4568-71-2

Usage

Uses

Used in Organic Synthesis:
3-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride is used as a catalyst for the acyloin condensation of aliphatic aldehydes, enabling the formation of various organic compounds. This reaction is crucial in the synthesis of complex organic molecules and contributes to the development of new pharmaceuticals and other chemical products.
Used in the Addition of Aldehydes to Unsaturated Compounds:
In the chemical industry, 3-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride is used as a catalyst for the addition of aliphatic and heterocyclic aldehydes to α,β-unsaturated ketones, nitriles, and esters. This process is essential for the synthesis of various chemical intermediates and final products, which can be utilized in different applications, such as pharmaceuticals, agrochemicals, and materials science.
Overall, 3-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride plays a significant role in the field of organic chemistry, acting as a catalyst to facilitate various reactions and contribute to the synthesis of a wide range of chemical compounds.

Purification Methods

Purify the chloride by recrystallisation from EtOH or H2O. If placed in a bath at 125o and heated at 2o/minute, the melting point is 140.5-141.4o. [Livermore & Sealock J Biol Chem 167 699 1947, Maier & Metzler J Am Chem Soc 79 4386 1957, Beilstein 27 III/IV 1758.]

InChI:InChI=1/C13H16NOS.ClH/c1-11-13(7-8-15)16-10-14(11)9-12-5-3-2-4-6-12;/h2-6,10,15H,7-9H2,1H3;1H/q+1;

Upstream product

• 137-00-8 5-hydroxyethyl-4-methylthiazole 
• 100-44-7 benzyl chloride 
• 67-56-1 methanol 
• 333385-00-5 methylhydroxyethyl thiazole 

Downstream Products

• 109339-13-1 3-benzyl-3a-methyl-hexahydro-furo[2,3-d]thiazole 
• 70770-03-5 4-(3,4-dimethoxyphenyl)-4-oxobutanenitrile 
• 123184-01-0 1-(4-fluorophenyl)-1,4-hexanedione 
• 113071-26-4 ethyl 3-benzoyl-3-(4-fluorophenyl)-2-(2-methylpropionyl)propionate 
• 131352-74-4 (E)-2,2'-(3,3'-dibenzyl-4,4'-dimethyl-3H,3'H-[2,2'-bithiazolylidene]-5,5'-diyl)bis(ethan-1-ol) 
• 6838-54-6 3-hydroxy-1,4-diphenyl-2-butanone 
• 726194-05-4 2,3,4-tribenzyl-γ-butyro-2-en-lactone 
• 6772-51-6 2-phenyl-3,4-dihydroisoquinolin-1(2H)-one 

Relevant academic research and scientific papers

Benzothiazolium salt and having Hydroxyalykyl antistatic agent containing same

PROBLEM TO BE SOLVED: To provide a thiazolium salt which possesses antistatic performance and whose cation is novel, and to provide an antistatic agent using the thiazolium salt. SOLUTION: The thiazolium salt is represented by formula (1) (wherein R1represents a hydrogen atom or a 1-20C alkyl group; R2represents a 1-20C alkyl group, a 2-20C alkenyl group, an aryl group, a 1-20C fluoroalkyl group, or a 7-20C aralkyl group; and R3represents a hydrogen atom or a 1-20C alkyl group; A-represents an anion, and n is an integer of 1 to 3). COPYRIGHT: (C)2013,JPOandINPIT

Methods of Treating or Preventing Cardiac Disease Associated With a High Fat Diet

The present invention relates to a method of treating or preventing cardiac disorders, myocardial inflammation or myocardial oxidative stress associated with a high fat diet or in a patient subjected to a high fat diet using the thiazolium compounds and compositions of the invention. The present invention also relates to a method of ameliorating weight gain, myocardial AGE accumulation associated, mitochondrial superoxide production, RAGE expression or PPARα expression with a high fat diet or in a patient subjected to a high fat diet using the thiazolium compounds and compositions of the invention.

Method and composition for rejuvenating hair, nails, tissues, cells and organs by ex-vivo or immersive treatment

A method and composition for the treatment of hair, nail, ex-vivo organ, ex-vivo cell or ex-vivo tissue to improve the biomechanical and diffusional characteristics comprising an effective amount of a compound selected from the group consisting of compounds of the formula

Method for treating fibrotic diseases or other indications IC

Provided, among other things, is a method of treating or ameliorating or preventing an indication of the invention in an animal, including a human comprising administering an effective amount of a compound of the formula I:

Preventing and reversing the formation of advanced glycosylation endproducts

The present invention relates to compositions and methods for inhibiting and reversing nonenzymatic cross-linking (protein aging). Accordingly, compositions are disclosed which comprise an agent capable of inhibiting the formation of advanced glycosylation endproducts of target proteins, and which additionally reverse pre-formed crosslinks in the advanced glycosylation endproducts by cleaving alpha-dicarbonyl-based protein crosslinks present in the advanced glycosylation endproducts. Certain agents useful are thiazolium salts. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated. A novel immunoassay for detection of the reversal of the nonenzymatic crosslinking is also disclosed.

Preventing and reversing advanced glycosylation endproducts

The present invention relates to compositions and methods for inhibiting and reversing nonenzymatic cross-linking (protein aging). Accordingly, a composition is disclosed which comprises a thiazolium compound capable of inhibiting, and to some extent reversing, the formation of advanced glycosylation endproducts of target proteins by reacting with the carbonyl moiety of the early glycosylation product of such target proteins formed by their initial glycosylation. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated. A novel immunoassay for detection of the reversal of the nonenzymatic crosslinking is also disclosed.

BASE-CATALYZED OXIDATION OF 2-(α-HYDROXYBENZYL)THIAMINE BY MOLECULAR OXYGEN

Oxidation of 2-(α-hydroxybenzyl)thiamine by molecular oxygen in the presence of an acetate buffer in methanol includes formation of an intermediate enamine and its subsequent oxidation with concurrent protonation.Using the dependence of the reciprocal rate constant for acetate-catalyzed oxidation on /-> the values of k1 and k-1/k2 have been calculated.Comparison of oxidation kinetics of 2-(α -hydroxybenzyl)thiamine, 2-(α-hydroxybenzyl)-3- benzyl-4-methyl-5-(2-hydroxyethyl)thiazolium chloride, and 2(α-hydroxybenzyl)-3-benzyl- 4-methylthiazolium chloride indicates that the reaction of the intermediate enamine with O2 is governed by the 3- and 5-substituents.It is assumed that the 5-hydroxyethyl group causes steric hindrance, and the amino group in position 4 of the pyrimidine fragment favors deprotonation of the Cα-hydroxy group.

OXIDATIVE DECOMPOSITION OF 2-(α-HYDROXYBENZYL)THIAMINE UNDER THE ACTION OF A BASE AND SUBSTITUTED QUINONES

The reaction of 2-(α-hydroxybenzyl)thiamine and its thiazolium structural analogs with substituted quinones in the presence of acetate buffer in deaerated methanolic solutions at 27 deg C and ionic strength of 0.15 is characterized by first-order kinetics with respect to the thiazolium salt and the acetate and by zero-order kinetics with resoect to quinone.The rate constant of the reaction catalyzed by the basic component of the buffer decreases in the following series of oxidants: 2-methyl-5-isopropyl-p-benzoquinone, trimethyl-p-benzoquinone, tetramethyl-p-benzoquinone.It was supposed that fast reversible formation of a complex between the deprotonated 2-(α-hydroxybenzyl)thiazole and the oxidant precedes electron transfer to the quinone.In the one-electron transfer stage, which determines the overall reaction rate, the 5-hydroxyethyl substituent exerts an adverse effect for steric reasons.

Preparation of vinylglyoxal derivatives, novel vinylglyoxal derivatives and their use

Vinylglyoxal derivatives of the general formula I STR1 where R is straight-chain or branched alkyl or alkenyl, cycloalkyl or unsubstituted or substituted phenyl, are prepared by a process in which bicyclo[2.2.1]hept-5-enecarbaldehyde of the formula V STR2 is either (a) subjected to autocondensation with formation of a compound of the formula VII STR3 or (b) reacted with a compound of the general formula II where R has the above meanings, with formation of a mixture of the compounds of the general formulae VIII (a) and (b) STR4 where R is as defined above, in the presence of a catalyst, and the compound of the formula VII or the compounds of the formulae VIII (a) and (b) is or are oxidized to the corresponding dicarbonyl compounds, after which gas-phase pyrolysis is carried out at from 500° to 700° C. and under reduced pressure, in particular less than 10-1 mbar, and, if desired, the resulting compound of the general formula I is further purified. These compounds can be used, for example, as monomer components in polymeric systems.