1,2-双(膦酰)乙烷 | 5518-62-7

• 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: 1,2-双(膦酰)乙烷
• 中文别名: 1,2-二膦基乙烷
• 英文名称: 1,2-diphosphinoethane
• 英文别名: 1,2-bis(phosphino)ethane；2-phosphanylethylphosphane
• CAS: 5518-62-7
• 化学式: C₂H₈P₂
• 分子量: 94.033
• InChiKey: FWFZRPMNAAFGBA-UHFFFAOYSA-N

物化性质

• 熔点：
  -62.4°C
• 沸点：
  109-110°C
• 闪点：
  109-110°C
• 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)：
  -0.4
• 重原子数：
  4
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险等级：
  4.2
• 危险类别码：
  R17,R36/37/38
• 危险品运输编号：
  UN 2845
• 包装等级：
  I
• 危险类别：
  4.2
• 储存条件：
  存储于阴凉干燥处。

SDS

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Section 1: Product Identification
Chemical Name: 1,2-Bis(phosphino)ethane, 99%
CAS Registry Number: 5518-62-7
Formula: H2PCH2CH2PH2
EINECS Number: none
Chemical Family: organophosphine ligand
Synonym: None

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title Compound 5518-62-7 100% no data no data

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Section 3: Hazards Identification
Harmful by inhalation, in contact with skin and if swallowed. May cause severe burns. Liquid has a pungent
Emergency Overview:
odor. Inhalation of vapors may lead to headache, fever, chills, muscle pain, nausea and dizziness.
Primary Routes of Exposure: Ingestion, eyes, skin, inhalation
Eye Contact: May cause mild to severe irritation of the eyes.
Skin Contact: Harmful in contact with skin. May cause mild irritation of the skin, or thermal burns if ignited.
Harmful by inhalation. Inhalation of vapors may lead to headache, fever, chills, muscle pain, nausea and
Inhalation:
dizziness.
Ingestion: Harmful if swallowed. May cause nausea and dizziness.
Harmful by inhalation, in contact with skin and if swallowed. Inhalation of vapors or ingestion may lead to
Acute Health Affects:
headache, fever, chills, muscle pain, nausea and dizziness.
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: not applicable
Autoignition Temperature: Pyrophoric
Explosion Limits: Pyrophoric
Extinguishing Medium: carbon dioxide, dry powder or foam
The pyrophoric liquid may reignite. Fire fighters should be equipped with an 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: Spontaneously flammable in air, especially in contact with organic matter such as paper or cloth.

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SECTION 6: Accidental Release Measures
'The material may ignite spontaneously in air. Avoid static discharge. Burning material may release
toxic fumes. In case of poor ventilation, leave the area unless fitted with a self-contained breathing apparatus.
Spill and Leak Procedures:
Small spills can be mixed with ground limestone, sodium bicarbonate, or other suitable absorbents, swept up,
and held in a closed metal can.

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SECTION 7: Handling and Storage
Store in a tightly sealed container under an inert atmosphere of nitrogen or argon. Keep away from heat.
Handling and Storage: Material should be transferred under an inert atmosphere of nitrogen or argon in a efficient fume hood. Fire
may occur in emptied container and transfer lines.

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SECTION 8: Exposure Controls and Personal Protection
Eye Protection: Wear chemical splash goggles and a full face shield.
Skin Protection: Wear protective clothing and flame proof insulated gloves over rubber gloves.
Ventilation: Material has a pungent odor. Always handle 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 has a pungent odor. Always handle material in an efficient fume hood.
Additional Protection: Wear a full face shield, flame resistant lab apron and suitable gloves.

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SECTION 9: Physical and Chemical Properties
Color and Form: colorless liq.
Molecular Weight: 92.02
Melting Point: no data
Boiling Point: 109-110°C
Vapor Pressure: no data
Specific Gravity: no data
Odor: unpleasant pungent odor
Solubility in Water: slightly soluble

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SECTION 10: Stability and Reactivity
Stability: air-sensitive, pyrophoric liquid
Hazardous Polymerization: no hazardous polymerization
Contact with air. Material may spontaneously ignite, especially in the presence of organic matter such as
Conditions to Avoid:
paper or cloth.
Incompatibility: oxidizing agents, halogens, air (pyrophoric), halocarbons, sulfur.
Decomposition Products: carbon dioxide, carbon monoxide, organic vapors, and phosphorus pentoxide.

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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 federal, state, and local regulations.

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SECTION 14: Transportation
Shipping Name (CFR): Pyrophoric liquids, organic, N.O.S.
Hazard Class (CFR): 4.2
Additional Hazard Class (CFR): NA
Packaging Group (CFR): I
UN ID Number (CFR): UN# 2845
Shipping Name (IATA): Forbidden
Hazard Class (IATA): NA
Additional Hazard Class (IATA): NA
Packaging Group (IATA): NA
UN ID Number (IATA): UN# 2845

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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：

  1,2-双(膦酰)乙烷 在 五氯化磷 作用下， 以 乙醚 为溶剂， 以73%的产率得到1,2-双(二氯磷基)-乙烷
  参考文献：
  名称：

  合成二氯膦的新方法

  摘要：

  描述了一种在温和条件下用五氯化磷氯化烷基膦来合成烷基二氯膦的新方法。

  DOI：

  10.1016/j.tetlet.2010.12.048
• 作为产物：
  描述：

  亚乙基二磷酸四乙酯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 1,2-双(膦酰)乙烷
  参考文献：
  名称：

  具有三（羟甲基）膦配体的水溶性铜（I）配合物的体外抗肿瘤活性。

  摘要：

  单阳离子亲水性配合物[Cu（thp）4]（+）3和[Cu（bhpe）2]（+）4是通过存在下不稳定的[Cu（CH3CN）4] [PF6]前体通过配体交换反应合成的过量的相关亲水性膦。针对一组几种人类肿瘤细胞系测试了复合物3和4。已经显示出复合物3的细胞毒性比顺铂高约1个数量级。对顺铂和多药耐药表型进行的化学敏感性测试表明，复合物3通过与参考药物不同的作用机理起作用。不同的短期增殖试验表明，溶酶体损伤是与复杂3细胞毒性相关的早期细胞事件，可能是由活性氧的产生增加所介导的。

  DOI：

  10.1021/jm701146c

文献信息

• A Universally Applicable Methodology for the Gram-Scale Synthesis of Primary, Secondary, and Tertiary Phosphines
  作者：N. Ian Rinehart、Alexander J. Kendall、David R. Tyler

  DOI：10.1021/acs.organomet.7b00684

  日期：2018.1.22

  to access a wide variety of phosphine oxides (an immediate precursor to phosphines). This synthetic approach saves the air-free handling until the last step (reduction to and isolation of the phosphine). Presented herein is a complete general procedure for the facile reduction of phosphonates, phosphinates, and phosphine oxides to primary, secondary, and tertiary phosphines using aluminum hydride reducing

  尽管有机膦的合成在一个世纪的上半叶已广为人知，但是即使对于资深的合成化学家来说，膦的合成仍然代表着艰巨的任务。膦作为一类化合物，其对空气的敏感性差异很大，并且误以为新手化学家尝试看似简单的合成是微不足道的，甚至是容易的，这会带来灾难性的结果。为了简化任务，我们之前已经开发出一种使用台式中间体访问各种氧化膦（膦的直接前体）的方法。这种合成方法可以节省无空气的处理，直到最后一步（还原并分离出膦）。本文介绍了将膦酸酯，次膦酸酯和膦氧化物轻松还原为伯，仲，和叔膦使用氢化铝还原剂。亲电还原剂（i Bu） 2 AlH和AlH 3在还原选择性和反应性方面被确定大大优于LiAlH 4。值得注意的是，即使LiAlH 4和（ i Bu） 2 AlH不能，AlH 3仍能还原具有极强抗性的三环己基氧化膦。使用这种新方法，可以以克级反应合成出代表性范围的伯，仲和叔膦（包括挥发性膦），而无需纯化步骤，可实现出色的收率和无与伦比的纯度。
• Synthesis and Reactivity of 1,2‐ and 1,3‐Diphosphanes that Contain Four Chiral Rhenium Fragments: Architecturally Novel Tetrametallo‐DMPE and ‐DMPP Species that are Unprivileged Ligands for Enantioselective Catalysis
  作者：Klemenz Kromm、Sandra Eichenseher、Markus Prommesberger、Frank Hampel、J. A. Gladysz

  DOI：10.1002/ejic.200500254

  日期：2005.8

  Reactions of enantiopure (S)-[(η 5 -C 5 H 5 )Re(NO)(PPh 3 )-(=CH 2 )] + PF 6 - [(S)-21 and PH 2 CH 2 (CH 2 ) n CH 2 PH 2 (0.5 equiv.) give (S R e S R e )-[(η 5 -C 5 H 5 )Re(NO)(PPh 3 )(CH 2 PH 2 CH 2 (CH 2 ) n -CH 2 PH 2 CH 2 }(Ph 3 P)(ON)Re(η 5 -C 5 H 5 )] 2 + 2PF 6 - [n = 0/1, (S R e S R e )-3/4; 65-62/77-58%]. Reaction of racemic 2 (BF 4 - salt) and PH 2 (CH 2 ) 2 PH 2 (0.5 equiv.) gives the meso and

  确定了 (SR e SR e SR e SR e )-7 的晶体结构并分析了其构象。(SR e SR e SR e SR e )-7/8 和 tBuOK 的反应得到空气敏感的双膦 (SR e SR e SR e SR e )-(η 5 -C 5 H 5 )Re(NO)-( PPh 3 )(CH 2 )} 2 (PCH 2 (CH 2 ) n CH 2 P}(CH 2 )(Ph 3 P)(ON)Re(η 5 -C 5 H 5 )} 2 [n = 0 /1, (SR e SR e SR e SR e )-9/10; 92/62%]. 添加 (a) PhIO 得到相应的二氧化物 (72/62%), 和 (b) [Rh(NBD) 2 ] + PF 6 - 得到相应的螯合物 [(PP)-Rh(NBD)] + PF 6 - (75/82%) (NBD = 降冰片二烯)。对映选择性. 当 (SR e
• Synthesis of Novel Tetrametallic and Trimetallic Compounds from Reactions of MMe₃ (M = Al, Ga) with 1,2-(H₂E)₂C₆H₄ (E = N, P)
  作者：Richard L. Wells、Hamid Rahbarnoohi、Paul B. Glaser、Louise M. Liable-Sands、Arnold L. Rheingold

  DOI：10.1021/om9600553

  日期：1996.7.9

  in the formation of the novel eight-membered tetrametallic ring compounds with the general formula (Me2M)4[(μ-PH)2(C6H4)]2} (M = Al (1), Ga (2)) in a nearly quantitative yield. Combining AlMe3 and 1,2-(H2P)2C6H4 in a 1:1 ratio also afforded 1. The reaction of AlMe3 with 1,2-(H2N)2C6H4 (2:1) yielded the novel asymmetric compound [(Me2Al)2AlMe(C6H4(NH)2)2]·AlMe3 (3). Compound 3 is composed of four aluminum

  MMe 3（M = Al，Ga）与1,2-（H 2 P）2 C 6 H 4的独立2：1反应导致形成通式为（ Me 2 M）4 [（μ-PH）2（C 6 H 4）] 2 }（M = Al（1），Ga（2））以接近定量的产率产生。以1∶1的比例结合AlMe 3和1,2-（H 2 P）2 C 6 H 4也得到1。AlMe的反应3与1,2-（H 2 N）2 C 6 H 4（2：1）生成新型不对称化合物[（Me 2 Al）2 AlMe（C 6 H 4（NH）2）2 ]·AlMe 3（3）。化合物3由四个化学上不等价的铝中心组成。GaMe 3与1,2-（H 2 N）2 C 6 H 4以3：2的比例反应，得到（Me 2 Ga）3 [（μ-NH）2（C 6H 4）（μ-NH）（C 6 H 4 NH 2）]}（4）。的合成和表征1 - 4，包括其固态结构，现介绍。
• Stabilized form of Tetrofosmin and its use
  申请人：ROTOP Pharmaka AG

  公开号：EP2899195A1

  公开（公告）日：2015-07-29

  The present invention provides a stabilized form of Tetrofosmin, which is stable at room temperature as well as in contact with oxygen, and a non-radioactive kit containing a stabilized form of Tetrofosmin for the preparation of a radiopharmaceutical composition in the field of diagnostic radiopharmaceuticals, especially for myocardial perfusion studies in patients with coronary artery diseases and in oncology.

  本发明提供了一种稳定的Tetrofosmin形式，该形式在室温下以及与氧气接触时具有稳定性，并且包含一种非放射性试剂盒，其中包含一种稳定的Tetrofosmin形式，用于在诊断放射药物领域中制备放射性药物组合物，特别是用于冠状动脉疾病患者和肿瘤学中的心肌灌注研究。
• [EN] STABILIZED FORM OF TETROFOSMIN AND ITS USE<br/>[FR] FORME STABILISÉE DE TÉTROFOSMINE ET SON UTILISATION
  申请人：ROTOP PHARMAKA GMBH

  公开号：WO2015114002A1

  公开（公告）日：2015-08-06

  The present invention provides astabilized form of Tetrofosmin, which is stable at room temperature as well as in contact with oxygen,and a non-radioactive kit containing a stabilized form of Tetrofosmin for the preparation of a radiopharmaceutical composition in the field of diagnostic radiopharmaceuticals, especially for myocardial perfusion studies in patients with coronary artery diseases and in oncology.

  本发明提供了一种稳定的Tetrofosmin形式，该形式在室温下以及与氧气接触时稳定，并且包含一种稳定的Tetrofosmin形式的非放射性试剂盒，用于制备放射性药物组合物，特别是用于冠状动脉疾病患者和肿瘤学患者的心肌灌注研究领域的诊断放射药物。