3453-84-7

Usage

Chemical Properties

White or light yellow crystalline powder

InChI:InChI=1/C9H12O3S/c1-6-4-8(3)9(5-7(6)2)13(10,11)12/h4-5H,1-3H3,(H,10,11,12)

Upstream product

• 7664-93-9 sulfuric acid 
• 52890-52-5 2,4,5-trimethylbenzophenone 
• 95-63-6 1,2,4-Trimethylbenzene 
• 4681-78-1 2,3,5,6-tetramethylbenzene-1-sulfonic acid 

Downstream Products

• 51307-74-5 5-sulfonyl-1,2,4-benzenetricarboxylic acid 
• 17851-27-3 1-ethyl-2,4,5-trimethylbenzene 
• 95111-55-0 2,5-dibromo-3,4,6-trimethyl-phenol 
• 58138-52-6 2-hydroxy-4,5-dimethylbenzoic acid 
• 15460-08-9 2-bromo-3,4,6-trimethyl-phenol 
• 5877-60-1 1-bromo-2,4,5-trimethyl-3,6-dinitro-benzene 
• 528-90-5 2,4,5-trimethylbenzoic acid 
• 7664-93-9 sulfuric acid 
• 5469-19-2 1-bromo-2,4,5-trimethylbenzene 
• 13059-46-6 2,4,5-trimethyl-3,6-dinitro-benzenesulfonic acid 
• 496-78-6 2,4,5-trimethylphenol 
• 95-63-6 1,2,4-Trimethylbenzene 
• 13250-07-2 phenyl-(2,4,5-trimethyl-phenyl)-sulfone 
• 92890-80-7 2,4,5-trimethylsulphonyl chloride 

Relevant academic research and scientific papers

Aromatic isomerization and related reactions. Part 61. Reactions of the tetra- and pentamethylbenzenesulfonic acids and hexamethylbenzene in concentrated sulfuric acid; the mechanism of the Jacobsen reaction

The chemical behaviour of the sulfonic acids of pentamethylbenzene (PMB) and the three tetramethylbenzenes (TeMB's( in concentrated aqueous sulphuric acid has been studied quantitatively using 1H AND 13C NMR and UV spectroscopy.PMB-sulfonic acid yields (protonated) hexamethylbenzene (HMB) and the 2,3,4,5- and 2,3,4,6-TeMB-1-sulfonic acids in an initial ratio of 9/1/8 up to a substrate conversion of 36percent; the ratio of HMB to the TeMB-1-sulfonic acids remains 1/1 and the only subsequent reaction is the relatively slow conversion of the 2,3,4,6- into the 2,3,4,5-TeMB-1-sulfonic acid which is the only stable TeMB-1-sulfonic acid isomer in concentrated sulfuric acid. 2,3,5,6-TeMB-1-sulfonic acid yields, as initial products, 2,3,5- and 2,4,5-trimethylbenzene(TrMB)-1-sulfonic acid together with PMB-1-sulfonic acid in a ratio of ca. 1/3/4.The subsequent products are the 2,3,4,6- and 2,3,4,5-TeMB-1-sulfonic acids, of which the former slowly isomerizes to the latter, together with some HMB. 2,3,4,6-TeMB-1-sulfonic acid yields the stable 2,3,4,5-isomer.It is proposed that the conversion proceeds via inter-molecular trans-methylations involving 1,3,5-TrMB and PMB as intermediates, the concentrations of which, however, are below the limits of NMR detection.Based on (i) the desulfonation-sulfonation equilibrium data of the TrMB-, TeMB- and PMB-sulfonic acids, (ii) the strong rate decrease for the conversion of both 2,3,4,6- and 2,3,5,6-TeMB-1-sulfonic acid in 98.4percent H2SO4 in the presence of added cyclohexane and (iii) the very strong electron-withdrawing and meta-directing effect of the SO3-/SO3H substituent, it is proposed that all the conversions proceed inter-molecularly, that the trans-methylating reagent is the polymethylbenzene (and not the corresponding sulfonate) and that the substrate undergoing methylation is most likely to be once again the polymethylbenzene rather than its sulfonate ion.

Mixed-Lanthanoid Metal-Organic Framework for Ratiometric Cryogenic Temperature Sensing

A ratiometric thermometer based on a mixed-metal LnIII metal-organic framework is reported that has good sensitivity in a wide temperature range from 4 to 290 K and a quantum yield of 22% at room temperature. The sensing mechanism in the europi

Synthesis, structure and proton conductivity of 2,4,5-trimethylbenzenesulfonic acid dihydrate

2,4,5-Trimethylbenzenesulfonic acid dihydrate was isolated in the monocrystalline state. Crystal and molecular structures of the compound were determined by X-ray diffraction analysis and vibrational spectroscopy. The compound crystal system is monoclinic

Reactions of overcrowded polymethylbenzenedisulfonic acids in concentrated aqueous sulfuric acid; protiodesulfonation and intramolecular sulfonic anhydride formation

The reaction of the three tetramethylbenzenedisulfonic acids and some lower homologues in concentrated aqueous sulfuric acid has been studied at 25 deg C. 3,4,5,6-Tetramethylbenzene-1,2-disulfonic acid undergoes both intramolecular disulfonic anhydride formation (the rate of which strongly increases upon increasing the sulfuric acid acidity) and protiodesulfonation (the rate of which decreases slightly with increasing acidity) while the other disulfonic acids only undergo protiodesulfonation.The observed rate order for protiodesulfonation within the tetramethylbenzenedisulfonic acids 1,3- >> 1,4-(SO3H)2> differs strongly from that predicted on the basis of the additivity principle of substituent effects > 1,4- > 1,2-(SO3H)2>.The strongly enhanced reactivity of the 1,2-disulfonic acid is ascribed to a greater releif of steric strain in the 1,2- than in the other disulfonic acids, the sulfo group being more bulky than the methyl.Also, within the group of tri- and tetra-methylbenzene-1,3-disulfonic acids, the rate of desulfonation increases with an increase in the degree of overcrowding around the sulfo group which is desulfonating.Mechanisms for the two types of reaction of the tetramethylbenzenedisulfonic acids are proposed, based on the variation of the rate constants with the sulfuric acid acidity.It is concluded that the substrate entity undergoing protiodesulfanation is the disulfonate dianion and further that the entity undergoing cyclization to the 1,2-disulfonic anhydride is the monoprotonated 1,2-disulfonic acid.