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

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

• 825-44-5 benzothiophene-1,1-dioxide 
• 20841-53-6 Benzonaphthto<1,2-d>thiophene 7,7-dioxide 
• 109601-52-7 benzo[b]naphtho[1,2-d]thiophene-5-carboxylic acid 
• 605-02-7 1-phenylnaphthalene 
• 20841-49-0 5,6-dihydrobenzonaphtho<1,2-d>thiophene 
• 271-63-6 7-Azaindole 
• 1264712-16-4 2-[1-(2-fluoro-phenyl)naphthalen-2-yloxy]tetrahydropyran 
• 1264712-17-5 1-(2-fluorophenyl)naphthalen-2-ol 
• 1264712-18-6 trifluoromethanesulfonic acid 1-(2-fluoro-phenyl)naphthalen-2-yl ester 
• 1264712-19-7 3-[1-(2-fluorophenyl)naphthalen-2-ylsulfanyl]propionic acid ethyl ester 
• 1993-03-9 o-fluorophenylboronic acid 
• 217438-58-9 2-((1-bromonaphthalen-2-yl)oxy)tetrahydro-2H-pyran 
• 36748-89-7 2-iodobenzothiophene 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 

Downstream Products

• 605-02-7 1-phenylnaphthalene 
• 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 
• 189097-35-6 5-bromobenzo[b]naphtha[1,2-d]thiophene 

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