1160-28-7

Usage

Chemical Properties

yellow to light brown powder

Upstream product

• 18704-37-5 quinoline-8-sulfonyl chloride 
• 63000-06-6 divinyltellane 
• 870-50-8 di-tert-butyl-diazodicarboxylate 
• 2801-16-3 sodium quinoline-8-thiolate 
• 126445-20-3 8-quinolyldisulphide ion 
• 64-17-5 ethanol 
• 32837-87-9 3-hydroxy-3-methyl-1-cyano-1-butyne 
• 754-34-7 1,1,1,2,2,3,3-heptafluoro-3-iodo-propane 

Downstream Products

• 104785-21-9 methyl N-phenylsulfonyl-8-quinolinesulfinimidate 
• 104765-37-9 C₁₇H₁₆N₂O₃S₂ 
• 70310-90-6 N,N'-bis(diphenyloxyphosphonyl)-8-quinolinesulfinamidine 
• 59195-20-9 8-vinylthioquinoline 
• 18704-37-5 quinoline-8-sulfonyl chloride 

Relevant academic research and scientific papers

Photochromic transformations in solutions of 8,8′-diquinolyl disulfide and di(mercaptoquinolinato)nickel(II)

The nature of intermediate species and their reactions were studied by laser pulse photolysis for a photochromic system consisting of 8,8′-diquinolyl disulfide (RSSR) and a planar NiII complex di(mercaptoquinolinato)nickel(II) (Ni(SR)2) in toluene and benzene solutions. Under exposure to laser radiation, disulfide RSSR dissociates to two RS? radicals, whose spectrum has an intense absorption band with a maximum at λ = 400 nm (ε = 8400 L mol-1 cm -1). The radicals disappear by recombination (2krec = 4.6 · 109 L mol-1 s-1). In the presence of the Ni(SR)2 complex, coordination of the radical (kcoord = 4.4 · 109 L mol-1 s-1) competes with recombination to form a radical complex RS?Ni(SR)2 having an intense absorption band with a maximum at 460 nm (ε = 16 600 L mol-1 cm-1). This species decays in the second-order reaction (2k = 4.6 · 104 L mol-1 s-1). Since the photochromic system returns to the initial state, the reaction of two radical complexes is assumed to produce radical recombination and reduction of the disulfide and Ni(SR)2 complex. Analysis of the kinetic data showed that some RS? radicals decay in the microsecond time interval due to the reaction with the RS?Ni(SR)2 radical complex (k = 3.1 · 109 L mol-1 s -1).

Synthesis of Symmetrical Thiosulfonates via Cu(OTf)2-Catalyzed Reductive Homocoupling of Arenesulfonyl Chlorides

A variety of symmetrical thiosulfonates are synthesized via Cu-catalyzed reductive homocoupling of aryl sulfonyl chlorides. This protocol uses organic amine acting as a mild reductant and low-cost copper as an effective catalyst. Such a reductive coupling process features a broad substrate scope and good functional group tolerance. Related thiosulfonate products can also be converted into diverse functional molecules.

Efficient regioselective synthesis of novel water-soluble 2h,3h-[1,4]thiazino[2,3,4-ij]quinolin-4-ium derivatives by annulation reactions of 8-quinolinesulfenyl halides

Regioselective synthesis of novel 2H,3H-[1,4]thiazino[2,3,4-ij]quinolin-4-ium derivatives has been developed by annulation reactions of 8-quinolinesulfenyl halides with vinyl chalcogenides (vinyl ethers, divinyl sulfide, divinyl selenide and phenyl vinyl

Synthesis, Characterization, and Theoretical Studies of cis -Dichloridobis(8-quinolinethiolato)tin(iv) and bis(8-Sulfanylquinolinium) Hexachloridostannate(iv) Derivatives

The structural characterisation of bis(8-sulfanylquinolinium) hexachloridostannate(iv) (2) is reported and the variable reaction behaviour of this compound in different solvents has been explored. In particular, attempted recrystallization of 2 from chloroform and dichloromethane affords two polymorphs of cis-dichloridobis(8-quinolinethiolato)tin(iv), 3m and 3t, respectively. Attempted recrystallization of 2 from methanol gives crystals of 8,8′-dithiodiquinolinium hexachloridostannate(iv) 4. When 2 is dissolved in dimethyl sulfoxide in the presence of air, it undergoes oxidation to afford diquinolinyl-8,8′-disulfide 5. The molecular structures of the isolated compounds 2-4 are unambiguously authenticated by single crystal X-ray diffraction studies. The electronic structure properties of all the isolated compounds 2-4 are thoroughly studied by DFT calculations.

Hydrazo coupling: The efficient transition-metal-free C-H functionalization of 8-hydroxyquinoline and phenol through base catalysis

Azodicarboxylate esters are common reagents in organic synthesis laboratories due to their utility in the Mitsunobu reaction. They can also be regarded as possible starting compounds for C-H functionalization, which up until now has been mainly achieved by transition-metal-catalyzed reactions. We have developed a novel reaction involving the quantitative coupling of 8-hydroxyquinoline or phenol with azodicarboxylate esters. The functionalization proceeds under mild base-catalyzed conditions selectively, and either the ortho-position of 8-hydroxyquinoline or para-position of the phenol/naphthol is involved in the reaction. This type of transformation can be considered as "hydrazo coupling" (by analogy with azo coupling). Herein, we discuss a plausible mechanism for this catalyzed substitution, backing up our findings with deuterium NMR experiments and by varying the starting compounds and bases. Using Boc-NN-Boc as a substrate, we have developed the convenient and efficient synthesis of (8-hydroxyquinolin-7-yl)hydrazines, as well as demonstrating a new stereoselective route for the synthesis of medicinally important 4-hydroxyphenylhydrazine for laboratory use, which almost doubles the yield of the common industrial process and reduces the number of synthetic steps. A new "one-pot" procedure for the synthesis of aromatic 8-hydroxyquinolin-7-yl hydrazones was applied.

Selective and simple phase transfer catalyzed synthesis of disulfides from thiols

Two novel methods of synthesis of disulfides from thiols or their Na salts in the phase transfer catalytic system CBr4/18-crown-6/benzene or toluene are developed and the products isolated in 67-8.8% yields.

Cyanoacetylene and Its Derivatives. XXI. Nucleophilic Addition of Mercaptoquinolines to Cyanoacetylenes

Reactions of 2-, 5- and 8-mercaptoquinolines with 3-phenylpropiolonitrile proceed in a regio- and stereoselective fashion, yielding 46-79% of (Z)-3-phenyl-3-quinolylthioacrylonitriles. Reactions of sodium 8-quinolinethiolate with 4-hydroxy-2-alkynenitriles result in formation of 4-hydroxy-3-(8-quinolylthio)-2-alkenenitriles.

Ion-radical perfluoroalkylation. Part 11. Perfluoroalkylation of thiols by perfluoroalkyl iodides in the absence of initiators

Perfluoroalkylation of aliphatic, aromatic and heterocyclic thiols by perfluoroalkyl iodides in the presence of Et3N appears to occur spontaneously under daylight or the usual laboratory lighting conditions at 20-22 deg C and is complete in 10-15 min to 2-3 h.An exception to this rule are thiols with a low nucleophilicity.The reaction is accompanied by thiol oxidation (2percent-3percent) and depends directly on the temperature, lighting, solvent polarity and electronic properties of the perfluoroalkylating agents and of the thiol substituents.At the same time, formation of diaryl disulphides frequently occurs contrary to above rules.The reaction mechanism is discussed. - Keywords: Ion-radical perfluoroalkylation; Thiols; Perfluoroalkyl iodides; Reaction mechanism; Nucleophilicity; NMR spectroscopy

Formation of Stable Aryldisulphide Ions in Dimethylacetamide from the Reaction of Sulphur with Thiolate Ions

The conditions for the formation of aryldisulphide ions, RS2- during the direct reaction of sulphur with thiolate ions RS- have been studied by the use of spectroelectrochemistry in dimethylacetamide.The series of derivatives examined was R = p-tolyl (1), phenyl (2), 8-quinolyl (3), 2- and 4-pyridyl (4), (5), N-oxido 4-pyridyl (6), 2- and 4-nitrophenyl (7), (8), and 2-(5-nitropyridyl) (9).Sulphur reaction leads to RS2- ions and preceded the oxidation to diaryldisulphide RS2R and polysulphide ions Sx-.With derivatives (1)-(3), both reactions are successive and practically stoicheiometric, while for derivatives containing electron-withdrawing groups (6)-(9), the equilibrium constants have been measured.Analysis of the reaction products by methylation of several solutions of thiolate ions in the presence of sulphur confirmed the possibility of obtaining aryldisulphide ions stabilized in aprotic dipolar media.