5570-18-3

Basic information

• Product Name: 2-Aminophenylboronic acid
• Synonyms: 2-Aminobenzeneboronic acid hydrochloride;2-AMINOPHENYLBORONIC ACID 2-AMINOPHENYLBORONIC ACID, HYDROCHLORIDE;2-Aminobenzeneboronicacid,96%;2-Aminophenylboronic acid HCl Salt;AMinobenzeneboronic acid;2-Boronoaniline;2-AMinophenylboronic acid(HCl forM);2-Aminophenylboronic acid 2-Aminobenzeneboronic acid
• CAS NO: 5570-18-3
• Molecular Formula: C₆H₈BNO₂
• Molecular Weight: 136.94
• Product Categories: Amines;blocks;BoronicAcids;Substituted Boronic Acids;Boronic Acid;Boronate Ester;Potassium Trifluoroborate
• Mol File: 5570-18-3.mol
• Article Data: 15

Chemical Properties

• Melting Point: 188-190°C
• Boiling Point: 346.9 °C at 760 mmHg
• Flash Point: 163.6 °C
• Appearance: /
• Density: 1.23 g/cm³
• Refractive Index: 1.558
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 8.83±0.53(Predicted)
• BRN: 2962939
• CAS DataBase Reference: 2-Aminophenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Aminophenylboronic acid(5570-18-3)
• EPA Substance Registry System: 2-Aminophenylboronic acid(5570-18-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36/37/39-37-36
• Hazardous Substances Data: 5570-18-3(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline powder

Uses

Different sources of media describe the Uses of 5570-18-3 differently. You can refer to the following data:
1. 2-Aminobenzeneboronic acid derivative is used in the synthesis of quinolines by reacting with alpha, beta unsaturated ketones. Its hydrochloride derivative is used in the preparation of designed boronate ligands for glucose-selective holographic sensors.
2. 2-Aminophenylboronic acid is used in the preparation of affinity sites for antibacterial drugs like ampicillin. A useful synthesis intermediate.

InChI:InChI=1/C18H21N3O3/c1-13-4-6-15(7-5-13)19-12-18(22)21-20-11-14-10-16(23-2)8-9-17(14)24-3/h4-11,19H,12H2,1-3H3,(H,21,22)/b20-11-

Synthetic route

2-nitrophenylboronic acid (5570-19-4) → 2-aminophenylboronic acid (5570-18-3)

Conditions	Yield
With hydrogenchloride; iron In ethanol; water at 50℃; for 3h; Inert atmosphere;	83%
With H2; catalyst: Pd/C In ethanol shaken for 15 h; filtd., the filtrate is evapd., the oily residue is recrystd. (methanol-water);	67%
With hydrogen; palladium 10% on activated carbon In ethanol under 750.075 Torr; for 8h;	50%

2-iodophenylamine (615-43-0) + water (7732-18-5) + bis(pinacol)diborane (73183-34-3) → 2-aminophenylboronic acid (5570-18-3)

Conditions	Yield
Stage #1: 2-iodophenylamine; bis(pinacol)diborane With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 18h; Inert atmosphere; Stage #2: water With sodium periodate; ammonium chloride In methanol at 20℃; for 18h;	78.1%

2-anilineboronic acid pinacol ester (191171-55-8) → 2-aminophenylboronic acid (5570-18-3)

Conditions	Yield
With boron trichloride In dichloromethane at 25℃; for 3h;	52%

nitric acid (7697-37-2) + phenylboronic acid (98-80-6) → 2-aminophenylboronic acid (5570-18-3)

Conditions	Yield
With palladium on activated charcoal; hydrogen; urea In acetic anhydride 1) HNO3, Ac2O, urea; 2) H2, Pd(C), EtOH;	31%

phenylboronic acid (98-80-6) + polymer; monomer(s): Actitex 1500-1, modified with [BF4][4-N2C6H4CH2Cl]; 4-halogenobenzenethiol → 2-aminophenylboronic acid (5570-18-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: HNO3; Ac2O; urea 2: H2 / Pd/C / ethanol View Scheme

phenylboronic acid (98-80-6) + Merrifield resin-CH2O(CH2)4S-CH2C6H4-Ph-4 → 2-aminophenylboronic acid (5570-18-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: HNO3; Ac2O; urea 2: H2 / Pd/C / ethanol View Scheme

tris(2-methylene(phenyl)imino phenyl)boroxin (17604-35-2) → 2-aminophenylboronic acid (5570-18-3) + 1-Hydroxy-2-phenyl-2,3-dihydro-1H-2,1-benzazaborol

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran refluxing for 1 h, decompn. of excess of LiAlH4 by water, filtering, extracting; recrystn. from benzene-hexane;

phenylboronic acid (98-80-6) → 2-aminophenylboronic acid (5570-18-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic anhydride; nitric acid / 3 h / -15 - 10 °C 2: iron; hydrogenchloride / ethanol; water / 3 h / 50 °C / Inert atmosphere View Scheme

phenylboronic acid (98-80-6) → 2-aminophenylboronic acid (5570-18-3)

Conditions	Yield
With nitric acid; palladium on carbon In ethanol; water

3-(6-bromo-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine (863783-61-3) + 2-aminophenylboronic acid (5570-18-3) → 2-[4-(5,6-Dimethyl-[2,2']bipyridin-3-yloxy)-quinolin-6-yl]-phenylamine

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 70℃; for 3h;	100%

3-(7-bromo-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine (863783-73-7) + 2-aminophenylboronic acid (5570-18-3) → 2-[4-(5,6-Dimethyl-[2,2']bipyridinyl-3-yloxy)-quinolin-7-yl]-phenylamine

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; dimethyl sulfoxide at 70℃; for 5h;	100%

2-aminophenylboronic acid (5570-18-3) → 1-hydroxy-3-methyl-1H-2,4,1-benzoxaborine (157524-26-0)

Conditions	Yield
With (CH3CO)2O In 1,4-dioxane under Ar, heated at 60°C for 17 h; the volatiles are removed by evapn. in vac.;	100%

trifluoromethylsulfonic anhydride (358-23-6) + 2-aminophenylboronic acid (5570-18-3) → 1-hydroxy-3-(trifluoromethyl)-1H-2,4,1-benzoxazaborine (157524-32-8)

Conditions	Yield
With H2O In 1,4-dioxane stirred at 0°C for 30 min, at room temp. for 3 h, the solvent isremoved by evapn. in vac. at 30°C, the residue is treated with water; evapn. at 30°C;	100%

2-aminophenylboronic acid (5570-18-3) + Acetic formic anhydride (2258-42-6) → 1-hydroxy-1H-2,4,1-benzoxazaborine (157524-27-1)

Conditions	Yield
In 1,4-dioxane under Ar, atirred at 11°C for 12 h; the volatiles are removed by evapn.;	100%

2-aminophenylboronic acid (5570-18-3) + C14H11ClN4O2 → 3-phenyl-3H-benzo[c]pyrazolo[4,3-f][2,7]naphthyridin-6(7H)-one

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene; tert-butyl alcohol at 75℃; for 18h; Suzuki Coupling; Inert atmosphere;	100%

5-nitrosalicylic acid (96-97-9) + 2-aminophenylboronic acid (5570-18-3) → C13H10BN2O6(1-)*H(1+)

Conditions	Yield
In acetonitrile at 49.84℃; for 1h;	99%

2-aminophenylboronic acid (5570-18-3) + ethyl (E)-crotonate (623-70-1) → 4-methyl-3,4-dihydroquinolin-2(1H)-one (30696-28-7)

Conditions	Yield
With [Rh(OH)(cod)]2; potassium carbonate In water at 50℃; for 5h; Inert atmosphere;	99%

2-bromo-pyridine (109-04-6) + 2-aminophenylboronic acid (5570-18-3) → 2-(2-pyridyl)aniline (29528-30-1)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 100℃; for 5h; Suzuki Coupling; Inert atmosphere;	98%

D-2-deoxyribose (452-51-7, 13046-70-3, 29780-54-9, 36792-87-7, 36792-88-8, 113890-35-0, 113890-38-3) + 2-aminophenylboronic acid (5570-18-3) → [2-[N-(deoxy-D-ribofuranosyl)amino]phenyl]boronic acid

Conditions	Yield
In ethanol at 20℃; for 24h; Substitution;	97%

D-Ribose (532-20-7, 613-83-2, 7261-25-8, 7687-39-0, 13221-22-2, 14795-83-6, 15761-67-8, 20074-49-1, 25545-03-3, 25545-04-4, 32445-75-3, 34436-17-4, 36441-93-7, 36468-53-8, 37110-85-3, 37388-49-1, 38029-69-5, 40461-77-6, 40461-89-0, 41546-19-4, 41546-20-7, 41546-21-8, 41546-26-3, 41546-29-6, 41546-30-9, 41546-31-0, 126872-16-0, 131064-98-7) + 2-aminophenylboronic acid (5570-18-3) → [2-[N-(D-ribofuranosyl)amino]phenyl]boronic acid

Conditions	Yield
In ethanol at 20℃; for 24h; Substitution;	97%

1-bromo-2-(4-cyanobenzyl)benzene + 2-aminophenylboronic acid (5570-18-3) → 4-((2'-amino-[1,1'-biphenyl]-2-yl)methyl)benzonitrile

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 12h; Inert atmosphere; Reflux;	97%

2-aminophenylboronic acid (5570-18-3) + 4-benzyl-2-iodo-1-methylbenzene → 5'-benzyl-2'-methyl-[1,1'-biphenyl]-2-amine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water for 12h; Inert atmosphere; Reflux;	97%

2-aminophenylboronic acid (5570-18-3) + benzalacetophenone (94-41-7) → 2,4-diphenylquinoline (1039-51-6)

Conditions	Yield
Stage #1: 2-aminophenylboronic acid; benzalacetophenone 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;	96%

2-aminophenylboronic acid (5570-18-3) + methyl 2-bromo-5-methylbenzoate (90971-88-3) → 8-methylphenanthridin-6(5H)-one (107622-36-6)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; water at 100℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere;	96%

1-bromo-9-methyl-9H-carbazole + 2-aminophenylboronic acid (5570-18-3) → 2-(9-methyl-9H-carbazol-1-yl)aniline

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; ethanol at 70℃; for 2h; Suzuki-Miyaura Coupling; Microwave irradiation; Inert atmosphere;	96%

(E)-3,4-dimethoxycinnamic chloride (39856-08-1, 141236-46-6) + 2-aminophenylboronic acid (5570-18-3) → C17H18BNO5

Conditions	Yield
With triethylamine In tetrahydrofuran at -5 - 20℃; for 2h;	95.1%

2-aminophenylboronic acid (5570-18-3) + 3-chlorobenzoate (535-80-8) → 2'-aminobiphenyl-3-carboxylic acid (177171-15-2)

Conditions	Yield
With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate; palladium diacetate; potassium carbonate In water at 100℃; for 12h; Suzuki-Miyaura coupling;	95%

6-chloropyridin-2-amine (45644-21-1) + 2-aminophenylboronic acid (5570-18-3) → 6-(2-amino-phenyl)-pyridin-2-ylamine

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium carbonate; palladium diacetate In water; acetonitrile at 100℃; for 10h; Suzuki-Miyaura cross-coupling;	95%

2-aminophenylboronic acid (5570-18-3) + 2-bromo-4-methyl-benzoic acid methyl ester (87808-49-9) → 9-methylphenanthridin-6(5H)-one

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; water at 100℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere;	95%

ethyl crotonate (10544-63-5) + 2-aminophenylboronic acid (5570-18-3) → 4-methyl-3,4-dihydroquinolin-2(1H)-one (30696-28-7)

Conditions	Yield
With [Rh(OH)(cod)]2; surfactant TPGS-750-M; potassium carbonate In water at 20℃; for 24h; Green chemistry;	95%

4-(trifluoromethyl)phenyl isothiocyanate (1645-65-4) + 2-aminophenylboronic acid (5570-18-3) → C14H10BF3N2OS

Conditions	Yield
In N,N-dimethyl-formamide Inert atmosphere;	95%

2-aminophenylboronic acid (5570-18-3) + salicylic acid (69-72-7) + cyanomethyl bromide (590-17-0) → 2-bromo-N-(2-(4-oxo-4H-benzo[d][1,3,2]dioxaborinin-2-yl)phenyl)acetimidamide

Conditions	Yield
for 2h; Inert atmosphere; Heating;	95%

2-aminophenylboronic acid (5570-18-3) + 4-[Bromo-(4-diethylcarbamoyl-phenyl)-methylene]-piperidine-1-carboxylic acid tert-butyl ester (209808-18-4) → 4-[(2-aminophenyl)[4-[(diethylamino)carbonyl]phenyl]methylene]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester (798550-18-2)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 90℃;	94%

2-bromobenzoic acid methyl ester (610-94-6) + 2-aminophenylboronic acid (5570-18-3) → 6(5H)-phenanthridinone (1015-89-0)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; water at 100℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere;	94%

5-(2-chlorophenyl)-4-iodo-2,6-dimethoxypyrimidine + 2-aminophenylboronic acid (5570-18-3) → 4-(2-aminophenyl)-5-(2-chlorophenyl)-2,6-dimethoxypyrimidine

Conditions	Yield
With triphenylphosphine; cesium fluoride; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 105℃; for 18h; Suzuki Coupling; Inert atmosphere;	94%

bromobenzene (108-86-1) + 2-aminophenylboronic acid (5570-18-3) → 2-phenylaniline (90-41-5)

Conditions	Yield
With potassium carbonate In water; isopropyl alcohol at 20℃; for 2h; Suzuki-Miyaura Coupling; Green chemistry;	94%

2-aminophenylboronic acid (5570-18-3) + C12H10BrF2N3O → N-(2'-amino-[1,1'-biphenyl]-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 1.5h; Inert atmosphere;	93.96%

2-aminophenylboronic acid (5570-18-3) + (S,S)-(-)-1,2-dicyclohexyl-ethane-1,2-diol (120850-91-1) → 2-aminophenylboronic acid (-)-1,2-dicyclohexyl-1,2-ethanediol

Conditions	Yield
In tetrahydrofuran stirred under N2; flash chromy. (silica, pre-absorption, Et2O/hexane); obtained as an oil;	93%
In tetrahydrofuran

2-aminophenylboronic acid (5570-18-3) + (1R,2R)-1,2-dicyclohexyl-1,2-ethanediol (120850-92-2) → 2-aminophenylboronic acid (-)-1,2-dicyclohexyl-1,2-ethanediol ester (616227-07-7)

Conditions	Yield
In tetrahydrofuran	93%

Upstream product

• 5570-19-4 2-nitrophenylboronic acid 
• 98-80-6 phenylboronic acid 
• 615-43-0 2-iodophenylamine 
• 7732-18-5 water 
• 73183-34-3 bis(pinacol)diborane 
• 17604-35-2 tris(2-methylene(phenyl)imino phenyl)boroxin 
• 7697-37-2 nitric acid 
• 191171-55-8 2-anilineboronic acid pinacol ester 

Downstream Products

• 153624-34-1 2'-amino-N-(3,4-dimethyl-5-isoxazolyl)-N'-(methoxyethoxymethyl)<1,1'-biphenyl>-2-sulfonamide 
• 473807-20-4 C₂₀H₃₄BNO₆Si 
• 191171-55-8 2-anilineboronic acid pinacol ester 
• 616227-06-6 2-aminophenylboronic acid (+)-pinanediol ester 
• 132198-53-9 2-phenyl-5H-[1,3]oxazolo[4,5-c]quinolin-4-one 
• 616227-08-8 2-aminophenylboronic acid (2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl-2,3-butanediol ester 
• 616227-07-7 2-aminophenylboronic acid (-)-1,2-dicyclohexyl-1,2-ethanediol ester 
• 1454-80-4 1,1'-biphenyl-2,2'-diamine 
• 35883-86-4 2-amino-2'-nitrobiphenyl 
• 177171-15-2 2-amino-3'-biphenylcarboxylic acid 
• 86-74-8 9H-carbazole 
• 1026423-97-1 {2'-[2-(3,4,5-trimethoxy-phenyl)-acetylamino]-biphenyl-3-yl}-acetic acid methyl ester 
• 928847-07-8 {2'-[3-(3,4,5-trimethoxy-phenyl)-propionylamino]-biphenyl-3-yl}-acetic acid methyl ester 

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