233-02-3

Basic information

• Product Name: naphtho[2,1-b]thiophene
• Synonyms: naphtho[2,1-b]thiophene;benzo[e][1]benzothiole;benzo[e]benzothiophene
• CAS NO: 233-02-3
• Molecular Formula: C₁₂H₈S
• Molecular Weight: 184.25692
• EINECS: 205-939-1
• Mol File: 233-02-3.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 340.2°Cat760mmHg
• Flash Point: 118.4°C
• Appearance: /
• Density: 1.252g/cm³
• Vapor Pressure: 0.000173mmHg at 25°C
• Refractive Index: 1.756
• CAS DataBase Reference: naphtho[2,1-b]thiophene(CAS DataBase Reference)
• NIST Chemistry Reference: naphtho[2,1-b]thiophene(233-02-3)
• EPA Substance Registry System: naphtho[2,1-b]thiophene(233-02-3)

Safety Data

• Hazardous Substances Data: 233-02-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 19, p. 2691, 1989 DOI: 10.1080/00397918908053063Tetrahedron Letters, 6, p. 301, 1965

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

Upstream product

• 109-99-9 tetrahydrofuran 
• 108871-15-4 naphtho[2,1-b]thiophene-6,9-dione 
• 91-60-1 2-Naphthalenethiol 
• 1428787-31-8 1-(2-acetothioethyl)naphthalene 
• 107-21-1 ethylene glycol 
• 3783-65-1 2-styrylthiophene 
• 1392144-28-3 C₂₆H₂₄N₄O₄S₃ 
• 135-19-3 β-naphthol 
• 78076-66-1 1,2-dihydronaphtho<2,1-b>thiophene 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 
• 5402-55-1 2-thiophenethanol 
• 1918-82-7 2-vinylthiophene 
• 85992-25-2 1-chloronaphtho<2,1-b>thiophene-2-carboxoyl chloride 
• 126331-91-7 C₁₂H₆Li₂ 

Downstream Products

• 16587-59-0 3-phenylnaphtho[2,1-b]thiophene 
• 78076-53-6 1-(4-methylphenyl)-1-(1'-naphthyl)ethane 
• 78076-57-0 1-(3',4'-dimethylphenyl)-2-(1'-naphthyl)ethane 
• 78076-64-9 1-p-Tolyl-naphtho[2,1-b]thiophene 
• 78076-55-8 2-(3',4'-dimethylphenyl)naphtho<2,1-b>thiophene 
• 78076-65-0 1-(4-Ethyl-phenyl)-naphtho[2,1-b]thiophene 
• 78076-59-2 1-Phenyl-1,2-dihydro-naphtho[2,1-b]thiophene 3,3-dioxide 
• 78076-60-5 1-p-Tolyl-1,2-dihydro-naphtho[2,1-b]thiophene 3,3-dioxide 
• 78076-61-6 1-(4-Ethyl-phenyl)-1,2-dihydro-naphtho[2,1-b]thiophene 3,3-dioxide 
• 78076-62-7 2-(3,4-Dimethyl-phenyl)-1,2-dihydro-naphtho[2,1-b]thiophene 3,3-dioxide 
• 78076-63-8 2-(2,5-Dimethyl-phenyl)-1,2-dihydro-naphtho[2,1-b]thiophene 3,3-dioxide 
• 205-43-6 Benzo[b]naphtho[1,2-d]thiophene 
• 136950-44-2 2-naphtho-<2',1'-b>-thienylthioglycolic acid p-nitrobenzyl ester 
• 136950-45-3 2-naphtho-<2',1'-b>-thienylthioglycolic acid p-bromophenacyl ester 

Relevant articles and documents

W(CO)5·THF-catalyzed electrocyclizations of aromatic enynes via vinylidene intermediates

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Insight into Regioselective Control in Aerobic Oxidative C-H/C-H Coupling for C3-Arylation of Benzothiophenes: Toward Structurally Nontraditional OLED Materials

The installation of (benzo)thiophene-containing biaryls via coupling reactions has become a staple in designing photoelectric materials. Undeniably, C-H/C-H cross-coupling reactions between two (hetero)aromatics would be a shortcut toward these structural fragments. While more reliable cross-coupling technologies are well-established to provide C2-arylated (benzo)thiophenes, efficient methods that arylate the C3-position remain underdeveloped. Herein we provide insight into the factors that determine regioselectivity switching for these cross-coupling reactions. X-ray crystallographic analysis gives solid evidence for the key roles of triflate in regioselective dearomatization and acetate in base-assisted anti-β-deprotonated rearomatization. The first isolation and X-ray characterization of a medium-sized dearomatized cyclometalated adduct involving both substrates provide extra insight into aerobic oxidative Ar-H/Ar-H cross-coupling reactions. The mechanistic breakthrough incubates the first example, enabling C-H/C-H-type C3-arylation of benzothiophenes. Finally, this chemistry is used to design blue-emitting thermally activated delayed fluorescence (TADF) materials with a helicene conformation that exhibit a high maximum external quantum efficiency of 25.4% in OLED.

Further insight into the photochemical behavior of 3-aryl-N-(arylsulfonyl)propiolamides: tunable synthetic route to phenanthrenes

Reported herein is further insight into the photochemical behaviour of 3-aryl-N-(arylsulfonyl)-propiolamides, which provides a straightforward way to access meaningful phenanthrenes. Mechanistic investigation indicated that aryl migration, C-C coupling, 1,3-hydrogen shift, desulfonylation and elimination were involved in the process. Moreover, this protocol allowed for scale-up using a flow reactor.