3497-00-5

Usage

Uses

Used in High-Refractive-Index Material Industry:
PHENYLTHIOPHOSPHONIC DICHLORIDE is used as a precursor for the synthesis of high-refractive-index materials. These materials are essential in the production of advanced optical components, such as lenses and filters, that require high light refraction for improved performance.
Used in Chemical Synthesis:
As a thiophosphonate, PHENYLTHIOPHOSPHONIC DICHLORIDE serves as a key intermediate in the synthesis of various organic and inorganic compounds. Its unique chemical structure allows it to participate in a range of reactions, making it a valuable building block for the development of new materials and pharmaceuticals.
Used in Research and Development:
Due to its reactivity and versatility, PHENYLTHIOPHOSPHONIC DICHLORIDE is often utilized in research and development laboratories for the exploration of new chemical reactions and the creation of novel compounds. Its properties make it an attractive candidate for studying various aspects of chemical reactivity and bonding.

Air & Water Reactions

Flammable. Decomposes to give hydrochloric acid in water, although this reaction is slow. The reaction becomes vigorous if the water is hot.

Reactivity Profile

PHENYLTHIOPHOSPHONIC DICHLORIDE is water reactive. Incompatible with strong oxidizing agents, alcohols, amines, alkali. Contact with active metals generates flammable hydrogen gas. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

Health Hazard

CORROSIVE and/or TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Fire will produce irritating, corrosive and/or toxic gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Contact with molten substance may cause severe burns to skin and eyes. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

EXCEPT FOR ACETIC ANHYDRIDE (UN1715), THAT IS FLAMMABLE, some of these materials may burn, but none ignite readily. May ignite combustibles (wood, paper, oil, clothing, etc.). Substance will react with water (some violently), releasing corrosive and/or toxic gases and runoff. Flammable/toxic gases may accumulate in confined areas (basement, tanks, hopper/tank cars, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water. Substance may be transported in a molten form.

Safety Profile

A corrosive. When heated to decomposition it emits toxic vapors of SOx and POx.

InChI:InChI=1/C6H5Cl2PS/c7-9(8,10)6-4-2-1-3-5-6/h1-5H

Upstream product

• 824-72-6 P,P-dichlorophenylphosphine oxide 
• 644-97-3 Dichlorophenylphosphine 
• 7782-50-5 chlorine 
• 71-43-2 benzene 
• 603-35-0 triphenylphosphine 

Downstream Products

• 2453-29-4 bis-aziridin-1-yl-phenyl-phosphine sulfide 
• 16906-06-2 phenyl-thiophosphonic acid O,O'-diallyl ester 
• 18995-01-2 N,N',P-triphenylphosphonothioic diamide 
• 20148-06-5 O-phenyl phenylphosphonothiochloridate 
• 33424-34-9 phenyl-thiophosphonic acid O-methyl ester-O'-(2-nitro-phenyl ester) 
• 102666-48-8 phenyl-thiophosphonic acid O,O'-bis-(2-dimethylaminomethyl-phenyl ester) 
• 6231-03-4 diethyl phenylphosphonothioate 
• 5075-13-8 O-ethyl phenylphosphonochloridothioate 
• 5395-21-1 phenyl-phosphonothioic acid dihydrazide 
• 3969-46-8 phenylphosphonothioic diamide 
• 109018-70-4 3,6-diphenyl-[1,2,4,5,3,6]tetraazadiphosphinane-3,6-disulfide 
• 55781-98-1 2-Phenyl-1,3,2-oxathiaphosphepan-2-sulfid 
• 73577-36-3 phenyl phosphonomorpholinylamidochloridothioate 
• 34670-65-0 7-phenoxy-1,4-diaza-7-phospha-bicyclo[2.2.1]heptane 7-sulfide 

Relevant academic research and scientific papers

Green synthesis of dichlorophenylphosphine sulfide using chloroaluminate ionic liquids as a catalyst

Triethylhydrogenammonium chloride-XAlCl3 Ionic Liquids (ILs) were used as a catalyst for the clean synthesis of dichlorophenylphosphine sulfide. Two synthesis routes were investigated; one of them was a reaction of sulfur and Dichlorophenylphosphine (DCPP), and another was a one-pot reaction of benzene, phosphorus, chloride, and sulfur. Effects of the ILs composition and reaction time and the quantity of the ILs on the reactions were studied. A simple product isolation procedure was achieved. The ILs showed reusable and low-consumption characters in the reaction of sulfur and DCPP. Thus the triethylhydrogenammonium chloride-XAlCl3 ILs gave this reaction a green character. Copyright Taylor & Francis Group, LLC.

Density, viscosity, and vapor pressure of dichlorophenylphosphine sulfide

The density and viscosity of dichlorophenylphosphine sulfide (C 6H5PSCl2) over a temperature range of (303.16 to 423.40) K were measured. The vapor pressure of dichlorophenylphosphine sulfide in the range of (417.83 to 448.12) K were measured by a static method. The density data were fitted to a second-order polynomial, the viscosity data were fitted to the Andrade equation, and the results of vapor pressure data were fitted to the Antoine equation. The density data and vapor pressure data of dichlorophenylphosphine sulfide were compared with literature values.

Structure and properties of halogen-free flame retardant and phosphorus-containing aromatic poly(1,3,4-oxadiazole)s fiber

In order to improve the flame retardance of aromatic polyoxadiazole (p-POD) fiber, a series of phosphorus-containing PODs (pho-POD) were synthesized by introducing triaryl phosphine oxide (TPO) units into the main chains of p-POD using hydrazine sulfate, terephthalic acid and bis(p-carboxy)phenyl phosphine oxide (BCPPO) as monomers, and then halogen-free flame resistant pho-POD fibers were obtained from wet spinning. The structure and properties of the pho-POD fibers were characterized and measured in detail using the methods of wide-angle X-ray diffraction (WAXD), scanning electron microscopy (SEM), thermogravimetric analysis (TGA), the limiting oxygen index (LOI), oxygen bomb calorimeter, Pyrolysis-Gas Chromatography/Mass Spectrometry (Py-GC/MS) etc. The results show that the introduction of TPO units resulted in the weakening of the crystallization ability, the formation of the poriferous and lax interior structure, the slight decrease in the thermal stability and mechanical properties of the POD fibers. However, the value of LOI obviously increased from 28% to 35%, and the gross heat of combustion (GHC) decreased from 19.72 MJ kg?1 to 17.84 MJ kg?1 with the increase in the content of the BCPPO. Moreover, the combustion residue of pho-POD fiber revealed a smooth, dense and non-porous carbon layer, which could effectively play a role of oxygen barrier and enhance the flame resistance. From the above results, it can be concluded that the flame resistance of the POD fiber could be improved significantly after introducing the TPO unit. The results of Py-GC/MS illustrate that the TPO unit of pho-POD could inhibit the production of volatile products, which could be confirmed that the mechanism of enhancing the flame retardancy by introducing TPO units was mainly the flame retardation of the condensed phase.

Synthesis of novel chiral 2-Oxo- And 2-thio-1,3,2-oxazaphospholidines via asymmetric cyclization of L-methionol with (thio)phosphoryl dichlorides

In order to search for novel antitumor and antiviral agents with high activity and low toxicity, a series of chiral 2-thio(oxo)-1,3,2- oxazaphospholidines were synthesized via the reaction of L-methionol with all kinds of (thio)phosphoryl dichlorides in THF in the presence of triethylamine at room temperature. The structures of all of the new compounds were confirmed by elemental analyses, 1H, 31P NMR, and 1R spectra.

Reactivity of X3P compounds with elemental sulfur, carbon disulfide or both, to yield X3PS, X3RCS2 or X3P.Sn.CS2 adducts

Kinetic constants k2 have been obtained for the reaction of sulfur with 25 PIII compounds in toluene or hexane. In the series PhnMe3-nP (n = 1-3) or PhnBu3-nP (n = 0-3), log k2 decreases linearly with Σχi (χi=Tolman's electronic parameter of each ligand on P), taken as a gauge for the donor strength of P. Dramatic deviations from additivity are observed for the series PhnP(OEt)3-n, PhnP(OEt)3-n, and BunP(OEt)3-n(n = 0-3); the deviation is smaller for PhnPCl3-n, and even smaller for PhnP(NEt2)3-n . The results are discussed in terms of P-coordination (PIV vs. PV), stability and geometry of the intermediate X3P.S8 or of the transition state leading to this adduct, emphasis being laid on the donor/acceptor character of the P site. A similar dependence on X governs the reactivity of X3P with S8, CS2 or both, to give X3PS, X3P.CS2 (binary red adduct) or X3P.Sn.CS2 (ternary yellow adduct) respectively; an explanation for this parallelism is proposed.

Studies on chiral thiophosphoric acids and their derivatives 16. - The asymmetric cyclization of L-(+)-prolinol with (thio)phosphoro(-no)dichloridates

The cyclizations of L-(+)-prolinol 5 with (thio)phosphoro(-no)dichloridates 6 give 1,2,3-azaphosphaoxabicyclo[3.3.0]octanes 7 consisting of unequal amounts of diastereoisomers, eight pairs of which have been successfully resolved by silica gel column chromatography or recrystallization. The influences of reaction temperature, solvent and substrate concentration upon the asymmetric induction have also been investigated.

DIE STRUKTUR VON ALKYL- UND ARYLPERTHIOPHOSPHONSAEUREANHYDRIDEN IN LOESUNG

The analysis of 1H-, 31P- and 13C-NMR spectra of different alkyl- and arylperthiophosphonic acid anhydrides shows that these compounds prefer a dimeric structure in solution.They exist as 2,4-diorganyl-2,4-dithioxo-1,3,2λ5,4λ5-dithiadiphosphetanes.Most of the perthiophosphonic acid anhydrides form configuration isomers which differ in the position of the thioxo groups relatively to the ring plane.The concentration of the trans-isomer is generally larger than that of the cis-isomer.The ratio of the concentration of both isomers is obviously determined by the polarity of the solvent used.Mixing of solutions of different perthiophosphonic acid anhydrides results in unsymmetrical compounds also existing in cis- and trans-configuration. 31P chemical shifts and geminal P-P coupling constants for symmetrical and unsymmetrical perthiophosphonic acid anhydrides are presented and discussed. - Key words: 31P chemical shifts; P-P coupling constants; perthiophosphonic acid anhydrides; mixed perthiophosphonic acid anhydrides; configuration isomers; 2,4-diorganyl-2,4-dithioxo-1,3,2λ5,4λ5-dithiadiphosphetanes.

Process for making alkyl or arylthiophosphonic acid

The disclosure relates to a process for making alkyl or arylthiophosphonic acid dichlorides by reacting alkyl or aryldichlorophosphanes with sulfur at a temperature above the melting point of sulfur and in the presence of a catalyst. More particularly, the reaction is effected at a temperature between the melting point of sulfur and the boiling point of the resulting alkyl or arylthiophosphonic acid dichloride and in the presence of a catalyst of the following general formula I or II STR1 in which R1, R2, R3 and R4 stand for identical or different alkyl, aryl, alkaryl, or aralkyl groups having from 1 to 22 carbon atoms and A stands for the anionic group of an organic or inorganic acid.

Process for preparing alkyl or aryl phosphorus halides and mixed isomers thereof

Alkyl or aryl phosphonic or phosphonothioic dihalides and phosphinic or phosphinothioic monohalides are prepared by reacting an alkyl halide or aryl halide respectively with a tri-valent phosphorus compound having at least two halogens attached thereto, and preferably three two halogens such as phosphorus trihalide, in the presence of P4 O10 or P4 S10 under at least autogenous pressure at a temperature of from 200° C. to 450° C. The compounds obtained are useful as constituents in insecticides, fungicides, pharmaceuticals, and as intermediates in preparation of other organophosphorus compounds.