15509-33-8

Basic information

• Product Name: 5-hydroxytoluene-2,4-disulphonic acid
• Synonyms: 5-hydroxytoluene-2,4-disulphonic acid;4-Hydroxy-6-methyl-1,3-benzenedisulfonic acid;Einecs 239-537-2
• CAS NO: 15509-33-8
• Molecular Formula: C₇H₈O₇S₂
• Molecular Weight: 268.26422
• EINECS: 239-537-2
• Mol File: 15509-33-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.792g/cm³
• Refractive Index: 1.635
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Water (Sparingly)
• PKA: -0.96±0.50(Predicted)
• CAS DataBase Reference: 5-hydroxytoluene-2,4-disulphonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-hydroxytoluene-2,4-disulphonic acid(15509-33-8)
• EPA Substance Registry System: 5-hydroxytoluene-2,4-disulphonic acid(15509-33-8)

Safety Data

• Hazardous Substances Data: 15509-33-8(Hazardous Substances Data)

Usage

Uses

4-Hydroxy-6-methyl-1,3-benzenedisulfonic Acid is a by-product during the synthesis of 4-Hydroxy-2-methylbenzenesulfonic Acid (H972825), which is derived from m-Cresol (C781915), one of the components that make up liquid rice hull smoke, and may contribute to its anti-inflammatory effects in mice.

InChI:InChI=1/C7H8O7S2/c1-4-2-5(8)7(16(12,13)14)3-6(4)15(9,10)11/h2-3,8H,1H3,(H,9,10,11)(H,12,13,14)

Upstream product

• 108-39-4 3-methyl-phenol 
• 75-15-0 carbon disulfide 
• 7790-94-5 chlorosulfonic acid 
• 111254-61-6 potassium 3-methylphenol-4-sulphonate 
• 99533-76-3 4-Hydroxy-2-methyl-benzene-1,3-disulfonic acid 
• 22356-80-5 2-hydroxy-4-methylbenzenesulfonic acid 
• 7134-05-6 5-methyl-1-hydroxybenzene-4-sulfonic acid 

Downstream Products

• 602-99-3 3-methyl-2,4,6-trinitrophenol 
• 861304-53-2 6-methyl-4-methoxy-1,3-benzenedisulfonyl chloride 
• 608-26-4 2-chloro-m-cresol 

Relevant articles and documents

Aromatic Sulphonation. Part 92. Sulphonation of the Three Methylphenols and the Six Dimethylphenols in Concentrated Aqueous Sulphuric Acid; and the Isomerization of Some of the Resulting Sulphonic Acids and of m-Xylene-2- and o-Xylene-3-sulphonic Acid

The isomer distributions for the mono- and di-sulphonation of the three methylphenols in 81.6-90.0percent sulphuric acid and of the six dimethylphenols in 84.9percent sulphuric acid at 35 deg C have been determined by means of 1H n.m.r. spectroscopy.Products that would result from demethylation, disproportionation, or ipso-substitution have not been observed.The monosulphonation isomer distribution of each of the three methylphenols is independent of the sulphuric acid concentration. 2,4-Dimethylphenol in 84.9percent H2SO4 yields 19percent 5- and 79percent 6-sulphonic acid, and 2,6-dimethylphenol yields 28percent 3- and 72percent 4-sulphonic acid.With the phenols (2), (3), (5),and (7), which have positions both ortho and para to the -OH substituent available for sulphodeprotonation, the yield of ortho-substitution is relatively high, viz. 44, 45, 36, and 27percent, respectively.The mono- and di-sulphonic acids of which the sulpho group is between the -OH and an -Me group are unstable under the reaction conditions employed, with the exception of the 3,5-dimethylphenol-2-sulphonic acid.It is proposed that their isomerization proceeds by protiodesulphonation followed by resulphonation to yield the more stable sulphonic acid isomer(s).From a kinetic analysis of the calculated first-order rate coefficients for protiodesulphonation, it is concluded that the unprotonated substrate species is the entity undergoing the protiodesulphonation.