1-丙基膦酸二乙酯 | 18812-51-6

• 物质功能分类: 有机原料 - 有机膦化合物
• 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: 1-丙基膦酸二乙酯
• 中文别名: 1-丙基磷酸二乙酯；1-丙烷磷酸二乙酯；丙基膦酸二乙酯
• 英文名称: diethyl propylphosphonate
• 英文别名: diethyl n-propylphosphonate；Propylphosphonsaeure-diethylester；Diethyl-propylphosphonat；diethyl 1-propylphosphonate；Propanphosphonsaeurediaethylester；1-diethoxyphosphorylpropane
• CAS: 18812-51-6
• 化学式: C₇H₁₇O₃P
• mdl: MFCD00015139
• 分子量: 180.184
• InChiKey: RUIKOPXSCCGLOM-UHFFFAOYSA-N

物化性质

• 沸点：
  94-96°C 12mm
• 密度：
  1.0079 g/cm3 (20 ºC)
• 闪点：
  94-96°C/12mm
• 稳定性/保质期：
  在常温常压下稳定，应避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 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：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2931900090
• 储存条件：
  常温下应密闭避光，并存放在通风干燥处。

SDS

Name:	Diethyl 1-Propanephosphonate Material Safety Data Sheet
Synonym:	None Known
CAS:	18812-51-6

Section 1 - Chemical Product MSDS Name:Diethyl 1-Propanephosphonate Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
18812-51-6	Diethyl 1-Propanephosphonate	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 foam, dry chemical, or carbon dioxide.

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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 only in a chemical fume hood. Wash clothing before reuse.
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:
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# 18812-51-6: 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: clear colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
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: C7H17O3P
Molecular Weight: 180.091

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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, reducing agents, acids, bases.
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# 18812-51-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Diethyl 1-Propanephosphonate - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
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# 18812-51-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 18812-51-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 18812-51-6 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：

  1-丙基膦酸二乙酯 在 氢溴酸 作用下， 反应 3.0h， 生成 丙基膦酸
  参考文献：
  名称：

  一种正丙基磷酸环酐的绿色合成方法

  摘要：

  一种正丙基磷酸环酐的绿色合成方法。本发明属于聚合物合成领域。本发明的目的是为了解决现有1‑丙基磷酸环酐反应温度高、条件苛刻、副产品处理难，以及部分原材料难以获取导致限制生产和反应时间长、成本高的技术问题。方法：步骤1：向溶剂中加入乙醇钠、亚磷酸二乙酯的甲苯溶液和溴丙烷，反应完成后加水静置分层，油层经脱溶和减压蒸馏，得到1‑丙基磷酸二乙酯；步骤2：向1‑丙基磷酸二乙酯中加入氢溴酸进行水解反应，得到丙基磷酸；步骤3：向丙基磷酸中加入乙酸酐，脱水反应，得到正丙基磷酸酐。本发明的方法经简单处理即可完成副产物溴化钠的高效去除，且原料简单易得、且价格低廉，合成步骤简单，生产成本低，适合工业化生产。

  公开号：

  CN114716480A
• 作为产物：
  描述：

  diethyl (3-chloropropyl)phosphonate 在 sodium tetrahydroborate 、 三乙基硼 、 三丁基氯化锡 、 sodium iodide 作用下， 以 正己烷 、 丙酮 、 甲苯 为溶剂， 生成 1-丙基膦酸二乙酯
  参考文献：
  名称：

  用于利用1-的CC键形成一种新的，有效的方法，2-和3-膦酰基取代从iodoalkylphosphonates衍生的基团和Ñ -Bu 3 SNH / ET 3乙/ O 2系统

  摘要：

  描述了利用衍生自碘代烷基膦酸酯的1-，2-和3-膦酰基取代的基团和催化或化学计量的n- Bu 3 SnH / Et 3 B / O 2试剂体系的新型，实用的高取代膦酸酯的合成方法。

  DOI：

  10.1016/s0040-4020(97)00405-5
• 作为试剂：
  描述：

  (+/-)-5-hydroxymethyl-3,5-dimethyl-4-(methoxymethoxy)-5H-thiophen-2-one 在 正丁基锂 、 1-丙基膦酸二乙酯 、 戴斯-马丁氧化剂 作用下， 以 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 3,5-dimethyl-4-(methoxymethoxy)-5H-thiophen-2-one
  参考文献：
  名称：

  Novel route to 5-position vinyl derivatives of thiolactomycin: olefination versus deformylation

  摘要：

  Vinyl and diene derivatives of thiolactomycin have been prepared via Horner-Wadsworth-Emmons olefination from protected 5-formyl-3,5-dimethylthiotetronic acid. Several 4-position protecting groups and a variety of phosphonates were evaluated, with MOM protection and beta-ketophosphonates yielding the highest ratio of the desired product to deformylated product. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.058

文献信息

• Synthesen von 2,3-Dioxoalkylphosphonaten und anderer neuartiger ?-Ketophosphonate sowie eines Phosphinopyruvamids ( = (Alkyloxyphosphinyl)pyruvamids)
  作者：Richard Neidlein、Helmut Feistauer

  DOI：10.1002/hlca.19960790329

  日期：1996.5.8

  Syntheses of 2,3-Dioxoalkylphonates and Other Novel β-Ketophosphonates As Well As of a Phosphinopyruvamide ( = (Alkyloxyphosphinyl)pyruvamide)

  2,3-二氧代烷基膦酸酯和其他新型β-酮膦酸酯以及膦酰丙酮酰胺（=（烷氧基膦基）丙酮酰胺）的合成
• Phosphonated Fluoroquinolones, Antibacterial Analogs Thereof, and Methods for the Prevention and Treatment of Bone and Joint Infections
  申请人：Delorme Daniel

  公开号：US20080287396A1

  公开（公告）日：2008-11-20

  The present invention relates to phosphonated fluoroquinolones, antibacterial analogs thereof, and methods of using such compounds. These compounds are useful as antibiotics for prevention and/or the treatment of bone and joint infections, especially for the prevention and/or treatment of osteomyelitis.

  本发明涉及磷酸化氟喹诺酮及其抗菌类似物，以及使用这些化合物的方法。这些化合物可用作抗生素，用于预防和/或治疗骨骼和关节感染，特别是用于预防和/或治疗骨髓炎。
• Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source
  作者：Stavros K. Kariofillis、Benjamin J. Shields、Makeda A. Tekle-Smith、Michael J. Zacuto、Abigail G. Doyle

  DOI：10.1021/jacs.0c02805

  日期：2020.4.22

  represents a valuable transformation, but typically requires harsh reaction conditions or reagents. We report a radical approach for the methylation of (hetero)aryl chlorides using nickel/photoredox catalysis wherein trimethyl orthoformate, a common laboratory solvent, serves as a methyl source. This method permits methylation of (hetero)aryl chlorides and acyl chlorides at an early and late stage with

  有机卤化物的甲基化代表了一种有价值的转化，但通常需要苛刻的反应条件或试剂。我们报告了一种使用镍/光氧化还原催化对（杂）芳基氯进行甲基化的激进方法，其中原甲酸三甲酯（一种常见的实验室溶剂）作为甲基源。该方法允许（杂）芳基氯和酰氯在早期和晚期甲基化，具有广泛的官能团兼容性。机理研究表明，原甲酸三甲酯通过从氯介导的氢原子转移产生的叔自由基 β 断裂作为甲基自由基的来源。
• Fragmentation-Related Phosphonylation of Nucleophiles Utilizing P-Alkyl 2,3-oxaphosphabicyclo[2.2.2]octene 3-oxide Precursors
  作者：Tamara Kovács、Laura Szandra Fülöp、György Keglevich

  DOI：10.1002/hc.21304

  日期：2016.3

  New P-alkyl 2,3-oxaphosphabicyclo-[2.2.2]octene 3-oxides were synthesized by the Bayer–Villiger oxidation of the corresponding 7-phosphanorbornene 7-oxides and were used as precursors for reactive alkylmetaphosphonates useful in the phosphonylation of alcohols. This is the first case that the reactivity of the two regioisomers formed by O-insertion was differentiated and that the fragmentation-related

  新的 P-烷基 2,3-氧杂磷杂双环-[2.2.2] 辛烯 3-氧化物是通过相应的 7-磷酰冰片烯 7-氧化物的 Bayer-Villiger 氧化合成的，并用作反应性烷基偏膦酸酯的前体，可用于醇的膦酰化. 这是第一个通过 O 插入形成的两种区域异构体的反应性不同的情况，并且在微波辅助条件下实现了导致膦酸酯的断裂相关的膦酰化。
• Synthesis of Cyclopropane-Containing Phosphorus Compounds by Radical Coupling of Butenylindium with Iodo Phosphorus Compounds
  作者：Kensuke Kiyokawa、Itaru Suzuki、Makoto Yasuda、Akio Baba

  DOI：10.1002/ejoc.201001471

  日期：2011.4

  by-product to be inert to the reaction system. In addition, the transmetalation of a (cyclopropylmethyl)stannane and InBr3 provided the dibutenylindium bromide as a single product, which smoothly coupled with the unstable phosphonyl radical species from the iodo phosphorus compound. A photochemical method (UV irradiation) was also applied and accelerated the coupling reaction. The cyclopropylmethylated

  通过（环丙基甲基）锡烷和 InBr3 之间的金属转移反应制备的 α-或 β-碘代磷化合物（如碘膦酸酯、碘代膦氧化物和碘代硫代膦酸酯）与丁烯基的自由基偶联，得到相应的环丙基甲基化产物。自由基反应是由丁烯基铟产生的自由基物种在少量氧气的辅助下引发的。Butenylindium 不仅可用作环丙基甲基化试剂，还可用作自由基引发剂。为了成功偶联，使用了锡/铟金属转移，其中卤化锡副产物对反应系统呈惰性非常重要。此外，（环丙基甲基）锡烷和 InBr3 的金属转移提供了二丁烯基溴化铟作为单一产品，其与来自碘磷化合物的不稳定膦酰基物种顺利偶联。还应用了光化学方法（紫外线照射）并加速了偶联反应。产生的环丙基甲基化膦酸酯是 Horner-Wadsworth-Emmons 反应的良好中间体，并产生带有环丙烷部分的官能化烯烃。

表征谱图