苯基膦酸二乙酯 | 1638-86-4

• 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 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯基膦酸二乙酯
• 中文别名: 二乙氧基苯膦；苯基亚磷酸二乙酯；苯基亚膦酸二乙酯
• 英文名称: diethyl phenylphosphonite
• 英文别名: phenylphosphonous acid diethyl ester；diethoxy(phenyl)phosphane
• CAS: 1638-86-4
• 化学式: C₁₀H₁₅O₂P
• mdl: MFCD00009086
• 分子量: 198.202
• InChiKey: RVDJLKVICMLVJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  64°C 0,7mm
• 密度：
  1.032 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• LogP：
  2.17 at 25℃
• 稳定性/保质期：

  常温常压下稳定，避免氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• TSCA：
  Yes
• 安全说明：
  S24/25
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P301+P312,P302+P352,P304+P340,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  请将容器密封保存，并储存在阴凉、干燥的地方。

SDS

Name:	Diethyl phenylphosphonite 99% Material Safety Data Sheet
Synonym:	Diethoxyphenylphosphin
CAS:	1638-86-4

Section 1 - Chemical Product MSDS Name:Diethyl phenylphosphonite 99% Material Safety Data Sheet
Synonym:Diethoxyphenylphosphin

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1638-86-4	Diethyl phenylphosphonite	99	216-676-7

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

---

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.

---

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:

---

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.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

---

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. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

---

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. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.)

---

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# 1638-86-4: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear, colorless
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
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: 1.0320 g/cm3
Molecular Formula: C10H15O2P
Molecular Weight: 198.20

---

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

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1638-86-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Diethyl phenylphosphonite - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

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.

---

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# 1638-86-4: No information available.
Canada
CAS# 1638-86-4 is listed on Canada's NDSL List.
CAS# 1638-86-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1638-86-4 is listed on the TSCA inventory.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  苯基膦酸二乙酯 在 porcine liver esterase 、 sodium hydroxide 、 phosphate buffer 作用下， 反应 16.0h， 生成 (S)-(-)-[ethoxy(phenyl)phosphoryl]acetic acid
  参考文献：
  名称：

  Enzyme-promoted kinetic resolution of racemic, P-chiral phosphonyl and phosphorylacetates

  摘要：

  A series of racemic methyl phosphonyl- and phosphorylacetates were hydrolyzed in the presence of porcine liver esterase (PLE) under kinetic resolution conditions to give the corresponding P-chiral phosphonyl- and phosphorylacetic acids and recovered esters in moderate to high enantiomeric purity (up to 95% ee). The Jones PLE active site model was applied to explain the enantioselectivity of this reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00258-4
• 作为产物：
  描述：

  双(二乙胺)苯膦 在 三乙胺 作用下， 以 乙醚 为溶剂， 生成 苯基膦酸二乙酯
  参考文献：
  名称：

  Andreev,N.A.; Grishina,O.N., Journal of general chemistry of the USSR, 1979, vol. 49, p. 1959 - 1964

  摘要：

  DOI：
• 作为试剂：
  描述：

  N-Boc-4-羟基哌啶 在 苯基膦酸二乙酯 、 水 、 C₄₂H₄₂F₄IrN₄⁽¹⁺⁾*F₆P^(1-) 、 sodium hydride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 43.0h， 生成 1-Boc-哌啶
  参考文献：
  名称：

  使用黄原酸盐光催化裂解醇的 C-O 键

  摘要：

  C-O 键的均裂裂解以提供烷基自由基是有机合成中有吸引力但具有挑战性的转变。在这里，我们描述了黄原酸盐的光催化脱氧 C-C 偶联反应，该反应可以很容易地从相应的醇中制备。该策略成功的关键是黄原酸盐的低氧化电位和使用合适的磷化氢来加速羰基硫的脱硫释放。

  DOI：

  10.1021/acs.orglett.1c04029

文献信息

• Photocontrolled Cobalt Catalysis for Selective Hydroboration of α,β‐Unsaturated Ketones
  作者：Frédéric Beltran、Enrico Bergamaschi、Ignacio Funes‐Ardoiz、Christopher J. Teskey

  DOI：10.1002/ange.202009893

  日期：2020.11.16

  In this way, we bias the reaction down two divergent pathways, giving contrasting products in the catalytic hydroboration of α,β‐unsaturated ketones. This includes direct access to previously elusive cyclic enolborates, via 1,4‐selective hydroboration, providing a straightforward and stereoselective route to rare syn‐aldol products in one‐pot. DFT calculations and mechanistic experiments confirm two

  摘要亲核试剂与 α,β-不饱和羰基化合物的 1,2 和 1,4 加成之间的选择性通常通过向底物或试剂中添加化学计量添加剂来改变，以增加其“硬”或“软”特性。在这里，我们展示了一种概念上不同的方法，该方法依赖于用可见光控制催化剂的配位范围。通过这种方式，我们使反应偏向两条不同的途径，从而在 α,β-不饱和酮的催化硼氢化中产生对比产物。这包括通过 1,4-选择性硼氢化反应直接获得以前难以捉摸的环状烯醇硼酸盐，为一锅法获得稀有的顺醇醛产品提供了一种直接且立体选择性的途径。DFT 计算和机械实验证实了两种不同的机制是有效的，支撑着这种不寻常的光控选择性开关。
• Multihydrido-complexes of osmium and related complexes
  作者：P. G. Douglas、B. L. Shaw

  DOI：10.1039/j19700000334

  日期：——

  A new route to tetrachloro-complexes of the type trans-[OsCl4L2] from mer-[OsCl3L3](L = tertiary phosphine or tertiary arsine) is described, which involves treatment with chlorine in the presence of light. The tetrachloro-osmium(III) complex trans-[OsCl4(PMe2Ph)2] reacts with tertiary phosphines, tertiary arsines, alkyl phosphites, or alkyl phosphonites (L′) to give [OsCl3(PMe2Ph)2L′]. Reduction of

  到所述类型的四氯络合物的新路由反式- [OSCL 4大号2 ]从聚体- [OSCL 3大号3 ]（L =叔膦或叔胂）中描述，其涉及用在光的存在下氯处理。四氯-（III）配合物反式-[OSCl 4（PMe 2 Ph）2 ]与叔膦，叔a，烷基亚磷酸酯或烷基亚膦酸酯（L'）反应，得到[OSCl 3（PMe 2 Ph）2 L ”]。的还原聚体[OSCL - 3大号3或[OSCl 3（PMe 2 Ph） 2 L']或硼氢化钠或氢化铝锂得到[OSH 4 L 3 ]或[OSH 4（PMe 2 Ph） 2 L']型四氢-配合物。反式-[OSCl 4（PMe 2 Ph） 2 ]的类似还原得到[OSH 6（PMe 2 Ph） 2 ]和[OSCl 4（PMe 2 Ph） 2 ] -的混合物。[OSH 4 L 3类型的四氢化物]与氯化氢反应生成fac- [OSCl 3 L 3 ]。四氢化物还与EtOD在苯中缓慢反
• Cs₂CO₃-Promoted One-Pot Synthesis of Alkynylphosphonates, -phosphinates, and -phosphine Oxides
  作者：Yulei Wang、Jiepeng Gan、Liu Leo Liu、Hang Yuan、Yuxing Gao、Yan Liu、Yufen Zhao

  DOI：10.1021/jo500312n

  日期：2014.4.18

  trialkyl phosphites, ethyl diphenylphosphinite, or diethyl phenylphosphonite has been developed under metal-free conditions, providing a practical and powerful tool for one-pot synthesis of valuable alkynylphosphonates, -phosphinates, and -phosphine oxides in good to excellent yields.

  在无金属条件下开发了一种新颖且有效的Cs 2 CO 3促进的各种1,1,1-二溴-1-烯烃与容易获得的亚磷酸三烷基酯，乙基二苯基亚膦酸酯或二乙基苯基亚膦酸酯的磷酸化或亚膦酰基化，提供了实用而有效的方法一锅合成有价值的炔基膦酸酯，-次膦酸酯和-膦氧化物的工具，产率很高。
• Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates
  作者：Hai Huang、Johanna Denne、Chou‐Hsun Yang、Haobin Wang、Jun Yong Kang

  DOI：10.1002/anie.201802082

  日期：2018.5.28

  A strategy for the direct functionalization strategy of inertial dialkyl phosphonates with hydroxy compounds to afford diverse mixed phosphonates with good yields and functional‐group tolerance has been developed. Mechanistic investigations involving both NMR studies and DFT studies suggest that an unprecedented highly reactive PV species (phosphoryl pyridin‐1‐ium salt), a key intermediate for this

  已经开发了一种惯性二烷基膦酸酯与羟基化合物直接官能化的策略，以提供具有良好收率和官能团耐受性的多种混合膦酸酯。涉及NMR研究和DFT研究的机理研究表明，在Tf 2存在的情况下，由膦酸二烷基酯原位生成了空前的高反应性P V物种（磷酰吡啶-1-盐），这是这种新的合成转化的关键中间体。O /吡啶。
• Carbon–phosphorus bond formation and transformation in the reaction of 1,2-diaza-1,3-butadienes with alkyl phenylphosphonites
  作者：Orazio A. Attanasi、Graziano Baccolini、Carla Boga、Lucia De Crescentini、Paolino Filippone、Fabio Mantellini

  DOI：10.1016/j.tet.2008.05.007

  日期：2008.7

  Abstract The reaction of 1,2-diaza-1,3-butadienes with dialkyl phenylphosphonites under solvent-free conditions proceeds via zwitterionic intermediate and gives, by precipitation, the stable ylidic α-phosphanylidene-hydrazones that, in turn, can be transformed into the corresponding 3-phenyl-2 H -1,2,3λ 5 -diazaphospholes. The latter compounds are converted by hydrolytic cleavage in methanol–water

  摘要 在无溶剂条件下，1,2-二氮杂-1,3-丁二烯与苯基亚膦酸二烷基酯的反应通过两性离子中间体进行，并通过沉淀得到稳定的内联α-亚膦亚基腙，进而可以转化为相应的 3-苯基-2 H -1,2,3λ 5 -二氮杂磷。后一种化合物在甲醇-水 (95:5) 中通过水解裂解转化为 E-肼基膦酸盐，可用于制备相应的 β-酮膦酸盐和 4-[烷氧基(苯基)磷酰基]-1,2-二氮杂- 1,3-丁二烯。这些特殊的 1,2-二氮杂-1,3-丁二烯在 4 位碳原子上带有烷氧基（苯基）磷酰基，也能够添加不同的亲核试剂，例如甲醇或硫脲，

表征谱图