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

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

Used in Chemical Synthesis:
2-Nitrophenylboronic acid is used as a catalyst for mild and selective dipolar cycloadditions of unsaturated carboxylic acids with azides. This application takes advantage of its ability to facilitate reactions under mild conditions, leading to the formation of desired products with high selectivity.
Used in Organic Reactions:
2-Nitrophenylboronic acid is used as a reactant in Suzuki-Miyaura cross-coupling reactions with aryl halides or nitroarenediazonium tetrafluoroborates. These reactions are crucial for the formation of carbon-carbon bonds, which are essential in the synthesis of complex organic molecules and pharmaceutical compounds.
Used in Transposition Reactions:
2-Nitrophenylboronic acid is used as a reactant in the transposition of allylic alcohols and Meyer-Schuster rearrangements. These reactions are important for the synthesis of various organic compounds, including those with potential applications in the pharmaceutical and chemical industries.
Used in Copper-Catalyzed Halogenation:
2-Nitrophenylboronic acid is used as a reactant in copper-catalyzed halogenation reactions. This application allows for the introduction of halogen atoms into organic molecules, which can be crucial for the development of new compounds with specific properties and applications.
Used in Oxidative Arylation:
2-Nitrophenylboronic acid is used as a reactant in the oxidative arylation of aminopyrazolyl disulfides. This reaction is significant for the synthesis of complex organic molecules with potential applications in various fields, including pharmaceuticals and materials science.

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

• 51207-30-8 2-ortho-nitrophenylthiophene 
• 5415-59-8 1-(2-nitrophenyl)naphthalene 
• 225381-85-1 N-(4-Methoxy-phenyl)-N'-[6-(2-nitro-phenyl)-thieno[3,2-d]pyrimidin-4-yl]-benzene-1,4-diamine 
• 859221-67-3 1-nitro-2-(3,3,5,5-tetramethylcyclohexa-1-enyl)benzene 
• 1190305-34-0 4,7-bis(2-nitrophenyl)benzo[c][1,2,5]thiadiazole 
• 1245526-43-5 2,6-di(2-nitrophenyl)-9,10-diphenylanthracene 
• 1245526-44-6 C₃₈H₂₄N₂ 
• 1323723-30-3 (R)-2-(3-nitrophenyl)-1-tosylpiperidine 
• 157524-37-3 C₆H₅B₂NO(OH)(C₆H₄(NH₂)) 
• 5840-40-4 2-nitrodiphenylmethane 
• 494795-55-0 tert-butyl 4-(2-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate 
• 4282-49-9 4-(2-nitrophenyl)-pyridine 
• 765937-82-4 3-[5-(2-nitrophenyl)-2-furyl]acrylic acid 

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