亚乙基二磷酸四乙酯 | 995-32-4

• 物质功能分类: 化学试剂 - 有机试剂 - 膦酸酯/膦酸盐
• 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: 亚乙基二磷酸四乙酯
• 英文名称: tetraethyl ethylenebis(phosphonate)
• 英文别名: tetraethyl ethylenediphosphonate；1,2-bis(diethoxyphosphoryl)ethane
• CAS: 995-32-4
• 化学式: C₁₀H₂₄O₆P₂
• mdl: MFCD00015133
• 分子量: 302.244
• InChiKey: RSQYXXACEZCDFS-UHFFFAOYSA-N

物化性质

• 沸点：
  200-202 °C14 mm Hg(lit.)
• 密度：
  1.146 g/mL at 25 °C(lit.)
• 闪点：
  >110°C
• 溶解度：
  可溶于乙腈（少量）、氯仿（少量）
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2915900090
• 危险性防范说明：
  P264,P280,P302+P352+P332+P313+P362+P364,P305+P351+P338+P337+P313
• 危险性描述：
  H315,H319
• 储存条件：
  请将容器密封保存，并存放在阴凉、干燥处。

SDS

Name:	Tetraethyl ethylenediphosphonate 95% Material Safety Data Sheet
Synonym:
CAS:	995-32-4

Section 1 - Chemical Product MSDS Name:Tetraethyl ethylenediphosphonate 95% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
995-32-4	Tetraethyl ethylenediphosphonate	95%	213-625-0

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.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation.
Chronic:
Not available.

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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.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
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 water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 995-32-4: Personal Protective Equipment Eyes: Not available.
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: Granules
Color: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 200 - 202 deg C @ 1
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: > 110 deg C (> 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.1460g/cm3
Molecular Formula: [-CH2P(O)(OC2H5)2]2
Molecular Weight: 302.25

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of phosphorus, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 995-32-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Tetraethyl ethylenediphosphonate - 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 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 995-32-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 995-32-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 995-32-4 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：

  亚乙基二磷酸四乙酯 在 盐酸 、 水 作用下， 以5.8 g的产率得到1,2-乙烯基二膦酸
  参考文献：
  名称：

  Flexible Diphosphonic Acids for the Isolation of Uranyl Hybrids with Heterometallic U^VI═O—Zn^II Cation–Cation Interactions

  摘要：

  A family of uranyl diphosphonates have been hydrothermally synthesized using various flexible diphosphonic acids and Zn(UO2)(OAc)(4)center dot 7H(2)O in the presence of bipy or phen. Single-crystal X-ray analyses indicate that these compounds represent the first examples of uranyl phosphonates with heterometallic U-VI=O-Zn-II cation cation interactions.

  DOI：

  10.1021/ic4009834
• 作为产物：
  描述：

  (甲酰基甲基)磷酸二乙酯 在 镍 氢气 、 sodium amide 、 三乙胺 作用下， 以 乙醇 、 氨 为溶剂， 反应 3.0h， 生成 亚乙基二磷酸四乙酯
  参考文献：
  名称：

  Tavs,P., Chemische Berichte, 1967, vol. 100, p. 1571 - 1574

  摘要：

  DOI：

文献信息

• [EN] NUCLEOSIDE PHOSPHONATE DERIVATIVES USEFUL IN THE TREATMENT OF HIV INFECTIONS<br/>[FR] DERIVES DE NUCLEOSIDE PHOSPHONATE UTILES DANS LE TRAITEMENT D'INFECTIONS VIH
  申请人：ANADYS PHARMACEUTICALS INC

  公开号：WO2005079812A1

  公开（公告）日：2005-09-01

  The present invention relates to a method of treating HIV infections by administering a nucleoside phosphonate derivative represented by formula (I).

  本发明涉及通过给予由式(I)表示的核苷酸膦酸衍生物来治疗HIV感染的方法。
• 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。
• Iodine atom transfer addition reaction of 1-iodoalkyl phosphonates to alkenes in the presence of α,α′-azoisobutyronitrile (AIBN): mechanistic aspects
  作者：Piotr Bałczewski、Marian Mikołajczyk

  DOI：10.1039/b005882n

  日期：——

  this work were to elucidate the mechanistic pathway of the title reaction, which constitutes the first example of a radical iodine atom transfer addition reaction of non-fluorine-containing phosphonates, and to determine whether 2-iodo-2-methylpropionitrile, 8, can serve as a competing iodine donor with the starting diethyl 1-iodoalkyl phosphonates, 1a,b. The title reaction was found to proceed with AIBN

  这项工作的目的是阐明标题反应的机理途径，该机理构成了不含氟的膦酸酯的自由基碘原子转移加成反应的第一个实例，并确定2-碘-2-甲基丙腈是否8可以与1-碘烷基膦酸二乙酯1a，b一起作为竞争的碘供体。发现标题反应是使用AIBN作为唯一的自由基引发剂进行的，不需要有毒的锡试剂作为助引发剂，并生成3-碘烷基膦酸二乙酯3a – e（繁殖步骤的最终产物，分离出的产率为59–95％ ），丁二酸琥珀酯，9，甲基膦酸二乙酯4，亚乙基双膦酸四乙酯 5（所有终止产物，产率0-10％）。使用TEMPO作为自由基陷阱证明了该反应的自由基特性。与AIBN和碘独立合成的8（引发步骤的中间体）在添加到反应混合物中时完全抑制了反应，表明它在转移阶段不作为碘供体，而是作为抑制剂。
• ESTERIFICATION OF PHOSPHONIC AND PHOSPHINIC ACID ANALOGUES OF GLUTAMIC AND ASPARTIC ACIDS WITH ETHYL ORTHOFORMATE-SCOPE AND LIMITATIONS OF THE METHOD
  作者：Ewa Żymańczyk-Duda、Barbara Lejczak、Paweł Kafarski

  DOI：10.1080/10426509608046348

  日期：1996.5.1

  Abstract Reaction of C-ethyl esters of phosphonic- and phosphinic acid analogues of glutamic and aspartic acids with ethyl orthoformate provides the mixtures of N-formylamino- and N-ethoxymethyleneimino-derivatives with nearly quantitative yields. Scope and limitations of this procedure were studied by means of GC/MS technique.

  摘要 谷氨酸和天冬氨酸的膦酸和次膦酸类似物的 C-乙酯与原甲酸乙酯的反应提供了 N-甲酰氨基和 N-乙氧基亚甲基亚氨基衍生物的混合物，收率几乎是定量的。该程序的范围和局限性通过 GC/MS 技术进行了研究。
• Organische Phosphorverbindungen XVII. Darstellung von Alkylen-bis-phosphonsäurechloriden und Alkylen-bis-thiophosphonsäurechloriden und deren Reaktion mit G<scp>RIGNARD</scp>-Verbindungen
  作者：Ludwig Maier

  DOI：10.1002/hlca.19650480114

  日期：——

  The synthesis and some physical properties of alkylene bis-(phosphonic dichlorides), Cl2P(O)(CH2)n(O)PCl2, and of alkylene bis-(phosphonothioic dichlorides), Cl2P(S)(CH2)n(S)PCl2, a new class of compounds, are reported. The reactions of alkylene bis-(phosphonothioic dichlorides) with GRIGNARD reagents and of CH3P(S)Br2 with di-GRIGNARD reagents are also described. Some physical properties of several

  亚烷基双-（膦酰二氯），Cl 2 P（O）（CH 2）n（O）PCl 2和亚烷基双-（硫代磷酸二氯），Cl 2 P（S）（CH）的合成及一些物理性质2）n（S）PCl 2是一种新型化合物。还描述了亚烷基双-（硫代硫代二氯化膦）与GRIGNARD试剂的反应以及CH 3 P（S）Br 2与di-GRIGNARD试剂的反应。已经确定了几种二膦二硫化物和两种环状叔膦硫化物的一些物理性质。