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14047-29-1

Basic Information
CAS No.: 14047-29-1
Name: 4-Carboxyphenylboronic acid
Article Data: 51
Cas Database
Molecular Structure:
Molecular Structure of 14047-29-1 (4-Carboxyphenylboronic acid)
Formula: C7H7BO4
Molecular Weight: 165.941
Synonyms: Benzoic acid, p-borono-;(4-formyloxyphenyl)boronic acid;p-Carboxyphenylboronic acid;Benzoic acid, 4-borono-;4-16-00-01683 (Beilstein Handbook Reference);Benzeneboronic acid, p-carboxy-;p-Boronobenzoic acid;p-Carboxybenzeneboronic acid;Benzoic acid, p-borono- (6CI,7CI,8CI);Benzoic acid, 4-borono- (9CI);4-Carboxybenzeneboronic acid;
EINECS: 604-189-6
Density: 1.406 g/cm3
Melting Point: 220 °C (dec.)(lit.)
Boiling Point: 406.383 °C at 760 mmHg
Flash Point: 199.574 °C
Solubility: N/A
Appearance: Off-white to light beige powder
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 36/37/38-20/21/22
Safety: 37/39-26-36
Transport Information: N/A
PSA: 77.76000
LogP: -0.93540
Synthetic route
99768-12-4

4-methoxycarbonylphenylboronic acid

14047-29-1

4-carboxyphenylboronic acid

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water for 3h; Concentration; Reagent/catalyst; Reflux;96.5%

(4-(diisopropylcarbamoyl)phenyl)boronic acid

14047-29-1

4-carboxyphenylboronic acid

Conditions
ConditionsYield
With lithium hydroxide monohydrate In tetrahydrofuran; water at 20℃; for 2h; Time;95.8%
4334-88-7

p-ethoxycarbonylphenylboronic acid

14047-29-1

4-carboxyphenylboronic acid

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water for 3h; Concentration; Reagent/catalyst; Reflux;95.2%
87199-17-5

4-formylphenylboronic acid,

14047-29-1

4-carboxyphenylboronic acid

Conditions
ConditionsYield
Stage #1: 4-formylphenylboronic acid, With potassium permanganate; sodium hydroxide In water for 2h;
Stage #2: In ethanol; water at 50℃; for 0.166667h;
95%
With sodium hydroxide; potassium permanganate In water90%
With potassium permanganate In water; acetonitrile
5084-80-0

tri(4-tolyl)boroxine

14047-29-1

4-carboxyphenylboronic acid

Conditions
ConditionsYield
With potassium permanganate; tetrabutylammomium bromide; sodium hydroxide In water at 20℃;93%
5720-05-8

4-methylphenylboronic acid

14047-29-1

4-carboxyphenylboronic acid

Conditions
ConditionsYield
With potassium permanganate; tetrabutylammomium bromide; sodium hydroxide; nickel dichloride In water at 20℃; Concentration;92%
With potassium permanganate; tetrabutylammomium bromide; sodium hydroxide In water at 20℃;82%
With potassium permanganate; tetrabutylammomium bromide; sodium hydroxide In water at 20℃;82%
1072960-67-8

4-carboxyphenyl boronic acid MIDA ester

14047-29-1

4-carboxyphenylboronic acid

Conditions
ConditionsYield
With sodium hydroxide; water In tetrahydrofuran at 23℃; for 0.166667h; Inert atmosphere;89%
7722-64-7

potassium permanganate

5720-05-8

4-methylphenylboronic acid

14047-29-1

4-carboxyphenylboronic acid

Conditions
ConditionsYield
With hydrogenchloride In sodium hydroxide oxidatio with KMnO4 in aq. NaOH followed by acidification with HCl;72%
121-43-7

Trimethyl borate

106-38-7

para-bromotoluene

14047-29-1

4-carboxyphenylboronic acid

Conditions
ConditionsYield
Stage #1: para-bromotoluene With iodine; magnesium In tetrahydrofuran for 12h; Heating;
Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 16h;
Stage #3: With ionic liquid In water for 0.5h; Further stages.;
70%
7647-01-0

hydrogenchloride

5720-05-8

4-methylphenylboronic acid

14047-29-1

4-carboxyphenylboronic acid

Conditions
ConditionsYield
Stage #1: 4-methylphenylboronic acid; water With potassium permanganate; sodium hydroxide
Stage #2: hydrogenchloride
70%
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Specification

The 4-Carboxyphenylboronic acid is an organic compound with the formula C7H7BO4. The IUPAC name of this chemical is 4-boronobenzoic acid. With the CAS registry number 14047-29-1, it is also named as p-Carboxybenzeneboronic acid. The product's categories are Blocks; BoronicAcids; Carboxes; Boronic Acid Series; Substituted Boronic Acids; Boronic Acids & Esters; Phenyls & Phenyl-Het; Boronic Acids; Heterocyclic Compounds; Boronic Acid; Aryl; Organoborons; B (Classes of Boron Compounds); Chiral Chemicals; Boronic Acids & Esters; Phenyls & Phenyl-Het. Besides, it is an off-white to light beige powder, which should be stored in a dark closed and well-ventilated place.

Physical properties about 4-Carboxyphenylboronic acid are: (1)ACD/LogP: 0.62; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1.055; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 4; (7)#H bond donors: 3; (8)#Freely Rotating Bonds: 4; (9)Polar Surface Area: 77.76 Å2; (10)Index of Refraction: 1.585; (11)Molar Refractivity: 39.564 cm3; (12)Molar Volume: 118.001 cm3; (13)Polarizability: 15.685×10-24cm3; (14)Surface Tension: 62.794 dyne/cm; (15)Density: 1.406 g/cm3; (16)Flash Point: 199.574 °C; (17)Enthalpy of Vaporization: 69.396 kJ/mol; (18)Boiling Point: 406.383 °C at 760 mmHg.

Uses of 4-Carboxyphenylboronic acid: it can be used to produce 4-(N-methoxy-N-methylcarbamoyl)phenylboric acid at temperature of 20 °C. This reaction is a kind of Acylation. It will need reagent 1-hydroxybenzotriazole, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide and solvent CH2Cl2 with reaction time of 72 hours. The yield is about 56%.

When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation, in contact with skin and if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: B(c1ccc(cc1)C(=O)O)(O)O
(2)InChI: InChI=1/C7H7BO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4,11-12H,(H,9,10)
(3)InChIKey: SIAVMDKGVRXFAX-UHFFFAOYAW
(4)Std. InChI: InChI=1S/C7H7BO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4,11-12H,(H,9,10)
(5)Std. InChIKey: SIAVMDKGVRXFAX-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 1740mg/kg (1740mg/kg)   "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964Vol. -, Pg. 693, 1964.
rat LD50 oral > 3gm/kg (3000mg/kg)   Acta Physiologica Polonica. Vol. 12, Pg. 173, 1961.