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825-55-8 Usage

Chemical Properties

white to light beige crystalline low melting mass

Synthesis Reference(s)

Tetrahedron, 38, p. 3347, 1982 DOI: 10.1016/0040-4020(82)80117-8Tetrahedron Letters, 25, p. 453, 1984 DOI: 10.1016/S0040-4039(00)99909-X

Check Digit Verification of cas no

The CAS Registry Mumber 825-55-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,2 and 5 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 825-55:
(5*8)+(4*2)+(3*5)+(2*5)+(1*5)=78
78 % 10 = 8
So 825-55-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H8S/c1-2-5-9(6-3-1)10-7-4-8-11-10/h1-8H

825-55-8 Well-known Company Product Price

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  • Alfa Aesar

  • (H60819)  2-Phenylthiophene, 95%   

  • 825-55-8

  • 1g

  • 205.0CNY

  • Detail
  • Alfa Aesar

  • (H60819)  2-Phenylthiophene, 95%   

  • 825-55-8

  • 5g

  • 848.0CNY

  • Detail
  • Aldrich

  • (520578)  2-Phenylthiophene  95%

  • 825-55-8

  • 520578-5G

  • 1,297.53CNY

  • Detail

825-55-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Phenylthiophene

1.2 Other means of identification

Product number -
Other names 2-PHENYLTHIOPHENE

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:825-55-8 SDS

825-55-8Synthetic route

2-Phenyl-2-thiophen-2-yl-4,5-dihydro-3λ5,2λ5-[1,3,2]oxazaborole

2-Phenyl-2-thiophen-2-yl-4,5-dihydro-3λ5,2λ5-[1,3,2]oxazaborole

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With N-Bromosuccinimide In methanol; dichloromethane; water Borax buffer;100%
2-bromothiophene
1003-09-4

2-bromothiophene

phenylboronic acid
98-80-6

phenylboronic acid

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With tri-tert-butyl phosphine; palladium diacetate; potassium hydroxide In tetrahydrofuran; water at 24℃; for 0.0833333h; Suzuki-Miyaura Coupling; Flow reactor;100%
With [Pd{κ2(C,C)-C6H4PPh2C(H)CO(C6H4-NO2-4)}Br(Ph-NCS)]; sodium carbonate In methanol at 85℃; for 2h; Reagent/catalyst; Suzuki-Miyaura Coupling;100%
With palladium diacetate; potassium fluoride; johnphos In tetrahydrofuran at 20℃; for 3h; Suzuki coupling;99%
2-Iodothiophene
3437-95-4

2-Iodothiophene

phenylboronic acid
98-80-6

phenylboronic acid

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With Tedicyp; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)) In xylene at 130℃; for 20h; Suzuki cross-coupling reaction;100%
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;99%
With caesium carbonate In water; N,N-dimethyl-formamide at 50℃; for 2h; Suzuki Coupling;99%
2-Iodothiophene
3437-95-4

2-Iodothiophene

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With potassium carbonate In methanol at 60℃; for 1h; Suzuki-Miyaura Coupling;99.8%
2-thienylphenyliodonium tosylate
91228-44-3

2-thienylphenyliodonium tosylate

phenylboronic acid
98-80-6

phenylboronic acid

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water for 0.0833333h; Ambient temperature;99%
With copper(l) iodide; sodium carbonate In 1,2-dimethoxyethane; water at 35℃; for 0.333333h;97%
thiophene boronic acid
6165-68-0

thiophene boronic acid

iodobenzene
591-50-4

iodobenzene

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;99%
Stage #1: thiophene boronic acid; iodobenzene With potassium phosphate In 1,2-dimethoxyethane at 80℃; for 6h; Suzuki-Miyaura Coupling; Inert atmosphere;
Stage #2: In 1,2-dimethoxyethane; water at 100℃; for 10h;
94%
With potassium phosphate; C24H44BClN2P2Pd In toluene at 80℃; for 1h; Catalytic behavior; Suzuki-Miyaura Coupling; Inert atmosphere;94%
2-bromothiophene
1003-09-4

2-bromothiophene

phenyl trimethylsiloxane
2996-92-1

phenyl trimethylsiloxane

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With sodium hydroxide; 4,4'-dichlorobenzophenone oxime-derived palladacycle at 120℃; under 7500.6 Torr; for 0.166667h; Hiyama coupling; microwave irradiation;99%
With potassium fluoride; propylene glycol; chloro-[2-(9-phenyl-1,10-phenanthrolin-2-yl)phenyl]palladium In dichloromethane at 100℃; for 12h; Hiyama Coupling; Inert atmosphere;91%
With sodium hydroxide In ethanol; water at 110℃; for 0.133333h; Hiyama coupling; Microwave irradiation;90%
thiophene boronic acid
6165-68-0

thiophene boronic acid

chlorobenzene
108-90-7

chlorobenzene

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With dichlorido(pyridine)[4-(4-nitrophenyl)-1,3-bis-(2,4,6-trimethylphenyl)-4,5-dihydro-3H-imidazol-2-ylidene]palladium(II); potassium carbonate In water; isopropyl alcohol at 20℃; for 6h; Suzuki-Miyaura Coupling;98%
With [PdCl{[(η5-C5H5)]Fe[(η5-C5H3)-N2C4H2-Cl]}(DCPAB)]; potassium tert-butylate at 120℃; for 12h; Suzuki coupling;92%
With 1,4-diaza-bicyclo[2.2.2]octane; caesium carbonate; palladium diacetate In N,N-dimethyl-formamide at 110℃; for 24h; Suzuki-Miyaura cross-coupling;88%
2-thienyl chloride
96-43-5

2-thienyl chloride

phenylboronic acid
98-80-6

phenylboronic acid

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With potassium tert-butylate; C38H29ClNPPd In isopropyl alcohol at 80℃; for 2h; Reagent/catalyst;98%
With [{Pd(μ-OH)Cl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)}2]; oxygen; potassium hydroxide In ethanol at 22℃; for 24h; Suzuki-Miyaura Coupling;97%
With di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; PdCl(π-allyl)(cyclohexyl-(1-methyl-2,2-diphenylcyclopropylphophine)); potassium carbonate In tetrahydrofuran; toluene at 80℃; for 2h; Suzuki-Miyaura Coupling; Inert atmosphere;95%
thiophene boronic acid
6165-68-0

thiophene boronic acid

bromobenzene
108-86-1

bromobenzene

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With tri-tert-butyl phosphine; palladium diacetate; potassium hydroxide In tetrahydrofuran; water at 24℃; for 0.0833333h; Suzuki-Miyaura Coupling; Flow reactor;97%
With caesium carbonate; copper(l) iodide; tetrabutylammomium bromide In dimethyl sulfoxide at 135 - 140℃; for 21h; Suzuki-Miyaura cross-coupling reaction;96%
With 1,4-diaza-bicyclo[2.2.2]octane; caesium carbonate; palladium diacetate In N,N-dimethyl-formamide at 110℃; for 12h; Suzuki-Miyaura cross-coupling;95%
sodium tetraphenyl borate
143-66-8

sodium tetraphenyl borate

2-thienylphenyliodonium tosylate
91228-44-3

2-thienylphenyliodonium tosylate

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
palladium dichloride In water for 0.00555556h; Suzuki coupling; microwave irradiation;97%
for 0.05h; Suzuki coupling; microwave irradiation;83%
With toluene-4-sulfonic acid In water at 50℃; for 2h; Suzuki coupling;81%
In water at 100℃; for 0.05h; Suzuki coupling reaction; microwave irradiation;80%
Thien-3-ylboronic acid
6165-69-1

Thien-3-ylboronic acid

(trifluoromethylsulfonyl)benzene
426-58-4

(trifluoromethylsulfonyl)benzene

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With potassium phosphate; palladium(II) acetylacetonate; ruphos In 1,4-dioxane; dimethyl sulfoxide at 80℃; for 16h; Suzuki-Miyaura Coupling; Sealed tube; Inert atmosphere;97%
bromobenzene
108-86-1

bromobenzene

bis(thien-2-yl)zinc
15106-95-3

bis(thien-2-yl)zinc

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With dichloro{bis[1-(dicyclohexylphosphanyl)piperidine]}palladium(II) In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 100℃; for 3h; Negishi cross-coupling reaction; In air;96%
With catalyst 1 (aliphatic, phosphine based pincer complex of palladium) In 1,4-dioxane; 1-methyl-pyrrolidin-2-one at 100℃; for 1h; Negishi cross-coupling reaction;89%
2-chloro-5-phenylthiophene
35717-20-5

2-chloro-5-phenylthiophene

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; PdCl2(1,1′-bis(di-tertbutylphosphino)ferrocene) In tetrahydrofuran at 65℃; for 8h; Reagent/catalyst; Temperature; Time; Inert atmosphere;96%
With sodium tetrahydroborate; dichloro[1,1′-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P′]palladium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 65℃; for 8h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere;96%
C10H13S(1+)*F6Sb(1-)

C10H13S(1+)*F6Sb(1-)

sodium tetra(thiophen-2-yl)borate

sodium tetra(thiophen-2-yl)borate

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran at 80℃; for 1h; Schlenk technique;96%
tributyl(thien-2-yl)stannane
54663-78-4

tributyl(thien-2-yl)stannane

phenyl bromide/chloride

phenyl bromide/chloride

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 6h; Catalytic behavior; Stille Cross Coupling;96%
2-thienyl chloride
96-43-5

2-thienyl chloride

phenyl trimethylsiloxane
2996-92-1

phenyl trimethylsiloxane

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With tBu2P-N=P(iBuPCH2CH2)3N; tetrabutyl ammonium fluoride; palladium diacetate at 80℃; for 1h; Hiyama coupling; Inert atmosphere; Neat (no solvent);95%
With sodium hydroxide; [[(t-Bu)2P(OH)(t-Bu)2PO]PdCl2] at 135℃; for 24h;44%
2-Iodothiophene
3437-95-4

2-Iodothiophene

benzene
71-43-2

benzene

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With 9,9′-(ethane-1,2-diylbis(azanediyl))bis(1Hphenalen-1-one); potassium tert-butylate In neat (no solvent) at 130℃; for 12h; Reagent/catalyst; Temperature; Time; Sealed tube;95%
With potassium tert-butylate at 110℃; for 3h;89%
With potassium tert-butylate at 130℃; for 12h; Sealed tube;82%
bromobenzene
108-86-1

bromobenzene

C10H19AlOS

C10H19AlOS

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With palladium diacetate; tris-(o-tolyl)phosphine In toluene at 20℃; for 5h; Inert atmosphere;95%
2-hydroxymethyl-5-phenylthiophene
439108-60-8

2-hydroxymethyl-5-phenylthiophene

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With potassium tert-butylate; oxygen In toluene at 80℃; for 14h;95%
2-Iodothiophene
3437-95-4

2-Iodothiophene

trimethyl(phenyl)stannane
934-56-5

trimethyl(phenyl)stannane

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With iodophenylbis(triphenylphosphine)palladium In N,N,N,N,N,N-hexamethylphosphoric triamide at 70℃; for 0.5h;94%
5-phenylthiophene-2-carboxaldehyde
19163-21-4

5-phenylthiophene-2-carboxaldehyde

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; air; triphenylphosphine In 1,4-dioxane for 48h; Heating;94%
With Pd-γ-Fe2O3 In cyclohexane at 130℃; for 24h; Inert atmosphere; Molecular sieve; Sealed tube;82%
Multi-step reaction with 2 steps
1: sodium tetrahydroborate; methanol / 1 h / 20 °C
2: potassium tert-butylate; oxygen / toluene / 14 h / 80 °C
View Scheme
3-chloro-1-methyl-1H-indole
124589-41-9

3-chloro-1-methyl-1H-indole

phenylboronic acid
98-80-6

phenylboronic acid

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
Stage #1: 3-chloro-1-methyl-1H-indole; phenylboronic acid With palladium diacetate; (R)-6-dicyclohexylphoshino-6'-diphenylphosphino-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1,1'-biphenyl In dodecane; butan-1-ol at 25℃; for 1h; Suzuki-Miyaura Coupling; Glovebox; Inert atmosphere;
Stage #2: With cesiumhydroxide monohydrate In dodecane; water; butan-1-ol at 25℃; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox;
94%
2-Bromo-5-phenyl-thiophene
29488-24-2

2-Bromo-5-phenyl-thiophene

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; palladium diacetate; triphenylphosphine In tetrahydrofuran at 20℃; for 2h; Reagent/catalyst; Time; Inert atmosphere;94%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 25℃; for 1h; Reagent/catalyst; Inert atmosphere;92%
With tetraethylammonium perchlorate; triethylamine In ethanol; dimethyl sulfoxide at 20℃; for 18h; Electrolysis; Green chemistry;90%
With Pd-γ-Fe2O3; potassium tert-butylate In isopropyl alcohol at 70℃; for 12h; Inert atmosphere; Sealed tube;84%
4-bromo-2-phenyl thiophene
38071-58-8

4-bromo-2-phenyl thiophene

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; palladium diacetate In tetrahydrofuran at 20℃; for 3h; Reagent/catalyst; Time; Inert atmosphere;94%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 25℃; Reagent/catalyst; Inert atmosphere;94%
2-Iodothiophene
3437-95-4

2-Iodothiophene

phenylacetylene
536-74-3

phenylacetylene

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 60℃; for 15h; Sonogashira Cross-Coupling; Inert atmosphere;94%
thiophene boronic acid
6165-68-0

thiophene boronic acid

4-iodophenylhydrazine
13116-27-3

4-iodophenylhydrazine

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
Stage #1: 4-iodophenylhydrazine With polystyrene-NHCO(CH2)4COOH; benzotriazol-1-ol; diisopropyl-carbodiimide In dichloromethane Solid phase reaction;
Stage #2: thiophene boronic acid With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In N,N-dimethyl-formamide at 90℃; for 24h; Suzuki coupling reaction;
Stage #3: With pyridine; copper diacetate In methanol at 20℃; for 2h; Oxidation;
93%
Stage #1: 4-iodophenylhydrazine With adipic acid-functionalized polystyrene; benzotriazol-1-ol; diisopropyl-carbodiimide; triethylamine In dichloromethane
Stage #2: thiophene boronic acid With potassium carbonate; tris-(dibenzylideneacetone)dipalladium(0) In N,N-dimethyl-formamide at 90℃; for 24h; Suzuki reaction;
Stage #3: With pyridine; copper diacetate In methanol at 20℃; for 2h; Further stages.;
2-thienyl chloride
96-43-5

2-thienyl chloride

tri(allyl)phenylsilane
2633-57-0

tri(allyl)phenylsilane

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
Stage #1: triallyl(phenyl)silane With tetrabutyl ammonium fluoride In tetrahydrofuran; water at 20℃; for 1h;
Stage #2: 2-thienyl chloride With XPhos; bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran; water at 80℃; for 12h;
93%
[2-(hydroxymethyl)phenyl](dimethyl)phenylsilane
853955-69-8

[2-(hydroxymethyl)phenyl](dimethyl)phenylsilane

2-Iodothiophene
3437-95-4

2-Iodothiophene

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With N-cyclohexyl-1-[2-(diphenylphosphanyl)phenyl]methanimine; potassium carbonate; palladium dichloride In water; dimethyl sulfoxide at 50℃; for 13h;93%
With potassium carbonate; N-cyclohexyl-1-[2-(diphenylphosphanyl)phenyl]methanimine; palladium dichloride In water; dimethyl sulfoxide at 50℃; for 13h;93%
2-phenylthiophene
825-55-8

2-phenylthiophene

2-Bromo-5-phenyl-thiophene
29488-24-2

2-Bromo-5-phenyl-thiophene

Conditions
ConditionsYield
With N-Bromosuccinimide In chloroform at 20℃; for 0.5h;100%
With N-Bromosuccinimide95%
With bromine; sodium acetate In acetic acid at 20℃;83%
2-phenylthiophene
825-55-8

2-phenylthiophene

C10H6(2)H2S

C10H6(2)H2S

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; deuterium In tetrahydrofuran at 55℃; under 750.075 Torr; for 22h; Inert atmosphere;100%
2-phenylthiophene
825-55-8

2-phenylthiophene

2-deuterio-5-phenylthiophene
35309-06-9

2-deuterio-5-phenylthiophene

Conditions
ConditionsYield
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); water-d2 In tetrahydrofuran; toluene at 90℃; for 2h; Microwave irradiation;98%
Stage #1: 2-phenylthiophene With tert.-butyl lithium In diethyl ether; pentane at -78 - 0℃;
Stage #2: With d(4)-methanol In diethyl ether; pentane at -78 - 20℃;
90%
With deuteromethanol; silver carbonate; johnphos at 50 - 80℃;85%
4-vinylbenzyl chloride
1073-67-2

4-vinylbenzyl chloride

2-phenylthiophene
825-55-8

2-phenylthiophene

2-phenyl-5-(4-vinylphenyl)thiophene

2-phenyl-5-(4-vinylphenyl)thiophene

Conditions
ConditionsYield
With NHC-Pd(II)-Im; potassium tert-butylate; copper(II) oxide In tetrahydrofuran at 130℃; for 3h; Inert atmosphere; Sealed tube;98%
2-phenylthiophene
825-55-8

2-phenylthiophene

methyl iodide
74-88-4

methyl iodide

2-methyl-5-phenylthiophene
5069-26-1

2-methyl-5-phenylthiophene

Conditions
ConditionsYield
Stage #1: 2-phenylthiophene With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 3h;
Stage #2: methyl iodide In tetrahydrofuran; hexane at 0 - 20℃; Further stages.;
97%
Stage #1: 2-phenylthiophene With n-butyllithium In tetrahydrofuran at -15℃; for 2h;
Stage #2: methyl iodide In tetrahydrofuran Further stages.;
86%
2-phenylthiophene
825-55-8

2-phenylthiophene

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

ethyl (R)-(5-phenylthiophen-2-yl)hydroxyacetate
1273326-28-5

ethyl (R)-(5-phenylthiophen-2-yl)hydroxyacetate

Conditions
ConditionsYield
Stage #1: glyoxylic acid ethyl ester With titanium(IV) isopropylate; (S)-6,6'-dibromo-1,1'-bi-2-naphthol In toluene at -40℃; for 0.166667h; Friedel Crafts alkylation;
Stage #2: 2-phenylthiophene In toluene at 0℃; for 7h; Friedel Crafts alkylation; optical yield given as %ee; enantioselective reaction;
96%
2-phenylthiophene
825-55-8

2-phenylthiophene

tributyltin chloride
1461-22-9

tributyltin chloride

tri-n-butyl(5-phenylthiophen-2-yl)stannane
137937-89-4

tri-n-butyl(5-phenylthiophen-2-yl)stannane

Conditions
ConditionsYield
Stage #1: 2-phenylthiophene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: tributyltin chloride In tetrahydrofuran at -78 - 20℃;
96%
Stage #1: 2-phenylthiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at 30℃; for 1h; Inert atmosphere;
Stage #2: tributyltin chloride In tetrahydrofuran; hexane at 20℃; for 20h; Cooling with ice;
Stage #1: 2-phenylthiophene With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 1.5h; Inert atmosphere;
Stage #2: tributyltin chloride In tetrahydrofuran at -78 - 20℃; for 13h; Inert atmosphere;

825-55-8Relevant articles and documents

-

Nilsson

, p. 679,681 (1966)

-

Preparation of Co-Pd bimetallic nanoparticles encapsulated in bamboo-like N-doped mesoporous carbon by a facile one-pot method for green Suzuki coupling

Wu, Li,Long, Yu,Ma, Jiantai,Lu, Gongxuan

, p. 3809 - 3821 (2019)

CoPd bimetallic nanoparticles (NPs) were successfully encapsulated in bamboo-like N-doped mesoporous carbon (bNMC) via a facile one-pot method through combination of dissolving chelation and carbonization reactions. The morphology, structure and composition of CoPd-bNMC was verified by detailed characterization including SEM, TEM, EDX, XPS, XRD, N2 adsorption–desorption, VSM, and ICP. The as-prepared CoPd/bNMC showed excellent activity and selectivity for Suzuki coupling under mild and green condition. Though the Pd content of CoPd/bNMC was half of Pd/bNMC, the catalytic performance of CoPd/bNMC was almost the same with Pd/bNMC, which was caused by its special bimetallic alloy structure, high BET surface area and pore volume. Importantly, CoPd/bNMC with magnetic property can be separated using external magnetic field and reused for five consecutive runs in the reaction of Suzuki crossing without significant loss of activity. It was found the Pd content only showed slight loss (2.3?wt.%) after five reused reactions, which was because CoPd bimetallic NPs were inside the bamboo-like N-doped mesoporous carbon.

Recyclable and ligandless suzuki coupling catalyzed by carbon nanotube-supported palladium nanoparticles synthesized in supercritical fluid

Pan, Horng-Bin,Yen, Clive H.,Yoon, Byunghoon,Sato, Masaki,Wai, Chien M.

, p. 3473 - 3478 (2006)

Carbon nanotube-supported palladium nanoparticles prepared by a supercritical fluid deposition method show high activities for catalyzing Suzuki coupling reactions, and the catalysts can be recycled and reused at least six times without losing activity. Copyright Taylor & Francis Group, LLC.

Synthesis and characterization of palladium nanoparticles immobilized on graphene oxide functionalized with triethylenetetramine or 2,6-diaminopyridine and application for the Suzuki cross-coupling reaction

Mirza-Aghayan, Maryam,Mohammadi, Marzieh,Boukherroub, Rabah

, (2021/11/22)

Graphene oxide (GO) was functionalized with two organic ligands, triethylenetetramine (TETA) or 2,6-diaminopyridine (DAP), followed by palladium nanoparticles (Pd NPs) for the synthesis of Pd NPs/GO-TETA and Pd NPs/GO-DAP nanocomposites, respectively. The two heterogeneous nanocomposites were fully characterized and their efficiency was investigated for C[sbnd]C bond formation for the synthesis of biaryl compounds via the Suzuki cross-coupling reaction of aryl halides with arylboronic acid derivatives. The obtained results indicated that the Pd NPs/GO-TETA nanocomposite was more effective in the Suzuki coupling reaction as compared to Pd NPs/GO-DAP. Thus, the Suzuki cross-coupling reaction of different aryl halides with arylboronic acid derivatives using Pd NPs/GO-TETA nanocomposite catalyst in the presence of Na2CO3 as base in DMF/H2O (1/1) as solvent at 90 °C was carried out to afford the desired biaryl compounds in high to excellent yields (81–100%) and short reaction times (10–90 min). Additionally, Pd NPs/GO-TETA nanocomposite can be recovered and reused for 8 consecutive runs without any apparent loss of its catalytic activity, proving its high stability and potential use in organic transformations.

Molecular engineered palladium single atom catalysts with an M-C1N3subunit for Suzuki coupling

Liu, Jia,Chen, Zhongxin,Liu, Cuibo,Zhang, Bao,Du, Yonghua,Liu, Chen-Fei,Ma, Lu,Xi, Shibo,Li, Runlai,Zhao, Xiaoxu,Song, Jingting,Sui, Xin Zhi,Yu, Wei,Miao, Ling,Jiang, Jianjun,Koh, Ming Joo,Loh, Kian Ping

supporting information, p. 11427 - 11432 (2021/05/19)

Single atom catalysis has emerged as a powerful technique for catalysis due to its outstanding performance and atom economy. Controlling the hybridization of the atom with its environment is crucial in determining the selectivity and/or yield of the reaction. However, the single atom environment is usually ill-defined and hard to predict because the pyrolysis process used in preparing SACs damages the original status of the precursors in the catalyst preparation. A molecular engineering approach to synthesize single atom catalysts (SACs) on a heterogeneous template provides a strategy to make SACs with a highly uniform coordinating environment. Herein, we report the preparation of a molecular engineered Pd single atom catalyst with a pre-defined M-N3C1 coordination (Pd-N3C1-SAC) using a structure-rigid Pd-N3C1 porphyrin as the precursor, which shows more efficient Suzuki coupling compared with the SAC with Pd-N4 coordination. The origin of the high activity of the Pd-N3C1-SAC is revealed through density functional theory calculations, where a lower reaction barrier for the rate-determining oxidative addition is identified. This journal is

Fe3O4-SAHPG-Pd0 nanoparticles: A ligand-free and low Pd loading quasiheterogeneous catalyst active for mild Suzuki–Miyaura coupling and C-H activation of pyrimidine cores

Azizollahi, Hamid,Eshghi, Hossein,García-López, José-Antonio

, (2020/09/17)

This paper reports a green magnetic quasiheterogeneous efficient palladium catalyst in which Pd0 nanoparticles have been immobilized in self-assembled hyperbranched polyglycidole (SAHPG)-coated magnetic Fe3O4 nanoparticles (Fe3O4-SAHPG-Pd0). This catalyst has been used for effective ligandless Pd catalyzed Suzuki–Miyaura coupling reactions of different aryl halides with substituted boronic acids at room temperature and in aqueous media. Herein, SAHPG is used as support; it also acts as a reducing agent and stabilizer to promote the transformation of PdII to Pd0 nanoparticles. Also, this environmental friendly quasiheterogeneous catalyst is employed for the first time in the synthesis of new pyrimido[4,5-b]indoles via oxidative addition/C-H activation reactions on the pyrimidine rings, which were obtained with higher yield and faster than when Pd(OAc)2 was used as the catalyst. Interestingly, the above-mentioned catalyst could be recovered in a facile manner from the reaction mixture by applying an external magnet device and recycled several times with no significant decrease in the catalytic activity.

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