二乙基(2-乙基氯)磷酸盐 | 10419-79-1

• 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: 二乙基(2-乙基氯)磷酸盐
• 英文名称: diethyl 2-chloroethylphosphonate
• 英文别名: diethyl (2-chloroethyl)phosphonate；diethyl chloroethylphosphonate；(2-chloro-ethyl)-phosphonic acid diethyl ester；2-Chlor-aethan-phosphonsaeure-(1)-diaethylester；(2-Chlor-aethyl)-phosphonsaeure-diaethylester；diethyl β-chloroethylphosphonate；1-chloro-2-diethoxyphosphorylethane
• CAS: 10419-79-1
• 化学式: C₆H₁₄ClO₃P
• mdl: MFCD00010358
• 分子量: 200.602
• InChiKey: GMDLEOVIACJWTD-UHFFFAOYSA-N

物化性质

• 沸点：
  92-94 °C (4 mmHg)
• 密度：
  1.15
• 闪点：
  98 °C
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：
  Xn
• 安全说明：
  S26,S37/39
• 危险类别码：
  R22,R36/37/38
• 海关编码：
  2931900090
• 储存条件：
  存放在阴凉干燥处即可。

SDS

Name:	Diethyl (2-Chloroethyl)phosphonate 95% Material Safety Data Sheet
Synonym:	(2-Chloroethyl)phosphonic Acid Diethyl Ester
CAS:	10419-79-1

Section 1 - Chemical Product MSDS Name:Diethyl (2-Chloroethyl)phosphonate 95% Material Safety Data Sheet
Synonym:(2-Chloroethyl)phosphonic Acid Diethyl Ester

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
10419-79-1	Diethyl (2-Chloroethyl)phosphonate	95%	unlisted

Hazard Symbols: XN
Risk Phrases: 22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed. Irritating to eyes, respiratory system and skin.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
Harmful if swallowed. Causes gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
Causes 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. 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:
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. Will burn if involved in a fire. 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 water spray, dry chemical, carbon dioxide, or chemical foam. Use agent most appropriate to extinguish fire. Cool containers with flooding quantities of water until well after fire is out.

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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. Remove all sources of ignition. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Wash clothing before reuse.
Storage:
Keep away from sources of ignition. 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# 10419-79-1: 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: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 92 - 94 deg C @ 4.00mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: 98 deg C ( 208.40 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.1500g/cm3
Molecular Formula: C6H14ClO3P
Molecular Weight: 200.62

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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:
Hydrogen chloride, phosphine, 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# 10419-79-1: SZ7110000 LD50/LC50:
CAS# 10419-79-1: Oral, rabbit: LD50 = 2 gm/kg; Oral, rat: LD50 = 1 gm/kg.
Carcinogenicity:
Diethyl (2-Chloroethyl)phosphonate - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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: XN
Risk Phrases:
R 22 Harmful if swallowed.
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 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 37/39 Wear suitable gloves and eye/face
protection.
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# 10419-79-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 10419-79-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 10419-79-1 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

制备方法与用途

类别：有毒物质

毒性分级：中毒

急性毒性（口服）：

• 大鼠 LD50：1000 毫克/公斤

可燃性危险特性：

• 可燃；火场分解产生有毒氯化物及磷氧化物气体

储运特性：

• 库房低温、通风、干燥
• 防火措施，与氧化剂分开存放

灭火剂：

• 水、二氧化碳、干粉、砂土

反应信息

• 作为反应物：
  描述：

  二乙基(2-乙基氯)磷酸盐 在 盐酸 作用下， 以 水 为溶剂， 反应 0.42h， 以79%的产率得到乙烯利
  参考文献：
  名称：

  微波辅助 水解 的 膦酸酯 二酯：制备膦酸的有效方案

  摘要：

  一种新型高效的无环核苷膦酸酯水解方法 二酯 （或通常是任何有机膦酸酯） 膦酸已经被开发出来。这种新颖的方法使用廉价盐酸以等摩尔的量表示分子中存在的酯基的数目，因此避免使用三甲基甲硅烷基卤化物，这是用于这些类型转化的标准试剂。此外，对反应混合物进行简单，轻松的后处理即可提供非常干净的产品，且收率很高（通常为77％至93％）。所述水解的另一个优点是膦酸酯 二酯事实是可以通过反应容器中的压力变化立即监控反应过程。这种“绿色”方法也已成功用于制备否则难以合成的（膦酰基甲氧基）乙基（PME）的导数 鸟嘌呤 （PMEG）和 黄嘌呤 （PMEHx），此外，该方法还可以使用重要的新型无环核苷膦酸酯，这些膦酸酯衍生自 2-氯次黄嘌呤 和从 黄嘌呤（例如PMEX）。

  DOI：

  10.1039/c2gc35547g
• 作为产物：
  描述：

  phosphorous acid diethyl ester-(2-chloro-ethyl ester) 生成 二乙基(2-乙基氯)磷酸盐
  参考文献：
  名称：

  Kabatschnik; Rossiskaja, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1948, p. 99

  摘要：

  DOI：

文献信息

• [EN] BICYCLIC COMPOUND AND USE THEREOF FOR INHIBITING SUV39H2<br/>[FR] COMPOSÉ BICYCLIQUE ET SON UTILISATION POUR INHIBER SUV39H2
  申请人：ONCOTHERAPY SCIENCE INC

  公开号：WO2017058503A1

  公开（公告）日：2017-04-06

  The present invention directs to a compound represented by formula (I).

  本发明涉及一种由化学式（I）表示的化合物。
• A free radical approach to functionalization of phosphonates utilizing novel 2- and 3-phosphonyl radicals
  作者：Piotr Bałczewski、Witold M. Pietrzykowski

  DOI：10.1016/0040-4020(96)00820-4

  日期：1996.10

  method for the phosphonyl C2,C3C bond formation under the free radical, reductive conditions is described. The new approach is based on the synthesis of novel 2- and 3- phosphonyl radicals 6, 9 derived from the corresponding 2- and 3-halo (XCl, Br, I) substituted phosphonates 7, 10 and their reaction with alkenes 4. Functionalized phosphonates 5, 8 possessing the 2+2 and 3+2 elongated carbon chain were

  为膦酰基C A一般方法2，C 3自由基，在还原条件下C键形成进行说明。这种新方法是基于新颖的合成2-和3-膦酰基6,9从相应的2-和3-卤代衍生（XCl，溴，I）取代的膦酸酯7,10和它们与烯烃反应4。官能膦酸酯5,8具有的2 + 2和3 + 2细长的碳链在24÷73％的产率获得。
• Efficient and ‘green’ microwave-assisted synthesis of haloalkylphosphonates via the Michaelis–Arbuzov reaction
  作者：Petr Jansa、Antonín Holý、Martin Dračinský、Ondřej Baszczyňski、Michal Česnek、Zlatko Janeba

  DOI：10.1039/c0gc00509f

  日期：——

  This paper deals with a novel, efficient and environmentally friendly synthesis of dialkyl haloalkylphosphonates via a microwave-assisted Michaelis–Arbuzov reaction. The approach is solventless, requires only one equivalent of each of the starting compounds, and provides high yields of pure products from which the impurities are easy to remove. The process has been optimised for batch and flow reactors

  本文研究了通过微波辅助的Michaelis-Arbuzov反应新颖，有效且环保的二烷基卤代烷基膦酸酯的合成方法。该方法是无溶剂的，每种起始化合物仅需要一个当量，并且可以提供高收率的纯产物，易于从其中除去杂质。该工艺已针对间歇式和流式反应器进行了优化，特别是对于合成氯乙烯的关键中间体的生产特别有利可图乙烯利 或无环核苷 膦酸酯 如 阿德福韦， 替诺福韦， 和 西多福韦。
• Oxaphospholene and oxaphosphinene heterocycles via RCM using unsymmetrical phosphonates or functional phosphinates
  作者：Pierre Fourgeaud、Camille Midrier、Jean-Pierre Vors、Jean-Noël Volle、Jean-Luc Pirat、David Virieux

  DOI：10.1016/j.tet.2009.11.049

  日期：2010.1

  New phosphorus heterocycles were synthesized using RCM reaction. They were prepared from unsymmetrical or polyfunctional insaturated precursor in 50 to 87% yields solving the problem of possible competitive side reactions. In parallel hydroxyphosphinate scaffolds represent a versatile starting material and could be of great interest for the synthesis of phosphosugar libraries.

  使用RCM反应合成了新的磷杂环。它们是由不对称或多官能的不饱和前体制备的，收率为50％至87％，解决了可能的竞争性副反应的问题。平行地，羟基次膦酸盐支架代表了通用的起始材料，并且对于磷酸糖文库的合成可能具有极大的兴趣。
• [EN] METHOD OF THE SYNTHESIS OF DIALKYL HALOALKYLPHOSPHONATES AND DIALKYL HALOALKYLOXYALKYLPHOSPHONATES<br/>[FR] PROCÉDÉ DE SYNTHÈSE DES DIALKYL HALOGÉNOALKYLPHOSPHONATES ET DES DIALKYL HALOGÉNOALKYLOXYALKYLPHOSPHONATES
  申请人：USTAV ORGANICKE CHEMIE A BIOCHEMIE AKADEMIE VED CESKE REPUBLIKY V V I

  公开号：WO2012013168A1

  公开（公告）日：2012-02-02

  The invention deals with the method of the synthesis of dialkyl haloalkylphosphonates and dialkyl haloalkyloxyalkylphosphonates via a microwave-heated Michaelis-Arbuzov reaction of trialkylphosphites with dihaloalkanes or bis(haloalkyl)ethers in a closed vessel, during which the reaction mixture, containing a dihaloalkane or bis(haloalkyl)ether and a trialkylphosphite, is heated with microwave radiation with the standard frequency (2.45 GHz) to reach a reaction temperature which is specific for each individual halogen. In the subsequent reaction of the first dihaloalkane or bis(haloalkyl)ether halogen atom with trialkyl phosphite, the desired dialkyl haloalkylphosphonate or dialkyl haloalkyloxyalkylphosphonate is formed, but the reaction of its halogen atom with the so-far present trialkylphosphite, leading to the creation of the relevant bisphosphonate, no longer takes place. In the case of an inhomogeneous reaction mixture, also the desired product in the amount of 0.1-5 molar % is added to the reaction mixture for its homogenization, which homogenizes it and thus precludes its uncontrollable overheating. The entire process of synthesis is more effective, faster, less expensive and more environmentally friendly than the methods described so far in the literature. The possibility of performing the described procedure also in a continuous-flow microwave reactor allows industrial production with minimal demands on an optimization of the reaction conditions for larger quantities, eliminates some security risks, dramatically reduces the spatial demands in production and reduces the need for the usage of large-tonnage industrial reactors.

  该发明涉及通过微波加热的Michaelis-Arbuzov反应，在封闭容器中合成二烷基卤代烷基膦酸酯和二烷基卤代烷氧基烷基膦酸酯的方法。在反应过程中，包含二烷基卤代烷基膦酸酯和三烷基膦酸酯的反应混合物通过微波辐射加热至标准频率（2.45 GHz）的反应温度，该温度对于每种卤素都是特定的。在第一个二烷基卤代烷基膦酸酯或二烷基卤代烷氧基烷基膦酸酯的卤原子与三烷基膦酸酯的反应中，形成所需的二烷基卤代烷基膦酸酯或二烷基卤代烷氧基烷基膦酸酯，但其卤原子与迄今为止存在的三烷基膦酸酯的反应，导致相关双膦酸酯的生成，不再发生。在反应混合物不均匀的情况下，还向反应混合物中添加所需产品的0.1-5摩尔%的量以使其均匀化，从而防止其不受控制地过热。整个合成过程比文献中迄今描述的方法更有效、更快、更经济、更环保。在连续流动微波反应器中执行所述程序的可能性使得工业生产具有最小的反应条件优化要求，消除了一些安全风险，显著减少了生产中的空间需求，并减少了对大吨位工业反应器的使用需求。

表征谱图