32446-47-2

Usage

Uses

3-ethyl-1,3-benzothiazol-3-ium bromide is a useful research chemical.

InChI:InChI=1/C9H10NS.BrH/c1-2-10-7-11-9-6-4-3-5-8(9)10;/h3-7H,2H2,1H3;1H/q+1;/p-1

Upstream product

• 95-16-9 1,3-Benzothiazole 
• 74-96-4 ethyl bromide 

Downstream Products

• 1394043-93-6 4-ethyl-2-phenyl-2,3-dihydro-4H-benzo[b][1,4]thiazin-3-one 
• 1394043-94-7 2-(4-bromophenyl)-4-ethyl-2,3-dihydro-4H-benzo[b][1,4]thiazin-3-one 

Relevant academic research and scientific papers

Unexpected reactivity of diaryl α-diketones with thiazolium carbenes: Discovery of a novel multicomponent reaction for the facile synthesis of 1,4-thiazin-3-ones

Diaryl α-diketones do not undergo polarity reversal in the presence of (benzo)thiazolium carbenes but are engaged in a novel multicomponent reaction with water to efficiently give medicinally relevant 1,4-thiazin-3-one heterocycles. Three different sets of conditions have been optimized to furnish the title compounds in fair to excellent yields depending on the electronic properties of α-diketone aromatic substituents and thiazolium or benzothiazolium substrate. A plausible reaction mechanism is also proposed based on the isolation and characterization of the postulated key intermediate and isotopic labeling experiments.

Formation and crystallographic elucidation of stable [4 + 2]-coordinate nickel(ii) N,S-heterocyclic carbene (NSHC) complexes

A series of square-planar N,S-heterocyclic carbene (NSHC) complexes trans-[NiX2(N-RBzTh)2] (BzTh = benzothiazolin-2-ylidene) (R/X = Bz/Br; Me/I; Et/I; Pri/I; Bui/I) have been synthesized and characterized by X-ray single-crystal diffraction analysis. These are the first crystallographically established NSHC complexes of nickel in the literature. The N,S-heterocyclic carbene (NSHC) rings invariably twist away from co-planarity with the metal coordination plane such that the N-substituent moves on top and below the metal to facilitate electrostatic γ-hydride interaction, thus giving an essentially [4 + 2] coordination at the Ni(ii) center. These compounds are active toward reductive Ullmann-type coupling reactions in Bu4NBr showing higher activities towards bromoanisole or bromotoluene than bromobenzene. The complex trans-[NiI2(N-Pr iBzTh)2] with the shortest Ni...H anagostic separation and a near-ideal orthogonal orientation between the carbene and metal planes gives the highest yields.

Selective Formation of Triose from Formaldehyde Catalyzed by Thiazolium Salt

In the self-condensation of formaldehyde catalyzed by thiazolium salts, dihydroxyacetone (triose), but not glycolaldehyde, was formed selectively and in high yield.This is of much interest as a facile and novel synthesis of triose from this C1 compound.A mechanism which can account for the selective formation of dihydroxyacetone is described.

Selective Formation of Triose from Formaldehyde catalysed by Ethylbenzothiazolium Bromide

Dihydroxyacetone was obtained selectively by condensation of formaldehyde using 3-ethylbenzothiazolium bromide as a catalyst in the presence of base.