1,2-二(二-2-吡啶基膦酰)乙烷 | 106308-26-3

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 1,2-二(二-2-吡啶基膦酰)乙烷
• 中文别名: 1,2-双(二-2-吡啶基膦)乙烷；2,2',2'',2'''-(1,2-乙二基二膦三基)四吡啶；1,2-双(二- 2 -吡啶基膦)乙烷
• 英文名称: 1,2-Bis(di-pyridin-2-ylphosphino)ethane
• 英文别名: 2,2',2'',2'''-(1,2-ethanediyldiphosphinidyne)tetrakispyridine；1,2-bis(bis(2-pyridyl)phosphine)ethane；1,2-bis[bis(2-pyridyl)phosphino]ethane；1,2-bis[di(2-pyridyl)phosphino]ethane；1,2-bis(di-2-pyridylphosphino)ethane；d2pype；1,2-Bis(di(pyridin-2-yl)phosphino)ethane；2-dipyridin-2-ylphosphanylethyl(dipyridin-2-yl)phosphane
• CAS: 106308-26-3
• 化学式: C₂₂H₂₀N₄P₂
• 分子量: 402.375
• InChiKey: GBLNXAZZONXIQE-UHFFFAOYSA-N

物化性质

• 熔点：
  134-135 °C(Solv: acetone (67-64-1))
• 沸点：
  576.7±45.0 °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)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090
• 储存条件：
  存于阴凉干燥处。

SDS

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Section 1: Product Identification
Chemical Name: 1,2-Bis(di-2-pyridylphosphino)ethane, min. 98%
CAS Registry Number: 106308-26-3
Formula: C22H20N4P2
EINECS Number: none
Chemical Family: organophosphine ligand
Synonym: 1,2-Bis(di-2-pyridylphosphano)ethane

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 106308-26-3 100% 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: Inhalation, skin, eyes
Eye Contact: Causes slight to mild irritation of the eyes.
Skin Contact: Causes irritation to the skin
Inhalation: Causes irritation to the nose, mucous membranes and respiratory tract
Ingestion: No information 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 available 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 chemical 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 organic fumes
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards

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SECTION 6: Accidental Release Measures
Small spills can be mixed with vermiculite, sodium carbonate or other suitable non-combustible adsorbent and
Spill and Leak Procedures:
swept up.

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SECTION 7: Handling and Storage
Handling and Storage: Store the material in a tightly sealed container. Keep in a cool, dry 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: 402.37
Melting Point: no data
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 and moisture stable
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: none
Incompatibility: oxidizing agents
Decomposition Products: carbon dioxide, carbon monoxide, phosphorus and nitrogen 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：

  (1,5-cylooctadiene)di-iodoplatinum(II) 、 1,2-二(二-2-吡啶基膦酰)乙烷 以 二氯甲烷 为溶剂， 以46%的产率得到cis-PtI2(C2H4(P(C5H4N)2)2)
  参考文献：
  名称：

  Coordination Chemistry of the 2-Pyridyldiphosphine Ligands, (py)₂P(CH(CH₂)₃CH)P(py)₂ and (py)₂P(CH₂)₂P(py)₂ (py = 2-Pyridyl), with Platinum(II) and Ruthenium(II). Ruthenium-Catalyzed Hydrogenation of Imines

  摘要：

  The synthesis and characterization of a range of Pt(II) and Ru(II) complexes containing the new 2-pyridyldi-phosphine ligand, d(py)pcp = (py)(2)P(CH(CH2)(3)CH)P(py)(2) (made as a racemate) and the previously reported d(py)pe = (py)(2)P(CH2)(2)P(py)(2) are given (py =2-pyridyl). The Pt complexes made were cis-PtX2(d(py)pcp) (X = Cl (1), I (2)), cis-PtX2(d(py)pe) (X = Cl (3), I (4)), [Pt(d(py)pcp)(2)][PF6](2) (5), and [Pt(d(py)pe)(2)][PF6](2) (6); these all contain P,P-bonded diphosphine ligand, as evidenced by P-31 NMR data and by crystallographic data in the case of 2 and 3. The X-ray structure of d(py)pe is also reported. The complexes RuX2(P,P,N-d(py)pcp)(PPh3) have cis-halogens and a P,P,N-bonding mode of the pyridyldiphosphine (which incorporates a four-membered P,N-chelate ring) with either a mer-arrangement (in 7a, X = Cl) or a fac-arrangement of the three P donor atoms (in 7b (X = Cl), 8 (X = Br), 9 (X = I)); cis-RuCl2(dppb)(P,N-PPh2(py)) (12) (dppb = Ph-2(CH2)(4)PPh2) is included because it has a donor set corresponding to that in 7b. Use of the purely P,P donor Ph2P(CH(CH2)(3)CH)PPh2 (dppcp), made as a racemate, affords trans-RuCl2(dppcp)(2) (10) and trans-RuCl2(dppcp)(dppb) (II). Crystallographic data for 7a, 7b, and 12 are reported together with the NMR data for all the Ru complexes. Preliminary results show that the Ru complexes 7b, 8, and 9 are effective precursors for catalytic H-2-hydrogenation of aldimines.

  DOI：

  10.1021/ic990002o
• 作为产物：
  描述：

  2-溴吡啶 、 1,2-双(二氯磷基)-乙烷 在 正丁基锂 作用下， 生成 1,2-二(二-2-吡啶基膦酰)乙烷
  参考文献：
  名称：

  Convenient synthetic routes to bidentate and monodentate 2-, 3- and 4-pyridyl phosphines: potentially useful ligands for water-soluble complex catalysts

  摘要：

  The monodentate and bidentate pyridyl phosphines, PR3 and R2P(CH2)(2)PR2, where R = 3- or 4-pyridyl can be prepared in high yields by treatment of butyllithium/TMEDA/3- or 4-bromopyridine with PCl3 or Cl2P(CH2)(2)PCl2 at low temperature. 1,2-Bis(di-2-pyridylphosphino)ethane is conveniently synthesised by an alternative route involving reaction of 1,2-dibromoethane with lithium di-2-pyridylphosphide. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(97)00722-5

文献信息

• 2-Pyridyl-phosphine and -diphosphine complexes of nickel(0), their reactivity (including aqueous solution chemistry), and some related, incidental methylphosphonium iodides
  作者：Matthew D. Le Page、Brian O. Patrick、Steven J. Rettig、Brian R. James

  DOI：10.1016/j.ica.2015.04.003

  日期：2015.5

  Ni(CO)2[2H-d(py)pcp]}2+ being isolated as the bis(triflate) salt; the dication decomposes in minutes with formation of [Ni(H2O)6]2+, CO, the phosphine dioxide, and deprotonated d(py)pcp. Some twenty-two Ni0 complexes, exemplified by Ni(P–P)2, Ni(PNx)2(P–P), Ni(PNx)4, and related PPh3- and Ph2P(CH2)2PPh2 (dppe)-containing species, are synthesized from Ni(1,5-COD)2 and their reactivity studied; for

  摘要Ni（CO）2L2型Ni0-二羰基（吡啶基膦）配合物的化学性质，其中L为P键结合的PPh3-npyn（n = 1-3，py = 2-吡啶基；缩写为PNx，x = 1– 3，1a–c）或L2是（P–P）螯合的py2P（CH2）2Ppy2或，是我们小组从较早的研究中进一步开发的[P–P配体分别缩写为d（py） pe和d（py）pcp]。由Ni（CO）2（PPh3）2的C6H6溶液合成配合物，并检测到Ni（CO）2（PPh3）（PNx）中间体（1a ∗ –c ∗）；X射线分析表明Ni（CO）2 [d（py）pcp]（2b）具有扭曲的四面体结构；从CDCl3溶液中的光诱导反应中分离出NiII物质[Ni2（CO）4（μ-PN2）2] Cl4。络合物2b在环境条件下通过吡啶基N原子的净双质子化作用溶于水，分离出Ni（CO）2 [2H-d（py）pcp]} 2+为双（三氟甲磺酸盐）盐；指示剂在几分钟内分解，形成[Ni（H2O）6]
• Certain bis(di-2 or 4-pyridyl-phosphino) alkanes #10 having anti-tumor
  申请人：Smithkline Beckman Corporation

  公开号：US04716230A1

  公开（公告）日：1987-12-29

  Heterocyclic phosphine compounds, pharmaceutical compositions containing an effective, tumor cell growth-inhibiting amount of such a compound, and a method for treating tumor cells sensitive to such a compound which comprises administering a tumor cell growth-inhibiting amount of such a compound to an animal afflicted by said tumor cells.

  含有有效的抗肿瘤细胞生长成分的杂环膦化合物，含有这种化合物的药物组合物，以及一种治疗对这种化合物敏感的肿瘤细胞的方法，包括向患有该肿瘤细胞的动物施用抗肿瘤细胞生长成分。
• [Ni(Et₂PCH₂NMeCH₂PEt₂)₂]²⁺ as a Functional Model for Hydrogenases
  作者：Calvin J. Curtis、Alex Miedaner、Rebecca Ciancanelli、William W. Ellis、Bruce C. Noll、M. Rakowski DuBois、Daniel L. DuBois

  DOI：10.1021/ic020610v

  日期：2003.1.1

  ligand in the proton exchange reactions observed for the various Ni complexes containing the PNP ligand. Similarly, structural studies of [Ni(PNBuP)(2)](BF(4))(2) and [Ni(PNP)(dmpm)](BF(4))(2) (where PNBuP is Et(2)PCH(2)N(Bu)CH(2)PEt(2) and dmpm is Me(2)PCH(2)PMe(2)) illustrate the importance of tetrahedral distortions about Ni in determining the hydride acceptor ability of Ni(II) complexes.

  Et（2）PCH（2）N（Me）CH（2）PEt（2）（PNP）与[Ni（CH（3）CN）（6）]（BF（4））（2）的反应结果在[Ni（PNP）（2）]（BF（4））（2）的形成中，它同时具有氢化物和质子受体位点。该络合物是用于将氢氧化为质子的电催化剂，与氢的化学计量反应形成[HNi（PNP）（PNHP）]（BF（4））（2），其中氢化物配体与Ni和质子键合与一个PNP配体的N侧基相连。使用热力学循环，与该反应有关的自由能已计算为-5 kcal / mol。氢化物配体和NH质子相互之间进行快速分子内交换，并与溶液中的质子进行分子间交换。[HNi（PNP）（PNHP）]（BF（4））（2）经历可逆的去质子化反应，在乙腈溶液中形成[HNi（PNP）（2）]（BF（4））（pK（a）= 10.6）。一种方便的合成方法来合成这种氢化物的PF（6）（-）盐包括PNP与Ni（COD）（2）反应形成N
• NMR and structural studies of gold(I) chloride adducts with bidentate 2-, 3- and 4-pyridyl phosphines
  作者：Susan J. Berners-Price、Richard J. Bowen、Trevor W. Hambley、Peter C. Healy

  DOI：10.1039/a809285k

  日期：——

  The 1∶2 adducts of gold(I) chloride with the diphosphine ligands, 1,2-bis(di-n-pyridylphosphino)ethane (dnpype) for n = 2, 3 and 4 have been synthesized and solution properties characterized by NMR spectroscopy, including variable temperature one dimensional 31P1H} and 2D [31P, 31P] COSY experiments. The results show the 3-pyridyl (d3pype) and 4-pyridyl (d4pype) adducts to exist as bis-chelated monomeric

  所述的金1个02加合物（我）氯化物与二膦配体，1,2-双（二- Ñ -pyridylphosphino）乙烷（d Ñ pype）为Ñ  = 2，3和4已被合成和溶液性质的特征在于NMR光谱学，包括可变温度一维31 P 1 H}和2D [ 31 P，31 P] COZY实验。结果显示3-吡啶基（d3pype）和4-吡啶基（d4pype）加合物以双螯合单体[Au（d3pype）2 ] +和[Au（d4pype）2 ] +的形式存在，而2-吡啶基（d2pype）加合物形成单体[Au（d2pype）的平衡混合物2 ] +，二聚体[Au（d2pype） 2 } 2 ] 2+和可能的四聚体[Au（d2pype） 2 } 4 ] 4+物种，其中d2pype配体通过磷原子在桥联和螯合模式下进行配位。存在的物质的相对百分比取决于温度和溶剂。由乙醇/己烷制得的4-吡啶基加合物的单晶X射线结构测定表明，该配合物结晶为[Au（d4pype）
• A novel coordination mode for a pyridylphosphine ligand. X-ray structures of [RuCl₂(NO)L] (<b>I</b>) and [RuCl₂(NO)L]·DMSO (<b>II</b>) (L = [(2-py)₂PC₂H₄POO(2-py)₂]^-)
  作者：Alzir A Batista、Salete L Queiroz、Peter C Healy、Robbie W Buckley、Sue E Boyd、Susan J Berners-Price、Eduardo E Castellano、Javier Ellena

  DOI：10.1139/v01-038

  日期：2001.5.1

  The ruthenium(II) complex, [RuCl₂(NO)L] (I), (L = [(2-py)₂PC₂H₄PO₂(2-py)]^-) was obtained from recrystallization of RuCl₃NO(d2pype) (d2pype = (2-py)₂PC₂H₄P(2-py)₂) in the presence of HNO₃, crystallizing in the monoclinic space group P2₁ (no. 4), with a = 8.012(4) Å, b = 14.454(4) Å, c = 9.353(3) Å, β = 105.77(3)°, and Z = 2. Crystals of the DMSO solvate of the complex (II) were obtained from (CD₃)₂SO solution, crystallizing in the monoclinic space group P2₁/c (no.14) with a = 9.7080(2) Å, b = 22.2920(5) Å, c = 11.5230(3) Å, β = 92.0450(10)°, and Z = 4. In both complexes, the geometry about the ruthenium atom is a distorted octahedron mainly as a result of the tridentate [P,N,O]-bonding mode of L. The ν (NO) bands at 1875 cm^–1 in both complexes are consistent with the linear disposition of the NO group and the Ru atom as is observed in the X-ray crystal structure (Ru-N1-O1 angle = 178.5(4)°).Key words: pyridylphosphine, nitrosyl, ruthenium complex, X-ray structure.

  [RuCl₂(NO)L] (I)是一种钌(II)配合物，其中L = [(2-py)₂PC₂H₄PO₂(2-py)]^-，通过RuCl₃NO(d2pype)（其中d2pype = (2-py)₂PC₂H₄P(2-py)₂）在HNO₃存在下重结晶而得，晶化于单斜晶系空间群P2₁（no. 4），晶胞参数为a = 8.012(4) Å，b = 14.454(4) Å，c = 9.353(3) Å，β = 105.77(3)°，Z = 2。配合物的DMSO溶剂化物(II)的晶体通过(CD₃)₂SO溶液得到，晶化于单斜晶系空间群P2₁/c (no.14)，晶胞参数为a = 9.7080(2) Å，b = 22.2920(5) Å，c = 11.5230(3) Å，β = 92.0450(10)°，Z = 4。在两种配合物中，钌原子周围的几何结构为畸变的八面体，主要是由于L的三齿配位方式[P，N，O]。两种配合物中的ν(NO)带位于1875 cm^–1，与NO基团和Ru原子的线性排列与X射线晶体结构中观察到的Ru-N1-O1角度为178.5(4)°一致。关键词：吡啶膦，亚硝基，钌配合物，X射线结构。