5570-19-4

Basic information

• Product Name: 2-Nitrophenylboronic acid
• Synonyms: RARECHEM AH PB 0142;O-NITROPHENYLBORONIC ACID;2-NITROPHENYLBORONIC ACID;2-NITROBENZENEBORONIC ACID;2-Borononitrobenzene~2-Nitrophenylboronic acid;2-Borononitrobenzene;2-Nitrophenylboronic acid O2NC6H4B(OH)2;2-Nitrophenylboronic Acid (contains varying amounts of Anhydride)
• CAS NO: 5570-19-4
• Molecular Formula: C₆H₆BNO₄
• Molecular Weight: 166.93
• EINECS: 1592732-453-0
• Product Categories: blocks;BoronicAcids;NitroCompounds;Substituted Boronic Acids;Boronic acids;B (Classes of Boron Compounds);Aryl;Boronic Acids;Boronic Acids and Derivatives
• Mol File: 5570-19-4.mol
• Article Data: 15

Chemical Properties

• Melting Point: 155-160°C
• Boiling Point: 374.78 °C at 760 mmHg
• Flash Point: 180.461 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.4 g/cm³
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol,Ether,Ethanol
• PKA: 7.83±0.53(Predicted)
• BRN: 3032097
• CAS DataBase Reference: 2-Nitrophenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Nitrophenylboronic acid(5570-19-4)
• EPA Substance Registry System: 2-Nitrophenylboronic acid(5570-19-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 5570-19-4(Hazardous Substances Data)

Usage

Uses

Boronic acid catalyst used for: Mild and selective dipolar cycloadditions of unsaturated carboxylic acids with azidesTransposition of allylic alcohols and Meyer-Schuster rearrangementsReactant involved in: Suzuki-Miyaura cross-coupling reactions with aryl halides or nitroarenediazonium tetrafluoroboratesCopper-catalyzed halogenationOxidative arylation of aminopyrazolyl disulfides

Synthetic route

phenylboronic acid (98-80-6) → 2-nitrophenylboronic acid (5570-19-4)

Conditions	Yield
With nitric acid; N,N-dimethyl-formamide; sodium nitrite at 45℃; Reagent/catalyst; Solvent; Temperature;	99%
With nitric acid; acetic anhydride at -15 - 10℃; for 3h;	42%
With nitric acid In water; acetic anhydride at -15 - 20℃; for 0.5h;	15%
With nitric acid; acetic anhydride; urea

Trimethyl borate (121-43-7) + o-nitroiodobenzene (609-73-4) → 2-nitrophenylboronic acid (5570-19-4)

Conditions	Yield
Stage #1: o-nitroiodobenzene With phenylmagnesium chloride In tetrahydrofuran at -78℃; Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran	89%
Stage #1: o-nitroiodobenzene With phenylmagnesium chloride In tetrahydrofuran at -78℃; for 0.5h; Stage #2: Trimethyl borate In tetrahydrofuran at 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0℃;	87%

o-nitroiodobenzene (609-73-4) → 2-nitrophenylboronic acid (5570-19-4)

Conditions	Yield
Stage #1: o-nitroiodobenzene With phenylmagnesium chloride In tetrahydrofuran at -60℃; for 0.0833333h; Stage #2: With Trimethyl borate In tetrahydrofuran at -60℃; for 0.5h; Stage #3: With hydrogenchloride In tetrahydrofuran at -20℃;	85%
Multi-step reaction with 2 steps 1.1: phenylmagnesium chloride / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere 1.2: 0.5 h / -78 °C / Inert atmosphere 2.1: hydrogenchloride / water / -20 °C / Inert atmosphere View Scheme

Trimethyl borate (121-43-7) + 2-nitrophenyl bromide (577-19-5) → 2-nitrophenylboronic acid (5570-19-4)

Conditions	Yield
Stage #1: 2-nitrophenyl bromide With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water for 0.5h; Inert atmosphere;	73%
Stage #1: 2-nitrophenyl bromide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: Trimethyl borate In tetrahydrofuran; hexane for 2h;	47%

phenylboronic acid (98-80-6) → 2-nitrophenylboronic acid (5570-19-4) + 4-nitrophenylboronic acid (24067-17-2)

Conditions	Yield
With nitric acid; urea	A 63% B n/a
With nitric acid; urea In acetic anhydride at -15℃; for 3h;
With nitric acid In acetic anhydride at -15℃;

tetrahydroxydiboron (13675-18-8) + 2-nitro-aniline (88-74-4) → 2-nitrophenylboronic acid (5570-19-4)

Conditions	Yield
Stage #1: 2-nitro-aniline With hydrogenchloride In water at 20℃; for 0.0166667h; Stage #2: With sodium nitrite In water at 0℃; for 0.25h; Stage #3: tetrahydroxydiboron With sodium acetate In water at 20℃; for 0.333333h;	28%

acetic anhydride (108-24-7) + phenylboronic acid (98-80-6) → 2-nitrophenylboronic acid (5570-19-4) + 4-nitrophenylboronic acid (24067-17-2)

Conditions	Yield
With nitric acid; urea

phenylboronic acid (98-80-6) → m-nitrobenzene boronic acid (13331-27-6) + 2-nitrophenylboronic acid (5570-19-4)

Conditions	Yield
With nitric acid; urea
With sulfuric acid; nitric acid

C8H10BNO4 → 2-nitrophenylboronic acid (5570-19-4)

Conditions	Yield
With hydrogenchloride In water at -20℃; Inert atmosphere;

nitrobenzene (98-95-3) → 2-nitrophenylboronic acid (5570-19-4)

Conditions	Yield
With tris(pentafluorophenyl)borate; boron trichloride In 1,2-dichloro-ethane at -10 - 50℃; for 6h; Solvent; Temperature; Time; Inert atmosphere; Sealed tube;

2-nitrophenylboronic acid (5570-19-4) + Ac-RRWWCR-amide → C51H69N19O9S

Conditions	Yield
With 4-methyl-morpholine; nickel diacetate In aq. buffer at 37℃; for 0.25h; pH=7.5;	99%

2-nitrophenylboronic acid (5570-19-4) + 3-iodo-1-tosyl-1H-indole-2-carbaldehyde (233770-15-5) → 2-formyl-3-(o-nitrophenyl)-1-tosylpyrrole (233770-18-8)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; barium dihydroxide In water; N,N-dimethyl-formamide at 80℃; for 0.0833333h;	98%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; barium dihydroxide In water; N,N-dimethyl-formamide at 80℃; for 5h;	98%

C16H18F3NO4S + 2-nitrophenylboronic acid (5570-19-4) → C21H22N2O4 (1221498-96-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 80℃; for 1h; Suzuki-Miyaura reaction;	98%

2-nitrophenylboronic acid (5570-19-4) + 1-benzyl-5-(trifluoromethanesulfonoyloxy)-3,6-dihydro-2H-pyridine-4-carboxylic acid ethyl ester (497843-21-7) → C21H22N2O4 (1221498-96-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 80℃; for 1h; Suzuki-Miyaura reaction;	98%

2-nitrophenylboronic acid (5570-19-4) + aniline (62-53-3) → 2-nitro-N-phenylaniline (119-75-5)

Conditions	Yield
With potassium fluoride In dimethyl sulfoxide at 130℃; for 2h; Ullmann-Goldberg Substitution; Inert atmosphere;	98%

2-nitrophenylboronic acid (5570-19-4) + 2-methoxy-5-(3,3,3-trifluoroprop-1-ynyl)benzonitrile → C17H11F3N2O3

Conditions	Yield
With copper diacetate In methanol at 28℃; for 3h; Inert atmosphere;	97%

8-bromo-7,10-dimethoxy-5-(methoxymethyl)phenanthridin-6(5H)-one (951307-21-4) + 2-nitrophenylboronic acid (5570-19-4) → 8-(nitrophenyl-2-yl)-7,10-dimethoxy-5-methoxymethylphenanthridin-6-one

Conditions	Yield
With potassium carbonate; triphenylphosphine; palladium diacetate In N,N-dimethyl-formamide at 150℃; for 16h; Suzuki coupling;	96%

2-nitrophenylboronic acid (5570-19-4) + benzyl bromide (100-39-0) → 2-nitrodiphenylmethane (5840-40-4)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 12h; Reflux; Inert atmosphere;	96%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene for 17h; Reflux; Inert atmosphere;	74.58%
With potassium carbonate; Pd(PPh3)4 In tetrahydrofuran; ethyl acetate	0.22 g (33%)

2-nitrophenylboronic acid (5570-19-4) → 1-nitro-2-(2-nitrophenyl)benzene (2436-96-6)

Conditions	Yield
With 1-butyl-3-methylpyridinium bis[(trifluoromethyl)sulfonyl]amide In water for 0.5h; Ullmann Condensation; Microwave irradiation; Green chemistry;	95%
With Cu(0)-rGO composite In N,N-dimethyl-formamide for 0.25h; Microwave irradiation;	94%
With water; copper diacetate

4,7-dibromobenzo[c][1,2,5]thiadiazole (15155-41-6) + 2-nitrophenylboronic acid (5570-19-4) → 4,7-bis(2-nitrophenyl)benzo[c][1,2,5]thiadiazole (1190305-34-0)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 50℃; Suzuki coupling; Inert atmosphere;	95%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 50℃; for 20h; Inert atmosphere;	39%

2-nitrophenylboronic acid (5570-19-4) + dihydrogen peroxide (7722-84-1) → 2-hydroxynitrobenzene (88-75-5)

Conditions	Yield
With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique;	95%

methyl 5-tert-butyl-2-(trifluoromethylsulfonyloxy)cyclohex-1-enecarboxylate + 2-nitrophenylboronic acid (5570-19-4) → C18H23NO4

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 100℃; for 4h; Suzuki Coupling;	95%

2-nitrophenylboronic acid (5570-19-4) + 6-bromopyridine-2-carboxylic acid ethyl ester (21190-88-5) → C14H12N2O4

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane at 80℃; for 16h; Inert atmosphere;	95%

2-nitrophenylboronic acid (5570-19-4) + 4-chloro-aniline (106-47-8) → N-(4-chlorophenyl)-2-nitroaniline (23008-56-2)

Conditions	Yield
With potassium fluoride In dimethyl sulfoxide at 130℃; for 2h; Ullmann-Goldberg Substitution; Inert atmosphere;	95%

2-nitrophenylboronic acid (5570-19-4) + C23H17Br → C29H21NO2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 8h; Reflux;	95%

+ 2-nitrophenylboronic acid (5570-19-4) → C34H27NO2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 8h; Reflux;	95%

methyl 5-bromo-2-furoate (2527-99-3) + 2-nitrophenylboronic acid (5570-19-4) → 5-(2-nitrophenyl)furan-2-carboxylic acid methyl ester (41019-36-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol; toluene for 6h; Suzuki reaction; Heating;	94%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane at 90℃; Inert atmosphere;	13%

2-chloro-6-nitro-benzoic acid methyl ester (80563-87-7) + 2-nitrophenylboronic acid (5570-19-4) → 7-amino-5H-phenanthridin-6-one (51336-10-8, 337960-27-7)

Conditions	Yield
Stage #1: 2-chloro-6-nitro-benzoic acid methyl ester; 2-nitrophenylboronic acid With caesium carbonate; bis(tri-t-butylphosphine)palladium(0) In 1,4-dioxane at 80℃; for 48h; Stage #2: With hydrogen; palladium on activated charcoal In methanol at 20℃; for 48h;	94%

2-nitrophenylboronic acid (5570-19-4) → 2-hydroxynitrobenzene (88-75-5)

Conditions	Yield
With iron(III) oxide; oxygen In tetrahydrofuran Irradiation;	94%
With iron(III) oxide; oxygen In tetrahydrofuran at 20℃; Irradiation;	94%
With C18H28Cl2CuN2O4 In water at 26℃; for 0.333333h;	93%

iodobenzene (591-50-4) + 2-nitrophenylboronic acid (5570-19-4) → 2-nitrobiphenyl (86-00-0)

Conditions	Yield
With potassium carbonate In water at 70℃; for 0.5h; Suzuki Coupling;	94%
With potassium carbonate In water at 60℃; for 3h; Catalytic behavior; Suzuki-Miyaura Coupling;	87%

2-nitrophenylboronic acid (5570-19-4) + 2-iodo-6-(trideuteriomethyl)-4,4,6-trimethylcyclohex-2-en-1-one (620943-77-3) → 6-(trideuteriomethyl)-4,4,6-trimethyl-2-(o-nitrophenyl)cyclohex-2-en-1-one (620943-78-4)

Conditions	Yield
With barium dihydroxide; tris(dibenzylideneacetone)dipalladium (0); johnphos In tetrahydrofuran at 35℃; for 5h; Suzuki coupling;	93%

2-iodo-6-(trideuteriomethyl)-4,4,6-trimethyl-cyclohex-2-en-1-one + 2-nitrophenylboronic acid (5570-19-4) → 6-(trideuteriomethyl)-4,6,6-trimethyl-2-(o-nitrophenyl)-cyclohex-2-en-1-one

Conditions	Yield
With barium dihydroxide; tris-(dibenzylideneacetone)dipalladium(0); johnphos In tetrahydrofuran; water at 35℃; for 5h;	93%

2-nitrophenylboronic acid (5570-19-4) + 2,5-dibromo-1-phenyl-1H-pyrrole (30068-54-3) → C22H15N3O4 (1245720-86-8)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene at 120℃; for 12h;	93%

tert-butyl 5-tert-butyl-2-(trifluoromethylsulfonyloxy)cyclohex-1-enecarboxylate + 2-nitrophenylboronic acid (5570-19-4) → C21H29NO4

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 100℃; for 4h; Suzuki Coupling;	93%

2-nitrophenylboronic acid (5570-19-4) + anthranilic acid (118-92-3) → 2-(2-nitrophenyl)-3,1,2-benzoxazaborininone

Conditions	Yield
In toluene for 16h; Inert atmosphere; Dean-Stark; Reflux;	93%

2-nitrophenylboronic acid (5570-19-4) + C22H12BrN → C28H16N2O2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water for 2h; Reflux;	93%

2-nitrophenylboronic acid (5570-19-4) + C8H4Br2O → C14H8BrNO3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; for 10h;	93%

2-nitrophenylboronic acid (5570-19-4) + ethyl 3-amino-1-bromoisoquinoline-4-carboxylate (125414-82-6) → ethyl 3-amino-1-(2-nitrophenyl)isoquinoline-4-carboxylate (1452824-40-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 95℃; for 12h; Suzuki Coupling; Inert atmosphere;	92%

2-nitrophenylboronic acid (5570-19-4) + 3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl trifluoromethanesulfonate (137058-15-2) → C18H17NO2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 100℃; for 4h; Suzuki Coupling;	92%

Upstream product

• 98-95-3 nitrobenzene 
• 121-43-7 Trimethyl borate 
• 577-19-5 2-nitrophenyl bromide 
• 13675-18-8 tetrahydroxydiboron 
• 88-74-4 2-nitro-aniline 
• 609-73-4 o-nitroiodobenzene 
• 98-80-6 phenylboronic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 93349-95-2 Methyl 5-(2-Nitrophenyl)nicotinate 
• 85107-45-5 2-(2-Nitro-phenyl)-[1,3,2]dioxaborinane 
• 41019-36-7 5-(2-nitrophenyl)furan-2-carboxylic acid methyl ester 
• 2436-96-6 1-nitro-2-(2-nitrophenyl)benzene 
• 859221-67-3 1-nitro-2-(3,3,5,5-tetramethylcyclohexa-1-enyl)benzene 
• 5840-40-4 2-nitrodiphenylmethane 
• 225381-85-1 N-(4-Methoxy-phenyl)-N'-[6-(2-nitro-phenyl)-thieno[3,2-d]pyrimidin-4-yl]-benzene-1,4-diamine 
• 1245526-43-5 2,6-di(2-nitrophenyl)-9,10-diphenylanthracene 
• 1245526-44-6 C₃₈H₂₄N₂ 
• 20013-55-2 4'-methoxy-2-nitrobiphenyl 
• 1421850-69-2 2,2'-(buta-1,3-diene-2,3-diyl)bis(nitrobenzene) 
• 1421850-73-8 C₂₄H₂₄N₂O₈ 
• 1421850-72-7 C₂₆H₂₈N₂O₈ 
• 1421850-71-6 C₂₀H₂₀N₂O₄ 

Relevant articles and documents

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