• Name

  3-Aminobenzeneboronic acid

• EINECS 250-189-0
• CAS No. 30418-59-8
• Article Data16
• CAS DataBase
• Density 1.23 g/cm³
• Solubility Soluble in water (partly miscible).
• Melting Point 98 °C
• Formula C₆H₈BNO₂
• Boiling Point 376 °C at 760 mmHg
• Molecular Weight 136.946
• Flash Point 181.2 °C
• Transport Information
• Appearance light yellow crystalline solid
• Safety 26-36/37/39
• Risk Codes 36/37/38
• Molecular Structure
• Hazard Symbols Xi
• Synonyms Benzeneboronicacid, m-amino- (6CI,7CI,8CI);Boronic acid, (3-aminophenyl)- (9CI);3-Aminophenyl(dihydroxy)borane;m-Aminobenzeneboronic acid;m-Aminophenylboronicacid;
• PSA 66.48000
• LogP -0.47020

Synthetic route

13331-27-6

m-nitrobenzene boronic acid

30418-59-8

3-Aminophenylboronic acid

Conditions

Conditions	Yield
Stage #1: m-nitrobenzene boronic acid With hydrogenchloride; 1,1,1,3',3',3'-hexafluoro-propanol; iron In water at 20℃; for 0.5h; Stage #2: With sodium hydrogencarbonate In water chemoselective reaction;	83%
With methanol; platinum Hydrogenation;
With barium dihydroxide; iron(II) hydroxide; water
With hydrogen; platinum(IV) oxide In methanol; water under 3102.97 Torr; for 0.75h;
With hydrogen In methanol at 20℃; under 775.743 Torr; for 20h;

1160186-73-1

potassium 3-aminophenyltrifluoroborate

7732-18-5

water

30418-59-8

3-Aminophenylboronic acid

Conditions

Conditions	Yield
With montmorillonite K10 at 25℃; for 1.5h;	78%

585-79-5

3-Bromonitrobenzene

13826-27-2

2,2'-bis(1,3,2-benzodioxaborole)

30418-59-8

3-Aminophenylboronic acid

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium acetate In dimethyl sulfoxide at 90℃; Solvent; Reagent/catalyst; Temperature; Inert atmosphere;	71%

3-aminophenylboronic acid hydrogen sulphate

30418-59-8

3-Aminophenylboronic acid

Conditions

Conditions	Yield
With sodium hydroxide In water pH=7.2;	66%

2-(3-aminophenyl)-4-{[tris-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silanyl]methyl}[1,3,2]dioxaborolane

30418-59-8

3-Aminophenylboronic acid

Conditions

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

98-80-6

phenylboronic acid

30418-59-8

3-Aminophenylboronic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: urea; nitric acid 2: iron (II)-hydroxide; barium hydroxide; water View Scheme

3-aminophenylboronic acid hydrochloric salt

30418-59-8

3-Aminophenylboronic acid

Conditions

Conditions	Yield
With NaF; Nafion solution In hydrogenchloride Electrochem. Process; on glassy carbon electrode according to Nicolas, M., et al., J. Eur. J. Org. Chem., 2000, 9, 1703-1710; NH2C6H4B(OH)2*HCl, NaF (40 mM) dissolvedin 0.2 M HCl; Nafion soln. added; mixt. vigorously stirred; potential w as scanned between 0.0 and +1.1 V...;
With NaF In hydrogenchloride Electrochem. Process; on glassy carbon electrode according to Nicolas, M., et al., J. Eur. J. Org. Chem., 2000, 9, 1703-1710; NH2C6H4B(OH)2*HCl, NaF (200 mM) dissolved in 0.5 M HCl; mixt. vigorously stirred; potential was scanned between 0.0 and +1.1 V in the unstirred soln.;

3-aminophenylboronic acid hemisulfate

30418-59-8

3-Aminophenylboronic acid

Conditions

Conditions	Yield
With sodium hydroxide In water at 0 - 5℃; pH=7.2;	21.7 g

591-19-5

3-bromoaniline

30418-59-8

3-Aminophenylboronic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / toluene / 150 h / Reflux; Large scale 2: n-butyllithium / tetrahydrofuran; hexane / -80 °C / Inert atmosphere 3: sodium hydroxide / water / 0 - 5 °C / pH 7.2 View Scheme
Multi-step reaction with 3 steps 1: toluene / Reflux; Large scale 2: n-butyllithium / tetrahydrofuran; hexane / -80 °C / Inert atmosphere 3: sodium hydroxide / water / 0 - 5 °C / pH 7.2 View Scheme

1020180-02-2

3-bromo-N-(diphenylmethylene)-benzenamine

30418-59-8

3-Aminophenylboronic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran; hexane / -80 °C / Inert atmosphere 2: sodium hydroxide / water / 0 - 5 °C / pH 7.2 View Scheme

30418-59-8

3-Aminophenylboronic acid

10357-27-4

4-nitrophenyl-α-D-mannopyranoside

4'-nitrophenyl α-D-mannopyranoside-2,3,4,6-di-O-(3"-aminophenylboronate)

Conditions

Conditions	Yield
In 1,4-dioxane	100%

Pd(0)

Pd(0)

Na2 CO3

Na2 CO3

228867-10-5

(R)-2-((5-bromopyridin-3-yloxy)methyl)pyrrolidine-1-carboxylic acid tert-butyl ester

30418-59-8

3-Aminophenylboronic acid

191162-60-4

5-(3-aminophenyl)-3-(1-BOC-2-(R)-pyrrolidinylmethoxy)pyridine

Conditions

Conditions	Yield
In toluene	100%

...Expand

863783-61-3

3-(6-bromo-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine

30418-59-8

3-Aminophenylboronic acid

3-[4-(5,6-Dimethyl-[2,2']bipyridin-3-yloxy)-quinolin-6-yl]-phenylamine

Conditions

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

863783-73-7

3-(7-bromo-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine

30418-59-8

3-Aminophenylboronic acid

3-[4-(5,6-Dimethyl-[2,2']bipyridin-3-yloxy)-quinolin-7-yl]-phenylamine

Conditions

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

927389-32-0

6-bromo-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

30418-59-8

3-Aminophenylboronic acid

927391-06-8

6-(3-aminophenyl)-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

Conditions

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 20 - 95℃; for 12h;	100%
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 100℃; for 17h; Inert atmosphere;

7591-01-7

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxane-3,4,5-triol

30418-59-8

3-Aminophenylboronic acid

4'-nitrophenyl α-D-mannopyranoside-2,3,4,6-di-O-(3"-aminophenylboronate)

Conditions

Conditions	Yield
In 1,4-dioxane dehydration (azeotropic distillation) of the 1:2 mixture of starting materials in dioxane;	100%

30418-59-8

3-Aminophenylboronic acid

126-30-7

2,2-Dimethyl-1,3-propanediol

220080-93-3

3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)aniline

Conditions

Conditions	Yield
In dichloromethane for 24h;	100%
In chloroform for 12h;	99%
In chloroform at 20℃; for 6h;	80.9%
In toluene at 20℃; for 12h;
In chloroform at 20℃;

3-Aminobenzeneboronic acid Chemical Properties

IUPAC Name: (3-aminophenyl)boronic acid
The MF of 3-Aminobenzeneboronic acid(30418-59-8): C₆H₈BNO₂
The MW of 3-Aminobenzeneboronic acid(30418-59-8): 136.94
EINECS: 250-189-0
mp: 98 °C
Density: 1.23 g/cm³ 
Flash Point: 181.2 °C 
Boiling Point: 376 °C at 760 mmHg 
Index of Refraction: 1.582   
Categories: Amines;blocks;BoronicAcids;Boronic acids;Boronic Acid;B (Classes of Boron Compounds)
Synonyms: M-APBA;M-AMINOPHENYLBORONIC ACID;3-AMINOPHENYLBORONIC ACID;3-AMINOBENZENEBORONIC ACID;TIMTEC-BB SBB004197;(m-aminophenyl)metaboric acid;3-Aminophenylboric Acid;3-AMINOBENZENEBORONIC ACID 1-HYDRATE
The Structure of 3-Aminobenzeneboronic acid(30418-59-8):

3-Aminobenzeneboronic acid Safety Profile

Hazard Codes: Xi
Risk Statements: 36/37/38
36/37/38:  Irritating to eyes, respiratory system and skin 
Safety Statements: 26-36/37/39
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36/37/39:  Wear suitable protective clothing, gloves and eye/face protection  
Hazard Note: Irritant