顺-1,2-双(二苯基膦)乙烯 | 983-80-2

• 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: 顺-1,2-双(二苯基膦)乙烯
• 中文别名: 顺式-1,2-双(二苯基膦)乙烯
• 英文名称: cis-1,2-bis-(diphenylphosphino)ethene
• 英文别名: cis-1,2-bis(diphenylphosphino)ethylene；cis-bis(diphenylphosphino)ethylene；dppv；[(Z)-2-diphenylphosphanylethenyl]-diphenylphosphane
• CAS: 983-80-2
• 化学式: C₂₆H₂₂P₂
• 分子量: 396.408
• InChiKey: NCKJIJSEWKIXAT-DQRAZIAOSA-N

物化性质

• 熔点：
  122-124 °C(lit.)
• 沸点：
  546.8±33.0 °C(Predicted)
• 稳定性/保质期：

  常温常压下稳定，避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2902909090
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338

SDS

Name:	Cis-1 2-Bis(Diphenylphosphino)Ethylene Material Safety Data Sheet
Synonym:
CAS:	983-80-2

Section 1 - Chemical Product MSDS Name:Cis-1 2-Bis(Diphenylphosphino)Ethylene Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
983-80-2	Cis-1,2-Bis(Diphenylphosphino)Ethylene		213-569-7

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
No information regarding eye irritation and other potential effects was found.
Skin:
No information regarding skin irritation and other potential effects was found.
Ingestion:
The toxicological properties of this substance have not been fully investigated.
Inhalation:
The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use agent most appropriate to extinguish fire.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use only in a well-ventilated area.
Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 983-80-2: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 122 - 124 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: (C6H5)2PCH=CHP(C7H5)2
Molecular Weight: 396.41

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stability unknown. Thermal decomposition may produce toxic fumes of phosphorous oxides and/or phosphine.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 983-80-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Cis-1,2-Bis(Diphenylphosphino)Ethylene - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 37/39 Wear suitable gloves and eye/face
protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 983-80-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 983-80-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 983-80-2 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  顺-1,2-双(二苯基膦)乙烯 在 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以71%的产率得到cis-1,2-bis(diphenylphosphoryl)ethylene
  参考文献：
  名称：

  Th（IV）与顺式-乙撑双（二苯基氧化膦）的配合物：X射线结构和NMR溶液研究

  摘要：

  摘要利用X射线晶体学，IR，NMR和CHN分析方法研究了Th（NO3）4与刚性二磷酰基配体顺式-乙撑双（二苯基膦氧化物）的络合作用。从甲醇溶液中生长出三个晶体多晶型物，其中1：3 Th（IV）-配体络合物是十配位的，并且该金属由三个二齿配体和两个硝酸根基团结合。还从非配位溶剂CHCl3中生长了另一种几何形状相似的金属-配体配合物。使用1H和31P NMR分析此络合物的CD3OD和CDCl3溶液表明，在甲醇-d4中，配体交换速率在NMR时间尺度上快，而在氯仿-d中在NMR时间尺度上慢。此外，据报道还描述了三种另外的晶体结构，分别描述了1：1和1：2 Th（IV）-配体配合物，即1：

  DOI：

  10.1016/j.poly.2015.05.016
• 作为产物：
  描述：

  双(二苯基磷)乙炔 在 (tolane)(trimethylphosphane)titanocene 氢气 作用下， 生成 顺-1,2-双(二苯基膦)乙烯
  参考文献：
  名称：

  Complexes acetyleniques de titane(II). Reactivite vis-a-vis de l'hydrogene moleculaire: Une nouvelle approche du titanocene

  摘要：

  DOI：

  10.1016/0022-328x(85)80096-6
• 作为试剂：
  描述：

  cyclopentyl tosylate 、 N-(quinolin-8-yl)cyclohex-1-enecarboxamide 在 iron(III)-acetylacetonate 、 四甲基乙二胺 、 4-甲氧基苯基溴化镁 、 顺-1,2-双(二苯基膦)乙烯 、 sodium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以77%的产率得到2-cyclopentyl-N-(quinolin-8-yl)cyclohex-1-enecarboxamide
  参考文献：
  名称：

  芳香族和烯烃甲酰胺与伯和仲烷基甲苯磺酸盐、甲磺酸盐和卤化物的铁催化定向烷基化

  摘要：

  在作为催化剂的 Fe(acac)3/二膦和作为碱的 ArZnBr 存在下，具有 8-喹啉酰胺基团作为导向基团的烯烃、芳烃和杂芳烃与伯和仲烷基甲苯磺酸盐、甲磺酸盐和卤化物烷基化。该反应对烯烃底物立体特异性地进行，并且在不损失起始二级甲苯磺酸酯的区域化学完整性的情况下发生，但会损失手性中心的立体化学。

  DOI：

  10.1021/ja5066015

文献信息

• Influence of the heavy-atom effect on singlet fission: a study of platinum-bridged pentacene dimers
  作者：Bettina S. Basel、Ryan M. Young、Matthew D. Krzyaniak、Ilias Papadopoulos、Constantin Hetzer、Yueze Gao、Nathan T. La Porte、Brian T. Phelan、Timothy Clark、Rik R. Tykwinski、Michael R. Wasielewski、Dirk M. Guldi

  DOI：10.1039/c9sc04410h

  日期：——

  The process of singlet fission (SF) produces two triplet excited states (T1 + T1) from one singlet excited exciton (S1) and a molecule in its ground state (S0). It, thus, possesses the potential to boost the solar cell efficiency above the thermodynamic Shockley-Queisser limit of 33%. A key intermediate in the SF mechanism is the singlet correlated triplet pair state 1(T1T1). This state is of great relevance

  单线态裂变（SF）的过程从一个单线态激发态激子（S1）和处于基态的分子（S0）产生两个三线态激发态（T1 + T1）。因此，它具有将太阳能电池效率提高到热力学肖克利-奎塞尔极限（33％）之上的潜力。SF机制中的关键中介是单重态相关的三重态对状态1（T1T1）。该状态具有极大的意义，因为它的形成是允许旋转的，因此非常快速有效。到目前为止，已经记录了形成1（T1T1）的三种根本不同的途径。但是，影响哪种机理与哪种生色团相关的因素仍然未知。为了独立地收获两个三重态激子，需要相关的三重态对状态与两个独立的三重态的去相关。SF过程的第二步意味着总自旋量子数发生变化。在二聚体的情况下，通常只有在两个戊烯之间的耦合足够弱的情况下才有可能。在这项研究中，我们提出了两个戊二烯牢固偶联的铂桥并五苯二聚体，因此最初预期自旋解相关产量（T1 + T1）将被三重态三重态an灭（TTA）击败而达到基态。两个铂桥联的并
• Di- and Trinuclear Metal Complexes Containing a β-Diketonate Dianion as a Bridging Ligand
  作者：Yukie Otani、Yukio Nakamura、Shinichi Kawaguchi、Seichi Okeya、Tetsu Hinomoto

  DOI：10.1246/bcsj.55.1467

  日期：1982.5

  The dinuclear palladium(II) complexes [(PP)Pd(C1–C3-β-dik(2−)-O,O′)Pd(PP)](ClO4)2 containing a β-diketonate dianion as a bridging ligand were prepared by the reactions of the mononuclear complexes ...

  双核钯(II)配合物[(PP)Pd(C1-C3-β-dik(2-)-O,O')Pd(PP)](ClO4)2 含有β-二酮酸二价阴离子作为桥连配体由单核配合物的反应制备...
• Cyclometallated thiosemicarbazone palladium(II) compounds: The first crystal and molecular structures of mononuclear complexes with a η1-diphosphine ligand
  作者：Javier Martínez、Luis A. Adrio、José M. Antelo、Juan M. Ortigueira、Ma Teresa Pereira、Jesús J. Fernández、Alberto Fernández、José M. Vila

  DOI：10.1016/j.jorganchem.2006.02.014

  日期：2006.6

  2-XC6H4C(Me)NN(H)C(S)NHR (R = Me, X = F, a; R = Et, X = F, b; R = Me, X = Cl, c; R = Et, X = Br, d) with potassium tetrachloropalladate(II) in ethanol, lithium tetrachloropalladate(II) in methanol or palladium(II) acetate in acetic acid, as appropriate, gave the tetranuclear cyclometallated complexes [Pd2-XC6H3C(Me)NNC(S)NHR}]4 (1a–1d). Reaction of 1a–1d with the diphosphines Ph2PCH2PPh2 (dppm), Ph2P(CH2)2PPh2

  硫代半脲酮2-XC 6 H 4 C（Me）NN（H）C（S）NHR的处理（R = Me，X = F，a ; R = Et，X = F，b ; R = Me，X = Cl，c； R = Et，X = Br，d），酌情用乙醇中的四氯钯酸（Ⅱ），甲醇中的四氯钯酸（Ⅱ）或乙酸中的乙酸钯（Ⅱ），得到四核环金属化配合物[Pd 2-XC 6 H 3 C（Me）NNC（S）NHR}] 4（1a – 1d）。的反应1A - 1d的与所述二膦博士2 PCH 2 PPH 2（dppm），Ph 2 P（CH 2）2 PPh 2（dppe），Ph 2 P（CH 2）3 PPh 2（dppp）或反式-Ph 2 PCHCHPPh 2（反式-dpe）以1：2的摩尔比得到双核环金属化配合物[Pd [2-XC 6 H 3 C（Me）NNC（S）-NHR]} 2（μ-diphosphine- P，P）]（2a – 5a，3b，3d，4c，5c）
• Chiral <i>cis</i>-Platinum Acetylide Complexes via Diphosphine Ligand Exchange: Effect of the Ligand
  作者：Amber L. Sadowy、Michael J. Ferguson、Robert McDonald、Rik R. Tykwinski

  DOI：10.1021/om800633h

  日期：2008.12.8

  Chiral, bidentate phosphine ligands (R,R-CHIRAPHOS, R-PROPHOS, S,S-BDPP, R,R-Me-DUPHOS, R,R-NORPHOS) react with trans-platinum acetylide complexes 1a and 1b, (Ph3P)2Pt(C≡CR)2 (R = TIPS, p-MeC6H4), via ligand exchange to generate chiral platinum acetylide complexes. The corresponding cis-platinum complexes are formed in all cases except for the reaction of 1b with S,S-BDPP, where the dimeric complex

  手性二齿膦配体（R，R -CHIRAPHOS，R- PROPHOS，S，S- BDPP，R，R- Me-DUPHOS，R，R- NORPHOS）与反铂乙炔化物络合物1a和1b（Ph 3 P）2 Pt（C≡CR）2（R = TIPS，p -MeC 6 H 4），通过配体交换产生手性的乙炔铂络合物。在所有情况下均形成相应的顺铂络合物，但1b与S，S- BDPP的反应除外，其中二聚体络合物4d'是产品。相反，1a和1b与配体S，S -DIOP，R -BINAP和R -SYNPHOS的反应未能以可观的收率得到所需的产物。圆二色光谱用于检查手性配体对乙炔铂骨架的手性的影响。报道了非手性络合物1a和手性衍生物4e的X射线晶体学分析。
• Synthesis and solution multinuclear nuclear magnetic resonance studies of homoleptic copper(I) complexes of Group 15 donor ligands
  作者：Jane R. Black、William Levason、Mark D. Spicer、Michael Webster

  DOI：10.1039/dt9930003129

  日期：——

  spectra, have been recorded from CH2Cl2 solutions of the complexes over the temperature range 300–175 K, including the first reported 63Cu resonances from arsenic and antimony donor ligand compounds. The effects of ligand size and geometry upon the 63Cu NMR spectra are discussed and typical copper chemical-shift ranges for Group 15 donor ligand compounds established. The structure of [Cu(cis-Ph2AsCHCHAsPh2)2]PF6

  均纯络合物[CuL 4 ] Y（L = PMe 3，PMe 2 Ph，PMePh 2，PPh 3，PPh 2 H，PPhH 2，AsMe 3，AsMe 2 Ph，AsMePh 2，AsPh 3，SbMe 3，SbEt 3或SbPh 3； Y = PF 6或BF 4）和[Cu（L–L）2 ] Y [L–L = Me 2 P（CH 2）2 PMe 2，o -C 6 H 4（PMe 2）2，Ph 2 P（CH 2）n PPh 2（n = 1-4），顺式-Ph 2 PCH CHPPh 2，o -C 6 H 4（PPh 2）2，o -C 6 H 4（AsMe 2）2，顺式-Ph 2 AsCH CHAsPh 2，o -C 6 H 4（SbMe 2）2，Me由[Cu（MeCN） 4 ] Y和L或L–L制备了2 Sb（CH 2） 3 SbMe 2或Ph 2 Sb（CH 2） 3 SbPh 2 ]。在300–175