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Usage

Uses

Used in Organic Semiconductors:
Naphtho[2,3-b]thiophene is utilized as a building block in the synthesis of organic semiconductors due to its unique electronic properties, which are crucial for the development of materials with specific electrical and optical characteristics.
Used in Dyes:
Naphtho[2,3-b]thiophene is also employed as a component in the creation of dyes, where its optical properties contribute to the color and stability of the dyes produced.
Used in Pharmaceuticals:
Naphtho[2,3-b]thiophene serves as a building block in the synthesis of pharmaceuticals, leveraging its chemical structure to contribute to the development of new drugs with potential therapeutic applications.
Used in Organic Electronics:
In the field of organic electronics, Naphtho[2,3-b]thiophene is used in the fabrication of organic light-emitting diodes (OLEDs) and organic photovoltaic (OPV) devices, where its electronic and optical properties are essential for enhancing the performance and efficiency of these devices.
Used in Advanced Materials Development:
Its unique properties make Naphtho[2,3-b]thiophene a valuable component in the development of advanced materials for various technological applications, including but not limited to electronic devices, sensors, and energy storage systems.

InChI:InChI=1/C12H8S/c1-2-4-10-8-12-11(5-6-13-12)7-9(10)3-1/h1-8H

Upstream product

• 64289-80-1 naphtho[2,3-b]thiophen-3-ol 
• 4968-81-4 naphtho[2,3-b]thiophene-4,9-dione 
• 33608-30-9 4,9-dihydro-naphtho[2,3-b]thiophene 
• 344417-46-5 2-(thiophene-2-ylmethyl)benzaldehyde 
• 116608-06-1 3-Benzyl-2-chloromethyl-thiophene 
• 112251-84-0 5,6,8a,9-tetrahydronaphtho<2,3-b>thiophene 
• 112251-85-1 4,4a,7,8-tetrahydronaphtho<2,3-b>thiophene 
• 337512-22-8 3-(2-thienoyl)cinnoline 
• 112251-74-8 endo 8-(2-thienyl)-bicyclo<4.2.0>oct-2-ene-7-ol 
• 31926-62-2 naphtho[2,3-b]thiophen-4-one 
• 62636-87-7 2-(thiophene-2-yl-methyl)-benzoic acid 
• 21579-98-6 [2-(thiophen-2-ylmethyl)phenyl]methanol 
• 46496-80-4 2-(thiophene-2-carbonyl)-benzoic acid 
• 5834-16-2 3-methyl-2-thiophenecarboxaldehdye 

Downstream Products

• 88220-32-0 2-(o-naphtho<2,3-b>thenyl)benzaldehyde 
• 88220-31-9 2-(o-hydroxymethylbenzyl)naphtho<2,3-b>thiophene 
• 88220-30-8 2-(o-carboxybenzyl)naphtho<2,3-b>thiophene 
• 243-46-9 benzo[b]naphtho[2,3-d]thiophene 
• 1610619-51-6 5,13-bis(4-methoxyphenyl)dinaphtho[2,3-b:2',3'-d]thiophene S,S-dioxide 
• 88220-29-5 2-naphtho<2,3-b>thienyl o-carboxyphenyl ketone 

Relevant academic research and scientific papers

Enhancing the Antiaromaticity ofs-Indacene through Naphthothiophene Fusion

Addressing the instability of antiaromatic compounds often involves protection with bulky groups and/or fusion of aromatic rings, thus decreasing paratropicity. We report four naphthothiophene-fuseds-indacene isomers, one of which is more antiaromatic tha

Palladium-catalyzed benzylic C(sp3)–H arylation of o-alkylbenzaldehydes

The palladium-catalyzed benzylic C(sp3)–H arylation of o-alkylbenzaldehyde derivatives was achieved utilizing 2-dimethylaminoethylamine as a novel transient directing group. The γ-C(sp3)–H arylation reaction efficiently afforded a variety of arylated o-alkylbenzaldehydes and polycyclic aromatic hydrocarbons (PAHs) in one pot, exhibiting high functional group tolerance with broad substrate scope. The aliphatic diamine auxiliary represents a simple, inexpensive, readily available, and removable directing group for C–H activation. The resultant o-benzylbenzaldehyde products could be diversely transformed into potentially important synthetic intermediates under mild conditions.

Cascade Oxidative C?H Annulation of Thiophenes: Heck-Type Pathway Enables Concise Access to Thienoacenes

The pursuit of efficient synthetic route to thienoacenes represents an appealing yet challenging task in the fields of both organic synthetic chemistry and organic functional materials. In this work, we disclose a rhodium-catalyzed cascade C?H annulation of phenacyl phosphoniums with (benzo)thiophenes via a Heck-type pathway to provide a new class of planar thienoacenes, which involves the formation of three Caryl-Caryl bonds and one Caryl?O bond in a single operation. The neutral S,O-heteroacenes exhibit superior stability and adopt a herringbone-like packing mode with efficient π–π stacking in the crystals, suggesting their potential in organic semiconducting materials. This work first exemplifies the superiority of cascade oxidative C?H annulation involving a Heck-type pathway in the development of concise access to heteroacenes.

Access to Hetero-Benzyl Scaffolds via Transient-Ligand-Enabled Direct γ-C(sp3)-H Arylation of 3-Methylheteroarene-2-Carbaldehydes

An efficient and straightforward method has been developed for the synthesis of β-benzyl-substituted 5-membered heterocyclic carbaldehydes via transient directing-group-enabled direct γ-C(sp3)-H arylation of 3-methylheteroarene-2-carbaldehydes. A wide range of 3-methylheteroarene carbaldehydes undergo coupling with a variety of aryl iodides, including less reactive iodo pyridine derivatives to provide a library of highly selective functionalized products in good to excellent yields. Some of these products have been successfully utilized in synthesizing useful synthetic intermediates.

Synthesis of annulated arenes and heteroarenes by hydriodic acid and red phosphorus mediated reductive cyclization of 2-(Hetero)aroylbenzoic acids or 3-(Hetero)arylphthalides

Annulated arenes and hetarenes were prepared in good to very good yields by hydriodic acid/red phosphorus mediated reductive cyclization of 3-(hetero)aryl phthalides. The reductive cyclization also proceeded successfully with 2-aroylbenzoic acids and 2-aroylnaphthoic acids.

Synthesis of Annulated Anthracenes, Carbazoles, and Thiophenes Involving Bradsher-Type Cyclodehydration or Cyclization-Reductive-Dehydration Reactions

A conventional BF3·OEt2-mediated Bradsher-type cyclodehydration of 2-arylmethyl benzaldehydes in CH2Cl2 at room temperature gave polycyclic aromatic and heteroaromatic compounds. Alternatively, these compounds could be synthesized in better yields from 2-arylmethylbenzoic acids by triflic-acid-mediated cyclization followed by reductive dehydration.

Indium-catalyzed construction of polycyclic aromatic hydrocarbon skeletons via dehydration

Polycyclic aromatic compounds can be synthesized from 2-benzylic- or 2-allylbenzaldehydes using a catalytic amount of In(III) or Re(I) complexes. By using this method, polycyclic aza-aromatic compounds can also be prepared efficiently. In these reactions, only water is formed as a side product.

Flash vacuum pyrolysis of 3-aroylcinnolines: Interesting routes toward polynuclear aromatic compounds

Flash vacuum pyrolysis of 3-aroylcinnolines 3 at 900°C and 0.02 Torr yielded phenanthrene and arylacetylene derivatives as the major products beside anthracene and diarylacetylene derivatives as minor products. Also, FVP of 3-(2-thienoyl)-cinnoline gave three isomeric naphthothiophenes, phenyl-2-thienylacetylene and phenylacetylene. On the other hand, 3-(2-furoyl)-cinoline gave dibenzofuran as a major product besides naphtho[1,2-b]furan and phenylacetylene.

GENERATION AND REACTIONS OF 2,3-DIHYDRO-2,3-bis-(METHYLENE)THIOPHENES

2,3-Dihydro-2,3-bis-(methylene)thiophene and its benzo derivate, generated flash-pyrolytically, polymerise or are trapped with HCl and PhSH but only the latter gives Diels-Alder adducts; electrocyclisation of the 3-phenylmethylene derivate is accompained by skeletal rearrangement to give naphthothiophene.

Acid-catalyzed rearrangement of cyclobutanols. A novel rearrangement

The acid-catalysed dehydration-rearrangement reaction of α-thienyl cyclobutanols 3 and 4 resulted in the formation of tetrahydronaphthothiophenes 5a and 6a.The rearrangement to the linearly fused PAH system instead of the expected angularly fused system reflects α-scission of the cyclobutyl ring.A mechanism based on deuterium labelling studies is propesed to account for the product formation.