654070-00-5

Usage

Uses

Used in Pharmaceutical Synthesis:
6-Iodobenzo[d]thiazole is utilized as a key intermediate in the synthesis of pharmaceutical compounds. Its unique structure and reactivity make it a valuable component in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Production:
In the agrochemical industry, 6-iodobenzo[d]thiazole serves as a building block for the creation of various agrochemicals. Its incorporation into these products can enhance their effectiveness in agricultural applications, such as pest control and crop protection.
Used in Materials Science:
6-Iodobenzo[d]thiazole is employed in materials science for the development of new materials with specific properties. Its chemical versatility allows for the engineering of materials with tailored characteristics for use in various industries, including electronics, plastics, and coatings.
Used in Organic Chemistry:
As a versatile organic compound, 6-iodobenzo[d]thiazole is used in organic chemistry for conducting various chemical reactions. Its ability to undergo nucleophilic substitution and participate in palladium-catalyzed couplings makes it a useful reactant in the synthesis of complex organic molecules.

Upstream product

• 533-30-2 1,3-benzothiazol-6-amine 
• 855282-75-6 2-chloro-6-iodobenzothiazole 
• 934-34-9 2(3H)-Benzothiazolone 
• 124-38-9 carbon dioxide 
• 1262983-59-4 C₆H₆INS 
• 2942-06-5 6-nitrobenzo[d]thiazole 
• 95-16-9 1,3-Benzothiazole 

Downstream Products

• 1338574-32-5 6-[4-(N,N-diphenylamino)phenylethynyl]benzothiazole 

Relevant academic research and scientific papers

New pentacyclic ring systems: Intramolecular cyclization of o,o′-disubstituted bibenzothiazoles

Efficient methods for the preparation of isomeric o,o′- diaminobibenzothiazoles (8a and 11a) and o,o′-diamino-2,2′- dimethylbibenzothiazoles (8b and 11b), potentially valuable building blocks for construction of hitherto unknown dithiazolo annulated pentacyclic heterocycles, have been developed. The dithiazolo annulated benzo[c]cinnolines 9a, 9b, and 12a were prepared from the corresponding diamines by oxidation with PhI(OAc) 2 in good yield. The dithiazolo annulated carbazoles 13 and 14 were efficiently prepared from the corresponding diamines by thermal cyclization in H3PO4. The unusual course of reduction and product formation of o,o′-dinitrosubstituted bibenzothiazoles 6a and 6b with SnCl2 under acidic conditions was rationalized by DFT quantum-mechanical calculations. It was suggested that cyclic products are formed from dinitroso derivatives and open-shell species immediately following on a reduction path.

CuTC mediated coupling of 6,7-disubstituted benzothiazoles

A synthesis of the halogeno derivatives of substituted benzothiazoles (2-6) is described, and dimerization using copper in different oxidation states is examined. Dimerization of iododerivatives (2) and (4) by copper(I) thiophen-2-carboxylate (CuTC) mediated coupling afforded the corresponding o,o'-disubstituted bibenzothiazoles (7) and (S) in excellent yield.{A figure is presented}.

Direct iodination of electron-deficient benzothiazoles: Rapid access to two-photon absorbing fluorophores with quadrupolar D-π-A-π-D architecture and tunable heteroaromatic core

Direct iodination of benzothiazoles under strong oxidative/acidic conditions leads to a mixture of iodinated heteroarenes with 1-2 major components, which are easily separable and which structures depend on the I2 equivalents used. Among the unexpected bu

Oxidative C-H Homocoupling of Push-Pull Benzothiazoles: An Atom-Economical Route to Highly Emissive Quadrupolar Arylamine-Functionalized 2,2′-Bibenzothiazoles with Enhanced Two-Photon Absorption

Copper(II)-catalyzed C-H/C-H coupling of dipolar 2-H-benzothiazoles end-capped with triphenylamine moieties affords highly fluorescent 2,2′-bibenzothiazoles with quadrupolar (D-π-A-π-D) architecture displaying large two-photon absorption (TPA) cross sections (543-1252 GM) in the near-infrared region. The notably higher TPA performance as compared to quadrupolar π-systems with a widely used 2,2′-bipyridine core, along with the ease of the synthesis and chelating N^N ability, makes the title biheteroaryl platform an attractive building block for a large scope of functional dyes exploiting nonlinear optical phenomena.

Synthesis of benzothiazoles from 2-aminobenzenethiols in the presence of a reusable polythiazolium precatalyst under atmospheric pressure of carbon dioxide

Synthesis of benzothiazoles from 2-aminobenzenethiols and carbon dioxide was carried out using poly(3,4-dimethyl-5-vinylthiazolium) iodide as a precatalyst to in situ generation of NHCs by deprotonation. The reaction was successfully carried out under mild conditions (1 atm of CO2 and 60–70 °C) with a broad substrate scope and functional group tolerance. The precatalyst salt was recovered and reused for several times without any loss of activity.

Benzothiazoles with tunable electron-withdrawing strength and reverse polarity: A route to triphenylamine-based chromophores with enhanced two-photon absorption

A series of dipolar and octupolar triphenylamine-derived dyes containing a benzothiazole positioned in the matched or mismatched fashion have been designed and synthesized via palladium-catalyzed Sonogashira cross-coupling reactions. Linear and nonlinear optical properties of the designed molecules were tuned by an additional electron-withdrawing group (EWG) and by changing the relative positions of the donor and acceptor substituents on the heterocyclic ring. This allowed us to examine the effect of positional isomerism and extend the structure-property relationships useful in the engineering of novel heteroaromatic-based systems with enhanced two-photon absorption (TPA). The TPA cross-sections (δTPA) in the target compounds dramatically increased with the branching of the triphenylamine core and with the strength of the auxiliary acceptor. In addition, a change from the commonly used polarity in push-pull benzothiazoles to a reverse one has been revealed as a particularly useful strategy (regioisomeric control) for enhancing TPA cross-sections and shifting the absorption and emission maxima to longer wavelengths. The maximum TPA cross-sections of the star-shaped three-branched triphenylamines are ～500-2300 GM in the near-infrared region (740-810 nm); thereby the molecular weight normalized δTPA/MW values of the best performing dyes within the series (2.0-2.4 GM?g-1?mol) are comparable to those of the most efficient TPA chromophores reported to date. The large TPA cross-sections combined with high emission quantum yields and large Stokes shifts make these compounds excellent candidates for various TPA applications, including two-photon fluorescence microscopy.

Hydrogen and halogen bonding patterns and π-π aromatic interactions of some 6,7-disubstituted 1,3-benzothiazoles studied by X-ray diffraction and DFT calculations

The structures of five 6,7-disubstituted 1,3-benzothiazole (1,3-benzothiazole = bta) derivatives: 6-chloro-7-nitro-bta (3), 6-iodo-7-nitro-bta (5), 6-amino-7-iodo-bta (6), 6-acetylamino-7-iodo-bta (7) and 6-amino-7-bromo-bta (8) are reported and investigated by X-ray crystallography and DFT calculations. The crystal structures of 3 and 5-8 are characterized by: (i) relatively weak C{single bond}H?O/N/Br and N{single bond}H?O/N/S hydrogen bonds, (ii) C{single bond}Cl?O and C{single bond}I?O/N halogen bonds and Br?Br interactions and (iii) π-π interactions. DFT optimized structures of 3, 5, 6 and 8 are in a good agreement with the corresponding X-ray molecular data. Calculated structure of 7 deviates from the experimental geometry because of more favourable intermolecular hydrogen bonding in crystal phase compared to the weak intramolecular hydrogen bond in the gas phase. The molecular electrostatic potential maps were used for predicting possible hydrogen and halogen bonding sites in structures of 3, 5, 6 and 8, and AIM analysis in order to characterize the nature and strength of intermolecular interactions in all of the examined crystal structures. Experimental results agree well with AIM analysis suggesting that the detected hydrogen and halogen bonds are weak and mostly of electrostatic origin.