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| CAS No.: | 25487-66-5 |
|---|---|
| Name: | 3-Carboxyphenylboronic acid |
| Article Data: | 18 |
| Cas Database | |
| Molecular Structure: | |
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| Formula: | C7H7BO4 |
| Molecular Weight: | 165.941 |
| 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; |
| EINECS: | -0 |
| Density: | 1.406 g/cm3 |
| Melting Point: | 243-247 °C(lit.) |
| Boiling Point: | 434.512 °C at 760 mmHg |
| Flash Point: | 216.585 °C |
| Solubility: | 2.5 g/100 mL in water |
| Appearance: | off-white crystalline powder |
| Hazard Symbols: |
 Xi, Xn
|
| Risk Codes: | 36/37/38-20/21/22 |
| Safety: | 37/39-26-36 |
| Transport Information: | N/A |
| PSA: | 77.76000 |
| LogP: | -0.93540 |
3-carboxyphenylboronic acid pinacol ester
dihydroxy-methyl-borane
3-Carboxyphenylboronic acid
| Conditions | Yield |
|---|---|
| With trifluoroacetic acid In dichloromethane at 20℃; | 99% |
(3‐cyanophenyl)boronic acid
3-Carboxyphenylboronic acid
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| With sodium hydroxide In water at 30 - 40℃; Temperature; | 61.2% |
| Conditions | Yield |
|---|---|
| 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; |
| Conditions | Yield |
|---|---|
| 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% |
tetrahydroxydiboron
3-Carboxyphenylboronic acid
| Conditions | Yield |
|---|---|
| In N,N-dimethyl-formamide at 20℃; for 0.25h; | 39% |
m-tolylboronic acid
3-Carboxyphenylboronic acid
| Conditions | Yield |
|---|---|
| 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.;; |
3-chlorobenzoate
3-Carboxyphenylboronic acid
| Conditions | Yield |
|---|---|
| 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; |
meta-aminobenzoic acid
3-Carboxyphenylboronic acid
| Conditions | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| 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 |
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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%.
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
