化学式（V）和/或（VI）的琥珀酸衍生物。
• OsXCl(phosphine)₂(diamine) and OsXCl(diphosphine)(diamine) (X = Cl, H) Complexes for Ketone Hydrogenation
  作者：Cinzia Barbato、Salvatore Baldino、Maurizio Ballico、Rosario Figliolia、Santo Magnolia、Katia Siega、Eberhardt Herdtweck、Paolo Strazzolini、Giorgio Chelucci、Walter Baratta

  DOI：10.1021/acs.organomet.7b00737

  日期：2018.1.8

  ethylenediamine (en), whereas the diphosphine derivatives trans-[OsCl2(dppf)(NN)] (NN = en (3), bn (4; bn = 1,4-butanediamine)) and trans-[OsCl2(dpbp)(en)] (5) were obtained from 1a, dppf or dpbp, and the corresponding NN ligand in CH2Cl2 or toluene. An X-ray diffraction study has been provided for 3. The isolation of the chiral derivatives trans-[OsCl2(diphosphine)((R,R)-dpen)] (diphosphine = dppf (6), dpbp (7)

  通过[OSCl 2（PPh 3）3 ]（1a）与乙二胺（en）反应制得O络合物反式-[OSCl 2（PPh 3）2（en）]（2），而二膦衍生物反式-[[ OSCL 2（DPPF）（NN）]（NN = EN（3），BN（4 ; BN = 1,4-丁二胺））和反式- [OSCL 2（DPBP）（烯）]（5从获得）1A，DPPF或dpbp，以及CH 2 Cl 2中相应的NN配体或甲苯。X射线衍射研究已经提供了3。分离了手性衍生物反式-[OSCl 2（diphOSphine）（（R，R）-dpen）]（diphOSphine = DPPF（6），dpbp（7），（R，R）-skewphOS（8））使1a与二膦和（R，R）-dpen在甲苯中反应。所述前体[OS中治疗2氯4（P（米间-甲苯基）3）5 ]（图1b）带连接，得到[OSCL2（P（米间-甲苯基）3）2（烯）]（9），而反应1B与DPPB和Ñ，Ñ
• Catalytic Enantioselective Hetero-dimerization of Acrylates and 1,3-Dienes
  作者：Stanley M. Jing、Vagulejan Balasanthiran、Vinayak Pagar、Judith C. Gallucci、T. V. RajanBabu

  DOI：10.1021/jacs.7b10055

  日期：2017.12.13

  counterion, and solvent effects uncovered during the course of these investigations show a unique role of a possible cationic Co(I) intermediate in these reactions. The rational evolution of a mechanism-based strategy that led to the eventual successful outcome and the attendant support studies may have further implications for the expanding use of low-valent group 9 metal complexes in organic synthesis

  1,3-二烯是普遍存在且易于合成的有机合成原料，丙烯酸烷基酯是最丰富且最便宜的原料碳源之一。据报道，这两种容易获得的前体的实用的、高度对映选择性的结合产生了有价值的、对映纯的跳过的1,4-二烯酯（具有两个构型确定的双键）。该过程使用市售的钴盐和手性配体。正如使用 20 种不同的底物（包括 17 种前手性 1,3-二烯和 3 种丙烯酸酯）所示，这种异二聚反应能够耐受许多常见的有机官能团（例如芳香族取代基、卤化物、分离的单和双官能团）。 -取代的双键、酯、甲硅烷基醚和甲硅烷基烯醇醚）。在这些研究过程中发现的配体、抗衡离子和溶剂效应等新颖结果表明，可能的阳离子 Co(I) 中间体在这些反应中具有独特的作用。导致最终成功结果的基于机制的策略的合理演变以及随之而来的支持研究可能会对低价第 9 族金属配合物在有机合成中的广泛使用产生进一步的影响。
• Preparation of monocarbonyl ruthenium complexes bearing bidentate nitrogen and phosphine ligands and their catalytic activity in carbonyl compound reduction
  作者：Steven Giboulot、Clara Comuzzi、Alessandro Del Zotto、Rosario Figliolia、Giovanna Lippe、Denise Lovison、Paolo Strazzolini、Sabina Susmel、Ennio Zangrando、Daniele Zuccaccia、Salvatore Baldino、Maurizio Ballico、Walter Baratta

  DOI：10.1039/c9dt02616a

  日期：——

  [RuCl2(CO)(PR3)(NN)] (R = Cy, NN = en 1, ampy 2; R = iPr; NN = en 3) have been prepared in a one pot reaction from [RuCl2(CO)(dmf)(PPh3)2], PR3 and the NN ligand in CH2Cl2. Treatment of [Ru(OAc)2(CO)(PPh3)2] with NN ligands in methanol gives the cationic derivatives [Ru(OAc)(CO)(PPh3)(NN)]OAc (NN = en 4, ampy 5) in which one acetate acts as a bidentate ligand, whereas the other is not coordinated. Diphosphine complexes

  单羰基配合物[RuCl 2（CO）（PR 3）（NN）]（R = Cy，NN = en 1，ampy 2 ; R = iPr; NN = en 3）已经由[RuCl 2（CO）（dmf）（PPh 3）2 ]，PR 3和CH 2 Cl 2中的NN配体。在甲醇中用NN配体处理[Ru（OAc）2（CO）（PPh 3）2 ]得到阳离子衍生物[Ru（OAc）（CO）（PPh 3）（NN）] OAc（NN = en 4，ampy 5），其中一种乙酸盐充当双齿配体，而另一种则没有配位作用。二膦配合物[RuCl 2（CO）（PP）（PPh 3）]（PP = dppb 6，dppf 7，（R）-BINAP 8，（R，S p）-Josiphos 9和（R，R）-Skewphos 10从[RuCl 2（CO）（dmf）（PPh 3）2 ]和PP配体在CHCl 3或甲苯中回流获得。[Ru（OAc）2（CO）（PPh