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Basic Information
| CAS No.: | 191171-55-8 |
|---|---|
| Name: | 2-Aminophenylboronic acid pinacol ester |
| Article Data: | 60 |
| Molecular Structure: | |
|
|
|
| Formula: | C12H18BNO2 |
| Molecular Weight: | 219.091 |
| 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; |
| Density: | 1.05 g/cm3 |
| Melting Point: | 63-68 °C(lit.) |
| Boiling Point: | 335.6 °C at 760 mmHg |
| Flash Point: | 156.8 °C |
| Solubility: | insoluble in water |
| Appearance: | cream crystalline powder |
| Hazard Symbols: |
 Xn,  Xi
|
| Risk Codes: | 36/37/38-20/21/22 |
| Safety: | 26-36 |
| PSA: | 44.48000 |
| LogP: | 2.14920 |
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Synthetic route
Conditions
| Conditions | Yield |
|---|---|
| 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% |
- 190788-59-1
2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene
- 191171-55-8
2-anilineboronic acid pinacol ester
Conditions
| Conditions | Yield |
|---|---|
| With 5%-palladium/activated carbon; hydrogen In ethyl acetate at 80℃; for 4h; Temperature; Solvent; Inert atmosphere; | 95.8% |
- 615-43-0
2-iodophenylamine
- 25015-63-8
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
- 191171-55-8
2-anilineboronic acid pinacol ester
Conditions
| Conditions | Yield |
|---|---|
| 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% |
- 615-36-1
2-bromoaniline
- 25015-63-8
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
- 191171-55-8
2-anilineboronic acid pinacol ester
Conditions
| Conditions | Yield |
|---|---|
| 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% |
Conditions
| Conditions | Yield |
|---|---|
| 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% |
- 76-09-5
2,3-dimethyl-2,3-butane diol
- 5570-18-3
2-aminophenylboronic acid
- 191171-55-8
2-anilineboronic acid pinacol ester
Conditions
| Conditions | Yield |
|---|---|
| In tetrahydrofuran | 76% |
| In tetrahydrofuran stirred under N2 overnight; evapn., chromy. (SiO2, EtOAc/toluene); | 76% |
- 615-43-0
2-iodophenylamine
- 73183-34-3
bis(pinacol)diborane
- 191171-55-8
2-anilineboronic acid pinacol ester
Conditions
| Conditions | Yield |
|---|---|
| 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% |
- 76-09-5
2,3-dimethyl-2,3-butane diol
- 121-43-7
Trimethyl borate
- 191171-55-8
2-anilineboronic acid pinacol ester
Conditions
| Conditions | Yield |
|---|---|
| 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
- 191171-55-8
2-anilineboronic acid pinacol ester
Conditions
| Conditions | Yield |
|---|---|
| With hydrogenchloride In octane; water at 20℃; for 24h; Inert atmosphere; | 46% |
- 95-51-2
2-Chloroaniline
- 25015-63-8
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
- 191171-55-8
2-anilineboronic acid pinacol ester
Conditions
| Conditions | Yield |
|---|---|
| With triethylamine; CyJohnPhos; palladium diacetate In 1,4-dioxane at 100℃; for 2h; | 7% |
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2-Aminophenylboronic acid pinacol ester
Chemistry
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;
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;
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
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