二甲基-乙烯基磷酸酯 | 4645-32-3

• 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: 二甲基-乙烯基磷酸酯
• 中文别名: 乙烯基磷酸二甲酯；二甲基乙烯基膦酸酯
• 英文名称: dimethylvinylphosphonate
• 英文别名: dimethyl ethenylphosphonate；vinyl phosphonic acid dimethyl ester；Dimethyl vinylphosphonate；1-dimethoxyphosphorylethene
• CAS: 4645-32-3
• 化学式: C₄H₉O₃P
• mdl: MFCD00015488
• 分子量: 136.087
• InChiKey: CQCXMYUCNSJSKG-UHFFFAOYSA-N

物化性质

• 沸点：
  197-202 °C(lit.)
• 密度：
  1.146 g/mL at 20 °C(lit.)
• 闪点：
  101°C
• 稳定性/保质期：
  | 存储冷藏 |

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  6.1
• 危险品标志：
  C
• 安全说明：
  S45,S53
• 危险类别码：
  R22,R45
• WGK Germany：
  1
• 海关编码：
  2931900090
• 危险品运输编号：
  UN 3265 8/PG 3
• 危险类别：
  6.1
• 包装等级：
  III
• 储存条件：
  | 2-8°C |

SDS

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Section 1: Product Identification
Chemical Name: Vinylphosphonic acid dimethyl ester, min. 90%
CAS Registry Number: 4645-32-3
Formula: CH2=CHP(O)(OCH3)2
EINECS Number: 225-076-4
Chemical Family: organic phosphonic acid
Synonym: Dimethylvinylphosphonate;1-dimethoxyphosphorylethylene; Ethenylphosphonic acid dimethyl

---

Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 4645-32-3 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Harmful by inhalation and if swallowed. Corrosive to skin, eyes and respiratory tract. Causes burns.
Primary Routes of Exposure: Ingestion, inhalation, skin, eyes
Eye Contact: Severe corrosive to eyes. Exposure can lead to permanent eye damage.
Skin Contact: Harmful in contact with skin. Causes burns. Contact can lead to redness, pain, blistering and scar formation.
Harmful by inhalation. Material is extremely destructive to the tissue of the mucous membranes and
Inhalation:
respiratory tract.
Ingestion: Harmful if swallowed. Causes burns to the mouth, throat and stomach.
Acute Health Affects: Harmful by inhalation and if swallowed. Corrosive to skin, eyes and respiratory tract. Causes burns.
Repeated or prolonged exposure to spray mist may produce respiratory tract irritation leading to frequent
Chronic Health Affects:
attacks of bronchial infection.
NTP: No
IARC: No
OSHA: No

---

SECTION 4: First Aid Measures
Immediately flush the eyes with copious amounts of water for at least 10-15 minutes. A victim may need
Eye Exposure:
assistance in keeping their eye lids open. Get immediate medical attention.
Wash the affected area with water. Remove contaminated clothes if necessary. Seek medical assistance if
Skin Exposure:
irritation persists.
Remove the victim to fresh air. Closely monitor the victim for signs of respiratory problems, such as difficulty
Inhalation:
in breathing, coughing, wheezing, or pain. In such cases seek immediate medical assistance.
Seek medical attention immediately. Keep the victim calm. Give the victim water (only if conscious). Induce
Ingestion:
vomiting only if directed by medical personnel.

---

SECTION 5: Fire Fighting Measures
Flash Point: 208.4°F
Autoignition Temperature: no data
Explosion Limits: no data
Extinguishing Medium: carbon dioxide, dry powder or foam
If this product is involved in a fire, fire fighters should be equipped with a NIOSH approved positive pressure
Special Fire Fighting Procedures:
self-contained breathing apparatus and full protective clothing.
Hazardous Combustion and If involved in a fire, this material may emit toxic and corrosive fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards.

---

SECTION 6: Accidental Release Measures
Ensure adequate ventilation and wear respiratory protection. Small spills can be mixed with vermiculite,
Spill and Leak Procedures: sodium carbonate or other suitable non-combustible adsorbent and swept up. Place in adequate container for
disposal. Do not let material enter drains.

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SECTION 7: Handling and Storage
Handling and Storage: Store cold, in a tightly sealed container. Keep away from heat and direct sunlight.

---

SECTION 8: Exposure Controls and Personal Protection
Eye Protection: Always wear approved safety glasses when handling a chemical substance in the laboratory.
Skin Protection: Wear protective clothing and gloves.
Ventilation: Handle the material in an efficient fume hood.
If ventilation is not available a respirator should be worn. The use of respirators requires a Respirator
Respirator:
Protection Program to be in compliance with 29 CFR 1910.134.
Ventilation: Handle the material in an efficient fume hood.
Additional Protection: No additional protection required.

---

SECTION 9: Physical and Chemical Properties
Color and Form: colorless liq.
Molecular Weight: 136.1
Melting Point: no data
Boiling Point: 197-202°C
Vapor Pressure: no data
Specific Gravity: 1.146g/cm3 (20°C)
Odor: none
Solubility in Water: soluble

---

SECTION 10: Stability and Reactivity
Stability: air and moisture stable (store cold)
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: none
Incompatibility: strong bases, oxidizing agents and fine powder metals
Decomposition Products: carbon monoxide, carbon dioxide and phosphorus oxides.

---

SECTION 11: Toxicological Information
RTECS Data: No information available in the RTECS files.
Carcinogenic Effects: no data
Mutagenic Effects: no data
Tetratogenic Effects: no data

---

SECTION 12: Ecological Information
Ecological Information: No information available

---

SECTION 13: Disposal Considerations
Disposal: Dispose of according to local, state and federal regulations.

---

SECTION 14: Transportation
Shipping Name (CFR): Corrosive liquid, Acidic, Organic, N.O.S.
Hazard Class (CFR): 8
Additional Hazard Class (CFR): NA
Packaging Group (CFR): III
UN ID Number (CFR): UN# 3265
Shipping Name (IATA): Corrosive liquid, Acidic, Organic, N.O.S.
Hazard Class (IATA): 8
Additional Hazard Class (IATA): NA
Packaging Group (IATA): III
UN ID Number (IATA): UN# 3265

---

SECTION 15: Regulatory Information
TSCA: Listed in the TSCA inventory
SARA (Title 313): Not reportable under SARA313.
Second Ingredient: none

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  二甲基-乙烯基磷酸酯 在 叔丁胺 作用下， 反应 16.5h， 以0.81 g的产率得到methylvinylphosphonate
  参考文献：
  名称：

  膦酸酯连接的氨基糖苷 - 辅酶 A 双底物的合成及其在参与氨基糖苷抗性的酶的机理研究中的应用

  摘要：

  只需五步！膦酸酯连接的氨基糖苷 - 辅酶 A 衍生物（见方案）的合成，包括在水中的迈克尔加成，仅用五个步骤就可以实现。

  DOI：

  10.1002/chem.200802172
• 作为产物：
  描述：

  磷酸三甲酯 生成 二甲基-乙烯基磷酸酯
  参考文献：
  名称：

  Process for the preparation of vinylphosphonic acid diesters and

  摘要：

  通过在酸性或碱性催化剂存在下加热具有公式CH.sub.3 COOCH.sub.2 CH.sub.2 P(O)(OR).sub.2的二烷基2-乙酰氧基乙磷酸酯，并将所得产物与具有公式R.sup.1 C(OR).sub.3的正酯反应，制备公式CH.sub.2 .dbd.CH--P(O)(OR).sub.2的乙烯磷酸二酯的方法。

  公开号：

  US04493803A1

文献信息

• 2‐Pyridyl Sulfoxide: A Versatile and Removable Directing Group for the Pd ^II ‐Catalyzed Direct CH Olefination of Arenes
  作者：Alfonso García‐Rubia、M. Ángeles Fernández‐Ibáñez、Ramón Gómez Arrayás、Juan Carlos Carretero

  DOI：10.1002/chem.201003633

  日期：2011.3.21

  Removable and versatile: The 2‐pyridylsulfinyl group has proved to be an efficient directing group in the PdII‐catalyzed aryl ortho CH olefination. This catalyst system enables the sequential double olefination to give asymmetrically di‐ortho‐functionalized arenes. The sulfinyl directing group can be easily cleaved, providing access to 1,3‐disubstituted arenes, or transformed into a thiol group.

  可移动的和多功能的：2-吡啶基亚硫组已被证明是在PD的有效定向基团II催化的芳基邻位Ç  ħ烯。这种催化剂系统使连续双烯给不对称二邻-功能化芳烃。亚硫酰基导向基团可以很容易地裂解，从而可以接近1,3-二取代的芳烃，或者可以转化为硫醇基团。
• Palladium-catalyzed ortho-olefination of 2-arylpyrrolidines: A tool for increasing structural complexity in nitrogen heterocycles
  作者：Pablo D. Legarda、Alfonso García-Rubia、Ramón Gómez Arrayás、Juan C. Carretero

  DOI：10.1016/j.tet.2018.05.076

  日期：2018.7

  of the (2-pyridyl)sulfonyl unit as directing functionality and readily removable N-protecting group has enabled an efficient and practical transformation of 2-arylpyrrolidine derivatives into more complex tricyclic frameworks via palladium-catalyzed ortho-olefination with electron deficient alkenes and subsequent cyclization upon N-deprotection under mild conditions. The key cross coupling step in the

  （2-吡啶基）磺酰基单元作为直接官能团和易于除去的N-保护基团的双重作用使得能够通过钯催化的与缺电子烯烃的邻位烯烃化反应将2-芳基吡咯烷衍生物有效而实用地转化为更复杂的三环骨架。和随后在温和条件下在N-脱保护下环化。在三氟甲磺酸N-氟-2,4,6-三甲基吡啶鎓（[F +]）的存在下，关键的交叉偶联步骤既高效又可耐受两个偶联伙伴处的各种空间和电子变化。通过的还原条件适当选择，Ñ-磺酰基脱保护基可以选择性地形成苯并-稠合的吡咯烷或稠合的吡咯烷基-苯并氮杂framework骨架。
• Product Control using Substrate Design: Ruthenium-Catalysed Oxidative C−H Olefinations of Cyclic Weinreb Amides
  作者：Riki Das、Manmohan Kapur

  DOI：10.1002/chem.201603126

  日期：2016.11.14

  A new class of Weinreb amides has been developed as directing groups for the ruthenium‐catalysed regioselective oxidative C−H olefination. The new Weinreb amides successfully inhibit the N−O bond reductive cleavage usually associated with the cationic ruthenium system, thereby keeping intact the synthetic utility of Weinreb amides. Mechanistic studies reveal interesting aspects of the directing group

  已开发出新型的Weinreb酰胺作为钌催化的区域选择性氧化CH H烯化反应的导向基团。新的Weinreb酰胺成功地抑制了通常与阳离子钌体系相关的N-O键还原性裂解，从而保持了Weinreb酰胺的合成效用。机理研究揭示了与相似结构的简单酰胺相比，Weinreb酰胺的指导基团功能的有趣方面。
• Weakly coordinating group directed rhodium-catalyzed unconventional site-selective C–H olefination of indolizines at the 8-position
  作者：Xue Feng、Jiaxin Tian、Ying Sun、Huayou Hu、Mingzhu Lu、Yuhe Kan、Danjun Fang、Chao Wang

  DOI：10.1016/j.cclet.2020.02.039

  日期：2021.1

  rhodium-catalyzed directing group promoted selective C–H olefination reaction of indolizines at the 8-position is reported. Di-olefination at 2,8-positions also achieved with silver hexafluoroantimonate as an additive under similar reaction conditions. Weakly coordinating groups, such as ketone, aldehyde, amide and ester, were used as directing groups. The ester group can be removed under acid conditions

  摘要报道了铑催化的导向基团促进了吲哚嗪在8位的选择性C–H烯化反应。在相似的反应条件下，用六氟锑酸银作为添加剂也可实现2,8位的二烯化。弱配位基团，例如酮，醛，酰胺和酯，被用作导向基团。酯基可在酸性条件下除去，因此用作无痕的导向基团。
• A Direct Approach to Orthogonally Protected α-Amino Aldehydes
  作者：Richard Lamb、Vincent L. Revil-Baudard、Samir Z. Zard

  DOI：10.1021/acs.orglett.9b02237

  日期：2019.8.16

  O-Neopentyl-xanthate 19 bearing a masked α-amino aldehyde, with the two functional groups orthogonally protected, reacts cleanly with many functional alkenes. The radical addition–transfer furnishes densely functionalized adducts that can be further transformed into an array of amino-substituted carbocycles and heteroaromatics. They are also easily converted into imidazolones.

  带有被掩蔽的α-氨基醛的O-新戊基黄原酸酯19，具有两个被正交保护的官能团，可以与许多官能烯烃干净地反应。自由基加成转移提供了高密度官能化的加合物，可以将其进一步转化为一系列氨基取代的碳环和杂芳族化合物。它们也容易转化为咪唑啉酮。