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239-35-0 Usage

Uses

1,2-Benzodiphenylene sulfide has been used in direct screening of sediment samples for polycyclic aromatic hydrocarbons by flow manifold coupled on-line to a fluorimetric detector.

General Description

1,2-benzodiphenylene sulfide is a rare constituent of coal tar. Photodeoxygenation of 1,2-benzodiphenylene sulfoxide, generates an intermediate capable of oxidizing the solvent benzene to phenol. Liquid-phase photolysis of 1,2-benzodiphenylene sulfide to generate atomic oxygen [O(3P)] or an equivalent active oxygen species has been reported.

Check Digit Verification of cas no

The CAS Registry Mumber 239-35-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,3 and 9 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 239-35:
(5*2)+(4*3)+(3*9)+(2*3)+(1*5)=60
60 % 10 = 0
So 239-35-0 is a valid CAS Registry Number.
InChI:InChI=1/C16H10S/c1-2-6-12-11(5-1)9-10-14-13-7-3-4-8-15(13)17-16(12)14/h1-10H

239-35-0 Well-known Company Product Price

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  • Aldrich

  • (255122)  1,2-Benzodiphenylenesulfide  99%

  • 239-35-0

  • 255122-25MG

  • 944.19CNY

  • Detail

239-35-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name naphtho[1,2-b][1]benzothiole

1.2 Other means of identification

Product number -
Other names benzo[b]naphto[2,1-d]thiophene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:239-35-0 SDS

239-35-0Synthetic route

2-[2-(1-chloro-vinyl)-phenyl]-benzo[b]thiophene

2-[2-(1-chloro-vinyl)-phenyl]-benzo[b]thiophene

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

Conditions
ConditionsYield
at 800℃; under 0.1 Torr; Cyclization; Pyrolysis;92%
1-Naphthalenethiol
529-36-2

1-Naphthalenethiol

1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

Conditions
ConditionsYield
With dichloro bis(acetonitrile) palladium(II); cesium pivalate; bis[2-(diphenylphosphino)phenyl] ether In N,N-dimethyl acetamide at 140℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;92%
cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

naphtho[1,2-b]thiophene
234-41-3

naphtho[1,2-b]thiophene

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;90%
2-(2-ethynylphenyl)benzo[b]thiophene

2-(2-ethynylphenyl)benzo[b]thiophene

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

Conditions
ConditionsYield
With silver(I) hexafluorophosphate; [dichloro(p-cymene)(triphenylphosphane)ruthenium(II)] In chlorobenzene at -78 - 120℃; for 20h; Inert atmosphere;90%
C16H10S

C16H10S

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

Conditions
ConditionsYield
With platinum(II) chloride In toluene at 100℃; for 12h; Inert atmosphere;85%
C16H12OS

C16H12OS

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

Conditions
ConditionsYield
With 5,10,15,20-tetraphenylporphyrinatochromium(III) hexafluoroantimonate In 1,2-dichloro-ethane at 100℃; for 2h; Inert atmosphere; Sealed tube;78%
3-styrylbenzothiophene
4565-13-3

3-styrylbenzothiophene

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

Conditions
ConditionsYield
With iodine In cyclohexane for 4h; Irradiation;72%
benzo[b]naphtho[2,1-d]iodol-11-ium trifluoromethanesulfonate
1469876-15-0

benzo[b]naphtho[2,1-d]iodol-11-ium trifluoromethanesulfonate

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

Conditions
ConditionsYield
With triethylammonium N-benzyldithiocarbamate; copper(II) sulfate In acetonitrile at 60℃; for 5h; Sealed tube; Inert atmosphere;71%
3-(2-(2-bromophenyl)-2-(phenylsulfonyl)ethyl)benzo[b]thiophene

3-(2-(2-bromophenyl)-2-(phenylsulfonyl)ethyl)benzo[b]thiophene

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;65%
1-naphthyl phenyl sulfide
7570-98-1

1-naphthyl phenyl sulfide

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

Conditions
ConditionsYield
With palladium(II) trifluoroacetate; silver(I) acetate; Trimethylacetic acid at 130℃; for 24h; Schlenk technique;60%
With palladium(II) trifluoroacetate; silver(I) acetate; potassium carbonate at 130℃; for 24h; Schlenk technique;56%
With n-butyllithium; potassium tert-butylate In tetrahydrofuran; diethyl ether; hexane at 20℃;36%
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate In tetrahydrofuran; diethyl ether at 25℃; for 0.0166667h; Inert atmosphere;32%
Benzo[b]thiophene
95-15-8

Benzo[b]thiophene

A

benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

B

benzo[b]naphtho[2,1-d]thiophene 11-oxide
121823-04-9

benzo[b]naphtho[2,1-d]thiophene 11-oxide

C

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

rac-(6aS,11S,11aR)-6a,11a-dihydrobenzo[b]naphtho[2,1-d]thiophene 11-oxide

rac-(6aS,11S,11aR)-6a,11a-dihydrobenzo[b]naphtho[2,1-d]thiophene 11-oxide

rac-(6aS,11R,11aR)-6a,11a-dihydrobenzo[b]naphtho[2,1-d]thiophene 11-oxide

rac-(6aS,11R,11aR)-6a,11a-dihydrobenzo[b]naphtho[2,1-d]thiophene 11-oxide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃;A 60%
B 0.026 g
C 0.018 g
D 0.045 g
E 0.015 g
C22H16S
1146542-57-5

C22H16S

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In CH3Cl at 65℃;42%
2-ethynyl-thiophene
4298-52-6

2-ethynyl-thiophene

2-(benzo[b]thiophen-2-yl)benzenamine
38210-45-6

2-(benzo[b]thiophen-2-yl)benzenamine

A

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

B

6-(thiophen-2-yl)benzo[b]naphtho[2,1-d]thiophene

6-(thiophen-2-yl)benzo[b]naphtho[2,1-d]thiophene

Conditions
ConditionsYield
With tris[2-phenylpyridinato-C2,N]iridium(III); tert.-butylnitrite In acetonitrile at 20℃; for 15h; Irradiation;A n/a
B 40%
1-Iodonaphthalene
90-14-2

1-Iodonaphthalene

2-bromothiophenol
6320-02-1

2-bromothiophenol

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

Conditions
ConditionsYield
With dichloro bis(acetonitrile) palladium(II); cesium pivalate; bis[2-(diphenylphosphino)phenyl] ether In N,N-dimethyl acetamide at 140℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;30%
2-(2-ethynylphenyl)benzo[b]thiophene

2-(2-ethynylphenyl)benzo[b]thiophene

A

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

B

aceanthrylene
202-03-9

aceanthrylene

Conditions
ConditionsYield
at 800℃; under 0.1 Torr; Cyclization; rearrangement; Pyrolysis;A 9%
B 24%
2-(cyclohex-1-en-1-yl)naphthalene
54607-03-3

2-(cyclohex-1-en-1-yl)naphthalene

A

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

B

benzo[b]naphtho[2,3-d]thiophene
243-46-9

benzo[b]naphtho[2,3-d]thiophene

C

2-phenylnaphthalene
612-94-2

2-phenylnaphthalene

Conditions
ConditionsYield
With hydrogen sulfide at 550℃; for 4.5h; Mechanism; Product distribution; object of study: sulfur bridging reaction;A 9.2%
B 2.8%
C 8%
3-(2-methylbenzoyl)benzothiophene
22720-67-8

3-(2-methylbenzoyl)benzothiophene

A

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

B

<1>benzothieno<2,3-b>-1,4-naphthoquinone
21503-35-5

<1>benzothieno<2,3-b>-1,4-naphthoquinone

Conditions
ConditionsYield
at 350℃;
1-chloro-benzo[b]naphtho[2,1-d]thiophene

1-chloro-benzo[b]naphtho[2,1-d]thiophene

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

Conditions
ConditionsYield
With pyridine; copper(I) oxide; acetic anhydride at 200℃;
7,8,9,10-tetrahydrobenzonaphtho<2,1-d>thiophene
16587-63-6

7,8,9,10-tetrahydrobenzonaphtho<2,1-d>thiophene

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

Conditions
ConditionsYield
With selenium at 300℃;
With selenium
1-chloro-7,8,9,10-tetrahydro-benzo[b]naphtho[2,1-d]thiophene
573722-57-3

1-chloro-7,8,9,10-tetrahydro-benzo[b]naphtho[2,1-d]thiophene

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

Conditions
ConditionsYield
With selenium at 300℃;
benzo[b]naphtho[2,1-d]thiophene-1,4-quinone
125847-44-1

benzo[b]naphtho[2,1-d]thiophene-1,4-quinone

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

Conditions
ConditionsYield
With tetrahydrofuran; lithium aluminium tetrahydride
2-methyl-3-benzoylbenzothiophene
65628-46-8

2-methyl-3-benzoylbenzothiophene

A

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

B

benzo[b]naphtho[2,3-d]thiophene
243-46-9

benzo[b]naphtho[2,3-d]thiophene

C

<1>benzothieno<2,3-b>-1,4-naphthoquinone
21503-35-5

<1>benzothieno<2,3-b>-1,4-naphthoquinone

D

3-benzyl-2-methylbenzothiophene

3-benzyl-2-methylbenzothiophene

Conditions
ConditionsYield
at 360℃; for 2.5h; Yield given. Further byproducts given. Title compound not separated from byproducts;A 2 % Turnov.
B 4 % Turnov.
C n/a
D 40 % Turnov.
2-methyl-3-benzoylbenzothiophene
65628-46-8

2-methyl-3-benzoylbenzothiophene

A

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

B

benzo[b]naphtho[2,3-d]thiophene
243-46-9

benzo[b]naphtho[2,3-d]thiophene

C

<1>benzothieno<2,3-b>-1,4-naphthoquinone
21503-35-5

<1>benzothieno<2,3-b>-1,4-naphthoquinone

D

3-benzyl-2-methylbenzothiophene

3-benzyl-2-methylbenzothiophene

E

11-hydroxybenzonaphtho<2,3-d>thiophene
91704-83-5

11-hydroxybenzonaphtho<2,3-d>thiophene

Conditions
ConditionsYield
at 420℃; for 0.5h; Product distribution; other temperatures; other time;A 4 % Turnov.
B 6 % Turnov.
C n/a
D 12.5 % Turnov.
E n/a
2-methyl-3-benzoylbenzothiophene
65628-46-8

2-methyl-3-benzoylbenzothiophene

A

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

B

benzo[b]naphtho[2,3-d]thiophene
243-46-9

benzo[b]naphtho[2,3-d]thiophene

C

3-benzyl-2-methylbenzothiophene

3-benzyl-2-methylbenzothiophene

D

11-hydroxybenzonaphtho<2,3-d>thiophene
91704-83-5

11-hydroxybenzonaphtho<2,3-d>thiophene

Conditions
ConditionsYield
at 360℃; for 2.5h; Further byproducts given. Title compound not separated from byproducts;A 2 % Turnov.
B 4 % Turnov.
C 40 % Turnov.
D n/a
at 360℃; for 2.5h; Yield given. Further byproducts given;A 2 % Turnov.
B 4 % Turnov.
C 40 % Turnov.
D n/a
3-(2-methylbenzoyl)benzothiophene
22720-67-8

3-(2-methylbenzoyl)benzothiophene

A

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

B

<1>benzothieno<2,3-b>-1,4-naphthoquinone
21503-35-5

<1>benzothieno<2,3-b>-1,4-naphthoquinone

C

11-hydroxybenzonaphtho<2,3-d>thiophene
91704-83-5

11-hydroxybenzonaphtho<2,3-d>thiophene

D

3-(2-methylbenzyl)benzothiophene
74881-99-5

3-(2-methylbenzyl)benzothiophene

Conditions
ConditionsYield
at 420℃; for 0.5h;A 64.5 % Turnov.
B n/a
C n/a
D 11 % Turnov.
at 420℃; for 0.5h; Product distribution; other temperatures; other time;A 64.5 % Turnov.
B n/a
C n/a
D 11 % Turnov.
at 360℃; for 2.5h; Yield given;A 36 % Turnov.
B n/a
C n/a
D 3 % Turnov.
at 420℃; for 0.5h; Title compound not separated from byproducts;A 64.5 % Turnov.
B n/a
C n/a
D 11 % Turnov.
2-(2-methylbenzoyl)benzothiophene
74882-00-1

2-(2-methylbenzoyl)benzothiophene

A

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

B

benzo[b]naphtho[2,3-d]thiophene
243-46-9

benzo[b]naphtho[2,3-d]thiophene

C

<1>benzothieno<2,3-b>-1,4-naphthoquinone
21503-35-5

<1>benzothieno<2,3-b>-1,4-naphthoquinone

D

6-hydroxybenzonaphtho<2,3-d>thiophene
91704-82-4

6-hydroxybenzonaphtho<2,3-d>thiophene

E

2-(2-methylbenzyl)benzothiophene
83656-83-1

2-(2-methylbenzyl)benzothiophene

Conditions
ConditionsYield
at 420℃; for 0.5h; Product distribution; other temperatures; other time;A 2.5 % Turnov.
B 30 % Turnov.
C n/a
D n/a
E 0.5 % Turnov.
2-(2-methylbenzoyl)benzothiophene
74882-00-1

2-(2-methylbenzoyl)benzothiophene

A

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

B

benzo[b]naphtho[2,3-d]thiophene
243-46-9

benzo[b]naphtho[2,3-d]thiophene

C

6-hydroxybenzonaphtho<2,3-d>thiophene
91704-82-4

6-hydroxybenzonaphtho<2,3-d>thiophene

D

2-(2-methylbenzyl)benzothiophene
83656-83-1

2-(2-methylbenzyl)benzothiophene

Conditions
ConditionsYield
at 420℃; for 0.5h; Further byproducts given;A 2.5 % Turnov.
B 30 % Turnov.
C n/a
D 0.5 % Turnov.
at 360℃; for 2.5h; Title compound not separated from byproducts;A 3.3 % Turnov.
B 2.2 % Turnov.
C n/a
D 19.5 % Turnov.
benzo[b]naphtho[2,1-d]thiophene 11-oxide
121823-04-9

benzo[b]naphtho[2,1-d]thiophene 11-oxide

benzene
71-43-2

benzene

A

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

B

phenol
108-95-2

phenol

Conditions
ConditionsYield
In acetonitrile at 20℃; Irradiation; Title compound not separated from byproducts.;
bituminous housecoal

bituminous housecoal

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

Conditions
ConditionsYield
With air Formation of xenobiotics; Heating;
11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

5-nitrobenzonaphtho<2,1-d>thiophene
76113-31-0

5-nitrobenzonaphtho<2,1-d>thiophene

Conditions
ConditionsYield
With nitric acid; acetic acid for 0.166667h; Heating;90%
With nitric acid; acetic acid for 2h; Ambient temperature;90%
With nitric acid In dichloromethane; water at 0℃; for 0.5h;76%
With sulfuric acid; nitric acid In acetic acid at 0℃; for 0.0833333h;67%
With nitric acid; acetic acid
11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

5-bromobenzonaphtho<2,1-d>thiophene
76113-28-5

5-bromobenzonaphtho<2,1-d>thiophene

Conditions
ConditionsYield
With bromine In chloroform for 3h; Ambient temperature;81%
Multi-step reaction with 3 steps
1: 90 percent / nitric acid, glacial acetic acid / 2 h / Ambient temperature
2: 80 percent / SnCl2*2H2O, HCl / various solvent(s) / 1 h / Heating
3: 1.) HCl, NaNO2, 2.) CuBr, 40percent HBr / 1.) H2O, 0 deg C, 2.) H2O, 80 deg C, 1 h
View Scheme
11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

acetyl chloride
75-36-5

acetyl chloride

5-acetylbenzonaphtho<2,1-d>thiophene
76113-35-4

5-acetylbenzonaphtho<2,1-d>thiophene

Conditions
ConditionsYield
With tin(IV) chloride In benzene for 2h; Heating;80%
11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

benzonaphtho<2,1-d>thiophene-5-sulfonic acid
76113-17-2

benzonaphtho<2,1-d>thiophene-5-sulfonic acid

Conditions
ConditionsYield
With chlorosulfonic acid In chloroform for 0.5h; Ambient temperature;80%
With chlorosulfonic acid In dichloromethane at 22℃; for 2h;3%
With chlorosulfonic acid In chloroform
[Rh(H)(Ph)(η5-pentamethylcyclopentadienyl)(PMe3)]
81971-46-2

[Rh(H)(Ph)(η5-pentamethylcyclopentadienyl)(PMe3)]

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

((CH3)5C5)Rh(P(CH3)3)(C16H10S)
177586-20-8

((CH3)5C5)Rh(P(CH3)3)(C16H10S)

Conditions
ConditionsYield
In Cyclohexane-d12 N2-atmosphere, sealed NMR tube; 68°C (70 h); evapn.; elem. anal.;75%
formaldehyd
50-00-0

formaldehyd

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

5-chloromethylbenzonaphtho<2,1-d>thiophene
76113-34-3

5-chloromethylbenzonaphtho<2,1-d>thiophene

Conditions
ConditionsYield
With hydrogenchloride; acetic acid; zinc(II) chloride at 60℃; for 10h;74%
1-chloro 4-iodobutane
10297-05-9

1-chloro 4-iodobutane

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

C20H18ClS(1+)*BF4(1-)

C20H18ClS(1+)*BF4(1-)

Conditions
ConditionsYield
With silver tetrafluoroborate In 1,2-dichloro-ethane at 25℃; Inert atmosphere;72%
11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

acetic anhydride
108-24-7

acetic anhydride

5-acetylbenzonaphtho<2,1-d>thiophene
76113-35-4

5-acetylbenzonaphtho<2,1-d>thiophene

Conditions
ConditionsYield
With aluminium trichloride In carbon disulfide 1.) 10 deg C, 1 h, 2.) 45 deg C, 3 h;69%
11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

2-phenylnaphthalene
612-94-2

2-phenylnaphthalene

Conditions
ConditionsYield
sulfided catalyst CMA-2 In methanol; benzene at 450℃; Product distribution;69%
nickel In ethanol at 78.3℃; for 1h; Rate constant;
4-chlorobutyl bromide
6940-78-9

4-chlorobutyl bromide

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

C20H18ClS(1+)*BF4(1-)

C20H18ClS(1+)*BF4(1-)

Conditions
ConditionsYield
With silver tetrafluoroborate In 1,2-dichloro-ethane at 25℃; Inert atmosphere;52%
11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

benzo[b]naphtho[2,1-d]thiophene 11,11-dioxide
20841-60-5

benzo[b]naphtho[2,1-d]thiophene 11,11-dioxide

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid for 12h; Reflux;48%
With dihydrogen peroxide; acetic acid
With dihydrogen peroxide In acetic acid for 1h; Heating;
11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

A

benzo[b]naphtho[2,1-d]thiophene-5,8-disulfonic acid

benzo[b]naphtho[2,1-d]thiophene-5,8-disulfonic acid

B

benzo[b]naphtho[2,1-d]thiophene-5,9-disulfonic acid

benzo[b]naphtho[2,1-d]thiophene-5,9-disulfonic acid

Conditions
ConditionsYield
With chlorosulfonic acid In dichloromethane at 0 - 22℃; Temperature;A 46%
B 40%
11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

A

2-phenylnaphthalene
612-94-2

2-phenylnaphthalene

B

methylphenylnaphthalene

methylphenylnaphthalene

Conditions
ConditionsYield
sulfided catalyst CMA-2 In methanol; benzene at 350℃; Product distribution;A 42%
B n/a
11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

chromium(0) hexacarbonyl
199620-14-9, 13007-92-6

chromium(0) hexacarbonyl

C16H10SCr(CO)3

C16H10SCr(CO)3

Conditions
ConditionsYield
boiling;;15%
boiling;;15%

239-35-0Relevant articles and documents

Palladium catalysis based one-pot synthesis method for DBTs (dibenzothiophenes)

-

Paragraph 0033-0038, (2020/05/12)

The invention discloses a palladium catalysis based one-pot synthesis method for DBTs (dibenzothiophenes). An inorganic base is added to an N,N-dimethylacetamide solution, with a palladium catalyst/ligand as a catalysis system, o-bromoiodobenzene derivatives or iodobenzene derivatives and thiophenol derivatives taken as raw materials are subjected to a reaction in nitrogen atmosphere, and DBTs areobtained through separation. The simple, economical and easily available raw materials are taken as substrates, all-position-substituted DBTs are synthesized on the basis of palladium catalyzed cascade reaction, and DBTs have great application prospect in medical synthesis intermediates and organic optoelectronic material science.

Synthetic Utility of Arylmethylsulfones: Annulative π-Extension of Aromatics and Hetero-aromatics Involving Pd(0)-Catalyzed Heck Coupling Reactions

Sankar, Elumalai,Raju, Potharaju,Karunakaran, Jayachandran,Mohanakrishnan, Arasambattu K.

, p. 13583 - 13593 (2017/12/26)

A straightforward and general method for the synthesis of annulated thiophene, dibenzothiophene, and carbazoles analogues has been achieved involving alkylation of 2-bromo-1-(phenylsulfonylmethyl)arene/heteroarene with arylmethyl bromides/heteroarylmethyl bromides using t-BuOK as a base in DMF, followed by Pd(0)-mediated intramolecular Heck coupling in the presence of K2CO3 in DMF at 80-140 °C. The attractive feature of this protocol is that a wide variety of π-conjugated heterocycles could be readily accessed by an appropriate choice of arylmethylsulfones and benzylic bromides.

Heterotetracenes: Flexible Synthesis and in Silico Assessment of the Hole-Transport Properties

Li, Yifan,Gryn'ova, Ganna,Saenz, Felipe,Jeanbourquin, Xavier,Sivula, Kevin,Corminboeuf, Clémence,Waser, Jér?me

supporting information, p. 8058 - 8065 (2017/06/19)

Thienoacenes and furoacenes are among the most frequent molecular units found in organic materials. The efficient synthesis of morphologically different heteroacenes and the rapid determination of their solid-state and electronic properties are still challenging tasks, which slow down progress in the development of new materials. Here, we report a flexible and efficient synthesis of unprecedented heterotetracenes based on a platinum- and gold-catalyzed cyclization–alkynylation domino process using EthynylBenziodoXole (EBX) hypervalent iodine reagents in the key step. The proof-of-principle in silico estimation of the synthesized tetracenes’ charge transport properties reveals their strong dependence on both the position and nature of the heteroatoms in the ring system. A broad range of mobility is predicted, with some compounds displaying performance potentially comparable to that of state-of-the-art electronic organic materials.

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