6409-58-1

Usage

Type of Compound

Sulfonic acid derivative

Structure

Benzene ring with two hydroxyl (-OH) groups and one sulfonic acid (-SO3H) group attached

Uses

+ Chemical intermediate in the synthesis of dyes, pigments, and pharmaceuticals
+ Reagent in analytical chemistry for the determination of various substances

Properties

+ Antioxidant capabilities
+ Potential use in the treatment of oxidative stress-related disorders

Interest

Held by researchers in various fields (industry and medicine) due to its versatile properties and potential applications.

InChI:InChI=1/C23H33NO4/c1-14(25)24-21(27)8-7-20-18-6-5-16-13-17(28-15(2)26)9-11-22(16,3)19(18)10-12-23(20,24)4/h5,17-20H,6-13H2,1-4H3

Upstream product

• 108-46-3 recorcinol 
• 103068-41-3 4-fluororesorcinol 
• 95-88-5 4-Chlororesorcinol 

Downstream Products

• 2321-07-5 fluorescein 
• 108-46-3 recorcinol 
• 2437-49-2 2,4,6-tribromoresorcinol 

Relevant academic research and scientific papers

Systematic evaluation of a new organic material: 1-methyl-1H-imidazol-3-ium-2,4,6-trinitrobenzene-1,3-bis(olate) for optoelectronics through spectral, structural, electrical, optical, quantum chemical and Hirshfeld surface studies

A new organic material, 1-methyl-1H-imidazol-3-ium-2,4,6-trinitrobenzene-1,3-bis(olate) (MITB), was synthesized and crystallized by solution growth-slow evaporation technique at ambient temperature. The characteristic functional groups in MITB were identified from FT-IR spectrum. 1H, 13C and DEPT-135 NMR spectroscopic techniques were used to ascertain types of carbons and protons in MITB. The compound crystallizes in the monoclinic system with a space group of P21/c. The electrostatic attraction between anions and cations stabilizes the crystal lattice and the N-H…O and C-H…O hydrogen bonds linking the cations and anions supplement the stable three dimensional networks. The material was thermally stable up to 178 °C. The molecular structure was optimized by Gaussian 09 program at B3LYP/6–311++G(d,p) level of basis set. Hydrogen bonding interactions are responsible for greater hyperpolarizability value of MITB and the value was found to be 34 times greater than that of reference material, urea. HOMO-LUMO, electrostatic potential surface and Mulliken atomic charges were calculated to explore covalent and non covalent interactions present in MITB. Hirshfeld surface analysis was carried out to estimate prominent covalent and non covalent interactions. Dielectric constant and dielectric loss have been determined to find MITB's suitability for optoelectronic applications.

Studies on synthesis, structural, luminescent and thermal properties of a new non-linear optical crystal: 4-amino-4H-1,2,4-triazol-1-ium-3-hydroxy-2,4,6-trinitrophenolate

A new organic proton transfer complex having NLO activity, 4-amino-4H-1,2,4-triazol-1-ium-3-hydroxy-2,4,6-trinitrophenolate (ATHTP), was crystallized to investigate the factors which stabilize the structure of the crystal. The compound crystallizes in triclinic system with space group P-1. Elemental analysis, thermal analysis, UV–Vis–NIR, FT-IR and NMR spectral analyses were carried out to characterize the crystal. Optical, spectral and thermal properties of the title crystal were analyzed to recommend the material for optical applications. Z-scan was used to measure the effective third-order nonlinear optical susceptibility and nonlinear refractive index. The crystal structure was determined using single crystal XRD method and the structure was optimized using Gaussian 09 program at B3LYP/6-311++G(d,p) level of basis set. This hydrogen bond interactions led to the increase in first-order hyperpolarizability of ATHTP and was 30 times greater than that of urea. Hirshfeld analyses surface analysis was carried out to explore intermolecular interactions in the crystalline state.

Reductive dehalogenation and dehalogenative sulfonation of phenols and heteroaromatics with sodium sulfite in an aqueous medium

Prototropic tautomerism was used as a tool for the reductive dehalogenation of (hetero)aryl bromides and iodides, or dehalogenative sulfonation of (hetero)aryl chlorides and fluorides, using sodium sulfite as the sole reagent in an aqueous medium. This protocol does not require a metal or phase transfer catalyst and avoids using organic solvent as the reaction medium. This method is especially suitable for substrates that readily tautomerize (such as 2-or 4-halogenated aminophenols and 4-halogenated resorcinols), for which dehalogenation or sulfonation proceeds under mild reaction conditions (≤60 °C). As sodium sulfite is an inexpensive, safe, and environmentally less hazardous reagent, this method has at least three potential applications: (i) in the deprotection of halogens as protecting groups, using sodium sulfite as a reducing agent; (ii) in the sulfonation of aromatic halides under mild reaction conditions avoiding hazardous and corrosive reagents/solvents; and (iii) in the transformation of toxic halogenated aromatics into less harmful compounds.

One step hair coloring compositions using salts

A hair coloring composition comprising the following two compositions which are mixed just prior to application to the hair: (a) a composition comprising a water-soluble peroxygen oxidizing agent; and (b) a composition comprising one or more oxidative hair coloring agents selected from the group consisting of an aromatic diamine, an amino phenol, a naphthol, a polyhydric phenol, a catechol and mixtures thereof; wherein the composition comprising one or more oxidative hair coloring agents further comprises al least one water soluble carbonate releasing salts; and optionally a water soluble ammonium salt, is described.

Transition metal complexes as dye forming catalysts in hair coloring compositions

A hair coloring composition comprising a first composition which comprises: (a) a dye forming transition metal salt or complex; which is first applied to the hair; and a second composition which comprises the following two compositions which are mixed just prior to application to the hair: (a) a composition comprising a water-soluble peroxygen oxidizing agent; and (b) a composition comprising one or more oxidative hair coloring agents selected from the group consisting of an aromatic diamine, an aminophenol, a polyhydric phenol a catechol and mixtures thereof.

Reactions of the dihydroxybenzenes and their methyl ethers with sulfur trioxide. The effect of initial sulfation on the sulfonation product distribution

The sulfation and sulfonation resulting from the reaction of the dihydroxybenzenes and their mono- and dimethyl ethers with SO3 in nitromethane have been studied, and their product distributions are reported.As to the non-hydroxy-substituent-containing substrates, 1,2-dimethoxybenzene (3) yields the 4-sulfonic acid (3-4-S) which, upon further sulfonation, yields a 1:4 mixture of the 3,5- and 4,5-S2.The 1,3- (6) and 1,4-isomer (9) yield initially the 4- and 2-S, respectively, and subsequently exclusively 6-4,6- and 9-2,5-S2, respectively.With the substrates containing one hydroxy substituent, the sulfonation isomer distribution is dependent on the SO3 to substrate ratio if the OH and OMe substituents are in ortho or para orientation, due to increasing sulfonation of the corresponding methoxyphenyl hydrogen sulfate.Thus, 2-methoxy- (2) and 4-methoxyphenol (8) with one equiv of SO3 at 0 deg C yield a 3:1 mixture of 2-4-S and 2-5-S and a 9:1 mixture of 8-2-S and 8-3-S, respectively, but, with >/= 4 equiv of SO3, the former reactant yields only 2-5-S and the latter only 8-3-S. 3-Methoxyphenol (5) yields initially a 1:1 mixture of the 4- and 6-sulfonic acid.Further sulfonation yields only 5-O,4,6-S3 which slowly cyclizes to the 1,3,2,4-benzodioxadithiin 2,2,4,4-tetraoxide derivative 11.As to the dihydroxy-containing substrates, 1,2-dihydroxybenzene (1) with 1 equiv of SO3 first yields the hydrogen sulfate 1-O-S which rearranges to 1-4-S; on using an excess of SO3, the eventual product is 1-O(2),4-S2.Similarly, the 1,4-isomer (7) with 1 equiv of SO3 yields initially 7-O-S which isomerizes to 7-2-S.With 6 equiv of SO3, initially 7-O,O-S2 is formed and subsequently its 2-sulfonic acid, which eventually cyclizes slowly to the 1,3,2,4-benzodioxadithiin 2,2,4,4-tetraoxide derivative 12.The 1,3-isomer 4 with 1 equiv of SO3 yields the 4-sulfonic acid.With 4 equiv of SO3, initially 4-O,O-S2 is formed and subsequently 4-4,O,O-S3, which is converted into both 4-O,O,4,6-S4 and the cyclization product 10.Eventually, small amounts of 4-O,2,4,6-S4 and 14-2,6-S2 are formed by transsulfonation.

Sulfonation and sulfation of 1,3-dihydroxybenzene and its methyl ethers in concentrated sulfuric acid

The homogeneous sulfonations of 1,3-dihydroxybenzene (1), its monomethyl (2) and dimethyl ether (3) in concentrated aqueous sulfuric acid at 25 deg C have been studied and isomer distributions and rate coefficients for the sulfonation of 1-3 and their monosulfonic acids are reported.The initial process, upon dissolution of the reactants, is protonation at C(4) and C(6).The subsequent sulfonation of the symmetrical reactants 1 and 3 yields the 4-sulfonic acids and that of 2 the 4- and 6-sulfonic acids, the ratio of which is 0.8 +/- 0.1 at 73.5percent H2SO4.The sulfonation of the 4-sulfonic acid of 1 (1-4-S) yields a mixture of 2,4- and 4,6-disulfonic acids, that of 2-4-S and 3-4-S yields the 4,6-S2 and that of 2-6-S gives a mixture of 2,6- and 4,6-S2.The disulfonic acids 1-2,4-S2 and 2-2,6-S2 both slowly isomerize to yield the 4,6-disulfonic acid isomers.At acid concentrations >= 82.2percent H2SO4, the disulfonic acids of 1 slowly yield 1-2,4,6-S3, whereas those of 2 and 3 are not further sulfonated.The absence of 2-2,4-S2 from 2-4-S and of 2-2,4,6-S3 is discussed in terms of conformer populations of the precursory sulfonic acid substrates.

Enzyme-activated oxidative process for coloring hair

An enzyme-based oxidative process for coloring hair wherein the hair is exposed to a solution having a pH of about 4 to about 10 and containing hydrogen peroxide, soybean peroxidase enzyme and one or more oxidation dye precursors.