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Usage

Uses

Used in Pharmaceutical Industry:
2,6-dimethyl-3-sulfonic acid is used as a catalyst for facilitating various organic reactions in the synthesis of pharmaceutical compounds. Its strong acidity and water solubility make it an effective agent for processes such as esterification and transesterification, which are crucial in the production of certain drugs.
Used in Dye Industry:
2,6-dimethyl-3-sulfonic acid is used as a catalyst in the synthesis of dyes. Its ability to catalyze reactions at mild conditions allows for the efficient production of a wide range of dye compounds, contributing to the coloration of textiles and other materials.
Used in Organic Synthesis:
2,6-dimethyl-3-sulfonic acid is used as a reagent in various organic synthesis processes. Its steric hindrance due to the dimethyl group attached to the sulfur atom affects its acidity and reactivity, making it a valuable component in the preparation of a diverse array of organic compounds.

Upstream product

• 87-62-7 2,6-dimethylaniline 
• 2198-53-0 N-(2,6-dimethylphenyl)acetamide 
• 952958-71-3 4-Acetylamino-3,5-dimethyl-benzenesulfonyl chloride 
• 385382-28-5 N-acetyl-2,6-dimethylbenzene-3-sulfonamide 

Downstream Products

• 81734-86-3 2,4-dimethyl-3-nitrosobenzenesulfonate 
• 70594-29-5 2-Amino-1.3-dimethyl-benzol-4.6-disulfonsaeure 

Relevant academic research and scientific papers

On the intermediacy of phenyl hydrogen sulfates in the sulfonation of phenols. Sulfonation of phenol, anisole, methyl phenyl sulfate, the 2-halogenophenols, a series of phenyl methanesulfonates together with 2,6-dimethylaniline and its N-methylsulfonyl derivative

The sulfonation of methyl phenyl sulfate (4) with concentrated aqueous sulfuric acid at 25 deg C yields the 4-sulfonic acid.This initial product then decomposes to give phenol-4-sulfonic acid, which is subsequently sulfonated to phenol-2,4-disulfonic acid.From the first-order-rate coefficients obtained for sulfonation of phenyl methanesulfonate (3) and (4) in 93,2percent H2SO4, for which acid concentration the sulfonating entity is H2S2O7, the ?p+ values of the OSO2Me and OSO2OMe substituents have been determined to be 0.40 and 0.46, respectively.The sulfonation of both 2-chlorophenyl (10) and 2-methylphenyl methanesulfonate (14) with 2.0 equiv of SO3 in nitromethane at 0.0 deg C yields the 4-sulfonic acid as the exclusive product, whereas 2-methoxyphenyl methanesulfonate (13), under the same conditions, forms exclusively the 5-sulfonic acid. 2-Chloro- (6), 2-bromo- (7) and 2-iodophenol (8) with 1.0 and 4.0 equiv of SO3 in nitromethane yield exclusively the 4-sulfonic acid, while 2-fluorophenol (5) with 2.0 and 5.0 equiv of SO3 yields in addition the 5-sulfonic acid to the extent of 4 and 30percent, respectively.In the reactions of 2,6-dimethylphenol (15) and 2,6-dimethylaniline (17) with at least 1 equiv of SO3 in nitromethane, the 3-SO3H/4-SO3H ratio was found to increase on increasing the relative amount of SO3.For both 15 and 17, the limiting 3-SO3H/4-SO3H ratio at high SO3/ArOH ratios is 86/14 and this value is considered to be the ratio for the sulfonation of both 2,6-dimethylphenyl hydrogen sulfate and 2,6-dimethylaniline-N-sulfonic acid.This assumption is supported by the observation that the sulfonation of 2,6-dimethylphenyl methanesulfonate (16) and N-(methylsulfonyl)-2,6-dimethylaniline (18) with SO3 leads to a similar 3-SO3H/4-SO3H ratio.

SPIN TRAPPING BY USE OF A WATER-SOLUBLE NITROSO COMPOUND

The preparation of sodium 2,4-dimethyl-3-nitrosobenzenesulfonate and its perdeuterio-analogue and their use in spin trapping in aqueous solutions are described.

Studies of Reactions of Amines with Sulfur Trioxide. VI. Thermal Reactions of Anilinium, Dimethylanilinium, and Trimethylanilinium Salts of Butylamidosulfuric Acid

When the title compounds were heated in an evacuated reaction vessel, both transsulfonation and rearrangement occurred.At lower temperatures (80-120 deg C) the corresponding phenylamidosulfates and sulfophenylamidosulfates (transsulfonation products) were the main products.Increasing temperature led to the formation of ring mono- and disulfonates (rearrangement products) at the expense of the transsulfonation products.The sulfonate group always migrated to the ortho and/or para position(s) to the amino group.In no case was any meta-product detected.There was no significant difference in the ease of transsulfonation among the anilinium salts studied exept 2,6-dimethyl- and 2,4,6-trimethylanilinium salts.On the other hand, the ease of rearrangement and the orientation of ring sulfonation depended strongly on the structure of the substrate anilines.The thermal reactions of 2,4,6-trimethylanilinium butylamidosulfate produced (2,4,6-trimethylphenylimido)bis(sulfate) in addition to (2,4,6-trimethylphenylamido)sulfate.This is the first isolation of an arylimidobis(sulfate) from such reactions.Mechanisms of the transsulfonation and rearrangement have been discussed.