852-20-0

Usage

Uses

Used in Medical Applications:
2,2'-thiobis[4-chloro-6-nitrophenol] is used as a therapeutic agent for the treatment of tyrosinemia, a rare genetic disorder. It functions by inhibiting the enzyme 4-hydroxyphenylpyruvate dioxygenase, which helps to reduce the levels of toxic metabolites associated with the disorder, thereby alleviating the symptoms and improving the patient's quality of life.
Used in Pharmaceutical Synthesis:
2,2'-thiobis[4-chloro-6-nitrophenol] is used as an intermediate in the synthesis of various pharmaceuticals. Its chemical properties make it a valuable component in the development of new drugs and medications.
Used in Agrochemical Synthesis:
2,2'-thiobis[4-chloro-6-nitrophenol] is also used as an intermediate in the synthesis of agrochemicals, contributing to the development of new products for agricultural applications.
Used in Research:
2,2'-thiobis[4-chloro-6-nitrophenol] is used as a research tool in the study of tyrosinemia and related metabolic disorders. It aids scientists in understanding the underlying mechanisms of these conditions and in the development of potential treatments and therapies.

Upstream product

• 97-24-5 4,4'-dichloro-2,2'-thiodiphenol 

Downstream Products

• 40654-56-6 5,5'-dichloro-3,3'-dinitro-2,2'-dihydroxydiphenyl sulfone 
• 283178-36-9 2,10-dichloro-6-(4'-methylphenoxy)-4,8-dinitrodibenzo[d,g][1,3,6,2]dioxathiaphosphocin-6-oxide 

Relevant academic research and scientific papers

Synthesis and spectral studies (see abstract)

Several novel bis(2-chloroethyl)aminophosphoryl-containing compounds have been prepared as potential anticancer agents. 2,10-Dichloro-6-[bis(2-chloroethyl)]amino-4,8-dinitrodibenzo[d,g][1,3,6,2]- dioxathiaphosphocin 6-oxide (5), 2-bis(2-chloroethyl)amino-1,3, 2-dioxaphosphorinane 2-oxide (13), and 8-bis(2-chloroethyl)amino-6H-dinaphtho[2,1-d:1prime;,2′]1,3,2- dioxaphosphocin 8-oxide (15) were synthesized from a reaction of equimolar quantities of the corresponding precursor diols 3, 12, and 14 with coreagent N,N-bis(2-chloroethyl)-phosphoramidic dichloride (1) at various temperatures in dry toluene/ether in the presence of triethylamine. In addition, 2-bis(2-chloroethyl)amino-2,3-dihydro-5-thiophenoxy-1H-1,3,2- benzodiazaphosphole 2-oxide (9) and 2-bis(2-chloroethyl)amino-1,2,3,4-tetrahydro-1,3,2-benzodiazaphosphorinane 2-oxide (11) were derived from 4-thiophenoxy-1,2-diphenyldiamine (8) and 2-aminobenzylamine (10) respectively, under similar conditions. Interestingly, attempted oxidation of 5 to the corresponding sulfone 7 by H2O2 (30%) in acetic acid yielded only sulfoxide 6 [2,10-dichloro-6-bis(2-chloroethyl)amino-4,8-dinitrodibenzo[d,g][1,3,6,2] dioxathiaphosphocin 6-oxide}. In an alternative approach, oxidation of 5,5′-dichloro-3,3′-dinitro-2,2′-dihydroxydiphenyl sulfide (3) with H2O2 (30%) in acetic acid formed the corresponding sulfone 4. However, attempted cyclization of 4 with 1, in the presence of triethylamine, to give the sulfone expected from 5 was unsuccessful. NMR analysis of 6 suggests the presence of two conformers in solution.

Synthesis and spectral studies of novel 2-chloroethyl dioxa / dioxathiaphosphocins and benzodiazaphosphole 2/6/8-oxides

A new class of phosphorates, 2, 10-dichloro-12-trichloromethyl-6-(2-chloroethyl)-12H-dibenzo [d,g] [1,3,2]dioxaphosphocin 6-oxide 3a, 2,10-dichloro-6-(2-chloroethyl) dibenzo [d,g] [1,3,6,2] dioxathiaphosphocin 6-oxide 3b, 8-(2-chloroethyl)-16H-dinaphtho[2,1-d:1,2′-g] 1,3,2-dioxaphosphocin 8-oxide 5, 2, 10-dichloro-6-(2-chloroethyl)-4,8-dinitrodibenzo[d,g] [1,3,6,2] dioxathiaphosphocin 6-oxide 9 and 2-(2-chloroethyl)2,3-dihydro-5-thiophenoxy-1H-1,3,2-benzodiazaphosphole 2-oxide 13 have been synthesized from reactions of equimolar quantities of diols (2a,2b,4,7)/diamine (12) with 2-chloroethyl phosphonyl dichloride 1 at various temperatures in dry toluene in the presence of triethylamine. Oxidation studies with H2O2 (30%) in acetic acid showed interesting results. Compound 9 on oxidation yielded only the corresponding 12-sulphoxide (10) and not its sulphone (11). But similar oxidation of 13 afforded sulphone (14), thus showing that steric and electronic factors control the oxidation process. Alternative approach for the preparation of 11 by oxidation of 7 to sulphone 8 and its cyclocondensation with 1 were unsuccessful due to the existence of strong intramolecular H-bonding. Their IR, 1H, 13C, 31P NMR and mass spectral data were analyzed.

A facile synthesis and antimicrobial activity of 2,10-dichloro-6- (aryloxy/thiophenoxy)-4,8-dinitrodibenzo[d,g][1,3,6,2]dioxathiaphosphocin-6- oxides

Novel 6-substituted 2,10-dichloro-4,8- dinitrodibenzo[d,g][1,3,6,2]dioxathiaphosphocin-6-oxides 4 were synthesized by reacting 5,5'-dichloro-3,3'-dinitro-2,2'-dihydroxydiphenyl sulfide (2) with different aryl phosphorodichloridates, trichloromethylphosphonic dichloride and O-2-chloroethyl phosphoryldichloride (3) in the presence of triethylamine at 55-60°. Some of these compounds are prepared by reacting the monochloride, 2,6,10-trichloro-4,8- dinitrodibenzo[d,g][1,3,6,2]dioxathiaphosphocin-6-oxide (5) in situ with substituted phenols and thiols. 5 is prepared by condensing 2 with phosphorus oxychloride. The 1H nmr chemical shifts of the dibenzodioxathiaphosphocin moiety indicates the presence of more than one conformer in solution. However the presence of more than one conformer in each example cannot be entirely eliminated. Interestingly 4d on oxidation to 12-sulphone by H2O2 in acetic acid medium yielded only 12-sulphoxide 6a. The ir, 1H, 13C, 31P nmr and mass spectral data are discussed. Some of these compounds were screened for antifungal activity against Curvularia lunata and Aspergillus niger and antibacterial activity on Bacillus subtilis and Klebsiella pneumoniae. A few of them possess significant activity.