852-20-0

Basic information

• Product Name: 2,2'-thiobis[4-chloro-6-nitrophenol]
• Synonyms: 2,2'-thiobis[4-chloro-6-nitrophenol];oxynide;DS-6;4-chloro-2-(5-chloro-2-hydroxy-3-nitrophenyl)sulfanyl-6-nitrophenol
• CAS NO: 852-20-0
• Molecular Formula: C₁₂H₆Cl₂N₂O₆S
• Molecular Weight: 377.15684
• EINECS: 212-708-9
• Mol File: 852-20-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,2'-thiobis[4-chloro-6-nitrophenol](CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-thiobis[4-chloro-6-nitrophenol](852-20-0)
• EPA Substance Registry System: 2,2'-thiobis[4-chloro-6-nitrophenol](852-20-0)

Safety Data

• Hazardous Substances Data: 852-20-0(Hazardous Substances Data)

Usage

General Description

2,2'-thiobis[4-chloro-6-nitrophenol], also known as NTBC, is a chemical compound commonly used in the treatment of tyrosinemia, a rare genetic disorder that inhibits the body's ability to break down the amino acid tyrosine. NTBC works by inhibiting the enzyme 4-hydroxyphenylpyruvate dioxygenase, which helps to reduce the levels of toxic metabolites associated with the disorder. It is a yellow crystalline compound that is sparingly soluble in water and used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. NTBC is also used as a research tool in the study of tyrosinemia and related metabolic disorders. However, it is important to handle NTBC with caution as it may be harmful if swallowed, inhaled, or absorbed through the skin, and it should be stored in a cool, dry place away from incompatible materials.

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 articles and documents

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.

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.