4862-09-3

Upstream product

• 100-53-8 phenylmethanethiol 
• 5275-46-7 2-nitro-2-nitrosopropane 
• 1158952-66-9 (iPr)2TpZn(nitrite-κ2O,O') 

Downstream Products

• 150-60-7 dibenzyl disulphide 
• 16302-98-0 petivericin 
• 16601-40-4 S-benzyl phenyl-methanethiosulfonate 
• 100-52-7 benzaldehyde 
• 1071983-16-8 C₂₆H₂₂NO₂PS 
• 1137591-10-6 C₂₇H₂₄NOPS₂ 

Relevant academic research and scientific papers

Dinitrogen tetroxide-impregnated charcoal (N2O 4/charcoal): Selective nitrosation of amines, amides, ureas, and thiols

Efficient N-nitrosation of amines, amides, and ureas, and also S-nitrosation of thiols were performed with dinitrogen tetroxide impregnated on activated charcoal (N2O4/charcoal) in CH 2Cl2 at room temperature. High selectivity was observed for N-nitrosation of dialkyl amines, N-alkylamides and N-alkylureas. Dealkylation and N-nitrosation of trialkylamines were also performed by this reagent. Copyright Taylor & Francis, Inc.

An efficient method for production and storage of unstable S- nitrosothiols under mild and heterogeneous condition with sodium nitrite and oxalic acid dihydrate

Thiols can be readily converted to their corresponding nitrosothiols with a combination of oxalic acid and sodium nitrite in t-butanol at room temperature (26-30 °C). The reaction mixture could be solidified with decreasing its temperature to, 15 °C and w

Conversion of nitrite to nitric oxide at zinc via S-nitrosothiols

Nitrite is an important reservoir of nitric oxide activity in the plasma and cells. Using a biomimetic model, we demonstrate the conversion of zinc-bound nitrite in the tris(pyrazolyl)borate complex iPr2TpZn(NO 2) to the corresponding S-nitrosothiol RSNO and zinc thiolate iPr2TpZn-SR via reaction with thiols H-SR. Decomposition of the S-nitrosothiol formed releases nitric oxide gas.

Establishment of the C-NO bond dissociation energy scale in solution and its application in analyzing the trend of NO transfer from C-nitroso compound to thiols

(Chemical Equation Presented) The first set of experimentally determined C-NO bond homolytic and heterolytic dissociation enthalpies in solution is derived by using direct titration calorimetry combined with appropriate electrode potentials through thermodynamic cycles. The homolytic bond dissociation energy scale (BDEs) of the corresponding C-NO bonds in the gas phase was also calculated at the MP2/6-311+G**//B3LYP/6-31G* level and BP86/6-31G*//B3LYP/6-31G* level of theory for the purpose of comparison. The C-NO and S-NO bond thermodynamic parameters were used to predict the trend of NO transfer from C-nitroso substrates to thiols in acetonitrile solution.

Silica-acetate complex of N2O4: A heterogeneous reagent for the selective nitration of phenols and nitrosation of thiols

Complexation of gaseous N2O4 with acylated silica gel affords an addition compound, which is an efficient heterogeneous reagent for the selective mono- and dinitration of phenol, substituted phenols and nitrosation of thiols.

Silica-polyethyleneglycols/N2O4 complexes as heterogeneous nitrating and nitrosating agents

Silica-chloride was reacted with different quantities of H(OCH2CH2)nOH (n = 2-4) to furnish silica-based linear polyethylene glycols and cyclic polyethylene glycolic ethers. The N2O4 complex of silica-tetraethylene glycolic ether (III) was selected and used as a stable, cheap, and heterogeneous silica-based reagent for the selective mono- and dinitration of phenols and nitrosation of thiols.

A kinetic study of S-nitrosothiol decomposition

Under anaerobic conditions S-nitrosothiols 1a-e undergo thermal decomposition by homolytic cleavage of the S-N bond; the reaction leads to nitric oxide and sulfanyl radicals formed in a reversible manner. The rate constants, k1, have been determined at different temperatures from kinetic measurements performed in refluxing alkane solvents. The tertiary nitrosothiols 1c (k1(69°C) = 13 × 10-3 min-1) and 1d (k1(69°C) 91 × 10-3 min-1) decomposed faster than the primary nitrosothiols 1a (k1(69°C) = 3.0 × 10-3 min-1) and 1b (k1(69°C) = 6.5 × 10-3 min-1). The activation energies (E#= 20.5 - 22.8 Kcal mol-1) have been calculated from the Arrhenius equation. Under aerobic conditions the decay of S-nitrosothiols 1a-e takes place by an autocatalytic chain-decomposition process catalyzed by N2O3. The latter is formed by reaction of dioxygen with endogenous and/or exogenous nitric oxide. The autocatalytic decomposition is strongly inhibited by removing the endogenous nitric oxide or by the presence of antioxidants, such as pcresol, β-styrene, and BHT The rate of the chain reaction is independent of the RSNO concentration and decreases with increasing bulkiness of the alkyl group; this shows that steric effects are crucial in the propagation step.

Dinitrogen tetroxide supported on polyvinylpyrrolidone (PVP-N2O4): A new nitrosating and coupling agent for thiols and a selective oxidant for sulfides and disulfides

Gaseous N2O4 was immobilized on polyvinylpyrrolidone to give a stable polymeric reagent. Thiols were converted to S-nitrosothiols (thionitrites) using this new nitrosating agent in n-hexane or CHCl3 at 10°C. With this reagent, thiols were also converted into their corresponding disulfides. Selective oxidation of sulfides to sulfoxides and disulfides to thiosulfonates can also be achieved by this reagent at room temperature. By using an excess of the reagent, the selective one-pot synthesis of thiosulfonates from thiols at room temperature was also performed.

S-nitrosothiol and disulfide formation through peroxynitrite-promoted oxidation of thiols

Peroxynitrite reacts with thiols 1 at acidic pH to give the corresponding S-nitrosothiols 2 and disulfides 3. The formation of nitrosothiols 2, the yield of which is strongly pH-dependent, can be rationalized in terms of acid-catalyzed decomposition of the undissociated HPN, probably through the intermediacy of the protonated form H2PN+, leading to a species, X-NO, capable of nitrosating the thiol function. In contrast, the formation of disulfides 3 occurs in a manner independent of the pH, without the intermediacy of sulfanyl radicals. Under basic conditions, the peroxynitrite anion (PN) oxidizes the thiolate ion to sulfanyl radicals, eventually leading to disulfide 3, or undergoes a thiol-catalyzed decomposition. The former is the exclusive reaction exhibited by peroxynitrite at pH > 13.

A convenient method for production of thionitrites and disulfides under mild and heterogeneous condition

Thiols can be readily converted to their corresponding thionitrite with a combination of inorganic acidic salts and sodium nitrite in dichloromethane at room temperature. Disulfides result from the homolytic cleavage of the sulfur-nitrogen bond of the unstable thionitrite and subsequent coupling of the resultant thiyl radicals.