6087-94-1

Usage

Uses

Used in Pharmaceutical Industry:
Bis(2-chloroethyl) chlorophosphate is used as an intermediate in the synthesis of Di-β,β''-Chloroethylphosphoric Acid (C366790) for its role in creating dialkyl hydrogen phosphates. These dialkyl hydrogen phosphates can undergo electrophilic trifluoromethylation, which leads to the production of trifluoromethyl phosphates. The addition of trifluoromethyl phosphates increases the lipophilicity of functional groups, enhancing the overall properties and effectiveness of the final pharmaceutical product.
Used in Chemical Synthesis:
In the chemical industry, bis(2-chloroethyl) chlorophosphate is used as a versatile building block for the creation of various organic compounds. Its reactivity with different functional groups allows for the development of a wide range of products, from pharmaceuticals to agrochemicals and other specialty chemicals. bis(2-chloroethyl) chlorophosphate's ability to participate in electrophilic trifluoromethylation reactions makes it a valuable asset in the synthesis of novel molecules with improved properties.

InChI:InChI=1/C4H8Cl3O3P/c5-1-3-9-11(7,8)10-4-2-6/h1-4H2

Upstream product

• 1070-42-4 di(2-chloroethyl)phosphite 
• 7782-50-5 chlorine 
• 1003-11-8 2-oxo-1,3,2-dioxaphospholane 
• 67-66-3 chloroform 
• 140-08-9 tris(2-chloro-ethyl)phosphite 
• 107-07-3 2-chloro-ethanol 
• 75-21-8 oxirane 
• 10025-87-3 trichlorophosphate 

Downstream Products

• 3040-56-0 bis(2-chloroethyl) phosphate 
• 53963-13-6 diphosphoric acid tetrakis-(2-chloro-ethyl ester) 
• 115752-37-9 (4-Amino-3-nitro-phenyl)-phosphoramidic acid bis-(2-chloro-ethyl) ester 
• 53461-82-8 bis-{2-[bis-(2-chloro-ethoxy)-phosphoryloxy]-ethyl} ether 

Relevant academic research and scientific papers

Reactivity of an electrophilic hypervalent iodine trifluoromethylation reagent with hydrogen phosphates - A mechanistic study

The electrophilic trifluoromethylation of hydrogen phosphates with the reagent trifluoromethyl-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole (1) was studied by means of initial rates determined for pseudo first order setups and subsequent Taft analysis of the calculated relative rates. A positive polar sensitivity factor, indicative of a negative charge forming during the rate-determining step, was found for the whole data set.

Ethyl octylphosphonofluoridate and analogs: Optimized inhibitors of neuropathy target esterase

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.

Process for preparing bis(2-haloalkyl) phosphoro-halidates

An improved process is disclosed for the preparation of bis(2-haloalkyl) phosphorohalidates. This process comprises the steps of reacting phosphorus trihalide with a stoichiometric excess of alkylene oxide to form tris(2-haloalkyl) phosphite, substantially eliminating the presence of unreacted alkylene oxide in the tris(2-haloalkyl) phosphite, and finally converting it to bis(2-haloalkyl) phosphorohalidate by reaction with halogen.