diethyl ester of 2-methylvinylphosphonic acid | 5954-65-4

• 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
• 英文名称: diethyl ester of 2-methylvinylphosphonic acid
• 英文别名: propenylphosphonate de diethyle；diethyl 1-propenylphosphonate；diethyl 2-butenylphosphonate；Propenyl-phosphonsaeure-diethylester；1-Propenphosphonsaeure-diethylester；Allyl-phosphonsaeure-diethylester；1-Diethoxyphosphorylprop-1-ene
• CAS: 5954-65-4
• 化学式: C₇H₁₅O₃P
• 分子量: 178.168
• InChiKey: VBHYLCOEVPIQKH-UHFFFAOYSA-N

物化性质

• 沸点：
  46 °C0.35 mm Hg(lit.)
• 闪点：
  224 °F
• 稳定性/保质期：
  在常温常压下，该物质是稳定的。

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 安全说明：
  S26,S36
• 储存条件：
  常温下应存放在避光、阴凉干燥处，并密封保存。

SDS

Name:	Diethyl(2-Propenyl)Phosphonate Material Safety Data Sheet
Synonym:	None Known
CAS:	5954-65-4

Section 1 - Chemical Product MSDS Name:Diethyl(2-Propenyl)Phosphonate Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5954-65-4	Diethyl(2-Propenyl)Phosphonate	ca. 100	unlisted

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. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately 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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. 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. Do NOT use mouth-to-mouth resuscitation.
Notes to Physician:
Treat symptomatically and supportively.

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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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Runoff from fire control or dilution water may cause pollution.
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. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
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:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 5954-65-4: 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: Liquid
Color: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 51 deg C @ .03mm Hg
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: C7H15O3P
Molecular Weight: 178.077

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, excess heat.
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# 5954-65-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Diethyl(2-Propenyl)Phosphonate - 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# 5954-65-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5954-65-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5954-65-4 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：

  diethyl ester of 2-methylvinylphosphonic acid 在 palladium dichloride 盐酸 、 水 、 氧气 作用下， 反应 20.0h， 以80%的产率得到丙酮基膦酸二乙酯
  参考文献：
  名称：

  Sturtz, Georges; Pondaven-Raphalen, Annick, Journal of Chemical Research, Miniprint, 1980, # 5, p. 2512 - 2523

  摘要：

  DOI：
• 作为产物：
  描述：

  乙基磷酸二乙酯 在 selenium 、 正丁基锂 、 双氧水 作用下， 以 吡啶 为溶剂， 生成 diethyl ester of 2-methylvinylphosphonic acid
  参考文献：
  名称：

  将元素硒添加到膦酸碳负离子中-这是合成乙烯基膦酸酯的关键步骤。1,4-二羰基体系的一种新的合成方法。

  摘要：

  描述了一种方便的乙烯基膦酸酯的合成方法，该方法包括将元素硒添加到膦酸酯碳负离子中，然后进行烷基化和亚硒酸酯消除。还报道了基于α-甲基硫代乙烯基膦酸二乙酯的1，4-二羰基体系的一般方法。

  DOI：

  10.1016/s0040-4039(01)81837-2

文献信息

• New selectivities from old catalysts. Occlusion of Grubbs’ catalysts in PDMS to change their reactions
  作者：M. Brett Runge、Martin T. Mwangi、Ned B. Bowden

  DOI：10.1016/j.jorganchem.2006.09.022

  日期：2006.12

  dissolved in methylene chloride also react by olefin isomerization with occluded catalysts. Eleven examples of substrates that exhibit dual reactivity by undergoing olefin isomerization with occluded catalysts and olefin metathesis with catalysts dissolved in methylene chloride are reported. Most of these substrates have olefins with allylic phosphine oxides, carbonyls, or ethers. Control experiments demonstrate

  本文介绍了Grubbs第一代和第二代催化剂在聚二甲基硅氧烷（PDMS）的疏水性基质中被吸附时的新选择性。通过用二氯甲烷溶胀，然后在真空下除去溶剂，可将催化剂封闭在毫米大小的PDMS平板中。催化剂均相溶解在PDMS中，但仍保持催化活性。许多通过烯烃复分解反应与自由溶解在二氯甲烷中的Grubbs催化剂反应的底物也通过烯烃异构化与封闭的催化剂反应。报道了通过封闭的催化剂进行烯烃异构化和用溶解在二氯甲烷中的催化剂进行烯烃复分解而表现出双重反应性的底物的十一个实例。这些底物中的大多数具有带有烯丙基氧化膦，羰基或醚的烯烃。对照实验表明，通过催化剂从钌卡宾分解为拟议的氢化钌，溶剂中发生了异构化。通过将封闭的Grubbs的第一代催化剂在90％的MeOH / H中加热至100°C来扩展这项工作在各种烯烃的存在下将2 O转化为用于未官能化烯烃的Grubbs催化剂转化为异构化催化剂。这项工作表明，PDMS中有机
• Stereochemical Assignment of the Protein-Protein Interaction Inhibitor JBIR-22 by Total Synthesis
  作者：Alan R. Healy、Miho Izumikawa、Alexandra M. Z. Slawin、Kazuo Shin-ya、Nicholas J. Westwood

  DOI：10.1002/anie.201411141

  日期：2015.3.23

  activity associated with a subfamily of the tetramic acid class of natural products. Despite the fact that members of this subfamily act as protein–protein interaction inhibitors that are of relevance to proteasome assembly, no synthetic work has been reported. This may be due to the fact that this subfamily contains an unnatural 4,4‐disubstitued glutamic acid, the synthesis of which provides a key challenge

  最近的报告强调了与特特拉姆酸类天然产物的一个亚科相关的生物活性。尽管该亚家族的成员充当与蛋白酶体组装相关的蛋白质-蛋白质相互作用抑制剂，但尚未报道合成工作。这可能是因为该亚家族含有非天然的 4,4-二取代谷氨酸，其合成提出了关键挑战。这种非天然氨基酸的掩蔽形式的高度立体选择性途径现在能够合成 JBIR-22 的两种可能的非对映体，并允许指定其相对和绝对立体化学。
• Amberlyst-15 catalyzed synthesis of alkyl/aryl/heterocyclic phosphonates
  作者：U.M. Rao Kunda、V.N. Reddy Mudumala、C.S. Reddy Gangireddy、B.R. Nemallapudi、K.N. Sandip、S.R. Cirandur

  DOI：10.1016/j.cclet.2011.01.033

  日期：2011.8

  A novel and efficient procedure for the synthesis of alkyl phosphonates through one pot condensation of alkyl halide and tri alkyl/aryl phosphite in the presence of amberlyst-15 as catalyst under solvent free conditions was applied. It demonstrated several advantages such as good yields of products, simple operation, convenient separation and inexpensive catalyst.

  在无溶剂条件下，采用琥珀酰-15作为催化剂，通过烷基卤化物和亚磷酸三烷基酯/亚芳基酯的一锅缩合，合成了一种新颖而有效的合成膦酸烷基酯的方法。它显示出许多优点，例如产物的产率高，操作简单，分离方便和催化剂便宜。
• Synthesis of α-Aminophosphonates by Umpolung-Enabled Cu-Catalyzed Regioselective Hydroamination
  作者：Shogo Nakamura、Soshi Nishino、Koji Hirano

  DOI：10.1021/acs.joc.2c02632

  日期：2023.1.20

  A copper-catalyzed regioselective hydroamination of α,β-unsaturated phosphonates has been developed to form corresponding α-aminophosphonates of interest in medicinal chemistry. The introduction of an umpolung, electrophilic amination strategy with the hydroxylamine derivative is the key to achieving the α-amination regioselectivity, which is otherwise difficult under the conventional nucleophilic

  已经开发了铜催化的 α,β-不饱和膦酸酯的区域选择性加氢胺化，以形成药物化学中感兴趣的相应 α-氨基膦酸酯。使用羟胺衍生物引入 umpolung 亲电胺化策略是实现 α-胺化区域选择性的关键，否则这在使用母胺的常规亲核加氢胺化条件下很难实现。还描述了使用手性双膦配体的不对称合成以及在相关甲硅烷基化反应中的应用。
• Horner,L. et al., Chemische Berichte, 1970, vol. 103, p. 2718 - 2728
  作者：Horner,L. et al.

  DOI：——

  日期：——