3216-47-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-3-methylbenzo(b)thiophene is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique chemical structure allows it to be a building block for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 2-chloro-3-methylbenzo(b)thiophene is utilized as a precursor in the production of agrochemicals, such as pesticides and herbicides. Its chemical properties make it suitable for the creation of effective and targeted agrochemicals.
Used in Dye and Pigment Production:
2-Chloro-3-methylbenzo(b)thiophene is employed in the manufacturing of dyes and pigments due to its color-producing properties. Its unique structure contributes to the development of a wide range of colors for various applications, including textiles, plastics, and inks.
Used in Organic Compound Synthesis:
As an intermediate, 2-chloro-3-methylbenzo(b)thiophene plays a crucial role in the synthesis of other organic compounds. Its reactivity and functional groups make it a valuable component in the creation of new and innovative organic molecules for various industries.
It is important to handle 2-chloro-3-methylbenzo(b)thiophene with care, as it can be harmful if ingested, inhaled, or in contact with the skin. Proper safety measures should be taken during its production, use, and disposal to minimize potential health risks.

InChI:InChI=1/C9H7ClS/c10-5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6H,5H2

Upstream product

• 50-00-0 formaldehyd 
• 95-15-8 Benzo[b]thiophene 
• 107-30-2 chloromethyl methyl ether 
• 7647-01-0 hydrogenchloride 
• 64-19-7 acetic acid 
• 5381-24-8 benzo[b]thiophen-3-yl methanol 
• 5381-20-4 benzothiophene-3-carboxaldehyde 
• 58432-15-8 3-(2-aminophenylthio)prop-1-yne 

Downstream Products

• 3216-48-6 2-(benzo[b]thiophen-3-yl)acetonitrile 
• 7388-06-9 2-[ethyl-(benzo[b]thiophen-3-ylmethyl)-amino]-ethanol; hydrochloride 
• 850855-58-2 3-benzo[b]thiophen-3-yl-2,2-dimethyl-1-phenyl-propan-1-one 
• 1455-18-1 3-methylbenzothiophene 
• 3133-78-6 3-methylbenzo[b]thiophene-2-carboxylic acid 
• 14585-66-1 3-(2-aminoethyl)-benzothiophene 
• 188974-11-0 N-<2-(benzothien-3-yl)ethyl>-N-ethyl-N-(2-hydroxy-2-phenyl)ethylamine 
• 188974-19-8 N-ethyl-N-<2-(benzothien-3-yl)ethyl>-N-<2-hydroxy-2-(3-bromophenyl)ethyl>amine 
• 188974-17-6 N-ethyl-N-<2-(benzothien-3-yl)ethyl>-N-<2-hydroxy-2-(3-nitrophenyl)ethyl>amine 
• 215594-40-4 N-ethyl-N-<2-(benzothien-3-yl)ethyl>-N-<2-hydroxy-2-(3,4-dichlorophenyl)ethyl>amine 

Relevant academic research and scientific papers

Synthesis of [1]Benzothieno[2,3- b ]quinolines via Transition-Metal-Free [3+3] Annulation of Nitroarenes and Benzo[ b ]thiophen-3-ylacetonitrile or 3-(Phenylsulfonylmethyl)benzo[ b ]thiophene Carbanions

Benzo[ b ]thiophen-3-ylacetonitriles or 3-(phenylsulfonylmethyl)benzo[ b ]thiophenes react with nitrobenzene derivatives in the presence of potassium tert -butoxide and chlorotrimethylsilane to form, in good yields, 11-cyano- or 11-(phenylsulfonyl)[1]benzothieno[2,3- b ]quinolines, respectively.

Thiophenol-mediated hydrogen atom abstraction: An efficient tin-free procedure for the preparation of cyclopentane derivatives

(Matrix Presented) An efficient procedure for running a cascade reaction involving 1,5-abstraction of a hydrogen atom followed by a radical cyclization is reported. Alkenyl radicals are generated from easily available terminal alkynes and thiophenol. This procedure eliminates the need of using the toxic tributyltin hydride and gives a greater amount of radical translocation products.

Method for synthesizing 3 - halo methyl benzofuran compounds

The invention provides a method for efficiently synthesizing a 3-halomethylation benzofuran class compound by one step through a 2-propargyloxy aniline class compound. Compared with an existing method, the method can adapt to substrates for a wide range, the compound is convenient and easy to obtain, the reaction condition is mild, the operation is easy and convenient, and the reaction efficiency is high. By means of the method, metal salt compounds do not need to be added, and the production and processing for drugs are facilitated.

IDO inhibitors

Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.

D1-like receptors distinguishing thieno-azecine regioisomers

Designing ligands with D1/D5 subtype selectivity is a challenge because of the high identity within the receptor helices. Based on the lead compounds 1-3, the thieno-benzazecine regioisomers 4 and 5 were synthesized and biologically evaluated for their affinity towards the five dopamine receptor subtypes utilizing a radioligand binding affinity technique. Within the D1-like family, compound 4 showed 20 fold selectivity for the D5 subtype over D1 subtype (Ki = 3 nM, D1: 60 nM), while its regioisomer, compound 5 with a reversed thiophene position, prefers the D1 subtype over the D5 subtype (Ki = 4 nM, D5: 15 nM). The benzothieno-benzazecine analog 6 was shown to be one of the few azecine derivatives with high affinity for both the D1- and the D2-like family members in the same order of magnitude (Ki = 1.5 nM for D2 and 1.9 nM for D5). Thorough analysis of the amino acid residues constituting the binding pockets of the target dopamine receptor subtypes revealed that at the D5 receptor, either serine S 6.62 and threonine T 7.33 residues or a water network, stabilized by anionic amino acids could contribute to the selectivity pattern of the synthesized compounds.

Preparation and reactions of heteroarylmethylzinc reagents

We report a general preparation of heteroarylmethylzinc chlorides by direct zinc insertion into heteroarylmethyl chlorides, along with a facile and straightforward synthesis of these heterocyclic chloromethyl precursors. We demonstrate that heteroarylmethylzinc reagents undergo various reactions including cross-couplings, allylations, acylations, and addition reactions to aldehydes, leading to polyfunctional heterocyclic products. Furthermore, these heteroaromatic zinc compounds prove to be versatile reagents for the preparation of various N- and O-heterocycles and give access to an analogue of a CB1 modifier.

Discovery of highly potent and selective D4 ligands by interactive SAR study

A series of thienylmethylphenylpiperazins was synthesized and tested for affinity towards the five subtypes of dopaminergic receptors. Compound 5f showed more than 1000 folds selectivity to D4 receptors; analogue 5e showed the highest affinity to D4 receptors with Ki 3.9 nM. An interactive SAR approach was adopted and lead to compound 14a with Ki (D4) as low as 0.03 nM. Molecular docking studies showed a potential, first to report arene cation interaction between the D4 unique residue Arg-186 and the ligands' arene moiety, explaining the importance of having a strong negative electrostatic potential at this area of the compound structure.

Simplifying nickel(0) catalysis: An air-stable nickel precatalyst for the internally selective benzylation of terminal alkenes

The synthesis and characterization of the air-stable nickel(II) complex trans-(PCy2Ph)2Ni(o-tolyl)Cl is described in conjunction with an investigation of its use for the Mizoroki-Heck-type, room temperature, internally selective coupling of substituted benzyl chlorides with terminal alkenes. This reaction, which employs a terminal alkene as an alkenylmetal equivalent, provides rapid, convergent access to substituted allylbenzene derivatives in high yield and with regioselectivity greater than 95:5 in nearly all cases. The reaction is operationally simple, can be carried out on the benchtop with no purification or degassing of solvents or reagents, and requires no exclusion of air or water during setup. Synthesis of the precatalyst is accomplished through a straightforward procedure that employs inexpensive, commercially available reagents, requires no purification steps, and proceeds in high yield.

Chemoenzymatic preparation of enantiopure l-benzofuranyl- and l-benzo[b]thiophenyl alanines

Lipase mediated DKR followed by a chemical and an enzymatic hydrolytic step were combined for the synthesis of enantiopure l-benzofuranyl- and l-benzothienyl alanines.

Structure-activity relationships for a novel series of dopamine D2-like receptor ligands based on N-substituted 3-aryl-8-azabicyclo[3.2.1]octan-3-ol

Discovering dopamine D2-like receptor subtype-selective ligands has been a focus of significant investigation. The D2R-selective antagonist 3-[4-(4-chlorophenyl)-4-hydroxypiperidinyl]methylindole (1, L741,626; K i(D2R/D3R) = 11.2:163 nM) has previously provided a lead template for chemical modification. Herein, analogues have been synthesized where the piperidine was replaced by a tropane ring that reversed the selectivity seen in the parent compound, in human hD2LR- or hD3R-transfected HEK 293 cells (31, Ki(D2R/D3R) = 33.4: 15.5 nM). Further exploration of both N-substituted and aryl ring-substituted analogues resulted in the discovery of several high affinity D2R/D3R ligands with 3-benzofurylmethyl-substituents (e.g., 45, Ki(D2R/D3R) = 1.7:0.34 nM) that induced high affinity not achieved in similarly N-substituted piperidine analogues and significantly (470-fold) improved D3R binding affinity compared to the parent ligand 1. X-ray crystallographic data revealed a distinctive spatial arrangement of pharmacophoric elements in the piperidinol vs tropine analogues, providing clues for the diversity in SAR at the D2 and D3 receptor subtypes.