双（二乙氧基磷酰基）乙炔 | 4851-53-0

• 物质功能分类: 化学试剂 - 有机试剂 - 炔烃
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 中文名称: 双（二乙氧基磷酰基）乙炔
• 中文别名: 双(二乙氧基磷酰基)乙炔,99%
• 英文名称: tetraethyl ethynyldiphosphonate
• 英文别名: bis(diethoxyphosphoryl)acetylene；1,2-bis(diethoxyphosphoryl)ethyne
• CAS: 4851-53-0
• 化学式: C₁₀H₂₀O₆P₂
• 分子量: 298.213
• InChiKey: YWEHVMWRXBROHK-UHFFFAOYSA-N

物化性质

• 沸点：
  181.5-182.5(2.5mm)
• 密度：
  1.12

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

SDS

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Section 1: Product Identification
Chemical Name: Bis(diethoxyphosphoryl)acetylene, 99%
CAS Registry Number: 4851-53-0
Formula: C10H20O6P2
EINECS Number: none
Chemical Family: organophosphine ligand
Synonym: 1,2-Bis(diethoxyphosphinyl)ethyne; (Diethoxy-phosphorylethynyl)-phosphonic acid diethyl ester

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 4851-53-0 100% 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: Ingestion, inhalation
Eye Contact: Causes slight to mild 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 available 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 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 powder 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 fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unususal 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 under an inert atmosphere of nitrogen or argon. Keep in a cool, dry, well
Handling and Storage:
ventilated 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: yellow liquid
Molecular Weight: 298.21
Melting Point: no data
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: no data
Solubility in Water: insoluble

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SECTION 10: Stability and Reactivity
Stability: moisture sensitive
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: prolonged exposure to moisture
Incompatibility: water, oxidizing agents and halogens
Decomposition Products: carbon monoxide, carbon dioxide, phosphorus 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：

  双（二乙氧基磷酰基）乙炔 在 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以35%的产率得到diethyl ethynylphosphonate
  参考文献：
  名称：

  Acheson, R. Morrin; Ansell, Peter J.; Murray, Jane R., Journal of Chemical Research, Miniprint, 1986, # 10, p. 3001 - 3019

  摘要：

  DOI：
• 作为产物：
  描述：

  diethyl ethynylphosphonate 在 次氯酸叔丁酯 、 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 4.0h， 生成 双（二乙氧基磷酰基）乙炔
  参考文献：
  名称：

  Acheson, R. Morrin; Ansell, Peter J.; Murray, Jane R., Journal of Chemical Research, Miniprint, 1986, # 10, p. 3001 - 3019

  摘要：

  DOI：
• 作为试剂：
  描述：

  3,5-二甲基吡啶 、 乙醇 、 苦味酸 在 双（二乙氧基磷酰基）乙炔 作用下， 以 水 为溶剂， 生成 3,5-dimethyl-1-ethylpyridinium picrate
  参考文献：
  名称：

  Acheson, R. Morrin; Ansell, Peter J.; Murray, Jane R., Journal of Chemical Research, Miniprint, 1986, # 10, p. 3001 - 3019

  摘要：

  DOI：

文献信息

• Base-Promoted Heterocyclization of Fluorinated Alkynylphosphonates with Select ortho-Aminobenzonitriles
  作者：Blazej Duda、Sergey N. Tverdomed、Boris I. Ionin、Gerd-Volker Röschenthaler

  DOI：10.1002/ejoc.201200379

  日期：2012.7

  The heterocyclization reactions of CF2-containing alkynylphosphonates with 2-aminobenzonitriles to give 2,3-difunctionalized 4-aminoquinolines were investigated. The influence of the R1 and R2 substituents and CF2X groups on the synthetic efficiency and specificity is also disclosed.

  研究了含 CF2 的炔基膦酸酯与 2-氨基苯甲腈的杂环化反应，得到 2,3-双官能化的 4-氨基喹啉。还公开了 R1 和 R2 取代基和 CF2X 基团对合成效率和特异性的影响。
• Boron azides in Staudinger oxidations and cycloadditions
  作者：Rebecca L. Melen、Alan J. Lough、Douglas W. Stephan

  DOI：10.1039/c3dt50791b

  日期：——

  and a cycloaddition reaction has taken place. However, if the Staudinger reaction is prohibited via phosphine oxidation as in the case of (EtO)2P(O)CCP(O)(OEt)2 then the unusual dimeric product 4 [2-(C6F5)2B-4-(P(O)OEt2)-2H-1,2,3-triazole-5-P(O)(OEt)(OB(C6F5)2)] is generated. The structures of 1b–d, 2b–d, 3 and 4 have been determined by X-ray diffraction.

  Cy 2 BN 3与三取代膦的斯托丁格反应（R 3 P）产生了硼-氮-磷连接系统Cy 2 BN PR 3（分别为Et，t Bu，Cy，Ph）（分别为1a-1d）。类似地，（C 6 F 5）2 BN 3与膦P t Bu 3，PPh 3，Ph 2 PC CPh和Ph 2 PC CPPh 2的反应产生（C 6 F 5）2 BNPR 3（分别为2a–d）。相反，（C反应6 ˚F 5）2 BN 3的Ph 2 P-Ç Ç p -tol在过量的Me存在3的SiN 3，得到双环产物3 [1-（C 6 ˚F 5）2乙-4-（对甲苯基）-1 H -1,2,3-三唑-5-P（NH）Ph 2 ]，其中施陶丁格和环加成反应均已发生。但是，如果史陶丁格反应是通过以下方式禁止的（EtO）2 P（O）C CP（O）（OEt）2的情况下进行膦氧化，然后生成不寻常的二聚产物4 [2-（C 6 F 5）2 B-4-（P（O）OEt
• (η⁵-Cyclopentadienyl)(η⁴-di- and tetra-phosphorylcyclobutadiene)cobalt(<scp>i</scp>): Synthesis, structure, and formation of 1-D coordination polymer
  作者：Shigeru Sasaki、Yoshihiro Tanabe、Masaaki Yoshifuji

  DOI：10.1039/b204779a

  日期：——

  (η5-Cyclopentadienyl)(η4-di- and tetra-phosphorylcyclobutadiene)cobalt(I) complexes were synthesized by the reaction of mono- and diphosphorylacetylenes with CpCo(CO)2, respectively. The tetraphosphoryl derivative has proved to work as a bis-bidentate ligand affording a one-dimensional coordination polymer with Ce(III).

  (η5-环戊二烯基)(η4-二磷酸酯和四磷酸酯环丁烯)钴(I)络合物是通过单磷酸乙炔和双磷酸乙炔与CpCo(CO)2反应合成的。四磷酸酯衍生物已被证明作为双二齿配体，与Ce(III)形成一维配位聚合物。
• Fluorinated Alkynylphosphonates in<i>C</i>,<i>C</i>-Cyclizations: Regioselective Formation of Polysubstituted Fluorinated Arylphosphonates
  作者：Blazej Duda、Sergey N. Tverdomed、Boris I. Ionin、Gerd-Volker Röschenthaler

  DOI：10.1002/ejoc.201402188

  日期：2014.6

  The regioselective C,C-cyclization of selected 1,4-bipolar substrates with fluorinated alkynylphosphonates provided polysubstituted benzenes and naphthalenes in up to 98 % yield. For the case in which tetraethyl ethynylbisphosphonate was used, an unexpected phosphonate–phosphoramidate rearrangement was, for the first time, observed, which occurred in excellent yield.

  选定的 1,4-双极底物与氟化炔基膦酸酯的区域选择性 C,C-环化以高达 98% 的产率提供多取代苯和萘。对于使用乙炔基双膦酸四乙酯的情况，首次观察到意外的膦酸-氨基磷酸酯重排，其产率非常好。
• Reaction of Malonic Acid Derivatives with Acetylenic Diphosphonates
  作者：A. Shekhadeh、N. G. Didkovskii、A. V. Dogadina、B. I. Ionin

  DOI：10.1007/s11176-005-0163-8

  日期：2005.1

  The primary addition products in the reactions of malonic esters, cyanoacetic esters, and malononitrile with acetylenediphosphonates in acetonitrile in the presence of anhydrous potassium carbonate are potassium derivatives, viz. esters and nitriles of the corresponding 2-alkoxycarbonyl(or 2-cyano) -3,4-bis(di-alkoxyphosphinoyl)-2-potassiobut-3-enoic acid. Further hydrogen replacement for potassium in the nitriles is accompanied by isomerization involving double-bond shift and geometry change. (E)- and (Z)-3,4-bis(dial-koxyphosphinoyl)-2-cyano-2-potassiobut-3-enenitriles (the alkoxy groups are CH3O and C2H5O) are crystalline compounds; they were isolated and characterized.

  在无水碳酸钾存在下，丙二酸酯、氰基乙酸酯和丙二腈与乙炔二磷酸酯在乙腈中的反应的主要加成产物是钾的衍生物，即相应的2-烷氧羧酸（或2-氰基）-3,4-双（二烷氧基膦酰基）-2-钾基丁-3-烯酸的酯和腈。在腈中对钾的进一步氢取代伴随着双键迁移和几何构型变化的异构化。（E）-和（Z）-3,4-双（烷氧基膦酰基）-2-氰基-2-钾基丁-3-烯腈（烷氧基为 CH3O 和 C2H5O）为结晶化合物；它们已被分离和表征。