双(2-氰基乙基)苯基膦 | 15909-92-9

• 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: 双(2-氰基乙基)苯基膦
• 英文名称: bis(2-cyanoethyl)phenylphosphine
• 英文别名: Bis(2-cyanoethyl)phenylphosphin；3-[2-cyanoethyl(phenyl)phosphanyl]propanenitrile
• CAS: 15909-92-9
• 化学式: C₁₂H₁₃N₂P
• mdl: MFCD00013827
• 分子量: 216.222
• InChiKey: LIYGDNBFEBKBBZ-UHFFFAOYSA-N

物化性质

• 熔点：
  72-73°C
• 沸点：
  176-178°C 0,5mm
• 密度：
  1.1043 g/cm3
• 闪点：
  176-178°C/0.5mm
• 稳定性/保质期：

  常温常压下稳定，避免与氧化物、空气及卤素接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  6.1
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R20/21/22,R36/37/38
• 危险品运输编号：
  UN 3439
• 海关编码：
  2926909090
• 包装等级：
  III
• 危险类别：
  6.1
• 储存条件：
  常温下应密闭避光保存，并保持通风和干燥。

SDS

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Section 1: Product Identification
Chemical Name: Bis(2-cyanoethyl)phenylphosphine, min. 97%
CAS Registry Number: 15909-92-9
Formula: (NCCH2CH2)2(C6H5)P
EINECS Number: none
Chemical Family: organophosphorus ligand
Synonym: None

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title Compound 15909-92-9 100% 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 mild to severe 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 information on the physiological effects of ingestion.
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. Prolonged exposure to air may
Handling and Storage:
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: colorless xtl.
Molecular Weight: 216.22
Melting Point: 72-73°
Boiling Point: 176-178°C/0.5 mm
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 and halogens
Decomposition Products: carbon dioxide, carbon monoxide, phosphorus pentoxide, 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 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：

  双(2-氰基乙基)苯基膦 在 aluminum oxide 盐酸 、 lithium aluminium tetrahydride 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 1-phenyl-1,2,3,6-tetrahydro-phosphinine
  参考文献：
  名称：

  Mathey,F.; Muller,G., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1969, vol. 269, p. 158 - 161

  摘要：

  DOI：
• 作为产物：
  描述：

  丙烯腈 、 苯基膦 在 氢氧化钾 作用下， 以 乙腈 为溶剂， 以82%的产率得到双(2-氰基乙基)苯基膦
  参考文献：
  名称：

  水性Heck反应中含阳离子胍官能团的膦配体的合成与研究。

  摘要：

  首次制备了具有强碱性和亲水性胍鎓官能团的膦2和3。这些配体与乙酸钯组合形成促进水性Heck反应的活性催化剂。

  DOI：

  10.1016/0040-4020(94)01101-5

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。
• 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)。
• 一种在空气氛围中具有高磷光量子产率的AuCu
  申请人：安徽医科大学

  公开号：CN112110955B

  公开（公告）日：2023-05-30

  本发明公开了一种在空气氛围中具有高磷光量子产率的AuCu14纳米团簇及其制备方法，其中AuCu14纳米团簇为混合配体保护的AuCu合金纳米团簇，包含1个Au原子、14个Cu原子、12个4‑叔丁基苯硫酚配体以及6个双(2‑氰基乙基)苯基膦配体组成，外围并配有一个SbF6‑反离子；所述AuCu14纳米团簇的精确结构中含有一个Au原子内核和8个Cu(I)原子组成的金属笼。该团簇在室温下，空气氛围中具有较高的磷光发光性能，其相对量子产率为71.35％。未来该团簇有望被设计用于LED、高分辨荧光纳米探针和防伪等实际应用领域。
• A Commercially Available Ruthenium Compound for Catalytic Hydrophosphination
  作者：Michael P. Cibuzar、Steven G. Dannenberg、Rory Waterman

  DOI：10.1002/ijch.201900070

  日期：2020.3

  available ruthenium compound, bis(cyclopentadienylruthenium dicarbonyl) dimer ([CpRu(CO)2]2), was explored. Styrene derivatives or Michael acceptors react readily with either primary or secondary phosphines in the presence of 0.1 mol % of [CpRu(CO)2]2 under photolysis with an inexpensive and commercially available UV/A 9 W lamp. In comparison to related photoactivated hydrophosphination reactions with [CpFe(CO)2]2

  探索了用市售钌化合物双（环戊二烯基钌二羰基）二聚体（[CpRu（CO）2 ] 2）进行的磷酸化。苯乙烯衍生物或迈克尔受体在0.1摩尔％[CpRu（CO）2 ] 2的存在下，可通过廉价和可商购的UV / A 9 W灯与伯或仲膦容易地反应。与以[CpFe（CO）2 ] 2为催化剂的相关光活化加氢磷酸化反应相比，这些钌催化的反应以相对较高的速率进行，且催化剂负载量较低。
• [EN] METHOD FOR PRODUCING AMIDINE DERIVATIVES<br/>[FR] PROCÉDÉ DE PRODUCTION DE DÉRIVÉS D'AMIDINE
  申请人：BIOCRYST PHARM INC

  公开号：WO2016029216A2

  公开（公告）日：2016-02-25

  The invention provides methods and intermediates useful in the synthesis of a compound of formula (I): or a pharmaceutically acceptable salt, solvate, ester or prodrug thereof; wherein the variables are as defined herein.

  本发明提供了用于合成式(I)化合物的方法和中间体，或其药学上可接受的盐、溶剂和前药酯；其中变量如本文所定义。