Product Name

  • Name

    2-Aminophenylboronic acid pinacol ester

  • EINECS
  • CAS No. 191171-55-8
  • Article Data60
  • CAS DataBase
  • Density 1.05 g/cm3
  • Solubility insoluble in water
  • Melting Point 63-68 °C(lit.)
  • Formula C12H18BNO2
  • Boiling Point 335.6 °C at 760 mmHg
  • Molecular Weight 219.091
  • Flash Point 156.8 °C
  • Transport Information
  • Appearance cream crystalline powder
  • Safety 26-36
  • Risk Codes 36/37/38-20/21/22
  • Molecular Structure Molecular Structure of 191171-55-8 (2-Aminophenylboronic acid pinacol ester)
  • Hazard Symbols HarmfulXn, IrritantXi
  • Synonyms 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamine;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline;
  • PSA 44.48000
  • LogP 2.14920

Synthetic route

2-bromoaniline
615-36-1

2-bromoaniline

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide for 12h; Reflux;98%
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); potassium acetate In dimethyl sulfoxide at 85℃; for 12h; Inert atmosphere;87%
With tris(trimethylphosphine)nickel(II) chloride; (2,2,2-trifluoroethoxy)trimethylsilane; cesium fluoride In toluene at 100℃; for 1h; Inert atmosphere;84%
2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene
190788-59-1

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In ethyl acetate at 80℃; for 4h; Temperature; Solvent; Inert atmosphere;95.8%
2-iodophenylamine
615-43-0

2-iodophenylamine

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
With dichlorobis(chlorodi-tert-butylphosphine) palladium(II); triethylamine In toluene for 2h; Inert atmosphere; Reflux;95%
With N(CH2CH3)3; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane (Ar); addn. of triethylamine, palladium compd. and borane deriv. to dioxane soln. of aniline deriv., heating at 100°C for 5 h;84%
With triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In further solvent(s) byproducts: C6H5NH2; (Ar); addn. of 2-IC6H4NH2 to suspn. of PdCl2(dppf) in 1-butyl-3-methylimidazolium tetrafluoroborate; stirring at 100°C; cooling to ambient temp., addn. of Et3N and then pinacolborane (2 equiv.); stirring at 100°C for 0.3 h; extn. with petroleum ether, removal of solvent;60%
2-bromoaniline
615-36-1

2-bromoaniline

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine In 1,4-dioxane at 100℃; for 12h;87%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine In 1,4-dioxane Inert atmosphere;84%
With triethylamine; CyJohnPhos; palladium diacetate In 1,4-dioxane at 80℃; for 1h;81%
2-Chloroaniline
95-51-2

2-Chloroaniline

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
With potassium phosphate tribasic heptahydrate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); XPhos In ethanol at 20℃; for 1h;84%
With tris(trimethylphosphine)nickel(II) chloride; (2,2,2-trifluoroethoxy)trimethylsilane; cesium fluoride In tetrahydrofuran at 100℃; for 12h; Inert atmosphere;80%
With (2,2,2-trifluoroethoxy)trimethylsilane; cesium fluoride; dichlorobis(trimethylphosphine)nickel In tetrahydrofuran at 100℃; for 12h; Inert atmosphere; Sealed tube;80%
With C52H67ClFeNPPd; potassium acetate In 1,4-dioxane at 110℃; for 3h; Suzuki-Miyaura coupling; Inert atmosphere;58%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

2-aminophenylboronic acid
5570-18-3

2-aminophenylboronic acid

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
In tetrahydrofuran76%
In tetrahydrofuran stirred under N2 overnight; evapn., chromy. (SiO2, EtOAc/toluene);76%
2-iodophenylamine
615-43-0

2-iodophenylamine

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
With pyridine; C50H44CuN4OP2(1+)*F6P(1-); N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation;71%
With bis-(dimethylamino)methane In water; acetone; acetonitrile at -5℃; for 0.25h; UV-irradiation; Flow reactor; chemoselective reaction;60%
With caesium carbonate In methanol for 24h; Reflux; Inert atmosphere;37%
With pyridine; cesium fluoride In dimethyl sulfoxide at 105℃; for 2h; Inert atmosphere; Schlenk technique;17%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

Trimethyl borate
121-43-7

Trimethyl borate

2-bis(trimethylsilyl)aminophenyl lithium

2-bis(trimethylsilyl)aminophenyl lithium

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
Stage #1: Trimethyl borate; 2-bis(trimethylsilyl)aminophenyl lithium In tetrahydrofuran at -70 - -60℃; Inert atmosphere;
Stage #2: 2,3-dimethyl-2,3-butane diol In tetrahydrofuran; methanol at 20℃;		52%
...Expand
C24H27BNO2P

C24H27BNO2P

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
With hydrogenchloride In octane; water at 20℃; for 24h; Inert atmosphere;46%
2-Chloroaniline
95-51-2

2-Chloroaniline

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
With triethylamine; CyJohnPhos; palladium diacetate In 1,4-dioxane at 100℃; for 2h;7%
2-iodophenylamine
615-43-0

2-iodophenylamine

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

A

aniline
62-53-3

aniline

B

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
With triethylamine; 1-butyl-3-methylimidazolium Tetrafluoroborate; palladium diacetate at 100℃; for 6h; Product distribution; Further Variations:; Catalysts; reaction time;A 33 % Chromat.
B 61 % Chromat.
...Expand
2-bromoaniline
615-36-1

2-bromoaniline

4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

2-nitrophenylboronic acid
5570-19-4

2-nitrophenylboronic acid

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / Pd/C / ethanol
2: 76 percent / tetrahydrofuran
View Scheme
phenylboronic acid
98-80-6

phenylboronic acid

polymer; monomer(s): Actitex 1500-1, modified with [BF4][4-N2C6H4CH2Cl]; 4-halogenobenzenethiol

polymer; monomer(s): Actitex 1500-1, modified with [BF4][4-N2C6H4CH2Cl]; 4-halogenobenzenethiol

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: HNO3; Ac2O; urea
2: H2 / Pd/C / ethanol
3: 76 percent / tetrahydrofuran
View Scheme
phenylboronic acid
98-80-6

phenylboronic acid

Merrifield resin-CH2O(CH2)4S-CH2C6H4-Ph-4

Merrifield resin-CH2O(CH2)4S-CH2C6H4-Ph-4

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: HNO3; Ac2O; urea
2: H2 / Pd/C / ethanol
3: 76 percent / tetrahydrofuran
View Scheme
aniline
62-53-3

aniline

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

A

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

B

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

C

3-aminophenylboronic acid pinacolate
210907-84-9

3-aminophenylboronic acid pinacolate

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin; 1,2,3,4,5,6,7,8,9,10,11,12-dodecahydrotriphenylene In tetrahydrofuran at 80℃; for 16h; Inert atmosphere; Glovebox; regioselective reaction;
...Expand
2-nitrophenyl bromide
577-19-5

2-nitrophenyl bromide

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: iron; ammonium chloride / water; ethanol / 1 h / 90 °C
2: bis[1,2-bis(diphenylphosphino)ferrocene]-palladium(0); triethylamine / 1,4-dioxane / 12 h / 100 °C
View Scheme
2-(bis(trimethylsilyl)amino)phenyl bromide
54807-57-7

2-(bis(trimethylsilyl)amino)phenyl bromide

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / -70 °C / Inert atmosphere
2.1: tetrahydrofuran / -70 - -60 °C / Inert atmosphere
2.2: 20 °C
View Scheme
2-bromoaniline
615-36-1

2-bromoaniline

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine / tetrahydrofuran / 0 - 60 °C / Inert atmosphere
1.2: -10 - 0 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / -70 °C / Inert atmosphere
3.1: tetrahydrofuran / -70 - -60 °C / Inert atmosphere
3.2: 20 °C
View Scheme
aniline
62-53-3

aniline

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

B

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

C

3-aminophenylboronic acid pinacolate
210907-84-9

3-aminophenylboronic acid pinacolate

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 3h; regioselective reaction;
...Expand
C10H13B2NO4

C10H13B2NO4

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
In chloroform at 20℃; for 1h; regioselective reaction;
[1,3,2]dioxaborolan-2-yl-phenyl-amine
17739-08-1

[1,3,2]dioxaborolan-2-yl-phenyl-amine

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

B

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

C

3-aminophenylboronic acid pinacolate
210907-84-9

3-aminophenylboronic acid pinacolate

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; triethylamine; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 3h; regioselective reaction;
...Expand
C14H21B2NO4

C14H21B2NO4

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
In chloroform at 20℃; for 1h; regioselective reaction;
aniline
62-53-3

aniline

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / tetrahydrofuran / 0.17 h / 80 °C
2: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; triethylamine; 4,4'-di-tert-butyl-2,2'-bipyridine / tetrahydrofuran / 12 h / 80 °C
3: chloroform / 1 h / 20 °C
View Scheme
aniline
62-53-3

aniline

A

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

B

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
214360-73-3

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

C

3-aminophenylboronic acid pinacolate
210907-84-9

3-aminophenylboronic acid pinacolate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / tetrahydrofuran / 0.17 h / 80 °C
2: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; triethylamine; 4,4'-di-tert-butyl-2,2'-bipyridine / tetrahydrofuran / 3 h / 80 °C
View Scheme
...Expand
[1,3,2]dioxaborolan-2-yl-phenyl-amine
17739-08-1

[1,3,2]dioxaborolan-2-yl-phenyl-amine

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; triethylamine; 4,4'-di-tert-butyl-2,2'-bipyridine / tetrahydrofuran / 12 h / 80 °C
2: chloroform / 1 h / 20 °C
View Scheme
C6H5NHBO2C2(CH3)4
857402-61-0

C6H5NHBO2C2(CH3)4

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; triethylamine; 4,4'-di-tert-butyl-2,2'-bipyridine / tetrahydrofuran / 3 h / 80 °C
2: chloroform / 1 h / 20 °C
View Scheme
nitrobenzene
98-95-3

nitrobenzene

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: boron trichloride; tris(pentafluorophenyl)borate / 1,2-dichloro-ethane / 6 h / -10 - 50 °C / Inert atmosphere; Sealed tube
2: triethylamine / 1,2-dichloro-ethane / 3 h / 40 °C / pH < 7
3: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 4 h / 80 °C / Inert atmosphere
View Scheme
(diphenylphosphino)phenylamine
6230-65-5

(diphenylphosphino)phenylamine

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 / octane / 6 h / 150 °C / Sealed tube; Inert atmosphere
2: hydrogenchloride / octane; water / 24 h / 20 °C / Inert atmosphere
View Scheme
tert-butyl 3-((5-bromothiazol-2-yl)carbamoyl)pyrrolidine-1-carboxylate

tert-butyl 3-((5-bromothiazol-2-yl)carbamoyl)pyrrolidine-1-carboxylate

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

tert-butyl 3-((5-(2-aminophenyl)thiazol-2-yl)carbamoyl)pyrrolidine-1-carboxylate

tert-butyl 3-((5-(2-aminophenyl)thiazol-2-yl)carbamoyl)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 110℃; for 24h; Inert atmosphere; Sealed tube;100%
C16H10BrCl

C16H10BrCl

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

C22H16ClN

C22H16ClN

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 100℃; for 18h;100%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

4-methyl-N-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzenesulfonamide
796061-07-9

4-methyl-N-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzenesulfonamide

Conditions
ConditionsYield
With pyridine at 0 - 25℃; for 3h;99%
In dichloromethane for 18h; Heating;33%
(S)-3-(1-bromovinyl)-2,2-dimethyl-1,4-dioxaspiro[4.4]nonane
1416570-55-2

(S)-3-(1-bromovinyl)-2,2-dimethyl-1,4-dioxaspiro[4.4]nonane

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

(R)-2-[1-(3,3-dimethyl-1,4-dioxaspiro[4.4]nonan-2-yl)vinyl]aniline
1416570-57-4

(R)-2-[1-(3,3-dimethyl-1,4-dioxaspiro[4.4]nonan-2-yl)vinyl]aniline

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 4h; Suzuki-Miyaura Coupling;99%
2,5-dibromothiophen
3141-27-3

2,5-dibromothiophen

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

2,2′-(thiophene-2,5-diyl)dianiline

2,2′-(thiophene-2,5-diyl)dianiline

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane; water at 100℃;99%
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane for 72h; Suzuki-Miyaura Coupling; Reflux;95%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 100℃; for 72h; Suzuki-Miyaura Coupling;77%
2-(6-bromo-5-fluorobenzo[d]thiazol-2-yl)-N-(2-(cyclopropylamino)-2-oxoethyl)acetamide

2-(6-bromo-5-fluorobenzo[d]thiazol-2-yl)-N-(2-(cyclopropylamino)-2-oxoethyl)acetamide

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

2-(6-(2-aminophenyl)-5-fluorobenzo[d]thiazol-2-yl)-N-(2-(cyclopropylamino)-2-oxoethyl)acetamide

2-(6-(2-aminophenyl)-5-fluorobenzo[d]thiazol-2-yl)-N-(2-(cyclopropylamino)-2-oxoethyl)acetamide

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane at 100℃; for 1h; Inert atmosphere;99%
3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl trifluoromethanesulfonate
137058-15-2

3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl trifluoromethanesulfonate

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

3',4',5',6'-tetrahydro-[1,1':2',1''-terphenyl]-2-amine

3',4',5',6'-tetrahydro-[1,1':2',1''-terphenyl]-2-amine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 100℃; for 2h; Inert atmosphere;99%
1,1-bis(diethylphosphono)ethylene
37465-31-9

1,1-bis(diethylphosphono)ethylene

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

C16H29NO6P2
1426661-69-9

C16H29NO6P2

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer In 1,4-dioxane; water at 110℃; for 6h; Inert atmosphere; Schlenk technique;98%
2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

Boc-(E)-ΔAbu(β-Br)-OMe
475288-42-7

Boc-(E)-ΔAbu(β-Br)-OMe

3-(tert-butoxycarbonyl)amino-4-methylquinolin-2-one
1036714-68-7

3-(tert-butoxycarbonyl)amino-4-methylquinolin-2-one

Conditions
ConditionsYield
With caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In tetrahydrofuran; water at 90℃; for 3h;97%
methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate
494799-19-8

methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

2-(2-aminophenyl)-3-cyclohexyl-1H-indole-6-carboxylic acid methyl ester
863578-19-2

2-(2-aminophenyl)-3-cyclohexyl-1H-indole-6-carboxylic acid methyl ester

Conditions
ConditionsYield
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water for 7h; Suzuki coupling; Heating;96%
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water for 9h; Heating / reflux;96%
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane; water at 20 - 100℃; for 78h;68%
3-(3-methyloxetan-3-yl)-acrylic acid ethyl ester

3-(3-methyloxetan-3-yl)-acrylic acid ethyl ester

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

4-(3-methyloxetan-3-yl)-3,4-dihydroquinolin-2(1H)-one

4-(3-methyloxetan-3-yl)-3,4-dihydroquinolin-2(1H)-one

Conditions
ConditionsYield
With [Rh(OH)(cod)]2; potassium carbonate In water at 20℃; for 24h; Microwave irradiation;96%
C12H10(2)H3F3O3S

C12H10(2)H3F3O3S

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

C17H16(2)H3N

C17H16(2)H3N

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 100℃; for 4h; Inert atmosphere;96%
2-bromo-3-chloro-5-(trifluoromethyl)pyridine
75806-84-7

2-bromo-3-chloro-5-(trifluoromethyl)pyridine

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]aniline
824953-11-9

2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]aniline

Conditions
ConditionsYield
With water; sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In dimethyl sulfoxide for 16h;95%
chloroacetyl chloride
79-04-9

chloroacetyl chloride

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

N-chloroacetyl-2-aminophenylboronic acid pinacol ester
1300115-16-5

N-chloroacetyl-2-aminophenylboronic acid pinacol ester

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃;95%
chloroacetyl chloride
79-04-9

chloroacetyl chloride

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

N-chloroacetyl-2-aminophenylboronic acid pinacol ester - potassium chloride (4/1)

N-chloroacetyl-2-aminophenylboronic acid pinacol ester - potassium chloride (4/1)

Conditions
ConditionsYield
With K2CO3 In acetonitrile byproducts: KCl; (inert atm.), to K2CO3 in CH3CN added dropwise under stirring 2-amino-phenylboronic acid pinacol ester, treated with 1 equiv. of chloroacetyl chloride dropwise in CH3CN, stirred at room temp. overnight; filtered, washed (CH3CN), evapd.(vac.), tritutated (pentane), dried (vac.), recrystd.;95%
5,5-dichloro-meldrum’s acid

5,5-dichloro-meldrum’s acid

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

2,2-dichloro-N-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide

2,2-dichloro-N-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide

Conditions
ConditionsYield
In ethyl acetate at 20℃; for 16h; Sealed tube;95%
1-(6-(1-(4-bromo-2,6-dimethylphenylimino)ethyl)pyridin-2-yl)ethanone
896712-63-3

1-(6-(1-(4-bromo-2,6-dimethylphenylimino)ethyl)pyridin-2-yl)ethanone

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

(4-bromo-2,6-dimethylphenyl)[1-(6-(1-(2-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenylimino)ethyl)pyridin-2-yl)ethylidene]amine
1020072-00-7

(4-bromo-2,6-dimethylphenyl)[1-(6-(1-(2-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenylimino)ethyl)pyridin-2-yl)ethylidene]amine

Conditions
ConditionsYield
In toluene byproducts: H2O; (N2/Ar, Schlenk) a soln. of amine and pyridine-compound in toluene and molecular sieves were kept at 100°C for 3 days; filtered, the solvent was rotary evapd., recrystd. from ethanol; elem. anal.;94%
C13H7BrClNO

C13H7BrClNO

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

C19H13ClN2O

C19H13ClN2O

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 110℃; for 5h;94%
benzalacetophenone
94-41-7

benzalacetophenone

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

2,4-diphenylquinoline
1039-51-6

2,4-diphenylquinoline

Conditions
ConditionsYield
Stage #1: benzalacetophenone; 2-anilineboronic acid pinacol ester With potassium hydroxide; chloro(1,5-cyclooctadiene)rhodium(I) dimer In toluene at 20℃; for 24h; Inert atmosphere;
Stage #2: With palladium 10% on activated carbon In toluene for 4h; Reflux; regiospecific reaction;		93%
2-chloro-5-methoxybenzaldehyde
13719-61-4

2-chloro-5-methoxybenzaldehyde

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

8-methoxy-phenanthridine
67342-93-2

8-methoxy-phenanthridine

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In dimethyl sulfoxide at 120℃; for 8h; Suzuki Coupling; Inert atmosphere;93%
3-chloro-5-(trifluoromethyl)-2-vinylpyridine

3-chloro-5-(trifluoromethyl)-2-vinylpyridine

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine
1512812-53-1

3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; chloro(2-dicyclohexylphosphino-2′,6′-di-i-propoxy-1,1′-biphenyl)(2′-amino-1,1′-biphenyl-2-yl)-palladium(II); potassium hydroxide; XPhos In 1,4-dioxane; water at 110℃; for 16h; Reagent/catalyst; Inert atmosphere; Sealed tube;93%
Multi-step reaction with 2 steps
1: potassium hydroxide; [Rh(cod)OH]2 / Inert atmosphere
2: XPhos; palladium diacetate; sodium t-butanolate / 1,4-dioxane / 16 h / 110 °C / Inert atmosphere
View Scheme
di(4-isocyanatophenyl)methane
101-68-8

di(4-isocyanatophenyl)methane

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

1,1'-(methylenebis(4,1-phenylene))bis(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-urea)

1,1'-(methylenebis(4,1-phenylene))bis(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-urea)

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 60℃; for 2h;93%
2-bromoanisole
578-57-4

2-bromoanisole

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

2-(2'-methoxyphenyl)aniline
1206-76-4

2-(2'-methoxyphenyl)aniline

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 6h;93%
2-bromothiophene
1003-09-4

2-bromothiophene

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

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

2-(thiophen-2-yl)aniline

Conditions
ConditionsYield
Stage #1: 2-bromothiophene; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane for 0.166667h;
Stage #2: 2-anilineboronic acid pinacol ester With sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 95℃; for 3h;		92%
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 95℃; for 3.16667h;92%
3,6-dibromopyridazine
17973-86-3

3,6-dibromopyridazine

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

2-[6-(2-aminophenyl)pyridazin-3-yl]aniline
1276656-60-0

2-[6-(2-aminophenyl)pyridazin-3-yl]aniline

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In water; N,N-dimethyl-formamide at 20 - 90℃; for 18h; Suzuki coupling; Inert atmosphere;92%
Methyl 2-(2-iodo-1H-indol-3-yl)acetate
275361-65-4

Methyl 2-(2-iodo-1H-indol-3-yl)acetate

2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

paullone
142273-18-5

paullone

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; caesium carbonate; copper(l) chloride In N,N-dimethyl-formamide at 80℃; for 2h; Suzuki coupling; Inert atmosphere;92%
2-anilineboronic acid pinacol ester
191171-55-8

2-anilineboronic acid pinacol ester

1,4-dibromo-2,5-bis(trimethylsilyl)benzene

1,4-dibromo-2,5-bis(trimethylsilyl)benzene

2,2′-(1,4-bis(trimethylsilyl)benzene-2,5-diyl)dianiline

2,2′-(1,4-bis(trimethylsilyl)benzene-2,5-diyl)dianiline

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 90℃; for 24h; Suzuki Coupling; Schlenk technique; Inert atmosphere;92%
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,2-dimethoxyethane at 90℃; for 24h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;92%

2-Aminophenylboronic acid pinacol ester Chemical Properties

The Molecular formula of 2-Aminophenylboronic acid pinacol ester(191171-55-8): C12H20BNO3
The Molecular Weight of 2-Aminophenylboronic acid pinacol ester(191171-55-8): 237.1
The Molecular Structure of 2-Aminophenylboronic acid pinacol ester(191171-55-8):
Melting point: 63-68 °C(lit.)
Boiling Point: 335.6 °C at 760 mmHg 
Flash Point: 156.8 °C 
Index of Refraction: 1.516 
Molar Refractivity: 63.07 cm3 
Molar Volume: 208.5 cm3 
Polarizability: 25 10-24cm3 
Surface Tension: 35.7 dyne/cm 
Density: 1.05 g/cm3 
Enthalpy of Vaporization: 57.87 kJ/mol 
Vapour Pressure: 0.000118 mmHg at 25°C 
storage temp.: Refrigerator (+4°C)
Water Solubility: Insoluble
BRN: 8548809
IUPAC Name: 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
Synonyms: 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ANILINE;2-Aminophenylboronic acid pinacol cyclic ester~2-(2-Aminophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(2-Aminophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-;2-AMINOPHENYLBORONIC ACID, PINACOL CYCLIC ESTER;2-AMINOPHENYLBORONIC ACID, PINACOL ESTER;2-AMINOBENZENEBORONIC ACID PINACOL ESTER;2-Aminobenzeneboronic acid pinacol cyclic ester;

2-Aminophenylboronic acid pinacol ester Safety Profile

The Hazard Codes of 2-Aminophenylboronic acid pinacol ester(191171-55-8):  Xi,Xn
The Risk Statements information of 2-Aminophenylboronic acid pinacol ester(191171-55-8):
20/21/22:  Harmful by inhalation, in contact with skin and if swallowed 
36/37/38:  Irritating to eyes, respiratory system and skin 
The Safety Statements information of 2-Aminophenylboronic acid pinacol ester(191171-55-8):
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36:  Wear suitable protective clothing 
WGK Germany: 3

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