4-膦酰丁烯酸三乙脂 | 20345-62-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 4-膦酰丁烯酸三乙脂
• 英文名称: triethyl 2-phosphono-2-butenoate
• 英文别名: triethyl 2-phosphonobut-2-enoate；1-Aethoxycarbonyl-propen-(1)-yl-phosphonsaeure-diaethylester；Ethyl 2-(diethoxyphosphinyl)but-2-enoate；ethyl 2-diethoxyphosphorylbut-2-enoate
• CAS: 20345-62-4
• 化学式: C₁₀H₁₉O₅P
• mdl: MFCD02258982
• 分子量: 250.232
• InChiKey: LKGVVQTVNFFWAT-UHFFFAOYSA-N

物化性质

• 沸点：
  133-135°C 0,4mm
• 密度：
  1,13 g/cm3
• 闪点：
  >110°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2931900090
• 安全说明：
  S24/25

SDS

Name:	Triethyl 4-Phosphonocrotonate 92% Predominantly Trans Material Safety Data Sheet
Synonym:	None known
CAS:	20345-62-4

Section 1 - Chemical Product MSDS Name:Triethyl 4-Phosphonocrotonate 92% Predominantly Trans Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
20345-62-4	Triethyl 4-Phosphonocrotonate	92	243-748-5

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. 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.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Use water spray to keep fire-exposed containers cool. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Containers may explode when heated.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Cool containers with flooding quantities of water until well after fire is out. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Remove all sources of ignition. Absorb spill using an absorbent, non-combustible material such as earth, sand, or vermiculite. Do not use combustible materials such as sawdust.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Keep away from heat, sparks and flame. Avoid ingestion and inhalation.
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# 20345-62-4: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear slightly yellow
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 135 deg C @ .40mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: > 112 deg C (> 233.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.1280g/cm3
Molecular Formula: C10H19O5P
Molecular Weight: 250.23

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, ignition sources, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of phosphorus, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 20345-62-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Triethyl 4-Phosphonocrotonate - 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.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 20345-62-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 20345-62-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 20345-62-4 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：

  4-膦酰丁烯酸三乙脂 、 亚甲基环己烷 在 二氯乙基铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 以52%的产率得到ethyl 4-(cyclohexen-1-yl)-2-diethoxyphosphoryl-3-methylbutanoate
  参考文献：
  名称：

  Ene reactions of 2-phosphonoacrylates

  摘要：

  DOI：

  10.1021/jo00169a013
• 作为产物：
  描述：

  2-膦酰丁酸三乙脂 在 苯基氯化硒 、 sodium hydride 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4-膦酰丁烯酸三乙脂
  参考文献：
  名称：

  Lewis酸介导的2-Phosphoo-2-alkenoates的Diels-Alder反应的研究。还原性加成产物烷基化在（±）-α-Alasken-8-全合成中的应用

  摘要：

  路易斯酸介导的三种2-膦酰基-2-链烷酸酯的Diels-Alder反应，包括2-膦酰基丙烯酸三乙酯（1），2-膦酰基丁-2-烯酸三乙酯（2）和2-（二乙氧基膦酰基）-3-甲基丁酯-乙基已经研究了2-烯酸酯（3）。在测试的几种路易斯酸中，氯化锡（IV）被证明对增强1与富电子二烯的反应的区域和立体选择性最有效，从而导致形成单一的区域和/或立体异构体丰产。带有β甲基的2的反应性比1的低得多，而3的反应性低。在研究条件下完全没有反应。在整个研究过程中，我们发现在高温下使用氯化锌可以有效地诱导2的环加成，尤其是Z-异构体的环加成。此外，将萘二甲酸锂（LN）诱导的还原烷基化过程应用于所得的Diels-Alder加合物4，以使季碳中心的膦酰基被各种烷基取代，从而得到烷基取代的酯12，因此几乎转向1和2转化为通常显示较差的狄尔斯-阿尔德反应性的相应的2-链烷酸2-烷基酯的有用合成等价物。该组合操作的应用促

  DOI：

  10.1021/jo9017292

文献信息

• Ene reactions of 2-phosphonoacrylates
  作者：Barry B. Snider、Gary B. Phillips

  DOI：10.1021/jo00169a013

  日期：1983.10
• Investigation on Lewis Acid Mediated Diels−Alder Reactions of 2-Phosphono-2-alkenoates. Application to Total Synthesis of (±)-α-Alasken-8-one via Reductive Alkylation of Resulting Adduct
  作者：Chuan-Cheng Liao、Jia-Liang Zhu

  DOI：10.1021/jo9017292

  日期：2009.10.16

  -enoate (3) have been investigated. Of several Lewis acids tested, tin(IV) chloride was shown to be the most effective at enhancing the regio- and stereoselectivity of the reactions of 1 with the electron-rich dienes to result in the formation of the single regio- and/or stereoisomers in good yields. Bearing the β methyl group(s), 2 displayed much less reactivity than 1 while 3 was completely unreactive

  路易斯酸介导的三种2-膦酰基-2-链烷酸酯的Diels-Alder反应，包括2-膦酰基丙烯酸三乙酯（1），2-膦酰基丁-2-烯酸三乙酯（2）和2-（二乙氧基膦酰基）-3-甲基丁酯-乙基已经研究了2-烯酸酯（3）。在测试的几种路易斯酸中，氯化锡（IV）被证明对增强1与富电子二烯的反应的区域和立体选择性最有效，从而导致形成单一的区域和/或立体异构体丰产。带有β甲基的2的反应性比1的低得多，而3的反应性低。在研究条件下完全没有反应。在整个研究过程中，我们发现在高温下使用氯化锌可以有效地诱导2的环加成，尤其是Z-异构体的环加成。此外，将萘二甲酸锂（LN）诱导的还原烷基化过程应用于所得的Diels-Alder加合物4，以使季碳中心的膦酰基被各种烷基取代，从而得到烷基取代的酯12，因此几乎转向1和2转化为通常显示较差的狄尔斯-阿尔德反应性的相应的2-链烷酸2-烷基酯的有用合成等价物。该组合操作的应用促