1438-74-0

Basic information

• Product Name: vinylphosphonic dichloride
• Synonyms: vinylphosphonic dichloride;Ethenyldichlorophosphine oxide;Ethenylphosphonic dichloride;Vinylphosphonic aciddichloride
• CAS NO: 1438-74-0
• Molecular Formula: C₂H₃Cl₂OP
• Molecular Weight: 144.924381
• EINECS: 215-871-4
• Mol File: 1438-74-0.mol

Chemical Properties

• Melting Point: -58 °C
• Boiling Point: 161.1°Cat760mmHg
• Flash Point: 51.2°C
• Appearance: /
• Density: 1.399g/cm³
• Vapor Pressure: 3.01mmHg at 25°C
• Refractive Index: 1.445
• CAS DataBase Reference: vinylphosphonic dichloride(CAS DataBase Reference)
• NIST Chemistry Reference: vinylphosphonic dichloride(1438-74-0)
• EPA Substance Registry System: vinylphosphonic dichloride(1438-74-0)

Safety Data

• Hazardous Substances Data: 1438-74-0(Hazardous Substances Data)

Usage

Uses

Used in Polymer Production:
Vinylphosphonic dichloride is utilized as a monomer in the production of polymers, contributing to the development of materials with specific properties tailored for different applications.
Used in Flame Retardants:
vinylphosphonic dichloride is employed as a key ingredient in the synthesis of flame retardants, enhancing the fire resistance of materials and ensuring safety in various industries.
Used in Adhesives and Coatings:
Vinylphosphonic dichloride is used as a reactive component in the formulation of adhesives and coatings, improving their bonding strength and durability.
Used in Specialty Polymers:
It serves as a versatile building block in the creation of specialty polymers designed for unique applications, such as high-performance materials in aerospace, automotive, and electronics industries.
Used in Organic Synthesis:
Vinylphosphonic dichloride acts as a valuable reaction intermediate in organic synthesis, enabling the production of a wide range of chemical compounds for various purposes.
Safety Precautions:
Due to its corrosive nature and potential to cause skin and eye irritation, vinylphosphonic dichloride should be handled with care. It is classified as a hazardous material, and its use should be confined to well-ventilated areas with appropriate personal protective equipment to ensure the safety of individuals involved in its manipulation.

InChI:InChI=1/C2H3Cl2OP/c1-2-6(3,4)5/h2H,1H2

Upstream product

• 690-12-0 (2-chloroethyl)phosphonic dichloride 
• 18291-41-3 vinylphosphonic acid bis(trimethylsilyl) ester 
• 75-44-5 phosgene 
• 4645-32-3 dimethylvinylphosphonate 
• 807292-23-5 butyl vinylphosphonate 
• 6294-34-4 bis(2-chloroethyl) 2-chloroethylphosphonate 
• 1746-03-8 vinylphosphonic acid 

Downstream Products

• 4645-32-3 dimethylvinylphosphonate 
• 682-30-4 Diethyl vinylphosphonate 
• 1746-03-8 vinylphosphonic acid 
• 727-16-2 vinyl-phosphonic acid diphenyl ester 
• 15849-99-7 Vinylthiophosphonsaeure-dichlorid 
• 53128-14-6 bis(4-methoxyphenyl) vinylphosphonate 
• 345898-58-0 C₁₅H₁₉ClNO₃P 
• 7283-64-9 dibenzyl vinylphosphonate 
• 882055-63-2 diethyl 3,3'-[(vinylphosphoryl)bis(oxy)]dibenzoate 
• 75998-96-8 2-(4-Chlorphenyl)-4-isopropyl-5-methoxycarbonyl-3-vinyl-3,4-dihydro-2H-1,2,4,3-triazaphosphol-3-oxid 

Relevant articles and documents

Synthesis and Evaluation of Non-Hydrolyzable Phospho-Lysine Peptide Mimics

The intrinsic lability of the phosphoramidate P?N bond in phosphorylated histidine (pHis), arginine (pHis) and lysine (pLys) residues is a significant challenge for the investigation of these post-translational modifications (PTMs), which gained attention rather recently. While stable mimics of pHis and pArg have contributed to study protein substrate interactions or to generate antibodies for enrichment as well as detection, no such analogue has been reported yet for pLys. This work reports the synthesis and evaluation of two pLys mimics, a phosphonate and a phosphate derivative, which can easily be incorporated into peptides using standard fluorenyl-methyloxycarbonyl- (Fmoc-)based solid-phase peptide synthesis (SPPS). In order to compare the biophysical properties of natural pLys with our synthetic mimics, the pKa values of pLys and analogues were determined in titration experiments applying nuclear magnetic resonance (NMR) spectroscopy in small model peptides. These results were used to compute electrostatic potential (ESP) surfaces obtained after molecular geometry optimization. These findings indicate the potential of the designed non-hydrolyzable, phosphonate-based mimic for pLys in various proteomic approaches.

Zwitterionic pyrrolidene-phosphonates: Inhibitors of the glycoside hydrolase-like phosphorylase: Streptomyces coelicolor GlgEI-V279S

We synthesized and evaluated new zwitterionic inhibitors against glycoside hydrolase-like phosphorylase Streptomyces coelicolor (Sco) GlgEI-V279S which plays a role in α-glucan biosynthesis. Sco GlgEI-V279S serves as a model enzyme for validated anti-Tuberculosis (TB) target Mycobacterium tuberculosis (Mtb) GlgE. Pyrrolidine inhibitors 5 and 6 were designed based on transition state considerations and incorporate a phosphonate on the pyrrolidine moiety to expand the interaction network between the inhibitor and the enzyme active site. Compounds 5 and 6 inhibited Sco GlgEI-V279S with Ki = 45 ± 4 μM and 95 ± 16 μM, respectively, and crystal structures of Sco GlgE-V279S-5 and Sco GlgE-V279S-6 were obtained at a 3.2 ? and 2.5 ? resolution, respectively.

Joint production method of ethephon and vinylphosphonic acid

The invention discloses a joint production method of ethephon and vinylphosphonic acid. The joint production method comprises the following steps of acylating bis(2-chloroethyl)-2-chloroethyl phosphonate by phosgene or thionyl chloride under the action of a catalyst to obtain a mixture of vinyl phosphonic chloride and 2-chloroethyl phosphonic chloride; separating the vinyl phosphonic chloride from the 2-chloroethyl phosphonic chloride in a reduced pressure distillation mode; hydrolyzing the vinyl phosphonic chloride and the 2-chloroethyl phosphonic chloride to obtain the vinylphosphonic acid and the ethephon. According to the joint production method disclosed by the invention, two products of the ethephon and the vinylphosphonic acid are synthesized by using the bis(2-chloroethyl)-2-chloroethyl phosphonate; a process is simple, and the purities of the two products are improved.

2-chloro ethyl phosphonic two chlorine gas phase method of synthesizing vinyl phosphine acid radical two chlorine shielding (by machine translation)

The present invention provides a the 2 [...] ethyl phosphonic two chlorine gas phase method of synthesizing vinyl phosphine acid radical two chlorine shielding, in the method, the alkaline earth metal or transition metal chloride load on the activated carbon, and is filled to the fixed bed reactor, in the 25 [...] 50mbar degree of vacuum, the 150 [...] 180 °C condition, so that the 2 [...] ethyl phosphonic b chlorine gasification, through the 180 [...] 250 °C fixed bed reactor, the role with the catalyst, to remove hydrogen chloride, cooling generating vinyl phosphine acid radical two chlorine product, hydrogen chloride forms hydrochloric acid exhaust gas by the water absorption. The process of the invention is simple, the operation is easy to control, reaction and separation process effectively combined, to realize the continuous synthesis process. (by machine translation)

High-load, oligomeric phosphonyl dichloride: facile generation via ROM polymerization and application to scavenging amines

A new ROMP-derived scavenging reagent, oligomeric phosphonyl dichloride (OPC), with high-load and selectivity is reported. This reagent can be readily generated via the ROM polymerization of bicyclo[2.2.1]hept-5-en-2-ylphosphonic dichloride, which is conveniently assembled from the Diels-Alder reaction of cyclopentadiene and vinyl phosphonic dichloride. The OPC has been exploited in the rapid, efficient scavenging of primary and secondary amines that are present in excess following a common benzoylation event at room temperature (30-60 min) or under microwave conditions in shorter duration (5 min).

Derivatives of [2-(8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)alkyl]phosphonic acid and methods of making them

Compounds of formula (I) or pharmaceutically acceptable salts thereof are provided: wherein: A is alkylenyl of 1 to 4 carbon atoms, or alkenylenyl of 2 to 4 carbon atoms; R1 and R2 are, independently, hydrogen or a C5 to C7 aryl optionally substituted with 1 to 2 substituents, independently, selected from the group consisting of —C(O)R3, halogen, cyano, nitro, hydroxyl, C1-C6 alkyl, and C1-C6 alkoxy, with the proviso that at least one of R1 and R2 is not hydrogen; R3 is, independently, hydrogen, —OR4, alkyl, aryl, or heteroaryl; R4 is hydrogen, alkyl, aryl, or heteroaryl; R5 and R6 are, independently, hydrogen, alkyl, hydroxyl, alkoxy, or C5 to C7 aryl; wherein any R3 to R6 group having an aryl or heteroaryl moiety can optionally be substituted on the aryl or heteroaryl moiety with 1 to about 5 substituents, independently, selected from the group consisting of halogen, cyano, nitro, hydroxyl, C1-C6 alkyl, and C1-C6 alkoxy. Methods of making these compounds as well as methods using the compounds for treating a variety of conditions are also disclosed.

A MILD AND FACILE SYNTHESIS OF ALKYL- AND ARYLPHOSPHONYL DICHLORIDES UNDER NEUTRAL CONDITIONS. REACTION OF BIS(TRIMETHYLSILYL) PHOSPHONATES WITH PCl5

Bis(trimethylsilyl) phosphonates, which are prepared from the dialkyl esters with chlorotrimethylsilane/sodium iodide, are transformed in high yields into the corresponding phosphonyl dichlorides on the treatment with phosphorus pentachloride under mild and neutral conditions.

Process for the preparation of phosphonic acid dihalides

A process for the preparation of phosphonic acid dihalides of the formula EQU1 IN WHICH R is α, β-unsaturated alkyl, α, β-unsaturated alkyl, phenyl or benzyl and may be further substituted, which comprises reacting corresponding phosphonic or pyrophosphonic acids or their functional derivatives with acid halides of the formula (CO)n Hal2 where n is 1 or 2.