220210-56-0

Basic information

• Product Name: 3-tert-Butoxycarbonylphenylboronic acid
• Synonyms: 3-(T-BUTOXYCARBONYL)PHENYLBORONIC ACID;3-(TERT-BUTOXYCARBONYL)BENZENEBORONIC ACID;3-(TERT-BUTOXYCARBONYL)PHENYLBORONIC ACID;T-BUTYL 3-BORONOBENZOATE;3-(Tert-Butoxycarbonyl)Phenylb;3-(tert-Butoxycarbonyl)benzeneboronic acid 98%;3-(T-BUTOXYCARBONYL)PHENYLBORBONIC ACID;tert-Butyl 3-boronobenzoate
• CAS NO: 220210-56-0
• Molecular Formula: C₁₁H₁₅BO₄
• Molecular Weight: 222.05
• EINECS: 1806241-263-5
• Product Categories: blocks;BoronicAcids;Carboxes;Boronic acids
• Mol File: 220210-56-0.mol
• Article Data: 0

Chemical Properties

• Melting Point: 96-102°C
• Boiling Point: 375 °C at 760 mmHg
• Flash Point: 180.6 °C
• Appearance: white to light yellow crystal powder
• Density: 1.15 g/cm³
• Vapor Pressure: 2.74E-06mmHg at 25°C
• Refractive Index: 1.517
• Storage Temp.: Keep Cold
• Solubility: soluble in Methanol
• PKA: 7.72±0.10(Predicted)
• CAS DataBase Reference: 3-tert-Butoxycarbonylphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-tert-Butoxycarbonylphenylboronic acid(220210-56-0)
• EPA Substance Registry System: 3-tert-Butoxycarbonylphenylboronic acid(220210-56-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-60-37
• Hazardous Substances Data: 220210-56-0(Hazardous Substances Data)

Usage

Chemical Properties

White to light yellow crystal powde

InChI:InChI=1/C11H15BO4/c1-11(2,3)16-10(13)8-5-4-6-9(7-8)12(14)15/h4-7,14-15H,1-3H3

Synthetic route

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + 4-Bromo-1-naphthylamine (2298-07-9) → tert-butyl 3-(4-aminonaphthalen-1-yl)benzoate

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 90℃; for 4h;	100%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + ((1-(3-bromophenyl)cyclopropyl)methoxy)(tert-butyl)dimethylsilane → C27H38O3Si

Conditions	Yield
With potassium phosphate; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In toluene at 100℃; for 3h; Inert atmosphere; Glovebox;	100%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + pinanediol (18680-27-8) → tert-butyl 3-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)benzoate (1154427-21-0)

Conditions	Yield
With magnesium sulfate In diethyl ether at 20℃; for 3h; Inert atmosphere;	99%
In tetrahydrofuran at 20℃; for 0.5h;	85%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + 5-iodopyrimidine (31462-58-5) → tert-butyl 3-(pyrimidin-5-yl)benzoate (1595294-71-5)

Conditions	Yield
With potassium carbonate In ethanol; water at 90℃; for 0.5h; Suzuki Coupling; Microwave irradiation;	99%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + 3-bromo-4-methylaniline (7745-91-7) → tert-butyl 5'-amino-2'-methyl-[1,1'-biphenyl]-3-carboxylate

Conditions	Yield
Stage #1: 3-bromo-4-methylaniline With potassium carbonate In water; toluene at 65℃; Inert atmosphere; Stage #2: 3-(tert-butoxycarbonyl)phenylboronic acid With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; toluene for 20h; Inert atmosphere; Reflux;	98%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + N-(1-Bromoisoquinolin-3-yl)-1-(2,2-difluorobenzo-[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (1152274-51-5) → tert-butyl 3-(3-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)isoquinolin-1-yl)benzoate (1152274-55-9)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 80℃;	97%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + C26H28BrNO (1373125-71-3) → C37H41NO3

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate In water; toluene at 90℃; for 14h; Heck-Suzuki cascade reaction; optical yield given as %de; diastereoselective reaction;	97%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) → benzoic acid (65-85-0)

Conditions	Yield
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); water In toluene at 90℃; for 1h; Microwave irradiation; Green chemistry;	96%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + C39H28IO3P → C50H41O5P

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 80℃; for 12h; Inert atmosphere;	96%
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 80℃; for 12h; Inert atmosphere;	96%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + 7-bromo-Nα-(tert-butoxycarbonyl)-D-tryptophanamide → (R)-Nα-tert-butoxycarbonyl-7-(3-(tert-butoxycarbonyl)phenyl)-tryptophanamide

Conditions	Yield
With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate; potassium phosphate; sodium tetrachloropalladate(II) In 1,4-dioxane; water at 100℃; for 0.5h; Suzuki-Miyaura Coupling; Sealed tube; Inert atmosphere;	96%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + 2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(2,2,2-trifluoroethoxy)benzofuran-5-yl trifluoromethanesulfonate → tert-butyl 3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(2,2,2-trifluoroethoxy)benzofuran-5-yl)benzoate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 110℃; Sealed tube; Inert atmosphere;	95%
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 110℃; Inert atmosphere; Sealed tube;	95%

2-bromo-3-picoline (3430-17-9) + 3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) → tert-butyl 3-(3-methylpyridin-2-yl)benzoate (1083057-12-8)

Conditions	Yield
Stage #1: 2-bromo-3-picoline With potassium carbonate In water; toluene at 65℃; Inert atmosphere; Stage #2: 3-(tert-butoxycarbonyl)phenylboronic acid With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; toluene for 18h; Inert atmosphere; Reflux;	92%
Stage #1: 2-bromo-3-picoline With potassium carbonate In water; toluene at 65℃; for 1h; Stage #2: 3-(tert-butoxycarbonyl)phenylboronic acid; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In water; toluene at 80℃; for 2h;	82%
Stage #1: 2-bromo-3-picoline With potassium carbonate In toluene at 65℃; for 1h; Inert atmosphere; Stage #2: 3-(tert-butoxycarbonyl)phenylboronic acid With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In toluene at 80℃; for 2h; Inert atmosphere;	82%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + methyl vinyl ketone (78-94-4) → tert-butyl 3-(3-oxobutyl)benzoate

Conditions	Yield
With potassium phosphate; chloro(1,5-cyclooctadiene)rhodium(I) dimer In 1,4-dioxane; water at 60℃; Glovebox;	89%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + 6-(ethoxy-1,1,2,2,2-d5)-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl trifluoromethanesulfonate → tert-butyl-3-(6-(ethoxy-1,1,2,2,2-d5)-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)benzoate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,3-dioxane; water at 100℃; for 16h; Inert atmosphere; Sealed tube;	87.57%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + 5-bromo-3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (875639-16-0) → 3-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-5-yl]-benzoic acid tert-butyl ester (875639-30-8)

Conditions	Yield
With sodium hydrogencarbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; acetonitrile at 90℃; for 0.5h; Suzuki Coupling;	87%
With sodium hydrogencarbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; acetonitrile at 90℃; for 0.5h; Microwave irradiation;	87%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + Fmoc-4-bromo-L-phenylalanine → (2S)-3-(4-{3-[(tert-butoxy)carbonyl]phenyl}phenyl)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid

Conditions	Yield
With potassium phosphate; 1,1'-bis(di-tertbutylphosphino)ferrocene; palladium diacetate In tetrahydrofuran at 50℃; for 16h; Suzuki-Miyaura Coupling; Inert atmosphere;	85%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + (R)-3-bromo-6-((4-hydroxy-1-(3-phenylbutanoyl)piperidin-4-yl)methyl)-2-methyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one → tert-butyl (R)-3-(6-((4-hydroxy-1-(3-phenylbutanoyl)piperidin-4-yl)methyl)-2-methyl-7-oxo-6,7-dihydro-2H-pyrazolo[4,3-d]pyrimidin-3-yl)benzoate

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 120℃; for 0.25h; Suzuki Coupling; Inert atmosphere; Microwave irradiation; Sealed tube;	85%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + 2-amino-5-bromo-3-(4'-chlorophenyl)pyridine → tert-butyl 3-[6-amino-5-(4-chlorophenyl)pyridin-3-yl]benzoate

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water Suzuki-Miyaura Coupling;	84%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + C28H21ClO4P2 → C39H34O6P2

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium phosphate; tri-tert-butyl phosphine In 1,4-dioxane at 80℃; for 10h; Suzuki-Miyaura Coupling; Inert atmosphere;	83%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + 2-amino-5-bromo-3-phenylmethylpyrazine (174680-55-8) → tert-butyl 3-(5-amino-6-benzylpyrazin-2-yl)benzoate

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane at 75℃; for 0.5h;	79%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + 4-bromo-5-(methylthio)-1,3-diphenyl-1H-pyrazole (32859-25-9) → tert-butyl 3-(5-(methylthio)-1,3-diphenyl-1H-pyrazol-4-yl)benzoate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene Inert atmosphere;	78%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + methyl 1-(3-bromo-5-methylphenyl)-5-(2-(1-methyl-1H-1,2,3-triazol-4-yl)cyclopropyl)-1H-pyrazole-4-carboxylate → methyl 1-(3'-(tert-butoxycarbonyl)-5-methyl-[1,1,-biphenyl]-3-yl)-5-(2-(1-methyl-1H-1,2,3-triazol-4-yl)cyclopropyl)-1H-pyrazole-4-carboxylate

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 90℃; for 6h; Inert atmosphere;	77%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + 5-bromo-2-methoxybenzaldehyde (25016-01-7) → 3'-formyl-4'-methoxybiphenyl-3-carboxylic acid tert-butyl ester

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water for 4h; Suzuki Coupling; Inert atmosphere; Sealed tube; Heating;	74%

5-bromo-2-aminopyrimidine (7752-82-1) + 3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) → tert-butyl 3-(2-aminopyrimidin-5-yl)benzoate

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 120℃; for 3h;	73.5%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + methyl 1-(6-bromopyridin-2-yl)-5-(2-(1-methyl-1H-1,2,3-triazol-4-yl)cyclopropyl)-1H-pyrazole-4-carboxylate → methyl 1-(6-(3-(tert-butoxycarbonyl)phenyl)pyridin-2-yl)-5-(2-(1-methyl-1H-1,2,3-triazol-4-yl)cyclopropyl)-1H-pyrazole-4-carboxylate

Conditions	Yield
With sodium carbonate In methanol; toluene at 110℃; for 2h; Inert atmosphere;	73.3%

4-chloro-3-methylpyridine (1681-36-3) + 3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) → tert-butyl 3-(3-methylpyridin-4-yl)benzoate (1189328-78-6)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 80℃; for 60h;	71.4%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + 2-bromo-3-chloropyridine (96424-68-9) → tert-butyl 3-(3-chloropyridin-2-yl)benzoate

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,2-dimethoxyethane; water at 80℃;	71%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + ethyl 2-(4-fluorophenyl)-6-nitro-5-(trifluoromethylsulfonyloxy)benzofuran-3-carboxylate (691857-51-9) → ethyl 5-(3-(tert-butoxycarbonyl)phenyl)-2-(4-fluorophenyl)-6-nitrobenzofuran-3-carboxylate (1217339-14-4)

Conditions	Yield
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 20 - 90℃;	69%
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃;	69%

3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) + 2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(3,3,3-trifluoropropyl)benzofuran-5-yl trifluoromethanesulfonate → tert-butyl 3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(3,3,3-trifluoropropyl)benzofuran-5-yl)benzoate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 90℃; for 16h;	67.7%

2,6-dichloropyridine-3-carboxylic acid (38496-18-3) + 3-(tert-butoxycarbonyl)phenylboronic acid (220210-56-0) → 6-(3-(tert-butoxycarbonyl)phenyl)-2-chloronicotinic acid (1391833-29-6)

Conditions	Yield
Stage #1: 2,6-dichloropyridine-3-carboxylic acid; 3-(tert-butoxycarbonyl)phenylboronic acid With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In dimethoxyethane-1,2; water at 90℃; Stage #2: With hydrogenchloride In dimethoxyethane-1,2; water; ethyl acetate pH=3 - 4;	67%

Downstream Products

• 1152274-55-9 tert-butyl 3-(3-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)isoquinolin-1-yl)benzoate 
• 1189328-78-6 tert-butyl 3-(3-methylpyridin-4-yl)benzoate 
• 903895-48-7 tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate