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3-Carboxyphenylboronic acid

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Name

3-Carboxyphenylboronic acid

EINECS -0
CAS No. 25487-66-5 Density 1.406 g/cm3
PSA 77.76000 LogP -0.93540
Solubility 2.5 g/100 mL in water Melting Point 243-247 °C(lit.)
Formula C7H7BO4 Boiling Point 434.512 °C at 760 mmHg
Molecular Weight 165.941 Flash Point 216.585 °C
Transport Information N/A Appearance off-white crystalline powder
Safety 37/39-26-36 Risk Codes 36/37/38-20/21/22
Molecular Structure Molecular Structure of 25487-66-5 (3-Carboxyphenylboronic acid) Hazard Symbols IrritantXi,HarmfulXn
Synonyms

Benzoic acid, m-borono- (6CI,7CI,8CI);Benzoic acid, 3-borono- (9CI);(3-formyloxyphenyl)boronic acid;Benzeneboronic acid, m-carboxy-;m-Carboxyphenylboronic acid;3-16-00-01283 (Beilstein Handbook Reference);m-Carboxybenzeneboronic acid;3-Boronobenzoic acid;3-hydroxyphenylboronic acid;

Article Data 18

3-Carboxyphenylboronic acid Synthetic route

269409-73-6

3-carboxyphenylboronic acid pinacol ester

13061-96-6

dihydroxy-methyl-borane

25487-66-5

3-Carboxyphenylboronic acid

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃;99%
150255-96-2

(3‐cyanophenyl)boronic acid

25487-66-5

3-Carboxyphenylboronic acid

Conditions
ConditionsYield
Stage #1: (3‐cyanophenyl)boronic acid With potassium hydroxide In ethylene glycol at 175℃; for 3h;
Stage #2: With hydrogenchloride In water; ethylene glycol pH=2 - 3;
89%
7722-64-7

potassium permanganate

17933-03-8

m-tolylboronic acid

25487-66-5

3-Carboxyphenylboronic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 30 - 40℃; Temperature;61.2%
13675-18-8

tetrahydroxydiboron

99-05-8

meta-aminobenzoic acid

25487-66-5

3-Carboxyphenylboronic acid

Conditions
ConditionsYield
Stage #1: meta-aminobenzoic acid With hydrogenchloride; sodium nitrite In water at 0℃; for 0.25h;
Stage #2: tetrahydroxydiboron With sodium acetate In water at 20℃; for 0.333333h;
52.5%
Stage #1: meta-aminobenzoic acid With hydrogenchloride; sodium nitrite In water at 0℃; for 0.25h;
Stage #2: tetrahydroxydiboron With potassium carbonate In water at 20℃; for 0.333333h;
124-38-9

carbon dioxide

626-00-6

1,3-Diiodobenzene

25487-66-5

3-Carboxyphenylboronic acid

Conditions
ConditionsYield
Stage #1: 1,3-Diiodobenzene With n-butyllithium In diethyl ether; hexane at -70℃; Inert atmosphere;
Stage #2: With Triisopropyl borate In diethyl ether; hexane at -70℃; for 0.25h; Inert atmosphere;
Stage #3: carbon dioxide Further stages;
50%
13675-18-8

tetrahydroxydiboron

3-carboxybenzenediazonium tetrafluoroborate

25487-66-5

3-Carboxyphenylboronic acid

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 0.25h;39%
17933-03-8

m-tolylboronic acid

25487-66-5

3-Carboxyphenylboronic acid

Conditions
ConditionsYield
With alkaline aqueous potassium permanganate
With potassium permanganate In sodium hydroxide
With permanganate(VII) ion In sodium hydroxide oxidation in alkaline soln.;;
With permanganate In sodium hydroxide aq. NaOH; oxidation in alkaline soln.;;
535-80-8

3-chlorobenzoate

25487-66-5

3-Carboxyphenylboronic acid

Conditions
ConditionsYield
With tetrahydroxydiboron; (chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)); potassium acetate; XPhos In ethanol at 80℃; for 5h; Inert atmosphere;
99-05-8

meta-aminobenzoic acid

25487-66-5

3-Carboxyphenylboronic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: ethanol; water / 0.03 h / 20 °C
1.2: 1.25 h / 0 - 20 °C
2.1: N,N-dimethyl-formamide / 0.25 h / 20 °C
View Scheme
124-38-9

carbon dioxide

98527-70-9

tris(3-bromo phenyl)boroxine

25487-66-5

3-Carboxyphenylboronic acid

Conditions
ConditionsYield
Stage #1: tris(3-bromo phenyl)boroxine With iodine; magnesium In tetrahydrofuran at 40 - 70℃; Inert atmosphere;
Stage #2: carbon dioxide In tetrahydrofuran at -20℃;
110 g

3-Carboxyphenylboronic acid Specification

The IUPAC name of m-Carboxyphenylboronic acid is 3-boronobenzoic acid. With the CAS registry number 25487-66-5, it is also named as Benzeneboronic acid, m-carboxy-. The product's categories are Blocks; Boronic Acids; Carboxes; Acids and Derivatives; Boron, Nitrile, Thio & TM-Cpds; Substituted Boronic Acids; Boronic Acids & Esters; Phenyls & Phenyl-Het; Aryl; Organoborons; B (Classes of Boron Compounds); Boronic Acids and Derivatives. It is off-white crystalline powder which should be stored at the temperature of 0-6°C.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.62; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 4; (8)#H bond donors: 3; (9)#Freely Rotating Bonds: 4; (10)Polar Surface Area: 77.76 Å2; (11)Index of Refraction: 1.585; (12)Molar Refractivity: 39.564 cm3; (13)Molar Volume: 118.001 cm3; (14)Polarizability: 15.685×10-24 cm3; (15)Surface Tension: 62.794 dyne/cm; (16)Density: 1.406 g/cm3; (17)Flash Point: 216.585 °C; (18)Enthalpy of Vaporization: 72.797 kJ/mol; (19)Boiling Point: 434.512 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

Uses of m-Carboxyphenylboronic acid: It can react with 3-bromo-pyridine to get 3-pyridin-3-yl-benzoic acid. This reaction which is a kind of Substitution//Suzuki reaction needs reagent aq. Na2CO3, catalytic agent Pd(PPh3)4 and solvent acetonitrile at temperature of 90 °C. The reaction time is 16 hours. The yield is 90%.

m-Carboxyphenylboronic acid can react with 3-bromo-pyridine to get 3-pyridin-3-yl-benzoic acid

When you are using this chemical, please be cautious about it as the following:
It is not onlt harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure. 
1. SMILES:B(c1cccc(c1)C(=O)O)(O)O
2. InChI:InChI=1/C7H7BO4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4,11-12H,(H,9,10)
3. InChIKey:DBVFWZMQJQMJCB-UHFFFAOYAT

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