381-45-3Relevant academic research and scientific papers
Trichloroisocyanuric acid-KF as an efficient reagent for one-pot synthesis of dialkylfluorophosphates from dialkylphosphites
Acharya,Gupta,Pardasani, Deepak,Dubey,Kaushik
, p. 3760 - 3765 (2008)
Trichloroisocyanuric acid-KF afforded dialkylfluorophosphates from dialkylphosphites at room temperature through a facile electrophilic- nucleophilic metathesis. Copyright Taylor & Francis Group, LLC.
Dichlorodimethylhydantoin-KF as an efficient reagent for one pot synthesis of dialkylfluorophosphates from dialkylphosphites
Gupta,Acharya,Dubey,Kaushik
, p. 226 - 229 (2008/09/16)
Organic-inorganic hybrid reagent dichlorodimethylhydantoin-KF (DCDMH-KF) mixture was explored as an efficient reagent for the direct conversion of dialkylphosphites to their corresponding dialkylfluorophosphates at room temperature and in shorter reaction times through a facile electrophilic-nucleophilic metathesis.
Single step fluorination of dialkylphosphites: trichloroacetonitrile-KF as an efficient reagent for the synthesis of dialkyl fluorophosphates
Gupta,Acharya,Pardasani,Dubey
, p. 2232 - 2235 (2008/09/19)
The use of trichloroacetonitrile and KF mixture is described as an efficient reagent for the direct conversion of dialkylphosphites to their corresponding dialkyl fluorophosphates via in situ formation of dialkyl chlorophosphates in one-pot.
Ethyl octylphosphonofluoridate and analogs: Optimized inhibitors of neuropathy target esterase
Wu,Casida
, p. 1070 - 1076 (2007/10/03)
The relation between organophosphorus-induced delayed neuropathy (OPIDN) and brain neuropathy target esterase (NTE) inhibition is further examined in hens by structure-activity studies leading to the most potent in vitro NTE inhibitors known, which are then examined for their neuropathic effects in vivo in hens. The principal compounds studied are alkyl alkylphosphonofluoridates and dialkyl phosphorofluoridates. Potencies that exceed those of any previous inhibitors under the standard in vitro NTE assay condition are achieved with alkyl octylphosphonofluoridates (ethyl, isopropyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, and 3-iodopropyl), 2-iodoethyl hexylphosphonofluoridate, and dialkyl phosphorofluoridates [ethyl, nonyl; di(2-iodoethyl); di(3-iodopropyl); dipentyl]. The concentration for 50% NTE inhibition (I50) of these compounds is 0.04-0.14 nM. Thirty-eight less active analogs including aryl phosphonates and aryl phosphates give I50s of 0.27-4730 nM. For highest potency the summation of length of the alkyl and alkoxy groups on phosphorus should be 12-16 atoms (carbons, oxygens, and phosphorus) (a terminal iodo substituent in this relationship is equivalent to a propyl group). In general, the phosphonofluoridates and phosphorofluoridates are more active than analogs with leaving groups other than fluorine, i.e., phenoxy, 4-nitrophenoxy, 4-cyanophenoxy, 3,4-dichlorophenoxy, and 4H-1,3,2-benzodioxaphosphorin. Considering the exceptional potencies of ethyl and 2-iodoethyl octylphosphonofluoridates (I50s of 0.04 and 0.09 nM, respectively), it is not surprising that at ip doses of 10-30 mg/kg they inhibit brain NTE by 82-97% 48 h after treatment. However, unexpectedly, only the ethyl but not the 2-iodoethyl compound induces OPIDN, possibly associated with the greater ease of aging for NTE inhibited with the ethyl than the 2-iodoethyl compound (as observed in vitro both spontaneously and on induction by potassium fluoride). The high potency of ethyl octylphosphonofluoridate and several analogs as NTE inhibitors suggests that they are useful probes in determining the toxicological features of this secondary lesion for organophosphorus poisoning.
Fluorination of phosphorus(+3) derivatives by xenon difluoride
Lermontov, S. A.,Popov, A. V.,Zavorin, S. I.,Sukhojenko, I. I.,Kuryleva, N. V.,et al.
, p. 233 - 236 (2007/10/02)
Xenon difluoride, XeF2, effectively fluorinates various phosphorous acid derivatives as well as hydrophosphoryl compounds.Arbuzov rearrangement is followed by i-Bu --> t-Bu isomerization in the case of i-BuOPF2.
THE FLUORINATION OF HYDROPHOSPHORYL COMPOUNDS USING 2-HYDROPERFLUOROPROPYL AZIDE
Lermontov, S. A.,popov, A. V.,Sukhozhenko, I. I.,Pushin, A. N.,Martynov, I. V.
, p. 839 - 841 (2007/10/02)
2-Hydroperfluoropropyl azide efficiently fluorinates hydrophosphoryl compounds to give the corresponding P(V) acid fluorides.
