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2-Thiopheneboronic acid
Cas No: 6165-68-0
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2-Thiopheneboronic acid
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Thiophene-2-boronicacid
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2-Thiopheneboronic acid 6165-68-0
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2-Thiopheneboronic acid
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6165-68-0 Usage

Uses

2-Thiopheneboronic acid can be used as reagent used for Palladium-catalyzed Suzuki-Miyaura cross-couplings;? Alkylation, boration, coupling reaction, Suzuki coupling, and halogenation of fluorenyl bromide ;Chain-growth catalyst transfer polycondensation of conjugated alternating copolymer; Ferric perchlorate-promoted reaction of fullerene to give fullerenyl boronic esters.

Uses

suzuki reaction

Chemical Properties

white to light yellow crystal powder
InChI:InChI=1/C4H5BO2S/c6-5(7)4-2-1-3-8-4/h1-3,6-7H

6165-68-0 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (B23071)  Thiophene-2-boronic acid, 98%    6165-68-0 1g 210.0CNY Detail
Alfa Aesar (B23071)  Thiophene-2-boronic acid, 98%    6165-68-0 5g 688.0CNY Detail
Alfa Aesar (B23071)  Thiophene-2-boronic acid, 98%    6165-68-0 25g 2992.0CNY Detail
Aldrich (436836)  2-Thienylboronicacid  ≥95.0% 6165-68-0 436836-1G 267.93CNY Detail
Aldrich (436836)  2-Thienylboronicacid  ≥95.0% 6165-68-0 436836-5G 820.17CNY Detail

6165-68-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Thiopheneboronic acid

1.2 Other means of identification

Product number -
Other names thiophen-2-ylboronic acid

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:6165-68-0 SDS

6165-68-0Synthetic route

2-thiopheneboronic acid MIDA ester
1158984-92-9

2-thiopheneboronic acid MIDA ester

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water at 23℃; for 0.333333h;99%
2-Iodothiophene
3437-95-4

2-Iodothiophene

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
Stage #1: 2-Iodothiophene With diisopropopylaminoborane; triethylamine; triphenylphosphine; palladium dichloride In tetrahydrofuran at 65℃; for 12h; Alcaraz-Vaultier borylation; Inert atmosphere;
Stage #2: With methanol In tetrahydrofuran at 0℃; Inert atmosphere; Further stages;
99%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

2-thiopheneboronic acid pinacol ester
193978-23-3

2-thiopheneboronic acid pinacol ester

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
With hydrogenchloride In water; acetone at 20℃;96%
2-bromothiophene
1003-09-4

2-bromothiophene

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
Stage #1: 2-bromothiophene With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; diisopropopylaminoborane; triethylamine; triphenylphosphine In tetrahydrofuran at 65℃; for 12h; Alcaraz-Vaultier borylation; Inert atmosphere;
Stage #2: With methanol In tetrahydrofuran at 0℃; Inert atmosphere; Further stages;
87%
With n-butyllithium; diethyl ether at -60℃; anschliessend Behandeln mit Tributylborat und Behandeln des Reaktionsgemisches mit wss. Salzsaeure;
Stage #1: 2-bromothiophene With Trimethyl borate In N,N-dimethyl-formamide at 20℃; Electrochemical reaction; Mg consumable anode, supporting electrolyte;
Stage #2: at 0℃; Acid hydrolysis; Further stages.;
With hydrogenchloride; borane; magnesium In tetrahydrofuran; ice-water
potassium (thiophen-2-yl)trifluoroborate

potassium (thiophen-2-yl)trifluoroborate

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
With water; silica gel at 20℃; for 3h; Inert atmosphere;84%
2-bromothiophene
1003-09-4

2-bromothiophene

methanol
67-56-1

methanol

diisopropylamine borane
55124-35-1

diisopropylamine borane

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
Stage #1: diisopropylamine borane With magnesium; phenylmagnesium bromide In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: 2-bromothiophene In tetrahydrofuran at 70℃;
Stage #3: methanol Further stages;
82%
thiophene
188290-36-0

thiophene

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
Stage #1: thiophene With n-butyllithium In tetrahydrofuran at -78 - -20℃;
Stage #2: With Triisopropyl borate In tetrahydrofuran at -78 - 20℃;
78%
Stage #1: thiophene With n-butyllithium In tetrahydrofuran at -78 - -20℃;
Stage #2: With Triisopropyl borate In tetrahydrofuran at -78 - 20℃;
Stage #3: With hydrogenchloride In tetrahydrofuran Further stages.;
78%
Stage #1: thiophene With n-butyllithium In tetrahydrofuran at 0℃; Inert atmosphere;
Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - 20℃;
Stage #3: With sulfuric acid In tetrahydrofuran
55%
Stage #1: thiophene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere;
Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
2-bromothiophene
1003-09-4

2-bromothiophene

Trimethyl borate
121-43-7

Trimethyl borate

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
Stage #1: 2-bromothiophene With n-butyllithium In diethyl ether; hexane at -78℃; for 4h; Inert atmosphere;
Stage #2: Trimethyl borate In diethyl ether; hexane at -78 - 20℃; Inert atmosphere;
Stage #3: With hydrogenchloride In water
78%
2-bromothiophene
1003-09-4

2-bromothiophene

diisopropopylaminoborane
22092-92-8

diisopropopylaminoborane

water
7732-18-5

water

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
Stage #1: 2-bromothiophene; diisopropopylaminoborane With magnesium In tetrahydrofuran at 65℃; for 4h; Inert atmosphere;
Stage #2: water With hydrogenchloride In tetrahydrofuran at 65℃; for 0.25h; Barbier Coupling Reaction; Inert atmosphere;
74%
borane
13283-31-3

borane

thiophen-2-yl magnesium bromide
5713-61-1

thiophen-2-yl magnesium bromide

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
With water In tetrahydrofuran slow addn. of 10 mmol of the Grignard reagent to a stirred soln. of borane in THF (40 mmol); the mixt. was poured into ice-water and acidified with 10% HCl;; extn. into ether three-times; the combined extracts were dried over NaSO4; removal of solvent under reduced pressure; trituration with petroleum ether; recrystn. from H2O;;68%
Trimethyl borate
121-43-7

Trimethyl borate

thiophen-2-yl magnesium bromide
5713-61-1

thiophen-2-yl magnesium bromide

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
Grignard reaction;65%
thiophene
188290-36-0

thiophene

triethyl borate
150-46-9

triethyl borate

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
Stage #1: thiophene With n-butyllithium In tetrahydrofuran; hexane at -78 - -20℃; for 1h; Inert atmosphere;
Stage #2: triethyl borate In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane Inert atmosphere;
65%
With n-butyllithium In tetrahydrofuran thiophene and n-BuLi in hexane mixed in THF at 0°C under N2; B(OEt)2 added dropwise at -70°C; temp. raised to room temp. and aq. H2SO4 added followed CH2Cl2; org. layer extd. with aq. NaOH; to aq. layer added aq. HCl and compd. extd. with dichloromethane;43%
2-thienyl chloride
96-43-5

2-thienyl chloride

Trimethyl borate
121-43-7

Trimethyl borate

A

thiophene
188290-36-0

thiophene

B

thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

C

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
With aluminium In N,N-dimethyl-formamide byproducts: Al(3+); Electrolysis; electrolysis carried out in a single-compartment cell at room temp., starting materials dissolved in DMF containing KBr or n-Bu4NBr, solvent andexcess B(OCH3)3 evaporated under vacuum, medium hydrolysed at 0° C with an HCl or H2SO4 soln.; extraction with Et2O (3 x 20 ml if the solvent evaporated or 3 x 60 ml otherwise), dried over sodium or magnesium sulfate and concentrated undervacuum, side product phenol formation avoided by work-up under inert at mosphere, recrystallized in CH2Cl2;A n/a
B n/a
C 59%
2-bromothiophene
1003-09-4

2-bromothiophene

Trimethyl borate
121-43-7

Trimethyl borate

A

thiophene
188290-36-0

thiophene

B

thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

C

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
With magnesium In N,N-dimethyl-formamide byproducts: Mg(2+); Electrolysis; electrolysis carried out in a single-compartment cell at room temp., starting materials dissolved in DMF containing KBr or n-Bu4NBr, solvent andexcess B(OCH3)3 evaporated under vacuum, medium hydrolysed at 0° C with an HCl or H2SO4 soln.; extraction with Et2O (3 x 20 ml if the solvent evaporated or 3 x 60 ml otherwise), dried over sodium or magnesium sulfate and concentrated undervacuum, side product phenol formation avoided by work-up under inert at mosphere, recrystallized in CH2Cl2;A n/a
B n/a
C 57%
With aluminium In N,N-dimethyl-formamide byproducts: Al(3+); Electrolysis; electrolysis carried out in a single-compartment cell at room temp., starting materials dissolved in DMF containing KBr or n-Bu4NBr, solvent andexcess B(OCH3)3 evaporated under vacuum, medium hydrolysed at 0° C with an HCl or H2SO4 soln.; extraction with Et2O (3 x 20 ml if the solvent evaporated or 3 x 60 ml otherwise), dried over sodium or magnesium sulfate and concentrated undervacuum, side product phenol formation avoided by work-up under inert at mosphere, recrystallized in CH2Cl2;A n/a
B n/a
C 56%
2-bromothiophene
1003-09-4

2-bromothiophene

triethyl borate
150-46-9

triethyl borate

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
Stage #1: 2-bromothiophene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;
Stage #2: triethyl borate In tetrahydrofuran; hexane at -78 - 20℃;
Stage #3: With hydrogenchloride; water Cooling;
45%
C12H19BLiNO2S

C12H19BLiNO2S

A

thiophene boronic acid
6165-68-0

thiophene boronic acid

B

Thien-3-ylboronic acid
6165-69-1

Thien-3-ylboronic acid

C

thiophene-2,3-diyldiboronic acid
1379794-79-2

thiophene-2,3-diyldiboronic acid

Conditions
ConditionsYield
Stage #1: C12H19BLiNO2S With thiophene; triethyl borate Inert atmosphere;
Stage #2: With sulfuric acid In water
A 9%
B 9%
C n/a
2-thienyl lithium
2786-07-4

2-thienyl lithium

diethyl ether
60-29-7

diethyl ether

boric acid tributyl ester
688-74-4

boric acid tributyl ester

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
anschliessend Behandeln mit wss. Salzsaeure;
Trimethyl borate
121-43-7

Trimethyl borate

2-thienylmagnesium iodide
89180-57-4

2-thienylmagnesium iodide

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
With diethyl ether at -75℃; Behandeln des Reaktionsgemisches mit wss. Schwefelsaeure;
2-thienyl chloride
96-43-5

2-thienyl chloride

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
Stage #1: 2-thienyl chloride With Trimethyl borate In N,N-dimethyl-formamide at 20℃; Electrochemical reaction; Al consumable anode, supporting electrolyte;
Stage #2: at 0℃; Acid hydrolysis; Further stages.;
With methanol; tetrakis(dimethylamido)diborane; chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); potassium acetate; XPhos at 20 - 60℃; for 5.0833h; Inert atmosphere; Sealed tube;
2-bromothiophene
1003-09-4

2-bromothiophene

boric acid tributyl ester
688-74-4

boric acid tributyl ester

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
With hydrogenchloride; n-butyllithium
With hydrogenchloride; n-butyllithium
2-bromothiophene
1003-09-4

2-bromothiophene

borane
13283-31-3

borane

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
With water; magnesium In tetrahydrofuran a 2.0 M soln. of borane (40 mmol) in THF was added to flame dried Mg turnings (12 mmol) at 0°C; slow addn. of the aryl bromide (10 mmol)in THF; stirring at room temp. for 12-16 h; the mixt. was poured into ice-water and acidified with 10% HCl;; extn. into ether three-times; the combined extracts were dried over NaSO4; removal of solvent under reduced pressure; trituration with petroleum ether; recrystn. from H2O;;
2-thiopheneboronic acid MIDA ester
1158984-92-9

2-thiopheneboronic acid MIDA ester

water
7732-18-5

water

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
In not given hydrolysis of appropriate N-methyliminodiacetic acid boronate;
C12H19BLiNO2S

C12H19BLiNO2S

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
Stage #1: C12H19BLiNO2S With thiophene; triethyl borate Inert atmosphere;
Stage #2: With sulfuric acid In water
2-thienyl lithium
2786-07-4

2-thienyl lithium

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
With triethyl borate In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Schlenk technique;10 g
dimethyl thiophen-2-ylboronate

dimethyl thiophen-2-ylboronate

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 20℃; Inert atmosphere; Schlenk technique;
With hydrogenchloride In water for 0.5h; Inert atmosphere;
thiophene
188290-36-0

thiophene

Trimethyl borate
121-43-7

Trimethyl borate

thiophene boronic acid
6165-68-0

thiophene boronic acid

Conditions
ConditionsYield
Stage #1: thiophene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: Trimethyl borate In tetrahydrofuran at -78℃; for 1h;
Stage #1: thiophene With n-butyllithium In tetrahydrofuran at -78℃; for 1h;
Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 1h;
thiophene boronic acid
6165-68-0

thiophene boronic acid

2,2'-Bithiophene
492-97-7

2,2'-Bithiophene

Conditions
ConditionsYield
With sodium carbonate; trans-PdBr(N-Succ)(PPh3)2 In tetrahydrofuran at 60℃; for 16h;100%
With copper fluorapatite In methanol at 20℃; for 2h; Green chemistry;95%
With C34H54N2O2; palladium diacetate; potassium carbonate; p-toluenesulfonyl chloride In water at 0 - 25℃; for 0.25h; Reagent/catalyst; Green chemistry;92%
7-[di(phenyloxy)phosphoryloxy]-8-(tert-butoxycarbonyl)-9-phenyl-8-azaspiro[4.5]deca-6,9-diene
908254-94-4

7-[di(phenyloxy)phosphoryloxy]-8-(tert-butoxycarbonyl)-9-phenyl-8-azaspiro[4.5]deca-6,9-diene

thiophene boronic acid
6165-68-0

thiophene boronic acid

8-(tert-butoxycarbonyl)-9-phenyl-7-(thien-2-yl)-8-azaspiro[4.5]deca-6,9-diene

8-(tert-butoxycarbonyl)-9-phenyl-7-(thien-2-yl)-8-azaspiro[4.5]deca-6,9-diene

Conditions
ConditionsYield
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; ethanol; water for 3h; Suzuki-Miyaura coupling; Heating;100%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

thiophene boronic acid
6165-68-0

thiophene boronic acid

2'-(2-thienyl)pyridine
3319-99-1

2'-(2-thienyl)pyridine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 18h; Inert atmosphere; Reflux;100%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; isopropyl alcohol at 80℃; for 0.666667h; Suzuki Coupling; Microwave irradiation;91%
With bis(triphenylphosphine)palladium(II) dichloride; potassium carbonate In 1,2-dimethoxyethane; water at 80℃; for 14h;86%
thiophene boronic acid
6165-68-0

thiophene boronic acid

4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

2-(4-nitrophenyl)thiophene
59156-21-7

2-(4-nitrophenyl)thiophene

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; tricyclohexylphosphine; dichloro bis(acetonitrile) palladium(II) at 85 - 90℃; for 5h; Suzuki-Miyaura reaction;100%
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate; palladium diacetate In N,N-dimethyl-formamide at 110℃; for 19h; Suzuki-Miyaura cross-coupling;93%
With potassium phosphate tribasic trihydrate; (2-mesityl-1H-inden-3-yl)dicyclohexyl phosphine; palladium diacetate; Aliquat 336 In water at 20 - 100℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere;86%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 70℃; for 10h; Suzuki-Miyaura reaction;73%
thiophene boronic acid
6165-68-0

thiophene boronic acid

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

2-(2-thienyl)benzaldehyde
99902-07-5

2-(2-thienyl)benzaldehyde

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water for 3.25h; Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;100%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water for 3.25h; Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere; Schlenk technique;89%
thiophene boronic acid
6165-68-0

thiophene boronic acid

(3-bromo-imidazo[1,2-a]pyrazin-8-yl)-methyl-amine

(3-bromo-imidazo[1,2-a]pyrazin-8-yl)-methyl-amine

PdCl2(dppf)CH2Cl2

PdCl2(dppf)CH2Cl2

Thiophen-2-yl-imidazo[1,2-a]pyrazin-8-ylamine
1027067-02-2

Thiophen-2-yl-imidazo[1,2-a]pyrazin-8-ylamine

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; methanol; water100%
thiophene boronic acid
6165-68-0

thiophene boronic acid

5-bromo-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecane-1-sulfonyl)-3-(2-nitrobenzyl)-1-propyl-1,3-dihydroindol-2-one
1007402-19-8

5-bromo-3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecane-1-sulfonyl)-3-(2-nitrobenzyl)-1-propyl-1,3-dihydroindol-2-one

3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecane-1-sulfonyl)-3-(2-nitrobenzyl)-1-propyl-5-thiophen-2-yl-1,3-dihydroindol-2-one
1007402-26-7

3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecane-1-sulfonyl)-3-(2-nitrobenzyl)-1-propyl-5-thiophen-2-yl-1,3-dihydroindol-2-one

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 80℃; for 5h; Suzuki coupling;100%
2-butynyl-[(2E)-4-hydroxy-2-butenyl]propanedioic acid dimethyl ester
852923-47-8

2-butynyl-[(2E)-4-hydroxy-2-butenyl]propanedioic acid dimethyl ester

thiophene boronic acid
6165-68-0

thiophene boronic acid

(4Z)-3-ethenyl-4-[1-(thiophen-2-yl)ethylidene]-1,1-cyclopentanedicarboxylic acid dimethyl ester
1061620-29-8

(4Z)-3-ethenyl-4-[1-(thiophen-2-yl)ethylidene]-1,1-cyclopentanedicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 80℃; for 3h; Inert atmosphere;100%
thiophene boronic acid
6165-68-0

thiophene boronic acid

2-bromoaniline
615-36-1

2-bromoaniline

2-(thiophen-2-yl)aniline
62532-99-4

2-(thiophen-2-yl)aniline

Conditions
ConditionsYield
With C11H8Cl4N2O3Pd; tetrabutylammomium bromide; potassium carbonate In methanol; water; N,N-dimethyl-formamide at 100℃; for 0.166667h; Suzuki Coupling;100%
With bis-triphenylphosphine-palladium(II) chloride; tetrabutylammomium bromide; potassium carbonate In chloroform; water at 80 - 100℃; for 0.166667h; Suzuki Coupling;99%
With 2-[5-(4-methylphenyl)isoxazol-3-yl]-5-(5-phenylisoxazol-3-yl)-1,3,4-oxadiazole·2PdCl2; tetrabutylammomium bromide; potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 0.0166667h; Suzuki Coupling;98%
thiophene boronic acid
6165-68-0

thiophene boronic acid

6-bromo-3,4-dihydroisoquinolin-1(2H)-one
147497-32-3

6-bromo-3,4-dihydroisoquinolin-1(2H)-one

6-(thiophen-2-yl)-3,4-dihydroisoquinolin-1(2H)-one
1309955-17-6

6-(thiophen-2-yl)-3,4-dihydroisoquinolin-1(2H)-one

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In ethanol; toluene Suzuki Coupling; Inert atmosphere; Reflux;100%
With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In water at 70℃; for 2.5h; Suzuki coupling; Inert atmosphere;83%
thiophene boronic acid
6165-68-0

thiophene boronic acid

2-(carboxymethyl)-5-iodobenzoic acid

2-(carboxymethyl)-5-iodobenzoic acid

2-(carboxymethyl)-5-(thiophen-2-yl)benzoic acid
1354742-82-7

2-(carboxymethyl)-5-(thiophen-2-yl)benzoic acid

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water at 150℃; for 0.5h; Suzuki coupling; Inert atmosphere; Microwave irradiation;100%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water at 150℃; for 0.5h; Suzuki Coupling; Microwave irradiation;
thiophene boronic acid
6165-68-0

thiophene boronic acid

N-(adamantan-1-yl)-5-bromo-1-pentyl-1H-indole-3-carboxamide
1378020-97-3

N-(adamantan-1-yl)-5-bromo-1-pentyl-1H-indole-3-carboxamide

N-(adamantan-1-yl)-1-pentyl-5-(thiophen-2-yl)-1H-indole-3-carboxamide
1378020-81-5

N-(adamantan-1-yl)-1-pentyl-5-(thiophen-2-yl)-1H-indole-3-carboxamide

Conditions
ConditionsYield
With palladium diacetate; sodium carbonate; triphenylphosphine In 1,2-dimethoxyethane; ethanol; water at 150℃; for 0.166667h; Suzuki coupling;100%
thiophene boronic acid
6165-68-0

thiophene boronic acid

C16H7F6I
1449478-78-7

C16H7F6I

C20H10F6S
1449478-93-6

C20H10F6S

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,2-dimethoxyethane; water for 9h; Suzuki-Miyaura Coupling; Reflux;100%
thiophene boronic acid
6165-68-0

thiophene boronic acid

6-(4-bromo-2-chlorophenyl)-8-ethyl-2-(4-(4-methylpiperazin-1-yl)phenylamino)pyrido[2,3-d]pyrimidin-7(8H)-one
1286738-68-8

6-(4-bromo-2-chlorophenyl)-8-ethyl-2-(4-(4-methylpiperazin-1-yl)phenylamino)pyrido[2,3-d]pyrimidin-7(8H)-one

C30H29ClN6OS
1286738-65-5

C30H29ClN6OS

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In water; N,N-dimethyl-formamide at 140℃; for 0.5h; Reagent/catalyst; Solvent; Inert atmosphere; Microwave irradiation;100%
piperidine
110-89-4

piperidine

thiophene boronic acid
6165-68-0

thiophene boronic acid

Glyoxilic acid
298-12-4

Glyoxilic acid

2-(piperidin-1-yl)-2-(thiophen-2-yl)acetic acid

2-(piperidin-1-yl)-2-(thiophen-2-yl)acetic acid

Conditions
ConditionsYield
In acetonitrile for 2.5h; Reflux;100%
thiophene boronic acid
6165-68-0

thiophene boronic acid

5-bromo-2,3-dimethylisoindolin-1-one
1345882-37-2

5-bromo-2,3-dimethylisoindolin-1-one

2,3-dimethyl-5-(thiophen-2-yl)isoindolin-1-one
1567837-17-5

2,3-dimethyl-5-(thiophen-2-yl)isoindolin-1-one

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In ethanol; toluene Suzuki Coupling; Inert atmosphere; Reflux;100%
thiophene boronic acid
6165-68-0

thiophene boronic acid

5-bromo-2-indolin-2-one
20870-78-4

5-bromo-2-indolin-2-one

5-(thiophen-2-yl)indolin-2-one
189748-08-1

5-(thiophen-2-yl)indolin-2-one

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In ethanol; toluene Suzuki Coupling; Inert atmosphere; Reflux;100%
thiophene boronic acid
6165-68-0

thiophene boronic acid

C12H10BrN3O

C12H10BrN3O

C16H13N3OS

C16H13N3OS

Conditions
ConditionsYield
With potassium phosphate; methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) In water; dimethyl sulfoxide at 20℃; for 20h; Reagent/catalyst; Solvent; Suzuki Coupling;100%
thiophene boronic acid
6165-68-0

thiophene boronic acid

2-(2-hydroxy-5-methylphenylsulfinyl)-4-methylphenol
27725-15-1

2-(2-hydroxy-5-methylphenylsulfinyl)-4-methylphenol

2,2'-sulfinylbis(4-methylphenol) 2-thienylboronic ester

2,2'-sulfinylbis(4-methylphenol) 2-thienylboronic ester

Conditions
ConditionsYield
With magnesium sulfate In tetrahydrofuran at 20℃; for 20h; Inert atmosphere;100%
thiophene boronic acid
6165-68-0

thiophene boronic acid

7-acetamido-4-bromo-8-methoxyquinoline

7-acetamido-4-bromo-8-methoxyquinoline

7-acetamido-4-(thiophen-2-yl)-8-methoxyquinoline

7-acetamido-4-(thiophen-2-yl)-8-methoxyquinoline

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; 1,2-bis-(diphenylphosphino)ethane In 1,4-dioxane; water at 80℃; Suzuki Coupling; Inert atmosphere;100%
thiophene boronic acid
6165-68-0

thiophene boronic acid

4-Chloro-2-nitroaniline
89-63-4

4-Chloro-2-nitroaniline

2-nitro-4-thiophen-2-yl-phenylamine
405170-93-6

2-nitro-4-thiophen-2-yl-phenylamine

Conditions
ConditionsYield
With potassium phosphate; (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1 ‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate In 1,4-dioxane; water for 20h; Sealed tube; Schlenk technique; Inert atmosphere;100%
thiophene boronic acid
6165-68-0

thiophene boronic acid

2-hydroxybromobenzene
95-56-7

2-hydroxybromobenzene

2-(2'-hydroxyphenyl)thiophene
106584-13-8

2-(2'-hydroxyphenyl)thiophene

Conditions
ConditionsYield
With bis(tri-t-butylphosphine)palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere;100%
thiophene boronic acid
6165-68-0

thiophene boronic acid

4-iodobenzoic acid
619-58-9

4-iodobenzoic acid

4-thiophen-2-yl-benzoic acid
29886-62-2

4-thiophen-2-yl-benzoic acid

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water for 12h; Suzuki Coupling; Reflux;99%
With tris(dibenzylideneacetone)dipalladium (0); Sasrin resin; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid 1) CH2Cl2, rt, 20 h; 2) DMF, rt, 20 h; 3) CH2Cl2, rt, 30 min; Yield given. Multistep reaction;
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-Iodothiophene
3437-95-4

2-Iodothiophene

thiophene boronic acid
6165-68-0

thiophene boronic acid

2,2'-Bithiophene
492-97-7

2,2'-Bithiophene

Conditions
ConditionsYield
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;99%
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In tetrahydrofuran; water for 24h; Suzuki cross-coupling; Inert atmosphere; Reflux;60%
With sodium phosphate; poly(N-vinyl-2-pyrrolidone); palladium In ethanol; water for 48h; Suzuki cross-coupling reaction; Heating;26%
With potassium fluoride In ethanol; water at 140℃; for 0.0333333h; Microwave irradiation;100 %Chromat.
thiophene boronic acid
6165-68-0

thiophene boronic acid

4-bromo-N,N-dimethylaniline
586-77-6

4-bromo-N,N-dimethylaniline

1-N,N-dimethylamino-4-(2-thienyl)benzene
88613-62-1

1-N,N-dimethylamino-4-(2-thienyl)benzene

Conditions
ConditionsYield
With potassium fluoride; tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine In tetrahydrofuran at 20℃; for 2h; Suzuki cross-coupling;99%
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In ethanol at 55℃; Suzuki Coupling;
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In ethanol at 55℃; Suzuki coupling;
thiophene boronic acid
6165-68-0

thiophene boronic acid

2-bromonaphthalene
580-13-2

2-bromonaphthalene

2-naphthalen-2-yl-thiophene
16939-09-6

2-naphthalen-2-yl-thiophene

Conditions
ConditionsYield
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;99%
With C18H9F5NOP(2-)*Pd(2+)*C3H7NO; caesium carbonate In N,N-dimethyl-formamide at 50℃; for 24h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;70%
thiophene boronic acid
6165-68-0

thiophene boronic acid

4-tolyl iodide
624-31-7

4-tolyl iodide

2-p-tolylthiophene
16939-04-1

2-p-tolylthiophene

Conditions
ConditionsYield
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;99%
With sodium carbonate In ethanol; water at 80℃; for 0.5h; Catalytic behavior; Suzuki-Miyaura Coupling;92%
With sodium carbonate; resin-plug bound Pd In N,N-dimethyl-formamide Suzuki coupling;75%
thiophene boronic acid
6165-68-0

thiophene boronic acid

para-iodoanisole
696-62-8

para-iodoanisole

2-(4-methoxyphenyl)thiophene
42545-43-7

2-(4-methoxyphenyl)thiophene

Conditions
ConditionsYield
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;99%
With potassium carbonate In ethanol; water at 70℃; for 1h; Catalytic behavior; Suzuki-Miyaura Coupling;93%
With potassium carbonate In water at 60℃; for 1h; Suzuki-Miyaura Coupling; Green chemistry;91%
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