三(2-氰乙基)膦 | 4023-53-4

• 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 - 有机膦及其衍生物
• 中文名称: 三(2-氰乙基)膦
• 英文名称: tris(2-cyanoethyl)phosphine
• 英文别名: 3-[bis(2-cyanoethyl)phosphanyl]propanenitrile
• CAS: 4023-53-4
• 化学式: C₉H₁₂N₃P
• mdl: MFCD00013828
• 分子量: 193.188
• InChiKey: CHZAMJVESILJGH-UHFFFAOYSA-N

物化性质

• 熔点：
  97-98°C
• 沸点：
  235°C 0,9mm
• 闪点：
  235°C/0.9mm
• 暴露限值：
  ACGIH: TWA 0.1 ppm; STEL 0.3 ppmOSHA: TWA 0.75 ppm; STEL 2 ppmNIOSH: IDLH 20 ppm; TWA 0.016 ppm; Ceiling 0.1 ppm
• 稳定性/保质期：
  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• TSCA：
  Yes
• 危险等级：
  6.1
• 危险品标志：
  Xi
• 安全说明：
  S36/37/39,S45
• 危险类别码：
  R20/21/22
• 危险品运输编号：
  UN3464
• 海关编码：
  2926909090
• 包装等级：
  II
• 危险类别：
  6.1
• 储存条件：
  请将药品存放在避光、通风干燥的地方，并密封保存。

SDS

Name:	TRIS-(2-CYANOETHYL)PHOSPHINE Material Safety Data Sheet
Synonym:
CAS:	4023-53-4

Section 1 - Chemical Product MSDS Name:TRIS-(2-CYANOETHYL)PHOSPHINE Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
4023-53-4	TRIS-(2-CYANOETHYL)PHOSPHINE		223-687-0

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
The toxicological properties of this material have not been investigated. Use appropriate procedures to prevent opportunities for direct contact with the skin or eyes and to prevent inhalation.

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Section 4 - FIRST AID MEASURES
Eyes: Not available.
Skin:
Not available.
Ingestion:
Not available.
Inhalation:
Not available.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
Not available.
Extinguishing Media:
Not available.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Not available.

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Section 7 - HANDLING and STORAGE
Handling:
Not available.
Storage:
Not available.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Exposure Limits CAS# 4023-53-4: Personal Protective Equipment Eyes: Not available.
Skin:
Not available.
Clothing:
Not available.
Respirators:
Not available.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Not available.
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
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:
Molecular Weight:

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Not available.
Incompatibilities with Other Materials:
Not available.
Hazardous Decomposition Products:
Not available.
Hazardous Polymerization: Not available.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 4023-53-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
TRIS-(2-CYANOETHYL)PHOSPHINE - 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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 4023-53-4: No information available.
Canada
CAS# 4023-53-4 is listed on Canada's NDSL List.
CAS# 4023-53-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 4023-53-4 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

Tris(2-氰乙基)膦是一种蛋白质交联剂，也可用于合成具有抗肿瘤活性的铜(I)配合物。

反应信息

• 作为反应物：
  描述：

  三(2-氰乙基)膦 在 sodium methylate 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 生成 3,3'-ethylphosphanediyl-bis-propionitrile
  参考文献：
  名称：

  Kuznetsov,E.V. et al., Journal of general chemistry of the USSR, 1963, vol. 33, p. 2564 - 2566

  摘要：

  DOI：
• 作为产物：
  描述：

  丙烯腈 在 phosphan 作用下， 生成 三(2-氰乙基)膦
  参考文献：
  名称：

  The Nucleophilicity of Phosphines

  摘要：

  DOI：

  10.1021/ja01507a009
• 作为试剂：
  描述：

  1-(3,4-dimethyl-1-phenyl-1-thioxo-1H-1λ⁵-phosphol-2-yl)-ethanone 在 三(2-氰乙基)膦 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 1-(3,4-dimethyl-1-phenyl-1H-phosphol-2-yl)-ethanone
  参考文献：
  名称：

  衍生出α-羰基等“芳族化合物”，磷酸三价

  摘要：

  2-乙酰基和2-乙氧基-磷的两步合成涉及通过叔丁基锂将单体的3,4-二甲基磷硫化物金属化，然后与乙酸乙酯和碳酸乙酯反应。由此获得的磷杂环硫化物通过PBU降低3或P（CH 2 CH 2 CN）3至phospholes 20 - 24。在2-乙酰基-磷系列中，通过1 H和31 P NMR监测从二烯系和从磷原子到羰基的可变电子转移。2-羧基磷脂25的主要分解途径与吡咯和噻吩衍生物26和27形成鲜明对比的是，质谱仪中的P involvesC涉及PC环内键裂解和CO的损失。这些事实妨碍强2 p π -3 p π在磷杂核电子离域。

  DOI：

  10.1016/0040-4020(76)87022-6

文献信息

• Use of tertiary phosphines in photographic silver dye bleach materials
  申请人：Ciba-Geigy AG

  公开号：US04357280A1

  公开（公告）日：1982-11-02

  A method of processing photographic silver dye bleach materials which have been exposed imagewise is provided. The process steps are (1) silver developing, (2) dye bleaching, (3) silver bleaching and (4) fixing. The treatment baths for the process steps (2), (3) and (4), or the combined treatment baths useful for process step (3) with at least one the process steps (2) or (4) contain water-soluble tertiary phosphines as silver ligands. These phosphines effect an acceleration of the dye and silver bleaching and they are further suitable stabilizers and optionally antioxidants which yield stable treatment baths.

  提供了一种处理已按图像曝光的摄影银染料漂白材料的方法。工艺步骤为：(1)银显影，(2)染料漂白，(3)银漂白和(4)定影。工艺步骤(2)、(3)和(4)的处理浴，或用于工艺步骤(3)与至少一个工艺步骤(2)或(4)的组合处理浴中含有作为银配体的水溶性三级磷化氢。这些磷化氢加速染料和银漂白，并且它们是进一步的稳定剂和可选的抗氧化剂，产生稳定的处理浴。
• [EN] NOVEL ZWITTERIONIC FLUORESCENT DYES FOR LABELING IN PROTEOMIC AND OTHER BIOLOGICAL ANALYSES<br/>[FR] NOUVEAUX COLORANTS ZWITTERIONIQUES FLUORESCENTS POUR LE MARQUAGE EN PROTEOMIQUE ET AUTRES ANALYSES BIOLOGIQUES
  申请人：UNIV MONTANA STATE

  公开号：WO2004009598A1

  公开（公告）日：2004-01-29

  The invention relates to compositions and methods useful in the labeling and identification of proteins. The invention provides for highly soluble zwitterionic dye molecules where the dyes and associated side groups are non-titratable and maintain their net zwitterionic character over a broad pH range, e.g. between pH 3 and 12. These dye molecules find utility in a variety of applications, including use in the field of proteomics.

  本发明涉及用于蛋白质标记和鉴定的有用的组合物和方法。本发明提供了一种高度可溶的两性离子染料分子，其中染料和相关侧链不具可滴定性，在广泛的pH范围内保持其净两性离子特性，例如在pH 3到12之间。这些染料分子在多种应用中具有实用价值，包括在蛋白质组学领域的使用。
• Photocatalytic properties of new cyclopentadienyl and indenyl rhodium(I) carbonyl complexes with water-soluble 1,3,5-triaza-7-phosphaadamantane (PTA) and tris(2-cyanoethyl)phosphine
  作者：Piotr Smoleński

  DOI：10.1016/j.jorganchem.2011.08.046

  日期：2011.12

  Reactions of [(η5-R)Rh(CO)2] (R = cp, ind) with water-soluble phosphines (L = 1,3,5-triaza-7-phosphaadamantane and tris(2-cyanoethyl)phosphine) give the new rhodium(I) complexes of the types [Rh(η5-cp)(CO)(PTA)] (1), [Rh(η5-cp)(CO)(P(CH2CH2CN)3)] (2), [Rh(η5-ind)(CO)(PTA)] (3) and [Rh(η5-ind)(CO)(P(CH2CH2CN)3)] (4) in isolated yields of 52–75%. All these compounds have been fully characterized by IR

  [（反应的η 5 -R）的Rh（CO）2用水溶性膦（L = 1,3,5三氮杂-7-磷和三（2-氰乙基）膦）]（R =厘泊，IND）得到类型的新铑（I）配合物的[Rh（η 5 -cp）（CO）（PTA）]（1），铑[Rh（η 5 -cp）（CO）（P（CH 2 CH 2 CN）3）]（2），的[Rh（η 5 -IND）（CO）（PTA）]（3）和铑[Rh（η 5 -IND）（CO）（P（CH 2 CH 2 CN）3 ]）（4）的孤立收益率为52–75％。所有这些化合物已通过IR，1 H，31 P 1 H}和13 C 1 H} NMR，FAB-MS光谱学和元素分析充分表征。反应磷化氢的取代是越大[（η 5 -IND）的Rh（CO）（L）]进行比较来[（η 5因为的茚基配体与灵活性-cp）的Rh（CO）（L）]容易进行η 5 - η 3配位异构化。所获得的络合物是在没有任何有机氢转移受体
• Preparation, Crystal Structures, and Behavior in Solution of Cobalt(III) Complexes Containing 2-Cyanoethylphosphines: <i>trans</i>-[Co(Me₂dtc)₂{P(CH₂CH₂CN)<i>_n</i>Ph₃₋<i>_n</i>}]BF₄ (<i>n</i> = 1–3; Me₂dtc⁻: <i>N</i>,<i>N</i>-Dimethyldithiocarbamate)
  作者：Keiko Kihara、Takayoshi Suzuki、Masakazu Kita、Yukinari Sunatsuki、Masaaki Kojima、Hideo D. Takagi

  DOI：10.1246/bcsj.20120148

  日期：2012.10.15

  A series of cobalt(III) complexes containing 2-cyanoethylphosphines, [Co(Me2dtc)2P(CH2CH2CN)nPh3−n}2]BF4 Me2dtc−: N,N-dimethyldithiocarbamate; n = 1 (1), 2 (2), and 3 (3)} have been prepared, and their molecular structures in the crystals and in solution have been characterized. X-ray analysis revealed that all complexes isolated as single-crystals were the trans-isomers. The Co–P bond lengths for the 2-cyanoethylphosphines in complexes 1–3 are almost invariant to the number of 2-cyanoethyl substituent groups. Unlike related complexes with other monodentate P-donor ligands, complexes 1–3 in solution showed dissociation and isomerization equilibriums, which were achieved immediately after dissolving the crystals. These characteristic features of the complexes would result from the weak σ-donor and π-acceptor abilities of 2-cyanoethylphosphines. Furthermore, mixing of complex 1 and NaN3 in acetonitrile gave cis-[Co(Me2dtc)2(N3)P(CH2CH2CN)Ph2}] quantitatively, and refluxing the mixture resulted in the phosphine–tetrazolate complex, [Co(Me2dtc)2(Ph2PCH2CH2CN4-κ2P,N1)] (4).

  制备了一系列含有2-氰乙基膦的钴(III)配合物[Co(Me2dtc)2P(CH2CH2CN)nPh3−n}2]BF4Me2dtc−：N,N-二甲基二硫代氨基甲酸酯；n=1(1)，2(2)和3(3)}，并对其晶体和溶液中的分子结构进行了表征。X射线分析表明，所有分离出的单晶配合物均为反式异构体。配合物1-3中2-氰乙基膦的Co–P键长度几乎不受2-氰乙基取代基数量的影响。与含有其他单齿P供体配体的相关配合物不同，溶液中的配合物1-3显示了解离和异构化平衡，这些平衡在晶体溶解后立即实现。这些配合物的特性可能是由于2-氰乙基膦的弱σ供体和π受体能力所致。此外，将配合物1与NaN3在乙腈中混合得到了定量的顺式-[Co(Me2dtc)2(N3)P(CH2CH2CN)Ph2}]，将混合物回流得到了膦-四唑配合物[Co(Me2dtc)2(Ph2PCH2CH2CN4-κ2P,N1)](4)。
• Dual Radical/Polar Pudovik Reaction:  Application Field of New Activation Methods
  作者：Delphine Semenzin、Guita Etemad-Moghadam、Dominique Albouy、Ousmane Diallo、Max Koenig

  DOI：10.1021/jo9622441

  日期：1997.4.1

  The Pudovik reaction (addition of organophosphorus compounds containing a labile P-H bond with alkenes and alkynes) can progess via a radical or (and) ionic mechanism. A comparative and systematic study including various reagents and different activation methods (heating, photochemical or ultrasonic irradiation, and dry medium supported reactions) is presented. Photolysis is the most efficient method

  Pudovik反应（含有不稳定的PH键的有机磷化合物与烯烃和炔烃的加成反应）可通过自由基或（和）离子机理进行。进行了比较和系统的研究，包括各种试剂和不同的激活方法（加热，光化学或超声辐射以及干燥介质支持的反应）。光解是用于自由基过程的最有效方法，但是在一些示例中，超声波辐照可能更合适，因为反应时间更短并且超声波不会引起副反应（特别是Z / E异构化）。在碱性固体载体上的干介质工艺是最佳的阴离子活化（产率，时间，选择性，纯化设备）。超声波由于其机械作用，在这些基本条件下，与传统的热方法相比，可以提高产量。无论对于膦反应性的不饱和底物，所有激活方法都是有效的，而适当的激活方法仅由对硫代膦（或氧化膦）反应性的不饱和体系的性质决定。