3-Nitrophenylboronic acid supplier

Name
3-Nitrophenylboronic acid
EINECS
CAS No. 13331-27-6
Article Data15
CAS DataBase
Density 1.4 g/cm³
Solubility soluble in hot water
Melting Point 289-291 °C
Formula C₆H₆BNO₄
Boiling Point 363.3 °C at 760 mmHg
Molecular Weight 166.929
Flash Point 173.5 °C
Transport Information
Appearance off-white powder
Safety 26-37/39-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Benzeneboronicacid, m-nitro- (6CI,7CI,8CI);Boronic acid, (3-nitrophenyl)- (9CI);3-Nitrobenzeneboronic acid;NSC 401539;NSC 59739;m-Nitrobenzeneboronic acid;m-Nitrophenylboronic acid;
PSA 86.28000
LogP -0.20220

Synthetic route

: 68716-48-3
4,4,5,5-tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane

: 13331-27-6
m-nitrobenzene boronic acid

Conditions

Conditions	Yield
With hydrogenchloride; polystyrene boronic acid In acetonitrile at 20℃; for 18h;	88%

: potassium 3-nitrophenyltrifluoroborate

: 13331-27-6
m-nitrobenzene boronic acid

Conditions

Conditions	Yield
With water; silica gel at 20℃; for 24h; Inert atmosphere;	86%
With water In tetrahydrofuran at 55℃; Kinetics; Reagent/catalyst;

: 5-(4-methoxyphenyl)-4,4-dimethyl-2-(3-nitrophenyl)[1,3,2]dioxaborolane

: 13331-27-6
m-nitrobenzene boronic acid

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 50℃; for 24h;	65%

: 13675-18-8
tetrahydroxydiboron

: 99-09-2
3-nitro-aniline

: 13331-27-6
m-nitrobenzene boronic acid

Conditions

Conditions	Yield
Stage #1: 3-nitro-aniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.25h; Stage #2: tetrahydroxydiboron With sodium acetate In water at 20℃; for 0.333333h;	64%

: 98-80-6
phenylboronic acid

: 13331-27-6
m-nitrobenzene boronic acid

Conditions

Conditions	Yield
nitration according to W. Seaman and J. R. Johnson, J. Am. Chem. Soc., 1931, 53, 711;	47%
With nitric acid at -15 - -9℃;	28%

: 13675-18-8
tetrahydroxydiboron

: 586-36-7
3-nitrophenyldiazonium tetrafluoroborate

: 13331-27-6
m-nitrobenzene boronic acid

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 0.25h;	38%

: 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

: C6H4LiNO2

: 13331-27-6
m-nitrobenzene boronic acid

Conditions

Conditions	Yield
With Trimethyl borate; hydrogen cation

: 585-79-5
3-Bromonitrobenzene

: 13331-27-6
m-nitrobenzene boronic acid

Conditions

Conditions	Yield
With n-butyllithium; Triisopropyl borate In tetrahydrofuran; hexane; toluene at -70 - -20℃;	13 % Chromat.

: C6H4BF3NO2(1-)

: 13331-27-6
m-nitrobenzene boronic acid

Conditions

Conditions	Yield
In phosphate buffer pH=6.9 - 7.0; Kinetics;

: 7732-18-5
water

: potassium 3-nitrophenyltrifluoroborate

: 13331-27-6
m-nitrobenzene boronic acid

Conditions

Conditions	Yield
With glass or Cs2CO3 In tetrahydrofuran; water Kinetics; hydrolysis at 55°C in THF/H2O in the presence of glass powder or Cs2CO3; not isolated;

: C17H18BN2O5Pol

: 13331-27-6
m-nitrobenzene boronic acid

Conditions

Conditions	Yield
With water; acetic acid In tetrahydrofuran at 20℃; for 2h;

: 99-09-2
3-nitro-aniline

: 13331-27-6
m-nitrobenzene boronic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: water / 0.03 h / 20 °C 1.2: 0.25 h / 0 °C 2.1: N,N-dimethyl-formamide / 0.25 h / 20 °C View Scheme

: 3262-89-3
triphenylboroxine

: 80283-99-4
2-nitrobenzo[d]isothiazol-3(2H)-one 1,1-dioxide

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

B: 98-95-3
nitrobenzene

Conditions

Conditions	Yield
With 1,1,1,3',3',3'-hexafluoro-propanol; magnesium sulfate at 60℃; for 17h; Reagent/catalyst;	A 24 %Chromat. B 38 %Chromat.

...Expand

: 619-42-1
4-methoxycarbonylphenyl bromide

: 13331-27-6
m-nitrobenzene boronic acid

: 89900-93-6
3'-nitro-[1,1'-biphenyl]-4-carboxylic acid methyl ester

Conditions

Conditions	Yield
With sodium carbonate; bis(dibenzylideneacetone)-palladium(0); C78H99N6P(6+)*6Br(1-) In methanol; water at 65℃; for 3h; Suzuki-Miyaura cross-coupling; Inert atmosphere;	100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 20 - 80℃; for 5h; Inert atmosphere;	21%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane at 85℃; Suzuki cross-coupling;	16%

: 13331-27-6
m-nitrobenzene boronic acid

: 223797-51-1
1-tert-butoxycarbonyl-4-(5-trifluoromethanesulfonyloxy-3-pyridyl)homopiperazine

: 223797-57-7
1-[5-(3-nitrophenyl)-pyridin-3-yl]-4-tert-butoxycarbonylhomopiperazine

Conditions

Conditions	Yield
With potassium carbonate; lithium chloride; trimethyleneglycol; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane for 2h; Heating / reflux;	100%

: 1-[3-bromo-2-hydroxy-5-(1 H-tetrazol-5-yl)-phenyl]-ethanone

: 13331-27-6
m-nitrobenzene boronic acid

: 1-[2-Hydroxy-3-nitro-5-(1H-tetrazol-5-yl)-biphenyl-3-yl]-ethanone

Conditions

Conditions	Yield
With sodium carbonate; Pd(PPh3)4 In ethanol; toluene	100%
With sodium carbonate; Pd(PPh3)4 In ethanol; toluene	1.22%

: 913067-90-0
N-(3-iodo-4-methyl-phenyl)-3-(trifluoromethyl)benzamide

: 13331-27-6
m-nitrobenzene boronic acid

: 1036376-84-7
N-(6-methyl-3'-nitrobiphenyl-3-yl)-3-(trifluoromethyl)benzamide

Conditions

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 90℃; for 16h; Heating / reflux;	100%

: 13331-27-6
m-nitrobenzene boronic acid

: 554-84-7
meta-nitrophenol

Conditions

Conditions	Yield
With dihydrogen peroxide In water at 30℃; Green chemistry;	99%
With 2,5-dimethylfuran; zinc(II) phthalocyanine; oxygen In tetrahydrofuran at 25℃; under 760.051 Torr; for 1.5h; Irradiation; Sealed tube; Schlenk technique;	98%
With water; 3-chloro-benzenecarboperoxoic acid In ethanol at 20℃; for 6h;	97%

: 13331-27-6
m-nitrobenzene boronic acid

: 99-90-1
para-bromoacetophenone

: 5002-11-9
1-(3'-nitrobiphenyl-4-yl)ethanone

Conditions

Conditions	Yield
With potassium carbonate In ethanol; water at 70℃; for 14h; Suzuki-Miyaura reaction;	99%
With lithium niobate; palladium diacetate; potassium carbonate In ethanol; water; paraffin oil at 87 - 88℃; for 0.2h; Suzuki Coupling;	99%
With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In water at 70℃; for 3.33h; Suzuki Coupling; Inert atmosphere;	96.5%

: 610-94-6
2-bromobenzoic acid methyl ester

: 13331-27-6
m-nitrobenzene boronic acid

: 83527-96-2
methyl 3’-nitro-[1,1’-biphenyl]-2-carboxylate

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane at 85℃; Suzuki cross-coupling;	99%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 20 - 80℃; for 6h; Inert atmosphere;	17%
With tetra-butylammonium acetate; Pd EnCat-30TM In ethanol Suzuki cross-coupling; microwave irradiation;

: 591-50-4
iodobenzene

: 13331-27-6
m-nitrobenzene boronic acid

3-nitro-1,1'-biphenyl: 3-nitro-1,1'-biphenyl

Conditions

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); tri-tert-butyl phosphine In 1,1,1,2,3,3,3-Heptafluoropropane; ethanol; 1,1,1,3,3-pentafluorobutane at 20℃; for 24h; Suzuki-Miyaura cross-coupling reaction; Inert atmosphere;	99%
With C22H24Cl2N6O2Pd2; potassium carbonate In ethanol; water for 4h; Catalytic behavior; Suzuki-Miyaura Coupling; Reflux;	99%
With potassium carbonate In water at 20℃; for 0.5h; Suzuki-Miyaura Coupling;	97%

: 942227-99-8
4-bromo-3,5-diphenylisothiazole

: 13331-27-6
m-nitrobenzene boronic acid

: 3,5-diphenyl-4-(3-nitrobenzene)isothiazole

Conditions

Conditions	Yield
With potassium carbonate; palladium diacetate In N,N-dimethyl-formamide at 20 - 110℃; for 0.916667h;	99%

: 425379-37-9
2-bromo-3,5-difluorobenzonitrile

: 13331-27-6
m-nitrobenzene boronic acid

: 731817-91-7
4,6-difluoro-3'-nitrobiphenyl-2-carbonitrile

Conditions

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In tetrahydrofuran; hexane; water at 50℃; for 4h;	99%

: 1262431-28-6
(E)-2-fluorovinyl 4-methylbenzenesulfonate

: 13331-27-6
m-nitrobenzene boronic acid

: 1262431-33-3
(E)-1-(2-fluorovinyl)-3-nitrobenzene

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium phosphate; tricyclohexylphosphine In 1,4-dioxane at 100℃; for 14h; Suzuki-Miyaura reaction; Inert atmosphere; stereoselective reaction;	99%

: 7633-38-7
di-tert-butyl fumarate

: 13331-27-6
m-nitrobenzene boronic acid

: 1378314-51-2
(S)-di-tert-butyl-2-(3-nitrophenyl)succinate

Conditions

Conditions	Yield
Stage #1: m-nitrobenzene boronic acid With chlorobis(ethylene)rhodium(I) dimer; (S,S)-1,7,7-trimethyl-2,5-diphenylbicyclo[2.2.1]hepta-2,5-diene; potassium tert-butylate In methanol; dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: di-tert-butyl fumarate In methanol; dichloromethane; isopropyl alcohol at 60℃; for 1h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%

Yield

Stage #1: m-nitrobenzene boronic acid With chlorobis(ethylene)rhodium(I) dimer; (S,S)-1,7,7-trimethyl-2,5-diphenylbicyclo[2.2.1]hepta-2,5-diene; potassium tert-butylate In methanol; dichloromethane at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: di-tert-butyl fumarate In methanol; dichloromethane; isopropyl alcohol at 60℃; for 1h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;

99%

: 1373125-72-4
C25H25BrFNO

: 13331-27-6
m-nitrobenzene boronic acid

: C31H29FN2O3

Conditions

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;	99%

: 5159-41-1
2-iodobenzyl alcohol

: 13331-27-6
m-nitrobenzene boronic acid

: 893743-35-6
(3'-nitro-[1,1'-biphenyl]-2-yl)methanol

Conditions

Conditions	Yield
With C22H24Cl2N6O2Pd2; potassium carbonate In ethanol; water for 4h; Catalytic behavior; Suzuki-Miyaura Coupling; Reflux;	99%

: 13331-27-6
m-nitrobenzene boronic acid

: 75-05-8
acetonitrile

: 619-24-9
3-nitrobenzonitrile

Conditions

Conditions	Yield
With N-iodo-succinimide; 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1,1,1,2,2,2-hexamethyldisilane; oxygen; copper diacetate; diisopropylamine at 20 - 150℃; Schlenk technique;	99%

: 13331-27-6
m-nitrobenzene boronic acid

: C19H15FeIN2

: 5-ferrocenyl-4-(3-nitrophenyl)-1-phenyl-1H-pyrazole

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium hydrogencarbonate In water; N,N-dimethyl-formamide at 110℃; for 4h; Suzuki-Miyaura Coupling; Inert atmosphere;	99%

: 56990-02-4
3,5-dibromobenzaldehyde

: 13331-27-6
m-nitrobenzene boronic acid

: 3,5-di(3-nitrophenyl)-benzaldehyde

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 24h; Schlenk technique; Inert atmosphere;	99%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 24h; Inert atmosphere;	80%

: 13331-27-6
m-nitrobenzene boronic acid

: 958-96-3
3,3'-dinitro-1,1'-biphenyl

Conditions

Conditions	Yield
With air In N,N-dimethyl-formamide at 20℃; for 16h; Green chemistry;	98%
With potassium permanganate; potassium carbonate In methanol; water at 20℃; Catalytic behavior; Reagent/catalyst;	97%
With [(μ4-Te)Fe3(CO)9Cu2(Me2Im)2]; oxygen In methanol at 25℃; for 24h; Kinetics;	97%

: 13331-27-6
m-nitrobenzene boronic acid

: 585-79-5
3-Bromonitrobenzene

Conditions

Conditions	Yield
With N-Bromosuccinimide; copper(I) bromide In acetonitrile at 80℃; for 1h;	98%
With N-Bromosuccinimide In acetonitrile at 80℃; for 12h;	98%
With tetrabutylammomium bromide; copper(ll) bromide In water at 100℃; Sealed tube;	80%

: 13331-27-6
m-nitrobenzene boronic acid

: 76757-90-9
N-(tert-butoxycarbonyl)-D-tyrosine methyl ester

: (R)-2-tert-Butoxycarbonylamino-3-[4-(3-nitro-phenoxy)-phenyl]-propionic acid methyl ester

Conditions

Conditions	Yield
With pyridine; copper diacetate; 4 A molecular sieve In dichloromethane at 25℃; for 18h;	98%

: 13331-27-6
m-nitrobenzene boronic acid

: 121-73-3
3-Chloronitrobenzene

Conditions

Conditions	Yield
With 1,3-dichloro-5,5-dimethylhydantoin; copper(l) chloride In acetonitrile at 80℃; for 2h;	98%
With N-chloro-succinimide In acetonitrile at 80℃; for 12h;	97%
With 1,3-dichloro-5,5-dimethylhydantoin; sodium methylate In methanol; water; acetonitrile at 60℃;	43 % Chromat.

: 13331-27-6
m-nitrobenzene boronic acid

: 870-50-8
di-tert-butyl (E)-azodicarboxylate

: di-tert-butyl 1-(3-nitrophenyl)hydrazine-1,2-dicarboxylate

Conditions

Conditions	Yield
With copper diacetate In tetrahydrofuran at 20℃; for 20h;	98%

: 13331-27-6
m-nitrobenzene boronic acid

: 4330-20-5
N-3-benzoylthymine

: 3-benzoyl-5-methyl-1-(3-nitrophenyl)pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With pyridine; air; copper diacetate In dichloromethane at 20℃; for 75h; Chan-Lam-Evans-modified Ullmann condensation;	98%

: 696-62-8
para-iodoanisole

: 13331-27-6
m-nitrobenzene boronic acid

: 53059-31-7
4-methoxy-3'-nitrobiphenyl

Conditions

Conditions	Yield
With potassium carbonate In water at 50℃; for 2h; Suzuki Coupling;	98%
With magnesium hydroxide; potassium hydroxide; barium(II) hydroxide; calcium hydroxide In water at 20℃; for 2h; Suzuki Coupling;	98%
With 0.1 % Cu/C; potassium carbonate In water at 50℃; for 3h; Suzuki Coupling; Green chemistry;	95%

: 395-44-8
o-trifluoromethylbenzyl bromide

: 13331-27-6
m-nitrobenzene boronic acid

: 886211-35-4
1-(3-nitrobenzyl)-2-(trifluoromethyl)benzene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 50℃; for 16h;	98%

: 76-09-5
2,3-dimethyl-2,3-butane diol

: 13331-27-6
m-nitrobenzene boronic acid

: 68716-48-3
4,4,5,5-tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane

Conditions

Conditions	Yield
With sodium sulfate In tetrahydrofuran at 20℃; for 24h; Schlenk technique; Inert atmosphere;	98%
In toluene at 120℃; for 1h;	92.1%
In benzene for 1h; Inert atmosphere; Reflux;	75%
With magnesium sulfate In tetrahydrofuran at 20℃; for 16h;	70%
In diethyl ether at 20℃; for 18h;	60%

: 1666-13-3
diphenyl diselenide

: 13331-27-6
m-nitrobenzene boronic acid

: 301329-93-1
(3-nitrophenyl)(phenyl)selane

Conditions

Conditions	Yield
With copper(II) oxide In dimethyl sulfoxide at 100℃; for 24h; Air atmosphere;	98%
With potassium carbonate In water at 70℃; for 9h;	88%
With iodine; dimethyl sulfoxide In neat (no solvent) at 100℃; for 0.166667h; Sealed tube; Microwave irradiation; Green chemistry;	86%
With potassium carbonate at 80℃; for 10h; Green chemistry;	85%
With sodium tetrahydroborate; 1,10-Phenanthroline; copper(ll) sulfate pentahydrate In ethanol at 20℃; for 8h;	79%

: 13331-27-6
m-nitrobenzene boronic acid

: 99-02-5
3'-Chloroacetophenone

: 371157-19-6
1-(3'-nitrobiphenyl-3-yl)ethanone

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate monohydrate; 2-(2-methoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole In 1,4-dioxane at 90℃; for 24h; Suzuki-Miyaura coupling; Inert atmosphere;	98%

: 1226548-51-1
(2S)-2-[(5-bromo-6-phenylfuro[2,3-d]pyrimidin-4-yl)amino]-2-phenylethanol

: 13331-27-6
m-nitrobenzene boronic acid

: 1226549-62-7
(2S)-2-{[5-(3-nitrophenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}-2-phenylethanol

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 100℃; for 2h; Inert atmosphere;	98%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 95℃; for 16h; Inert atmosphere;	75%
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; sodium carbonate In 1,4-dioxane; water Suzuki Coupling; Inert atmosphere; Reflux;	43%

: 15249-31-7
N-phenyl-N-methyl-2-propynamide

: 13331-27-6
m-nitrobenzene boronic acid

: 1238625-89-2
N-methyl-3-(3-nitrophenyl)-N-phenylpropiolamide

Conditions

Conditions	Yield
With palladium diacetate; potassium carbonate; silver(l) oxide In acetonitrile at 70℃; for 12h; Sonogashira coupling;	98%

3-Nitrophenylboronic acid Chemical Properties

IUPAC Name: (3-Nitrophenyl)boronic acid
Molecular Formula: C₆H₆BNO₄Molecular Weight: 166.94g/mol
Melting Point: 289-291 ºC
Freely Rotating Bonds: 4
Polar Surface Area: 64.28 Å²
Index of Refraction: 1.573
Molar Refractivity: 39.32 cm³
Molar Volume: 119.2 cm³
Polarizability: 15.58× 10^-24cm³
Surface Tension: 57.8 dyne/cm
Density:1.4 g/cm³
Flash Point: 173.5 °C
Enthalpy of Vaporization: 64.29 kJ/mol
Boiling Point: 363.3 °C at 760 mmHg
Vapour Pressure: 6.5E-06 mmHg at 25°C
The Cas Register Number of 3-Nitrophenylboronic acid is 13331-27-6 .The chemical synonyms of 3-Nitrophenylboronic acid (CAS No.13331-27-6) are (3-Nitrophenyl)-boronicaci ; M-Nitro-benzeneboronicaci ; M-Nitrobenzeneboronicacid ; 3-Nitrophenylboric acid ; 3-Nitrophenylboronic acid ; 3-Nitrobenzeneboronic acid ; Akos brn-0128 ; M-Nitrophenylboronic acid .Product categories of 3-Nitrophenylboronic acid (CAS No.13331-27-6) are Blocks ; Boronicacids ; Boronic acid series ; Substituted boronic acids ; Organometallics ; Boronic acids ; Boronic acid ; Aryl ; Organoborons ; B (classes of boron compounds) .The molecular structure of 3-Nitrophenylboronic acid (CAS No.13331-27-6) is.

3-Nitrophenylboronic acid Toxicity Data With Reference

mouse LD50:180mg/kg

U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#01859,

3-Nitrophenylboronic acid Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39: Wear suitable gloves and eye/face protection.
S36: Wear suitable protective clothing.
WGK Germany: 3
RTECS: CY8980000
TSCA: T
HS Code: 29310095

Product Name

3-Nitrophenylboronic acid

Synthetic route

3-Nitrophenylboronic acid Chemical Properties

3-Nitrophenylboronic acid Toxicity Data With Reference

3-Nitrophenylboronic acid Safety Profile

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