4-Aminophenylboronic acid pinacol ester supplier

Name
4-Aminophenylboronic acid pinacol ester
EINECS 629-061-7
CAS No. 214360-73-3
Article Data85
CAS DataBase
Density 1.05 g/cm³
Solubility Insoluble in water
Melting Point 165-169 °C(lit.)
Formula C₁₂H₁₈BNO₂
Boiling Point 340 °C at 760 mmHg
Molecular Weight 219.091
Flash Point 159.4 °C
Transport Information
Appearance almost white to light beige crystalline powder
Safety 26-36-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2-(4-Aminophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzeneamine;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine;
PSA 44.48000
LogP 2.14920

Synthetic route

: 171364-83-3
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene

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

Conditions

Conditions	Yield
With C36H56Cl3CrN2O; magnesium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In tetrahydrofuran at 60℃; for 24h; Inert atmosphere;	99%
With 5%-palladium/activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 4h;	98%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 4h;	97%

: 106-40-1
4-bromo-aniline

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
With 10H-phenothiazine; caesium carbonate In acetonitrile for 48h; Irradiation; Sealed tube; Inert atmosphere;	97%
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In dimethyl sulfoxide at 150℃; for 0.366667h; microwave irradiation;	85%
With bis(tri-t-butylphosphine)palladium(0); potassium acetate In water at 20℃; for 24h; Reagent/catalyst; Miyaura Borylation Reaction; Inert atmosphere;	85%

: 73183-34-3
bis(pinacol)diborane

: 540-37-4
p-aminoiodobenzene

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

Conditions

Conditions	Yield
With caesium carbonate In methanol for 60h; Reflux; Inert atmosphere;	96%
With pyridine; C50H44CuN4OP2(1+)*F6P(1-); N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation;	87%
With 10H-phenothiazine; caesium carbonate In acetonitrile for 48h; Irradiation; Sealed tube; Inert atmosphere;	80%

: C18H34BNO2Si2

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

Conditions

Conditions	Yield
With hydrogenchloride; water In methanol at 20℃; for 1h;	91%

: 106-40-1
4-bromo-aniline

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

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

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In 1,4-dioxane at 120℃; for 12h; Time; Schlenk technique; Inert atmosphere;	90%
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In 1,4-dioxane at 120℃; for 12h; Schlenk technique; Inert atmosphere;	90%
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In 1,4-dioxane at 120℃; for 12h; Inert atmosphere;	89%

: 864754-08-5
2,2,2-trifluoro-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamide

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

Conditions

Conditions	Yield
	87.1%

: 540-37-4
p-aminoiodobenzene

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

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

Conditions

Conditions	Yield
With dichlorobis(chlorodi-tert-butylphosphine) palladium(II); triethylamine In toluene for 2h; Inert atmosphere; Reflux;	83%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine In 1,4-dioxane at 90℃; for 1.5h; Inert atmosphere;	80%
With triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 80℃; for 8h;	75 %Chromat.

: 73852-88-7
2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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

Conditions

Conditions	Yield
With bis(triphenylphosphine)nickel(II) chloride; lithium hexamethyldisilazane In toluene at 100℃; for 2h; Glovebox; Sealed tube;	80%
Multi-step reaction with 2 steps 1: chlorotris(triphenylphosphine)cobalt(I); bis[2-(diphenylphosphino)phenyl] ether / toluene / 12 h / 100 °C 2: hydrogenchloride; water / methanol / 1 h / 20 °C View Scheme

: 5419-55-6
Triisopropyl borate

: 5089-33-8
2-(4-bromophenyl)-1,1,1,3,3,3-hexamethyldisilazane

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

Conditions

Conditions	Yield
Stage #1: 2-(4-bromophenyl)-1,1,1,3,3,3-hexamethyldisilazane With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran at -78 - 25℃; for 4.5h; Inert atmosphere; Stage #3: With 2,3-dimethyl-2,3-butane diol; acetic acid In tetrahydrofuran at 20℃; for 0.75h; pH=5; Inert atmosphere;	79%

: (4-aminophenyl)boronic acid hydrochloride

: 76-09-5
2,3-dimethyl-2,3-butane diol

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

Conditions

Conditions	Yield
With magnesium sulfate In tetrahydrofuran at 20℃; for 5h;	76%

: 76-09-5
2,3-dimethyl-2,3-butane diol

: 53847-33-9
4-bromo-N-(diphenylmethylidene)aniline

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

Conditions

Conditions	Yield
Stage #1: 4-bromo-N-(diphenylmethylidene)aniline With C12H27Mg(1-)*Li(1+) In tetrahydrofuran at -20℃; for 1h; Inert atmosphere; Green chemistry; Large scale; Stage #2: With Trimethyl borate In tetrahydrofuran at -20 - 25℃; for 2.5h; Inert atmosphere; Green chemistry; Large scale; Stage #3: 2,3-dimethyl-2,3-butane diol Reagent/catalyst; Temperature; Green chemistry; Large scale; Further stages;	70%

Yield

Stage #1: 4-bromo-N-(diphenylmethylidene)aniline With C12H27Mg(1-)*Li(1+) In tetrahydrofuran at -20℃; for 1h; Inert atmosphere; Green chemistry; Large scale;
Stage #2: With Trimethyl borate In tetrahydrofuran at -20 - 25℃; for 2.5h; Inert atmosphere; Green chemistry; Large scale;
Stage #3: 2,3-dimethyl-2,3-butane diol Reagent/catalyst; Temperature; Green chemistry; Large scale; Further stages;

70%

: 371-40-4
4-fluoroaniline

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); lithium hexamethyldisilazane In toluene at 80℃; for 12h; Inert atmosphere; Schlenk technique;	68%
With tetramethylammonium fluoride; 2-mercaptopyridine sodium salt In acetonitrile at 30 - 35℃; for 24h; Irradiation; Inert atmosphere;	52%

: 106-50-3
1,4-phenylenediamine

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
With tert.-butylnitrite In acetonitrile at 80℃; for 2h;	62%
With tert.-butylnitrite In acetonitrile at 80℃; for 2h;	62%
With tert.-butylnitrite In acetonitrile at 80℃; for 2h;	62%
With tert.-butylnitrite In acetonitrile at 80℃; for 2h;	62%
Stage #1: 1,4-phenylenediamine With hydrogenchloride; methanol; sodium nitrite In water at 0 - 5℃; for 0.5h; Sandmeyer Reaction; Green chemistry; Stage #2: bis(pinacol)diborane In water at 20℃; for 1h; Sandmeyer Reaction; Green chemistry;	53%

: 4-amino-N,N,N-trimethylbenzenaminium trifluoromethanesulfonate

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); potassium tert-butylate; 1,3-dicyclohexyl-1H-imidazol-3-ium chloride In 2-ethoxy-ethanol; toluene at 50℃; for 24h; Schlenk technique; Inert atmosphere;	62%

: 106-47-8
4-chloro-aniline

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
With Co(1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene)2Cl2; potassium methanolate In tert-butyl methyl ether at 50℃; for 8h;	60%
With potassium acetate In isopropyl alcohol at 82℃; for 2h; Suzuki-Miyaura Coupling;	75 %Chromat.

: 76-09-5
2,3-dimethyl-2,3-butane diol

: 5419-55-6
Triisopropyl borate

: 756822-47-6
(4-(bis(trimethylsilyl)amino)phenyl)magnesium bromide

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

Conditions

Conditions	Yield
Stage #1: Triisopropyl borate; (4-(bis(trimethylsilyl)amino)phenyl)magnesium bromide In tetrahydrofuran at -70 - -60℃; for 5h; Inert atmosphere; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h; Stage #3: 2,3-dimethyl-2,3-butane diol In tetrahydrofuran at 20℃;	59%

...Expand

: 627093-70-3
6-methyl-1-oxo-2-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]-1,2-dihydrobenzo[b][1,6]naphthyridine-4-carboxylic acid

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

Conditions

Conditions	Yield
With triethylamine In DMF (N,N-dimethyl-formamide); toluene Reduced pressure;	45%

: 61676-62-8
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 106-40-1
4-bromo-aniline

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

Conditions

Conditions	Yield
Stage #1: 4-bromo-aniline With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20℃; for 24h;	42.2%

: 102879-36-7
4-Amino-thiobenzoesaeure-S-ethylester

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
With [Rh(OH)(cod)]2; tributylphosphine; potassium acetate at 80℃; for 24h; Inert atmosphere; Glovebox;	32.4%

: 106-40-1
4-bromo-aniline

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / 0 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 2.2: 4.5 h / -78 - 25 °C / Inert atmosphere 2.3: 0.75 h / 20 °C / pH 5 / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: triethylamine / tetrahydrofuran / 0 - 60 °C / Inert atmosphere 1.2: -10 - 0 °C 2.1: magnesium; iodine / tetrahydrofuran / 2 h / 50 °C / Inert atmosphere; Reflux 3.1: tetrahydrofuran / 5 h / -70 - -60 °C / Inert atmosphere 3.2: 2 h / 20 °C 3.3: 20 °C View Scheme

: 62-53-3
aniline

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

A: 191171-55-8
2-anilineboronic acid pinacol ester

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

C: 210907-84-9
3-aminophenylboronic acid pinacolate

Conditions

Conditions	Yield
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

: 100-01-6
4-nitro-aniline

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 2-(4-biphenylyl)-5-phenyloxazole; tert.-butylnitrite / acetonitrile / 4 h / 20 °C 2: 5%-palladium/activated carbon; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr View Scheme

: 73183-34-3
bis(pinacol)diborane

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 2-(4-biphenylyl)-5-phenyloxazole; tert.-butylnitrite / acetonitrile / 4 h / 20 °C 2: 5%-palladium/activated carbon; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr View Scheme

: 330793-01-6
(4-tert-butoxycarbonylaminophenyl)boronic acid pinacol ester

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

Conditions

Conditions	Yield
With hydrogenchloride In ethyl acetate at 20℃; for 4h;

: 76-09-5
2,3-dimethyl-2,3-butane diol

: 89415-43-0
(4-aminophenyl)boronic acid

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

Conditions

Conditions	Yield
With magnesium sulfate In tetrahydrofuran at 20℃; for 5h;

: 106-50-3
1,4-phenylenediamine

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: formic acid; sodium cyanoborohydride / methanol / 16 h / 0 - 20 °C / pH 3 - 4 / Inert atmosphere 1.2: 0 °C / Inert atmosphere 2.1: bis(1,5-cyclooctadiene)nickel(0); 1,3-dicyclohexyl-1H-imidazol-3-ium chloride; potassium tert-butylate / toluene; 2-ethoxy-ethanol / 24 h / 50 °C / Schlenk technique; Inert atmosphere View Scheme

: 24524-95-6
S-(p-nitrobenzoyl)mercaptoethane

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tin(II) chloride dihdyrate / ethyl acetate / 4 h / Inert atmosphere; Reflux 2: [Rh(OH)(cod)]2; tributylphosphine; potassium acetate / 24 h / 80 °C / Inert atmosphere; Glovebox View Scheme

: 108-24-7
acetic anhydride

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

: 214360-60-8
N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide

Conditions

Conditions	Yield
at 20℃; for 1h;	100%
In dichloromethane at 20℃; for 10h;	87%
for 1h;

: 155820-88-5
1-bromo-4-(2,2,2-trifluoroethyl)benzene

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

: 4-[4'-(2,2,2-trifluoroethyl)-4-biphenylyl]amine

Conditions

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 100℃; for 17h; Suzuki coupling;	100%

: 82417-45-6
dichlorobenzenesulfonyl chloride

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

: 912675-28-6
2,3-dichloro-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzenesulfonamide

Conditions

Conditions	Yield
With pyridine at 20℃; for 15h;	100%
With pyridine In dichloromethane at 20 - 25℃; for 20h;	77%
With pyridine In dichloromethane at 20 - 25℃; for 20h;	77%

: 6-chloro-2-ethoxy-N-methylnicotinamide

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

: 1138322-13-0
6-(4-aminophenyl)-2-ethoxy-N-methylnicotinamide

Conditions

Conditions	Yield
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; ethanol; water for 16h; Inert atmosphere; Reflux;	100%

: 89891-65-6
7-bromo-2-chloroquinoxaline

: 1008-91-9
4-(piperazin-1-yl)pyridine

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

: 1271847-04-1
4-[3-(4-pyridin-4-yl-piperazin-1-yl)-quinoxalin-6-yl]-phenlamine

Conditions

Conditions	Yield
Stage #1: 7-bromo-2-chloroquinoxaline; 4-(piperazin-1-yl)pyridine With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 20 - 160℃; Microwave irradiation; Stage #2: 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline With potassium carbonate; tris-(o-tolyl)phosphine; palladium diacetate In 1-methyl-pyrrolidin-2-one at 140℃; Microwave irradiation;	100%

...Expand

: 1252598-01-8
C11H13BrN4O

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

: 1252597-72-0
C17H19N5O

Conditions

Conditions	Yield
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In dimethyl ether, 1,2- at 130℃; for 1h; Microwave irradiation;	100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,2-dimethoxyethane at 130℃; for 1h; Microwave irradiation;	100%

: 79-22-1
methyl chloroformate

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

: 844500-75-0
methyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate

Conditions

Conditions	Yield
With pyridine In 1,2-dichloro-ethane at 0 - 60℃;	100%

: 1437281-38-3
6-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-2-chloroquinoxaline

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

: 1437281-40-7
4-(6-(2-((tert-butyldimethylsilyl)oxy)ethoxy)quinoxalin-2-yl)aniline

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 4h; Reflux;	100%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 4h; Reflux;	100%

: 529-20-4
2-methylphenyl aldehyde

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

: (E)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-(o-tolyl)methanimine

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 18h; Inert atmosphere; Molecular sieve;	100%

: 79-14-1
glycolic Acid

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

: C14H20BNO4

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 36h;	100%

: 576-83-0
2,4,6-trimethylphenyl bromide

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

: 66818-61-9
2′,4′,6′-trimethylbiphenyl-4-amine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane for 17h; Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;	100%

: 619-44-3
methyl 4-iodobenzoate

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

: 5730-76-7
methyl 4’-amino-[1,1’-biphenyl]-4-carboxylate

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 10h;	100%

: 124-63-0
methanesulfonyl chloride

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

: 380430-57-9
4-(methylsulfonylamino)phenyl boronic acid

Conditions

Conditions	Yield
Stage #1: methanesulfonyl chloride; 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline With pyridine In dichloromethane at 0 - 20℃; Stage #2: With water In dichloromethane	99%

: 69922-27-6
1-fluoro-2-isocyanato-4-(trifluoromethyl)benzene

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

: 796967-62-9
N-(2-fluoro-5-trifluoromethylphenyl)-N'-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]urea

Conditions

Conditions	Yield
In 1,2-dichloro-ethane at 20℃;	98.8%
In tetrahydrofuran at 20℃; for 0.5h;	85%
In dichloromethane at 20℃;

: 329-01-1
1-isocyanato-3-trifluoromethyl-benzene

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

: 796967-48-1
N-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]-N'-(3-trifluoromethylphenyl)urea

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃;	98%
In dichloromethane at 20℃;
With triethylamine In dichloromethane at 20℃;

: 5402-73-3
2,5-dichlorobenzenesulphonyl chloride

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

: 1426214-54-1
2,5-dichloro-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzenesulfonamide

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 1h;	98%
With pyridine In dichloromethane at 20 - 25℃; for 16h;	17.9 g
With pyridine In dichloromethane at 20 - 25℃; for 16h;	17.9 g

: 128-63-2
1,3,6,8-tetrabromopyrene

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

: 1610471-69-6
4,4’,4’’,4’’’-(pyrene-1,3,6,8-tetrayl) tetra aniline

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 115℃; Inert atmosphere;	98%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water for 72h; Schlenk technique; Inert atmosphere; Reflux;	94%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 115℃; for 72h; Inert atmosphere;	90%

: 108-30-5
succinic acid anhydride

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

: 480424-98-4
4-oxo-4-[(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)amino]butanoic acid

Conditions

Conditions	Yield
In chloroform at 20℃; for 4h;	98%

: 50978-45-5
3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide

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

: N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)formamide

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.166667h; Solvent; Time;	98%

: 5-bromo-2-(2-fluorophenyl)thiazole

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

: 4-[2-(2-fluorophenyl)thiazol-5-yl]phenylamine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane at 100℃; for 2h; Inert atmosphere;	98%

: [5,15-dibromo-10,20-bis(2,6-dioctoxyphenyl)porphinato]zinc(II)

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

: C91H124N6O4Zn

Conditions

Conditions	Yield
Stage #1: [5,15-dibromo-10,20-bis(2,6-dioctoxyphenyl)porphinato]zinc(II) With tetrakis(triphenylphosphine) palladium(0) In toluene at 20℃; for 0.5h; Sonogashira Cross-Coupling; Stage #2: 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline With sodium carbonate In ethanol; water; toluene at 100℃; for 5h; Sonogashira Cross-Coupling;	97.22%

: 103-71-9
phenyl isocyanate

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

: 819056-67-2
N-phenyl-N'-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]urea

Conditions

Conditions	Yield
In toluene at 50℃; for 16h;	97%
With triethylamine In dichloromethane at 20℃;	70%
With 4-methyl-morpholine In tetrahydrofuran

: 1173205-24-7
5-chloro-3-cyclopropyl-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidine

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

: 1173205-23-6
4-(3-cyclopropyl-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl)aniline

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 140℃; for 0.75h; Suzuki coupling; Microwave irradiation;	97%

: 1202885-77-5
2-chloro-7-(2,2-dimethoxyethyl)-4-morpholin-4-yl-7H-pyrrolo[2,3-d]pyrimidine

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

: 1202885-78-6
4-[7-(2,2-dimethoxyethyl)-4-morpholin-4-yl-7H-pyrrolo[2,3-d]pyrimidin-2-yl]aniline

Conditions

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 130℃; for 0.5h; Suzuki Coupling; Microwave irradiation;	97%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 130℃; for 0.5h; Suzuki coupling; Microwave irradiation;	97%

: 1101819-64-0
4-[1-(benzenesulfonyl)cyclopropyl]-2-chloro-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine

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

: 1101819-63-9
4-[4-[1-(benzenesulfonyl)cyclopropyl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]aniline

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; ethanol; water; N,N-dimethyl-formamide at 80 - 95℃; for 5h; Inert atmosphere;	97%

: 3-chloro-5-(3,4-dimethoxyphenyl)pyrazin-2-amine

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

: 3-(4-aminophenyl)-5-(3,4-dimethoxyphenyl) pyrazin-2-amine

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 100℃; for 4h;	96.8%

: 1195-45-5
para-fluorophenyl isocyanate

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

: 819056-61-6
N-(4-fluorophenyl)-N'-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]urea

Conditions

Conditions	Yield
at 20℃;	96%
In dichloromethane at 20℃;
In dichloromethane Alkaline conditions;
In dichloromethane at 0 - 20℃; Alkaline conditions;

4-Aminophenylboronic acid pinacol ester Specification

The 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline with cas registry number of 214360-73-3 is also called 4-Aminophenylboronic acid pinacol ester. It is almost white to light beige crystalline powder which is insoluble in water.It belongs to the following categories: boron compounds; substituted boronic acids; boronic acid; b (classes of boron compounds); boronic acids esters; chiral chemicals. Both its systematic name and IUPAC name are the same which is called 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline.

The physical properties about this chemical are: (1)#H bond acceptors: 3; (2)#H bond donors: 2; (3)#Freely Rotating Bonds: 2; (4)Index of Refraction: 1.516; (5)Molar Refractivity: 63.07 cm³; (6)Molar Volume: 208.5 cm³; (7)Surface Tension: 35.7 dyne/cm; (8)Density: 1.05 g/cm³; (9)Flash Point: 159.4 °C; (10)Enthalpy of Vaporization: 58.35 kJ/mol; (11)Boiling Point: 340 °C at 760 mmHg; (12)Vapour Pressure: 8.87E-05 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. Therefore, it is better to wear suitable protective clothing, gloves and eye/face protection during using it. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O1B(OC(C)(C)C1(C)C)c2ccc(N)cc2;
(2)InChI: InChI=1/C12H18BNO2/c1-11(2)12(3,4)16-13(15-11)9-5-7-10(14)8-6-9/h5-8H,14H2,1-4H3;
(3)InChIKey: ZANPJXNYBVVNSD-UHFFFAOYAY

Product Name

4-Aminophenylboronic acid pinacol ester

Synthetic route

4-Aminophenylboronic acid pinacol ester Specification

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