2-Nitrophenylboronic acid supplier

Name
2-Nitrophenylboronic acid
EINECS 611-304-3
CAS No. 5570-19-4
Article Data19
CAS DataBase
Density 1.4 g/cm³
Solubility
Melting Point 155-160 °C
Formula C₆H₆BNO₄
Boiling Point 374.78 °C at 760 mmHg
Molecular Weight 166.929
Flash Point 180.461 °C
Transport Information
Appearance Off-white powder
Safety 26
Risk Codes 22-36/37/38
Molecular Structure
Hazard Symbols Xn
Synonyms Benzeneboronicacid, o-nitro- (6CI,7CI,8CI);Boronic acid, (2-nitrophenyl)- (9CI);o-Nitrophenylboronicacid;2-Nitrophenylboronic acid;
PSA 86.28000
LogP -0.20220

Synthetic route

: 98-80-6
phenylboronic acid

: 5570-19-4
2-nitrophenylboronic acid

Conditions

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

: 121-43-7
Trimethyl borate

: 609-73-4
o-nitroiodobenzene

: 5570-19-4
2-nitrophenylboronic acid

Conditions

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%

: 609-73-4
o-nitroiodobenzene

: 5570-19-4
2-nitrophenylboronic acid

Conditions

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

: 121-43-7
Trimethyl borate

: 577-19-5
2-nitrophenyl bromide

: 5570-19-4
2-nitrophenylboronic acid

Conditions

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%

: 98-80-6
phenylboronic acid

A: 5570-19-4
2-nitrophenylboronic acid

B: 24067-17-2
4-nitrophenylboronic acid

Conditions

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℃;

: 13675-18-8
tetrahydroxydiboron

: 88-74-4
2-nitro-aniline

: 5570-19-4
2-nitrophenylboronic acid

Conditions

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%

: 108-24-7
acetic anhydride

: 98-80-6
phenylboronic acid

A: 5570-19-4
2-nitrophenylboronic acid

B: 24067-17-2
4-nitrophenylboronic acid

Conditions

Conditions	Yield
With nitric acid; urea

...Expand

: 98-80-6
phenylboronic acid

A: 13331-27-6
m-nitrobenzene boronic acid

B: 5570-19-4
2-nitrophenylboronic acid

Conditions

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

: C8H10BNO4

: 5570-19-4
2-nitrophenylboronic acid

Conditions

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

: 98-95-3
nitrobenzene

: 5570-19-4
2-nitrophenylboronic acid

Conditions

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;

: 5570-19-4
2-nitrophenylboronic acid

: Ac-RRWWCR-amide

: C51H69N19O9S

Conditions

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

: 5570-19-4
2-nitrophenylboronic acid

: 233770-15-5
3-iodo-1-tosyl-1H-indole-2-carbaldehyde

: 233770-18-8
2-formyl-3-(o-nitrophenyl)-1-tosylpyrrole

Conditions

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

: 5570-19-4
2-nitrophenylboronic acid

: 1221498-96-9
C21H22N2O4

Conditions

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

: 5570-19-4
2-nitrophenylboronic acid

: 497843-21-7
1-benzyl-5-(trifluoromethanesulfonoyloxy)-3,6-dihydro-2H-pyridine-4-carboxylic acid ethyl ester

: 1221498-96-9
C21H22N2O4

Conditions

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

: 5570-19-4
2-nitrophenylboronic acid

: 62-53-3
aniline

: 119-75-5
2-nitro-N-phenylaniline

Conditions

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

: 5570-19-4
2-nitrophenylboronic acid

: 2-methoxy-5-(3,3,3-trifluoroprop-1-ynyl)benzonitrile

: C17H11F3N2O3

Conditions

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

: 951307-21-4
8-bromo-7,10-dimethoxy-5-(methoxymethyl)phenanthridin-6(5H)-one

: 5570-19-4
2-nitrophenylboronic acid

: 8-(nitrophenyl-2-yl)-7,10-dimethoxy-5-methoxymethylphenanthridin-6-one

Conditions

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

: 5570-19-4
2-nitrophenylboronic acid

: 100-39-0
benzyl bromide

: 5840-40-4
2-nitrodiphenylmethane

Conditions

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%)

: 5570-19-4
2-nitrophenylboronic acid

: 2436-96-6
1-nitro-2-(2-nitrophenyl)benzene

Conditions

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

: 15155-41-6
4,7-dibromobenzo[c][1,2,5]thiadiazole

: 5570-19-4
2-nitrophenylboronic acid

: 1190305-34-0
4,7-bis(2-nitrophenyl)benzo[c][1,2,5]thiadiazole

Conditions

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%

: 5570-19-4
2-nitrophenylboronic acid

: 7722-84-1
dihydrogen peroxide

: 88-75-5
2-hydroxynitrobenzene

Conditions

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

: methyl 5-tert-butyl-2-(trifluoromethylsulfonyloxy)cyclohex-1-enecarboxylate

: 5570-19-4
2-nitrophenylboronic acid

: C18H23NO4

Conditions

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

: 5570-19-4
2-nitrophenylboronic acid

: 21190-88-5
6-bromopyridine-2-carboxylic acid ethyl ester

: C14H12N2O4

Conditions

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

: 5570-19-4
2-nitrophenylboronic acid

: 106-47-8
4-chloro-aniline

: 23008-56-2
N-(4-chlorophenyl)-2-nitroaniline

Conditions

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

: 5570-19-4
2-nitrophenylboronic acid

: C23H17Br

: C29H21NO2

Conditions

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

: 5570-19-4
2-nitrophenylboronic acid

C34H27NO2: C34H27NO2

Conditions

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

: 2527-99-3
methyl 5-bromo-2-furoate

: 5570-19-4
2-nitrophenylboronic acid

: 41019-36-7
5-(2-nitrophenyl)furan-2-carboxylic acid methyl ester

Conditions

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%

: 80563-87-7
2-chloro-6-nitro-benzoic acid methyl ester

: 5570-19-4
2-nitrophenylboronic acid

: 51336-10-8, 337960-27-7
7-amino-5H-phenanthridin-6-one

Conditions

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%

: 5570-19-4
2-nitrophenylboronic acid

: 88-75-5
2-hydroxynitrobenzene

Conditions

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%

: 591-50-4
iodobenzene

: 5570-19-4
2-nitrophenylboronic acid

: 86-00-0
2-nitrobiphenyl

Conditions

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%

: 5570-19-4
2-nitrophenylboronic acid

: 620943-77-3
2-iodo-6-(trideuteriomethyl)-4,4,6-trimethylcyclohex-2-en-1-one

: 620943-78-4
6-(trideuteriomethyl)-4,4,6-trimethyl-2-(o-nitrophenyl)cyclohex-2-en-1-one

Conditions

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

: 5570-19-4
2-nitrophenylboronic acid

: 6-(trideuteriomethyl)-4,6,6-trimethyl-2-(o-nitrophenyl)-cyclohex-2-en-1-one

Conditions

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

: 5570-19-4
2-nitrophenylboronic acid

: 30068-54-3
2,5-dibromo-1-phenyl-1H-pyrrole

: 1245720-86-8
C22H15N3O4

Conditions

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

: 5570-19-4
2-nitrophenylboronic acid

: C21H29NO4

Conditions

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

: 5570-19-4
2-nitrophenylboronic acid

: 118-92-3
anthranilic acid

: 2-(2-nitrophenyl)-3,1,2-benzoxazaborininone

Conditions

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

: 5570-19-4
2-nitrophenylboronic acid

: C22H12BrN

: C28H16N2O2

Conditions

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

: 5570-19-4
2-nitrophenylboronic acid

: C8H4Br2O

: C14H8BrNO3

Conditions

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

: 5570-19-4
2-nitrophenylboronic acid

: 125414-82-6
ethyl 3-amino-1-bromoisoquinoline-4-carboxylate

: 1452824-40-6
ethyl 3-amino-1-(2-nitrophenyl)isoquinoline-4-carboxylate

Conditions

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

: 5570-19-4
2-nitrophenylboronic acid

: 137058-15-2
3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl trifluoromethanesulfonate

: C18H17NO2

Conditions

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

2-Nitrophenylboronic acid Specification

The 2-Nitrophenylboronic acid, with the CAS registry number 5570-19-4, is also known as Boronic acid, B-(2-nitrophenyl)-. It belongs to the product categories of Blocks; Boronic Acids; Nitro Compounds; Substituted Boronic Acids; Boronic Acids; B (Classes of Boron Compounds); Aryl; Boronic Acids; Boronic Acids and Derivatives. This chemical's molecular formula is C₆H₆BNO₄ and molecular weight is 166.93. What's more, its IUPAC name is the same with its product name. It should be stored in a cool, dry and well-ventilated place.

Physical properties about 2-Nitrophenylboronic acid are: (1)ACD/LogP: 1.319; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.32; (4)ACD/LogD (pH 7.4): 1.18; (5)ACD/BCF (pH 5.5): 5.90; (6)ACD/BCF (pH 7.4): 4.32; (7)ACD/KOC (pH 5.5): 123.79; (8)ACD/KOC (pH 7.4): 90.66; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 86.28 Å²; (13)Index of Refraction: 1.574; (14)Molar Refractivity: 39.322 cm³; (15)Molar Volume: 119.225 cm³; (16)Polarizability: 15.588×10^-24cm³; (17)Surface Tension: 57.826 dyne/cm; (18)Density: 1.4 g/cm³; (19)Flash Point: 180.461 °C; (20)Enthalpy of Vaporization: 65.639 kJ/mol; (21)Boiling Point: 374.78 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

Uses of 2-Nitrophenylboronic acid: it is used to produce other chemicals. For example, it can react with 5-bromo-nicotinic acid methyl ester to get 5-(2-nitro-phenyl)-nicotinic acid methyl ester. This reaction needs reagent NEt₃ and solvent dimethylformamide at temperature of 100 °C. The reaction time is 3 hours. The yield is 61 %.

2-Nitrophenylboronic acid can react with 5-bromo-nicotinic acid methyl ester to get 5-(2-nitro-phenyl)-nicotinic acid methyl ester.

When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health and it is harmful if swallowed. It is irritating to eyes, respiratory system and skin. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: [O-][N+](=O)c1ccccc1B(O)O
(2) InChI: InChI=1S/C6H6BNO4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4,9-10H
(3) InChIKey: SFUIGUOONHIVLG-UHFFFAOYSA-N

Product Name

2-Nitrophenylboronic acid

Synthetic route

2-Nitrophenylboronic acid Specification

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