6374-26-1

Basic information

• Product Name: Diethyl phosphor(isothiocyanatidate)
• Synonyms: Diethyl phosphor(isothiocyanatidate)
• CAS NO: 6374-26-1
• Molecular Formula: C₅H₁₀NO₃PS
• Molecular Weight: 195.18
• Mol File: 6374-26-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Diethyl phosphor(isothiocyanatidate)(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl phosphor(isothiocyanatidate)(6374-26-1)
• EPA Substance Registry System: Diethyl phosphor(isothiocyanatidate)(6374-26-1)

Safety Data

• Hazardous Substances Data: 6374-26-1(Hazardous Substances Data)

Upstream product

• 505-14-6 thiocyanogen 
• 762-04-9 phosphonic acid diethyl ester 
• 2901-90-8 bis(diethoxyphosphoryl)disulphide 
• 151-50-8 potassium cyanide 
• 598-02-7 Diethyl phosphate 
• 592-87-0 lead(II) thiocyanate 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 814-49-3 diethyl chlorophosphate 
• 89430-21-7 Phosphoric acid benzo[1,3,2]dioxaphosphol-2-yl ester diethyl ester 
• 4972-37-6 methanesulfonic phosphoric anhydride, diethyl ester 
• 1147550-11-5 ammonium thiocyanate 
• 89430-31-9 C₁₁H₁₄NO₆P₂S⁽¹⁺⁾*CNS^(1-) 
• 540-72-7 sodium thiocyanide 
• 89430-18-2 Phosphoric acid 2,2-diisothiocyanato-1,3-dioxa-2λ⁵-phospha-indan-2-yl ester diethyl ester 

Downstream Products

• 66608-35-3 2,4-bis-(N'-diethoxyphosphoryl-thioureido)-toluene 
• 112626-21-8 N-[2-(4-chloro-phenylsulfanyl)-ethyl]-N'-diethoxyphosphoryl-thiourea 
• 598-02-7 Diethyl phosphate 
• 542-90-5 ethyl isothiocyanate 
• 4697-37-4 ethyl metaphosphate 
• 108753-09-9 cyclohexylthiocarbamoyl-amidophosphoric acid diethyl ester 
• 110475-25-7 N-diethoxyphosphinyl-N'-4-chloroanilinothiourea 
• 119013-34-2 bis-[4-(N'-diethoxyphosphoryl-thioureido)-phenyl]-methane 
• 109220-41-9 phenethylthiocarbamoyl-amidophosphoric acid diethyl ester 
• 58100-68-8 o-Phenylen-di(thiocarbamoyl)diphosphorsaeureamid-tetraethylester 
• 108629-76-1 (2-mercapto-phenylthiocarbamoyl)-amidophosphoric acid diethyl ester 
• 20446-91-7 (3-phenyl-thiohydrazinocarbonyl)-amidophosphoric acid diethyl ester 
• 108629-77-2 (3-hydroxy-phenylthiocarbamoyl)-amidophosphoric acid diethyl ester 
• 110378-14-8 o-tolylthiocarbamoyl-amidophosphoric acid diethyl ester 

Relevant articles and documents

Microwave-assisted solvent-free synthesis of pseudohalophosphates

A rapid, efficient, solvent-free, and catalyst-free procedure has been developed for the synthesis of pseudohalophosphates from phosphorochloridate and sodium (or potassium) pseudohalides under microwave irradiation. Diethyl, diisobutyl, and diphenyl phosphorazidates, phosphorocyanidates, and phosphor(isothiocyanidate)s 2a-2i were prepared in good yields under mild conditions. Copyright

Phase-transfer catalyzed pseudohalogenation of phosphorochloridates

Pseudohalogenation of phosphorochloridates by sodium pseudohalides with different phase transfer catalysts and solvents was optimized. Dialkyl and diaryl phosphorazidates phosphorocyanidates, and phosphor(isotniocyanidate)s were prepared in good yields from phosphorochloridates under two kinds of mild phase-transfer catalyzed conditions respectively.

Pseudohalogenation of phosphites

A new type of Atherton-Todd reaction for a convenient pseudohalogenation of phosphites has been developed. Direct azidation, cyanation, and thiocyanation of (RO)2P(O)H (R = Et, i-Bu, Ph) were accomplished readily with sodium pseudohalides in acetonitrile under mild modified Atherton-Todd conditions. The corresponding phosphorochloridates were demonstrated by GC/MS to be the intermediates. Pseudohalogenations of ethyl phenylphosphinate and diphenylphosphine oxide were also investigated.

Synthesis of N-(thio)phosphoryl-N′-2-benzoxazolyl semicarbazides

We prepared the benzoxazole derivatives bearing the (thio) phosphoryl moiety by addition reactions of 2-hydrazionbenzoxazole with isothiocyanato (thio) phosphates and characterized their structures by elementary analysis and 1H NMR and IR spectral data. From the results of biological activity screening, we found that these compounds possess some herbicidal, and plant growth regulator activities, and especially good fungicidal activity against Puccinia recondita.

NOVEL REACTIONS OF PENTACOORDINATE PHOSPHORUS SYSTEMS DERIVED FROM PYROCATECHOL

Monocyclic chlorophosphoranes 1 and 2 have been used as models for investigations of nucleophilic displacement reactions at the pentacoordinate phosphorus atom.The chlorine ligands of 1 and 2 can be exchanged by nucleophiles under very mild conditions.Synthesis of the pentacoordinate phosphorus systems 4 and 5 via the reactions of 1 and 2 with a variety of nucleophiles is demonstrated.Special attention is paid to the reactions of chlorophosphoranes with such nucleophiles as organic phosphorus acids and thiocyanates.

Anhydrides of Phosphorus and Sulfur Acids, 2. Mixed Anhydrides of Phosphoric, Phosphonic, and Phosphinic Acids with Sulfonic Acids and Sulfuric Monoimidazolide. New Methods of Synthesis, Novel Structures, Phosphorylating Properties

New applications of methods leading to anhydrides RR'P(O)OSO2R'' (1) are described: a) Reaction of acids RR'P(O)OH (2) with sulfonic imidazolides. b) Reaction of phosphorus imidazolides 4 with sulfonic acids and sulfonic anhydrides.New methods of synthesis of anhydrides 1 have been developed. c) Reaction of phosphorus acid silyl esters RR'P(O)OSiMe3 (9) with methanesulfonic and trifluoromethanesulfonic anhydrides. d) Reaction of bis(trimethylsilyl) tert-butylphosphonate (10) with methanesulfonic acid leading to tBuP(O)(OSO2Me)2 (11). e) Reaction of stannyl phosphate (EtO)2P(O)OSnMe3 (15) with methanesulfonic anhydride. f) Reaction of phosphorus acid silyl esters 9 with trimethylsilyl trifluoromethanesulfonate.All methods result in high yields and can be adapted to a variety of anhydrides 1 derived from phosphoric, phosphonic, and phosphinic acids on the one hand and methanesulfonic, trifluoromethanesulfonic acids and sulfuric monoimidazolide on the other.Phosphonium intermediates have been demonstrated by low temperature FT 31P NMR spectroscopy for reaction b) and c).The anhydrides 1 are readily converted into imidazolides 4 by the reaction with N-(trimethylsilyl)imidazole which proceeds via two distinct phosphonium intermediates.With neutral and weakly basic nucleophiles, the anhydrides 1 behave as phosphorylating agents.

SYNTHESIS OF ISOTHIOCYANATOPHOSPHORANES AND ISOTHIOCYANATOPHOSPHONIUM SALTS VIA OXIDATIVE ADDITION OF THIOCYANOGEN AND LIGAND SUBSTITUTION. NOVEL REAGENTS FOR CONVERTING HYDROXY GROUPS INTO THIOCYANATE AND ISOTHIOCYANATE FUNCTIONS UNDER MILD CONDITIONS

The oxidative addition of thiocyanogen to triphenilphosphine has been investigated by (31)P NMR spectroscopy showing the formation of the isothiocyanatophosphonium salt 8.The analogous reaction between thiocyanogen and alkyl o-phenylene phosphites 7 leads to diisothiocyanatophosphoranes 9.The same products were prepared via ligand substitution from the corresponding chlorophosphonium salt 12 and alkyldichloro-o-phenylene phosphoranes 13 by the action of potassium thiocyanate in the presence of 18-crown-6-ether or more conveniently using lead thiocyanate.The phosphonium salt 8 and phosphoranes 9 were employed as convenient novel reagents for converting hydroxy groups into thiocyanate and isothiocyanate function with high stereoselectivity under very mild conditions.The efficient synthesis of acylisothiocyanates RCONCS,R2P(O)NCS and R2P(S)NCS via addition of thiocyanogen to mixed anhydrides is of special interest.

THIOCYANATION OF DIALKYL PHOSPHITES AND THEIR STRUCTURAL ANALOGUES BY THIOCYANOGEN (SCN)2: MECHANISM AND STEREOCHEMISTRY

The thiocyanation of organophosphorus compounds containing >P(X)H functional groups (X=O,S) has been reinvestigated.The reaction was shown to be highly stereospecific and proceeds with the retention of configuration at P via the thiocyanidate >P(O)SCN structure.The thiocyanidates rearrange into the isothiocyanidates >P(O)NCS with a rate depending on structure of substrates and reaction conditions.The thiocyanation reaction of dialkyl phosphite and their structural analogues offers an excellent route to the isothiocyanidates >P(X)NCS and in some cases also the thiocyanidates >P(X)SCN.

P-Phenylene bis[imino(thiocarbonyl)] diphosphoramidic acid esters as anthelmentic agents

There are provided substituted p-phenylene bis[imino(thiocarbonyl)] diphosphoramidic acid esters, a method for the preparation of said esters and unsubstituted derivatives thereof and a method for controlling helminths in warm-blooded animals by administering to said animals an anthelmintically effective amount of said unsubstituted or substituted p-phenylene bis[imino(thiocarbonyl)] diphosphoramidic acid ester.