205-43-6

Basic information

• Product Name: BENZO(B)NAPHTHO(1,2-D)THIOPHENE
• Synonyms: BENZO(B)NAPHTHO(1,2-D)THIOPHENE;7-thiabenzo(c)fluorene;Benzo[b]naphtho[1,2-d]thiophene (purity);Benzo[b]naptho[2,1-d]thiophene;39696, Benzo[b]naphtho[1,2-d]thiophene ( purity);BENZO[B]NAPHTHO[1,2-D]THIOPH;naphtho[2,1-b][1]benzothiole;naphtho[2,1-b]benzothiophene
• CAS NO: 205-43-6
• Molecular Formula: C₁₆H₁₀S
• Molecular Weight: 234.32
• Product Categories: Alphabetic;B;BA - BH
• Mol File: 205-43-6.mol
• Article Data: 26

Chemical Properties

• Melting Point: 185℃ (acetic acid )
• Boiling Point: 220°C/0.2mmHg(lit.)
• Flash Point: 163°C
• Appearance: /
• Density: 1.292g/cm³
• Vapor Pressure: 2.44E-07mmHg at 25°C
• Refractive Index: 1.809
• Storage Temp.: 2-8°C
• BRN: 9635
• CAS DataBase Reference: BENZO(B)NAPHTHO(1,2-D)THIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZO(B)NAPHTHO(1,2-D)THIOPHENE(205-43-6)
• EPA Substance Registry System: BENZO(B)NAPHTHO(1,2-D)THIOPHENE(205-43-6)

Safety Data

• RTECS: DI2340000
• Hazardous Substances Data: 205-43-6(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C16H10S/c1-2-6-12-11(5-1)9-10-15-16(12)13-7-3-4-8-14(13)17-15/h1-10H

Synthetic route

3-[1-(2-fluorophenyl)naphthalen-2-ylsulfanyl]propionic acid ethyl ester (1264712-19-7) → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 50℃; for 8h; Inert atmosphere;	99%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + naphtho[2,1-b]thiophene (233-02-3) → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;	88%

2-[2-(benzo[b]thiophen-3-yl)benzyl]-1,3-dioxolane → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
With trifluorormethanesulfonic acid at 0 - 20℃; for 0.666667h;	88%

2-iodobenzothiophene (36748-89-7) + bicyclo[2.2.1]hepta-2,5-diene (121-46-0) + 2-bromobenzoic-acid (88-65-3) → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
With palladium diacetate; caesium carbonate; tricyclohexylphosphine In 1,4-dioxane at 130℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere;	68%

3-(2-formyl-phenyl)-benzo[b]thiophene-2-carbaldehyde (912952-83-1) → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran McMurry cyclisation; Heating;	67%

(E)-3-(2-styrylphenyl)benzo[b]thiophene-2-carbaldehyde → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
With iron(III) chloride In 1,2-dichloro-ethane at 50℃; for 6h; regioselective reaction;	67%

2-iodophenyl 2-naphthyl sulfide (1520814-76-9) → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); copper diacetate; sodium pivalate In N,N-dimethyl-formamide at 150℃; for 5h; Inert atmosphere;	53%

2-styryl-benzo[b]thiophene (36634-77-2) → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
Irradiation;	51%

2-naphthyl phenyl sulfide (7570-96-9) → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
With n-butyllithium; potassium tert-butylate In tetrahydrofuran; diethyl ether at 20℃; for 0.5h; Schlenk technique;	40%
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate In tetrahydrofuran; diethyl ether at 25℃; for 0.0166667h; Inert atmosphere;	30%

benzothiophene-1,1-dioxide (825-44-5) → Benzonaphthto<1,2-d>thiophene 7,7-dioxide (20841-53-6) + benzothioxantene dioxide (86043-93-8) + Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
at 195℃;

tetrahydro(8,9,10,11)benzo(b)naphto<1,2-d>thiophene (18428-06-3) → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
With selenium at 300℃;
With tetrachloromethane; N-Bromosuccinimide; dibenzoyl peroxide Erwaermen der Reaktionsgemische mit Kaliumacetat und Essigsaeure.;

Benzonaphthto<1,2-d>thiophene 7,7-dioxide (20841-53-6) → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether
With lithium aluminium tetrahydride In diethyl ether Heating;

benzo[b]naphtho[1,2-d]thiophene-5-carboxylic acid (109601-52-7) → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
With barium dihydroxide; copper at 350℃;

benzo[b]naphtho[1,2-d]thiophene-5,6-dicarboxylic acid-anhydride (859744-62-0) → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
With barium dihydroxide; copper at 350℃;

1-phenylnaphthalene (605-02-7) → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
With hydrogen sulfide; pre sulfided Harshaw Cr-0101 T catalyst (chromia alumina catalyst) In toluene at 500℃;	1.05 g
With hydrogen sulfide; aluminum oxide; chromium(III) oxide In toluene at 500℃; Product distribution; other temperatures;	1.05 g

2-bromo-1-chlorobenzene (694-80-4) + 2-Naphthalenethiol (91-60-1) → 2-chlorophenyl 2-naphthyl sulfide + Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
With potassium tert-butylate; ammonia 1) 15 min, 2) irradiation, 180 min.; Yield given. Multistep reaction. Yields of byproduct given;

1-Bromo-2-iodobenzene (583-55-1) + 2-Naphthalenethiol (91-60-1) → (2-bromophenyl)(naphthalen-2-yl)sulfane (15861-51-5) + Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
With potassium tert-butylate; ammonia 1) 15 min, 2) irradiation, 180 min.; Yield given. Multistep reaction. Yields of byproduct given;

1,2-Diiodobenzene (615-42-9) + 2-Naphthalenethiol (91-60-1) → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
With potassium tert-butylate; ammonia 1) 15 min, 2) irradiation, 180 min.; Yield given. Multistep reaction;

5,6-dihydrobenzonaphtho<1,2-d>thiophene (20841-49-0) → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
palladium on activated charcoal dehydrogenation;

5,6-dihydro-benzothiophene → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
With tetrachloromethane; N-Bromosuccinimide; dibenzoyl peroxide Erwaermen der Reaktionsgemische mit Kaliumacetat und Essigsaeure.;

dihydrogen peroxide (7722-84-1) + acetic anhydride (108-24-7) + acetic acid (64-19-7) + Benzo[b]thiophene (95-15-8) → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

tetrahydrofuran (109-99-9) + 3,10-dibromo-benzo[b]naphtho[1,2-d]thiophene-7,7-dioxide + lithium alanate → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

1,2,3,4,5,6-hexahydro-benzo[b]naphtho[1,2-d]thiophen-4-ol → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
palladium on activated charcoal In Triethylene glycol dimethyl ether for 24h; Heating;

7-Azaindole (271-63-6) + C17H13S(1+)*BF4(1-) → C8H8N2*H(1+)*BF4(1-) + Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
In [D3]acetonitrile at 20℃; for 24h; Title compound not separated from byproducts.;

7-Azaindole (271-63-6) + C18H15S(1+)*BF4(1-) → C9H10N2*H(1+)*BF4(1-) + Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
In [D3]acetonitrile at 20℃; for 24h; Title compound not separated from byproducts.;

2,3,5,6-tetrahydronaphtho[2,1-b]benzo[b]thiophen-4(1H)-one (354816-86-7) → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4 / methanol; CH2Cl2 / 2 h / 20 °C 2: Pd-C / triethylene glycol dimethyl ether / 24 h / Heating View Scheme

11c-nitro-2,3,4a,5,11b,11c-hexahydro-1H-benzo[b]naphtho[1,2-d]thiophen-4-one → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: DBN / tetrahydrofuran / 0.5 h / 0 °C 2: NaBH4 / methanol; CH2Cl2 / 2 h / 20 °C 3: Pd-C / triethylene glycol dimethyl ether / 24 h / Heating View Scheme

6A,11b-dihydro-benzo[b]naphtho[1,2-d]thiophene-7,7-dioxide (19076-30-3) → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: Br2 / CCl4 2: LiAlH4 / diethyl ether / Heating View Scheme

benzo[b]naphtho[1,2-d]thiophene-5-carboxylic acid ethyl ester (111273-73-5) → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol. KOH-solution 2: barium hydroxide; copper / 350 °C View Scheme

(+/-)-4c-chlorocarbonyl-4t-phenyl-1,2,3,4-tetrahydro-[1r]naphthoic acid ethyl ester (102237-39-8) → Benzo[b]naphtho[1,2-d]thiophene (205-43-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride / 175 °C / 0.01 Torr 2: methanol. KOH-solution 3: barium hydroxide; copper / 350 °C View Scheme

Benzo[b]naphtho[1,2-d]thiophene (205-43-6) → 5-bromobenzo[b]naphtha[1,2-d]thiophene

Conditions	Yield
With bromine In dichloromethane at 0℃;	91%
With bromine In chloroform
With N-Bromosuccinimide In dichloromethane at 20℃; for 2h;

1-chloro 4-iodobutane (10297-05-9) + Benzo[b]naphtho[1,2-d]thiophene (205-43-6) → C20H18ClS(1+)*BF4(1-)

Conditions	Yield
With silver tetrafluoroborate In 1,2-dichloro-ethane at 25℃; Inert atmosphere;	75%

dimethylsilicon dichloride (75-78-5) + Benzo[b]naphtho[1,2-d]thiophene (205-43-6) → 7,7-dimethyl-7H-benzo[b]naphtho[1,2-d]silole

Conditions	Yield
Stage #1: Benzo[b]naphtho[1,2-d]thiophene With N,N,N,N,-tetramethylethylenediamine; lithium In tetrahydrofuran at 20℃; for 2h; Schlenk technique; Inert atmosphere; Stage #2: dimethylsilicon dichloride In tetrahydrofuran at -78 - 20℃; Inert atmosphere; Schlenk technique;	74%

4-chlorobutyl bromide (6940-78-9) + Benzo[b]naphtho[1,2-d]thiophene (205-43-6) → C20H18ClS(1+)*BF4(1-)

Conditions	Yield
With silver tetrafluoroborate In 1,2-dichloro-ethane at 25℃; Inert atmosphere;	50%

Benzo[b]naphtho[1,2-d]thiophene (205-43-6) → benzo[b]naphtho[1,2-d]thiophene-6-boronic acid (1383607-09-7)

Conditions	Yield
Stage #1: Benzo[b]naphtho[1,2-d]thiophene With n-butyllithium In tetrahydrofuran; hexane at -80 - 20℃; for 2h; Inert atmosphere; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -80 - 20℃; for 18h; Inert atmosphere;	49%

Benzo[b]naphtho[1,2-d]thiophene (205-43-6) → Benzonaphthto<1,2-d>thiophene 7,7-dioxide (20841-53-6)

Conditions	Yield
With dihydrogen peroxide; acetic acid for 12h; Reflux;	35%
With dihydrogen peroxide; acetic acid
With dihydrogen peroxide In acetic acid
With 3-chloro-benzenecarboperoxoic acid

Benzo[b]naphtho[1,2-d]thiophene (205-43-6) → (+)-(10S,11R)-cis-10,11-Dihydroxy-10,11-dihydrobenzo[b]naphtho[1,2-d]thiophene

Conditions	Yield
With Sphingomonas yanoikuyae B8/36; oxygen at 30℃; for 18h;	2%

Benzo[b]naphtho[1,2-d]thiophene (205-43-6) → 1-phenylnaphthalene (605-02-7) + 1-phenyl-1,2,3,4-tetrahydronaphthalene (3018-20-0) + 5-phenyl-1,2,3,4-tetrahydronaphthalene (67064-63-5) + tetrahydro(1,2,3,4)benzo(b)naphto<1,2-d>thiophene (90501-14-7)

Conditions	Yield
With hydrogen; aluminum oxide; nickel molybdenum In dodecane at 250℃; under 30400 Torr; Rate constant; Product distribution;
With hydrogen; Procatalyst HR 346+3 percent H2S+ 97 percent H2 In dodecane at 250℃; under 30400 Torr; Rate constant; Product distribution;
With hydrogen; Procatalyst HR 346+3 percent H2S+97 percent H2 In dodecane at 250℃; under 30400 Torr;

Benzo[b]naphtho[1,2-d]thiophene (205-43-6) → 5-Nitro-benzo[b]naphtho[1,2-d]thiophene (189097-16-3)

Conditions	Yield
With copper(II) nitrate In acetic acid

Benzo[b]naphtho[1,2-d]thiophene (205-43-6) → Benzo[b]naphtho[1,2-d]thiophene-5-sulfonic acid

Conditions	Yield
With chlorosulfonic acid In chloroform

Benzo[b]naphtho[1,2-d]thiophene (205-43-6) → 1-phenylnaphthalene (605-02-7)

Conditions	Yield
nickel In ethanol at 78.3℃; for 1h; Rate constant;

Upstream product

• 18428-06-3 tetrahydro(8,9,10,11)benzo(b)naphto<1,2-d>thiophene 
• 20841-53-6 Benzonaphthto<1,2-d>thiophene 7,7-dioxide 
• 859744-62-0 benzo[b]naphtho[1,2-d]thiophene-5,6-dicarboxylic acid-anhydride 
• 605-02-7 1-phenylnaphthalene 
• 694-80-4 2-bromo-1-chlorobenzene 
• 91-60-1 2-Naphthalenethiol 
• 583-55-1 1-Bromo-2-iodobenzene 
• 615-42-9 1,2-Diiodobenzene 
• 7722-84-1 dihydrogen peroxide 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 95-15-8 Benzo[b]thiophene 
• 109-99-9 tetrahydrofuran 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 

Downstream Products

• 605-02-7 1-phenylnaphthalene 
• 189097-35-6 5-bromobenzo[b]naphtha[1,2-d]thiophene 
• 3018-20-0 1-phenyl-1,2,3,4-tetrahydronaphthalene 
• 67064-63-5 5-phenyl-1,2,3,4-tetrahydronaphthalene 
• 90501-14-7 tetrahydro(1,2,3,4)benzo(b)naphto<1,2-d>thiophene 

Relevant articles and documents

Synthesis method of benzo[b] naphtho [2,3-d] thiophene

The present invention discloses a method for synthesizing benzo [b] naphthio [2,3-d] thiophene, comprising the following steps: 2-aminobenzo [d] thiazole as a raw material, under the action of alkali and haloalkanes, to prepare 2- (methylthio) aniline; using 2- (methylthio) aniline to prepare (2-iophenyl) (methyl) thiane preparation of 1-iodo-2-(methylsulfonyl) benzene; using 1-iodo-2-(methylsulfonyl) benzene; using 1-iodo-2-(methylsulfonyl) Benzene and compound S5 were prepared to obtain 1-(2-(methyl sulfoxide phenyl)) naphthalene, and 1-(2-(methyl sulfoxidephenyl)) naphthalene was used to obtain benzo[b]naphthalene [2,3-d]thiophene. The present invention employs a green route to obtain high yield, high quality benzo [b] naphthalene [2,3-d] thiophene.

Site-Selective Acceptorless Dehydrogenation of Aliphatics Enabled by Organophotoredox/Cobalt Dual Catalysis

The value of catalytic dehydrogenation of aliphatics (CDA) in organic synthesis has remained largely underexplored. Known homogeneous CDA systems often require the use of sacrificial hydrogen acceptors (or oxidants), precious metal catalysts, and harsh reaction conditions, thus limiting most existing methods to dehydrogenation of non- or low-functionalized alkanes. Here we describe a visible-light-driven, dual-catalyst system consisting of inexpensive organophotoredox and base-metal catalysts for room-temperature, acceptorless-CDA (Al-CDA). Initiated by photoexited 2-chloroanthraquinone, the process involves H atom transfer (HAT) of aliphatics to form alkyl radicals, which then react with cobaloxime to produce olefins and H2. This operationally simple method enables direct dehydrogenation of readily available chemical feedstocks to diversely functionalized olefins. For example, we demonstrate, for the first time, the oxidant-free desaturation of thioethers and amides to alkenyl sulfides and enamides, respectively. Moreover, the system's exceptional site selectivity and functional group tolerance are illustrated by late-stage dehydrogenation and synthesis of 14 biologically relevant molecules and pharmaceutical ingredients. Mechanistic studies have revealed a dual HAT process and provided insights into the origin of reactivity and site selectivity.

Helicene synthesis by Br?nsted acid-catalyzed cycloaromatization in HFIP [(CF3)2CHOH]

A facile synthesis of carbo- and heterohelicenes was achieved via tandem cycloaromatization of bisacetal precursors, which were readily prepared through C-C bond formation by Suzuki-Miyaura coupling. This cyclization was efficiently realized by a catalytic amount of trifluoromethanesulfonic acid (TfOH) in a cation-stabilizing solvent, 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP), which readily allowed gram-scale syntheses of higher-order helicenes, double helical helicenes, and heterohelicenes.