833486-94-5

Basic information

• Product Name: 4-AMINO-3-NITROPHENYLBORONIC ACID, PINACOL ESTER
• Synonyms: SALOR-INT L480630-1EA;2-NITRO-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ANILINE;4-AMINO-3-NITROPHENYLBORONIC ACID, PINACOL ESTER;2-(4-Amino-3-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-nitro-4-(tetraMethyl-1,3,2-dioxaborolan-2-yl)aniline;2-(4-Amino-3-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 4-Amino-3-nitrophenylboronic Acid Pinacol Ester
• CAS NO: 833486-94-5
• Molecular Formula: C₁₂H₁₇BN₂O₄
• Molecular Weight: 264.09
• Product Categories: Heterocyclic Compounds;B (Classes of Boron Compounds);Boronic Acids Esters
• Mol File: 833486-94-5.mol
• Article Data: 21

Chemical Properties

• Melting Point: 157.1-172.4 °C
• Boiling Point: 404°C at 760 mmHg
• Flash Point: 198.1°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 9.74E-07mmHg at 25°C
• Refractive Index: 1.54
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Dimethylformamide
• PKA: -0.76±0.56(Predicted)
• CAS DataBase Reference: 4-AMINO-3-NITROPHENYLBORONIC ACID, PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-3-NITROPHENYLBORONIC ACID, PINACOL ESTER(833486-94-5)
• EPA Substance Registry System: 4-AMINO-3-NITROPHENYLBORONIC ACID, PINACOL ESTER(833486-94-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 833486-94-5(Hazardous Substances Data)

Usage

General Description

4-Amino-3-Nitrophenylboronic Acid, Pinacol Ester is a chemical compound often used for research purposes. It contains the elements Carbon (C), Hydrogen (H), Nitrogen (N), Oxygen (O), and Boron (B). The inclusion of a nitro group (NO2) gives the compound a greater degree of reactivity, which can be particularly useful in synthesis reactions. Its proper handling and storage require careful attention due to its reactivity. As with all chemicals, appropriate safety measures should be taken when handling, including the use of personal protective equipment. Its specific applications can vary, but like many boronic acids and their derivatives, it is often used in coupling reactions, such as Suzuki-Miyaura cross-coupling reactions.

InChI:InChI=1/C12H17BN2O4/c1-11(2)12(3,4)19-13(18-11)8-5-6-9(14)10(7-8)15(16)17/h5-7H,14H2,1-4H3

Synthetic route

4-Bromo-2-nitroaniline (875-51-4) + bis(pinacol)diborane (73183-34-3) → 4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5)

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl-formamide at 85℃; for 5h;	92%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane for 2h; Inert atmosphere;	91.9%
With potassium acetate; 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 85℃;	86%

4-Chloro-2-nitroaniline (89-63-4) + bis(pinacol)diborane (73183-34-3) → 4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5)

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 1.5h;	63%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 4,6-dichloro-5-methoxypyrimidine (5018-38-2) → 4-(6-chloro-5-methoxypyrimidin-4-yl)-2-nitroaniline

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 80℃; for 3h; Suzuki Coupling;	100%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 2-chloro-4,6-diphenyl-1,3,5-triazine (3842-55-5) → C21H15N5O2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 12h; Reflux;	100%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 2-bromo-5-methoxy-1,3-benzothiazole (2941-58-4) → 2-(4'-amino-3-nitrophenyl)-6-methoxybenzothiazole (132064-21-2)

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 2-bromo-6-methoxy-1,3 benzothiazole With potassium carbonate In water; N,N-dimethyl-formamide for 1h; Suzuki-Miyaura Coupling; Inert atmosphere; Stage #2: With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; N,N-dimethyl-formamide at 80℃; for 2h; Suzuki-Miyaura Coupling; Inert atmosphere;	99%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 6-hydroxy-2-bromo-benzothiazole (808755-67-1) → 2-(4'-amino-3-nitrophenyl)-6-hydroxybenzothiazole (1448780-05-9)

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 6-hydroxy-2-bromo-benzothiazole With potassium carbonate In water; N,N-dimethyl-formamide for 1h; Suzuki-Miyaura Coupling; Inert atmosphere; Stage #2: With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; N,N-dimethyl-formamide at 80℃; for 1.5h; Temperature; Time; Suzuki-Miyaura Coupling; Inert atmosphere;	98%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 4-iodo-5-methyl-1,2-oxazole (7064-38-2) → 4-(5-methylisoxazol-4-yl)-2-nitroaniline

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 4-iodo-5-methyl-1,2-oxazole With caesium carbonate In 1,4-dioxane; water at 0.2℃; for 0.25h; Stage #2: With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; water at 100℃; for 0.5h; Inert atmosphere;	96%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 2,7-dibromo-2',7'-di-[5-[3,4-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]phenyl]-1,3,4-oxadiazole-2-yl]-9,9'-spirobifluorene (1274238-86-6) → 2,7-di-(4-amino-3-nitrophenyl)-2',7'-di-[5-[3,4-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]phenyl]-1,3,4-oxadiazole-2-yl]-9,9'-spirobifluorene (1274238-87-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water for 12h; Suzuki coupling; Inert atmosphere; Reflux;	94%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one (1110641-70-7) → 3-[(S)-1-(4'-amino-3'-nitrobiphenyl-4-yl)ethyl]-(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-[1,3]oxazinan-2-one (1114573-37-3)

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one With sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water at 100℃; Inert atmosphere; Stage #2: With citric acid In water pH=5 - 6;	93%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + methyl 3-[methyl(propan-2-yl)amino]-2-[(trifluoromethane)sulfonyloxy]quinoxaline-6-carboxylate (1394973-22-8) → methyl 2-(4-amino-3-nitrophenyl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (1396753-37-9)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 90℃; for 0.666667h; Inert atmosphere;	93%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) → 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzene-1,2-diamine (851883-08-4)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethyl acetate under 3102.97 Torr;	91%
With hydrogen; palladium 10% on activated carbon In methanol; dichloromethane at 20℃;
With hydrogen; palladium 10% on activated carbon In methanol under 2475.25 Torr; for 2h;

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 1-bromo-2,6-difluorobenzene (64248-56-2) → 2',6'-difluoro-3-nitro-[1,1'-biphenyl]-4-amine (1259026-54-4)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane; water at 90℃; for 18h; Suzuki coupling; Inert atmosphere;	91%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 3-(2-(1H-indol-3-yl) ethyl)-6-bromoquinazolin-4(3H)-one → 3-(2-(1H-indol-3-yl)ethyl)-6-(4-amino-3-nitrophenyl)quinazolin-4(3H)-one

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 3-(2-(1H-indol-3-yl) ethyl)-6-bromoquinazolin-4(3H)-one With potassium carbonate In 1,4-dioxane; water at 100℃; for 0.25h; Suzuki-Miyaura Coupling; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere;	89.4%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 7-bromo-4-{[4-(difluoromethyl)piperidine-1-yl]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepine (1257320-91-4) → 4-(4-{[4-(difluoromethyl)piperidin-1-yl]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-2-nitroaniline (1257320-92-5)

Conditions	Yield
With caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; water at 90℃; for 12h;	86%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 3-bromo-4-fluorobenzaldehyde (77771-02-9) → 4'-amino-6-fluoro-3'-nitro-[1,1'-biphenyl]-3-carbaldehyde

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 98℃; for 18h; Inert atmosphere;	86%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 6-bromo-3-(2-morpholino-2-oxoethyl)quinazolin-4(3H)-one → 6-(4-amino-3-nitrophenyl)-3-(2-morpholino-2-oxoethyl)quinazolin-4(3H)-one

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 6-bromo-3-(2-morpholino-2-oxoethyl)quinazolin-4(3H)-one With potassium carbonate In 1,4-dioxane; water at 100℃; for 0.25h; Suzuki-Miyaura Coupling; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere;	86%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 5-bromo-furan-2-carboxylic acid ((S)-cyclohexyl-methylcarbamoyl-methyl)-amide (1191923-17-7) → 5-(4-amino-3-nitro-phenyl)-furan-2-carboxylic acid ((S)-cyclohexyl-methylcarbamoyl-methyl)-amide (1222809-30-4)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 100℃; for 4h;	85%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + C70H101BrN2O4 (1268673-68-2) → C76H106N4O6 (1435751-05-5)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 8h; Suzuki Coupling;	85%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + (1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-2-en-3-yl trifluoromethanesulfonate → 4-((1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-2-en-3-yl)-2-nitroaniline

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere;	83%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 6-bromo-3-methyl-2-(morpholinomethyl)quinazolin-4(3H)-one → 6-(4-amino-3-nitrophenyl)-3-methyl-2-(morpholinomethyl)quinazolin-4(3H)-one

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 6-bromo-3-methyl-2-(morpholinomethyl)quinazolin-4(3H)-one With potassium carbonate In 1,4-dioxane; water at 100℃; for 0.25h; Suzuki-Miyaura Coupling; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere;	82.8%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 6-bromo-3-butyl-4(3H)-quinazolinone → 6-(4-amino-3-nitrophenyl)-3-butylquinazolin-4(3H)-one

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 6-bromo-3-butylquinazolin-4(3H)-one With potassium carbonate In 1,4-dioxane; water at 100℃; for 0.25h; Suzuki-Miyaura Coupling; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere;	82.3%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 6-bromo-3-(2-(4-morpholino)ethyl)quinazolin-4(3H)-one → 6-(4-amino-3-nitrophenyl)-3-(2-morpholinoethyl)quinazolin-4(3H)-one

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 4h; Inert atmosphere;	82.2%
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 6-bromo-3-(2-(4-morpholino)ethyl)quinazolin-4(3H)-one With potassium carbonate In 1,4-dioxane; water at 100℃; for 0.25h; Suzuki-Miyaura Coupling; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere;	81.1%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 6-bromo-3-N-methylquinazoline-4(3H)-one (57573-59-8) → 6-(4-amino-3-nitrophenyl)-3-methylquinazolin-4(3H)-one

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 6-bromo-3-N-methylquinazoline-4(3H)-one With potassium carbonate In 1,4-dioxane; water at 100℃; for 0.25h; Suzuki-Miyaura Coupling; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere;	82.1%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 6-bromo-3-(2-(piperidin-1-yl)ethyl)quinazolin-4(3H)-one → 6- (4-amino-3-nitrophenyl)-3-(2-(piperidin-1-yl)ethyl)quinazolin-4(3H)-one

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 6-bromo-3-(2-(piperidin-1-yl)ethyl)quinazolin-4(3H)-one With potassium carbonate In 1,4-dioxane; water at 100℃; for 0.25h; Suzuki-Miyaura Coupling; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere;	81.3%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 6-bromo-3-(3-morpholinylpropyl)-4(3H)-quinazolinone (878743-68-1) → 6-(4-amino-3-nitrophenyl)-3-(3-morpholinopropyl)quinazolin-4(3H)-one

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 6-bromo-3-(3-morpholinylpropyl)-4(3H)-quinazolinone With potassium carbonate In 1,4-dioxane; water at 100℃; for 0.25h; Suzuki-Miyaura Coupling; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere;	80.3%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + methyl iodide (74-88-4) → N-methyl-2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;	80%
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h;	80%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 4-bromo-2,2-difluoro-1,3-benzodioxole (144584-66-7) → 4-(2,2-difluorobenzo[d][1,3]dioxol-4-yl)-2-nitroaniline (1259026-52-2)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane; water at 90℃; for 18h; Suzuki coupling; Inert atmosphere;	79%

Upstream product

• 89-63-4 4-Chloro-2-nitroaniline 
• 73183-34-3 bis(pinacol)diborane 
• 875-51-4 4-Bromo-2-nitroaniline 

Downstream Products

• 956822-01-8 C₂₁H₂₆N₈O₃ 
• 912971-25-6 tert-butyl 4-(4-amino-3-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate 
• 1016645-42-3 [{[2-(4-amino-3-nitrophenyl)-4-methyl-1,3-thiazol-5-yl]carbonyl}(pyridin-2-ylmethyl)amino]acetic acid 
• 1016645-41-2 methyl [{[2-(4-amino-3-nitrophenyl)-4-methyl-1,3-thiazol-5-yl]carbonyl}(pyridin-2-ylmethyl)amino]acetate 
• 1222809-30-4 5-(4-amino-3-nitro-phenyl)-furan-2-carboxylic acid ((S)-cyclohexyl-methylcarbamoyl-methyl)-amide 
• 863328-18-1 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2-amine 
• 1257320-92-5 4-(4-{[4-(difluoromethyl)piperidin-1-yl]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-2-nitroaniline 
• 1351585-61-9 4-methyl-2-nitro-5-(2-(pyridin-4-yl)-1H-benzo[d]imidazol-5-yl)aniline 
• 1351585-62-0 4-methyl-5-(2-(pyridin-4-yl)-1H-benzo[d]imidazol-5-yl)benzene-1,2-diamine 
• 167959-19-5 2-nitro-4-(pyridin-3-yl)benzenamine 
• 851883-08-4 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzene-1,2-diamine 
• 934984-14-2 ethyl 6-(3,4-diaminophenyl)-7-(diethylamino)-2-oxo-2H-chromene-3-carboxylate 

Relevant articles and documents

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