4-Carboxyphenylboronic acid supplier

Name
4-Carboxyphenylboronic acid
EINECS 604-189-6
CAS No. 14047-29-1
Article Data51
CAS DataBase
Density 1.406 g/cm³
Solubility
Melting Point 220 °C (dec.)(lit.)
Formula C₇H₇BO₄
Boiling Point 406.383 °C at 760 mmHg
Molecular Weight 165.941
Flash Point 199.574 °C
Transport Information
Appearance Off-white to light beige powder
Safety 37/39-26-36
Risk Codes 36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xn,Xi
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;
PSA 77.76000
LogP -0.93540

Synthetic route

: 99768-12-4
4-methoxycarbonylphenylboronic acid

: 14047-29-1
4-carboxyphenylboronic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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 water	90%
With potassium permanganate In water; acetonitrile

: 5084-80-0
tri(4-tolyl)boroxine

: 14047-29-1
4-carboxyphenylboronic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

: 7732-18-5
water

: 14047-29-1
4-carboxyphenylboronic acid

Conditions

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

...Expand

: 87199-17-5
4-formylphenylboronic acid,

A: 14047-29-1
4-carboxyphenylboronic acid

B: 123-08-0
4-hydroxy-benzaldehyde

Conditions

Conditions	Yield
With [(hydrotris(3,5-diphenyl-pyrazol-1-yl)borate)FeII(benzilate)]; oxygen In benzene at 20℃; for 0.333333h;	A 10% B 70%

: 124-38-9
carbon dioxide

: 624-38-4
para-diiodobenzene

: 14047-29-1
4-carboxyphenylboronic acid

Conditions

Conditions	Yield
Stage #1: para-diiodobenzene With n-butyllithium In diethyl ether; hexane at -70℃; for 0.5h; Inert atmosphere; Stage #2: With Triisopropyl borate In diethyl ether; hexane at -70℃; for 0.25h; Inert atmosphere; Stage #3: carbon dioxide Further stages;	52%

: 87199-16-4
3-Formylphenylboronic acid

: 14047-29-1
4-carboxyphenylboronic acid

Conditions

Conditions	Yield
With potassium permanganate

: 586-76-5
4-Bromobenzoic acid

: 14047-29-1
4-carboxyphenylboronic acid

Conditions

Conditions	Yield
Stage #1: 4-Bromobenzoic acid With n-butyllithium In tetrahydrofuran; hexane; toluene at -70℃; for 1.5h; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane; toluene at -70 - -20℃; Further stages.;	41 % Chromat.
Multi-step reaction with 3 steps 1.1: thionyl chloride / 2.5 h / Reflux 1.2: 2 h / 20 °C / Cooling with ice 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -75 °C / Inert atmosphere 2.2: 3.25 h / 20 °C / Inert atmosphere 3.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 2 h / 20 °C View Scheme

: C68H42B2F78O7Si2

: 14047-29-1
4-carboxyphenylboronic acid

Conditions

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

: 4294-57-9
para-methylphenylmagnesium bromide

: 14047-29-1
4-carboxyphenylboronic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) B(OMe)3, (ii) aq. H2SO4 2: KMnO4 View Scheme

: 126747-14-6
4-cyanophenylboronic acid

: 14047-29-1
4-carboxyphenylboronic acid

Conditions

Conditions	Yield
With potassium hydroxide In methanol; water

: 106-38-7
para-bromotoluene

: 14047-29-1
4-carboxyphenylboronic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: iodine; magnesium / tetrahydrofuran / 5 h / Inert atmosphere; Reflux 1.2: -30 - 20 °C 1.3: 1 h / 20 °C 2.1: potassium permanganate; sodium hydroxide; tetrabutylammomium bromide / water / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: magnesium / diethyl ether / 3 - 4 h / Reflux 1.2: -12 - 20 °C 2.1: potassium permanganate; sodium hydroxide View Scheme
Multi-step reaction with 2 steps 1.1: iodine; magnesium / tetrahydrofuran / 5 h / Inert atmosphere; Reflux 1.2: 20 °C / Inert atmosphere; Cooling 1.3: 1 h / 20 °C 2.1: potassium permanganate; sodium hydroxide; tetrabutylammomium bromide / water / 20 °C View Scheme

: 40881-45-6
4-tolylboronic dimethyl ester

: 14047-29-1
4-carboxyphenylboronic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / tetrahydrofuran; water / 5 h / 20 °C 2: sodium hydroxide; potassium permanganate; tetrabutylammomium bromide / water / 20 °C / Cooling with ice View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / tetrahydrofuran; water / 5 h 2: sodium hydroxide; potassium permanganate; tetrabutylammomium bromide / water / 20 °C View Scheme

: 51934-41-9
4-iodobenzoic acid ethyl ester

: 14047-29-1
4-carboxyphenylboronic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 2: sodium hydroxide / tetrahydrofuran; water / 3 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C 2: sodium hydroxide / tetrahydrofuran; water / 3 h / Reflux View Scheme

: 619-42-1
4-methoxycarbonylphenyl bromide

: 14047-29-1
4-carboxyphenylboronic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 2: sodium hydroxide / tetrahydrofuran; water / 3 h / Reflux View Scheme

Reaxys ID: 31937714: Reaxys ID: 31937714

: 14047-29-1
4-carboxyphenylboronic acid

: 619-58-9
4-iodobenzoic acid

: 14047-29-1
4-carboxyphenylboronic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / 5.5 h / Reflux 2: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 3: sodium hydroxide / tetrahydrofuran; water / 3 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / 5.5 h / Reflux 2: n-butyllithium / tetrahydrofuran / 1 h / -78 °C 3: sodium hydroxide / tetrahydrofuran; water / 3 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / 6 h / Reflux 2: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 3: sodium hydroxide / tetrahydrofuran; water / 3 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / 6 h / Reflux 2: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 3: sodium hydroxide / tetrahydrofuran; water / 3 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / 6 h / Reflux 2: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 3: sodium hydroxide / tetrahydrofuran; water / 3 h / Reflux View Scheme

: 619-44-3
methyl 4-iodobenzoate

: 14047-29-1
4-carboxyphenylboronic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 2: sodium hydroxide / tetrahydrofuran; water / 3 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 2: sodium hydroxide / tetrahydrofuran; water / 3 h / Reflux View Scheme

: 124-38-9
carbon dioxide

: 7519-90-6
tris(4-iodo phenyl)boroxine

: 14047-29-1
4-carboxyphenylboronic acid

Conditions

Conditions	Yield
Stage #1: tris(4-iodo phenyl)boroxine With isopropylmagnesium chloride In tetrahydrofuran at -10℃; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran at 0℃;	90.8 g

: 124-38-9
carbon dioxide

: 7519-94-0
2,4,6-tris(4-bromophenyl)boroxin

: 14047-29-1
4-carboxyphenylboronic acid

Conditions

Conditions	Yield
Stage #1: 2,4,6-tris(4-bromophenyl)boroxin With iodine; magnesium In tetrahydrofuran at 40 - 70℃; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran at -20℃;	118 g

: 13675-18-8
tetrahydroxydiboron

: 619-58-9
4-iodobenzoic acid

: 14047-29-1
4-carboxyphenylboronic acid

Conditions

Conditions	Yield
With [{Pd(μ-Cl){κ2-P,C-P(iPr)2(OC6H3-2-Ph)}}2]; sodium acetate In dichloromethane; water at 40℃; for 6h; Inert atmosphere;

: 13675-18-8
tetrahydroxydiboron

: 74-11-3
para-chlorobenzoic acid

: 14047-29-1
4-carboxyphenylboronic acid

Conditions

Conditions	Yield
With [{Pd(μ-Cl){κ2-P,C-P(iPr)2(OC6H3-2-Ph)}}2]; sodium acetate In dichloromethane; water at 40℃; for 6h; Inert atmosphere;

: 14047-29-1
4-carboxyphenylboronic acid

: 71-36-3
butan-1-ol

: 91345-47-0
n-butyl ester 4-carboxyphenyl boronic acid

Conditions

Conditions	Yield
With hydrogenchloride In water for 5h; Reflux;	100%
With hydrogenchloride

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

: 14047-29-1
4-carboxyphenylboronic acid

: 180516-87-4
4-carboxyphenylboronic acid pinacol ester

Conditions

Conditions	Yield
In tetrahydrofuran; toluene	100%
In tetrahydrofuran; toluene at 45℃;	100%
In hexane at 70℃; for 3h; Temperature; Time; Concentration;	93.7%

: 2-bromothioanisole

: 14047-29-1
4-carboxyphenylboronic acid

: 330942-85-3
4-[(2-methylthio)phenyl]benzoic acid

Conditions

Conditions	Yield
With hydrogenchloride; potassium carbonate; dichlorobis(triphenylphosphine)palladium[II] In 1,4-dioxane	100%

: 2-bromothioanisole

: 14047-29-1
4-carboxyphenylboronic acid

: 4-[(2-ethylthio)phenyl]benzoic acid

Conditions

Conditions	Yield
With hydrogenchloride; potassium carbonate; dichlorobis(triphenylphosphine)palladium[II] In 1,4-dioxane	100%

: 19614-16-5
2-bromo-1-(methylsulfanyl)benzene

: 14047-29-1
4-carboxyphenylboronic acid

: 330942-85-3
4-[(2-methylthio)phenyl]benzoic acid

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane for 2h; Inert atmosphere; Reflux;	100%
Stage #1: 2-bromo-1-(methylsulfanyl)benzene; 4-carboxyphenylboronic acid With potassium carbonate; bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane; water for 2h; Heating / reflux; Stage #2: With hydrogenchloride; water

: 14047-29-1
4-carboxyphenylboronic acid

: 99-96-7
4-hydroxy-benzoic acid

Conditions

Conditions	Yield
With water; oxygen; sodium sulfite at 50℃; for 1h; Green chemistry;	100%
With N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃; for 48h; Catalytic behavior; Reagent/catalyst; Irradiation; Green chemistry;	99%
With N-ethyl-N,N-diisopropylamine In water; acetonitrile for 28h; Irradiation;	99%

: 626-55-1
3-Bromopyridine

: 14047-29-1
4-carboxyphenylboronic acid

: 4-pyridine-3-yl-benzoic acid hydrochloride

Conditions

Conditions	Yield
Stage #1: 3-Bromopyridine; 4-carboxyphenylboronic acid With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; acetonitrile at 150℃; under 9000.9 Torr; for 0.333333h; Inert atmosphere; Microwave irradiation; Stage #2: With hydrogenchloride In water; acetonitrile pH=1; Inert atmosphere;	100%

: 67-56-1
methanol

: 14047-29-1
4-carboxyphenylboronic acid

: 99768-12-4
4-methoxycarbonylphenylboronic acid

Conditions

Conditions	Yield
With sulfuric acid for 30h; Reflux;	99%
In thionyl chloride at 50℃; for 2.5h; Inert atmosphere;	92%
sulfuric acid for 8h; Heating / reflux;	90%

: 14047-29-1
4-carboxyphenylboronic acid

: 288067-35-6
4-bromo-2-hydroxy-benzonitrile

: 1261983-31-6
C14H9NO3

Conditions

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene for 24h; Heating / reflux;	99%

: 1093169-72-2
4-iodophenyl-1-piperidin-1-ylethanone

: 14047-29-1
4-carboxyphenylboronic acid

: 1093169-75-5
4'-(2-oxo-2-piperidino-ethyl)biphenyl-4-carboxylic acid

Conditions

Conditions	Yield
With palladium diacetate; potassium carbonate In water; acetone at 65℃; for 1h; Suzuki coupling; Inert atmosphere;	99%

: 14047-29-1
4-carboxyphenylboronic acid

: tris(4-iodophenyl)phosphine oxide

: 4',4''',4'''''-(oxo-λ5-phosphanetriyl)tris([1,1'-biphenyl]-4-carboxylic acid)

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Suzuki-Miyaura Coupling;	99%

: 623-00-7
4-bromobenzenecarbonitrile

: 14047-29-1
4-carboxyphenylboronic acid

: 5728-46-1
4′‐cyano‐[1,1′‐biphenyl]‐4‐carboxylic acid

Conditions

Conditions	Yield
Stage #1: 4-bromobenzenecarbonitrile; 4-carboxyphenylboronic acid With sodium carbonate; palladium on activated charcoal In methanol; water at 77℃; Stage #2: With hydrogenchloride In methanol; water pH=4 - 4.5;	98%
With sodium carbonate In ethanol; water at 20℃; for 1h; Suzuki-Miyaura Coupling; Green chemistry;	80%
Stage #1: 4-bromobenzenecarbonitrile; 4-carboxyphenylboronic acid With potassium carbonate In 1,4-dioxane; ethanol; water at 120℃; for 0.333333h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; ethanol; water at 0 - 85℃; for 25h; Suzuki-Miyaura Coupling; Inert atmosphere;	78%
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane for 1h; Suzuki coupling; Heating;

: 945244-49-5
1-(benzo[d][1,3]dioxol-5-yl)-N-(3-bromo-4-methylphenyl)cyclopropanecarboxamide

: 14047-29-1
4-carboxyphenylboronic acid

: 945240-59-5
4-[5-(1-benzo[1,3]dioxol-5-ylcyclopropyl)carbonylamino-2-methylphenyl]benzoic acid

Conditions

Conditions	Yield
With potassium carbonate; Pd-FibreCat 1007 In N,N-dimethyl-formamide at 80℃; for 3h;	98%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h;	98%

: 1120-87-2
4-bromopyridin

: 14047-29-1
4-carboxyphenylboronic acid

: 4385-76-6
4-(4-pyridinyl)benzoic acid

Conditions

Conditions	Yield
With sodium carbonate In ethanol; water at 90℃; Suzuki coupling; Inert atmosphere;	98%
With potassium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; acetonitrile at 100℃; for 24h; Inert atmosphere;	90%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,2-dimethoxyethane at 100℃; for 4h; Inert atmosphere;	71%

: 14047-29-1
4-carboxyphenylboronic acid

: C7H5(131)IO2

Conditions

Conditions	Yield
With copper(I) oxide; 1,10-Phenanthroline; [131I]-sodium iodide; triethylamine In water; acetonitrile at 25℃; for 1h; Chan-Lam Coupling;	98%

: 14047-29-1
4-carboxyphenylboronic acid

: 7-bromo-2-(morpholinomethyl)-4H-imidazol[2,1-c][1,4]benzoxazine

: 4-[2-(morpholinomethyl)-4H-imidazo[2,1-c][1,4]benzoxazin-7-yl]benzoic acid

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; acetonitrile at 90℃; for 18h; Suzuki Coupling; Inert atmosphere;	98%

: 626-41-5
3,5-dibromophenol

: 14047-29-1
4-carboxyphenylboronic acid

: 3,5-bis(4-carboxyphenyl)-1-hydroxybenzene

Conditions

Conditions	Yield
With bis(triphenylphosphine)palladium(II) chloride; potassium carbonate In water; acetonitrile at 100℃; for 48h; Schlenk technique; Inert atmosphere;	98%

: europioum(III) chloride

: terbium(III) chloride

: 14047-29-1
4-carboxyphenylboronic acid

: 7732-18-5
water

: 0.5Tb(3+)*0.5Eu(3+)*C7H6BO4(1-)*C7H7BO5(2-)*2H2O

Conditions

Conditions	Yield
at 20℃;	98%

...Expand

: gadolinium(III) chloride

: europioum(III) chloride

: 14047-29-1
4-carboxyphenylboronic acid

: 7732-18-5
water

: 0.5Gd(3+)*0.5Eu(3+)*C7H6BO4(1-)*C7H7BO5(2-)*2H2O

Conditions

Conditions	Yield
at 20℃;	98%

...Expand

: 116-69-8
3-bromophthalic acid

: 14047-29-1
4-carboxyphenylboronic acid

: biphenyl-2,3,4'-tricarboxylic acid

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); Davisil 500 Angstroem beads; sodium carbonate In water for 1.5h; Suzuki cross coupling reaction; Heating;	97%

: 14047-29-1
4-carboxyphenylboronic acid

: 7722-84-1
dihydrogen peroxide

: 99-96-7
4-hydroxy-benzoic acid

Conditions

Conditions	Yield
With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique;	97%

: 14047-29-1
4-carboxyphenylboronic acid

: C19H21N3O3

: C26H24BN3O5

Conditions

Conditions	Yield
In acetonitrile at 80℃; for 2h;	97%

: yttrium(III) chloride

: europioum(III) chloride

: 14047-29-1
4-carboxyphenylboronic acid

: 7732-18-5
water

: 0.5Eu(3+)*0.5Y(3+)*C7H6BO4(1-)*C7H7BO5(2-)*2H2O

Conditions

Conditions	Yield
at 20℃;	97%

...Expand

: gadolinium(III) chloride

: terbium(III) chloride

: 14047-29-1
4-carboxyphenylboronic acid

: 0.5Tb(3+)*0.5Gd(3+)*C7H6BO4(1-)*C7H7BO5(2-)*2H2O

Conditions

Conditions	Yield
at 20℃;	97%

...Expand

: 174-78-7
2-oxa-6-azaspiro[3.3]heptane

: 14047-29-1
4-carboxyphenylboronic acid

: (4-(2-oxa-6-azaspiro[3.3]heptane-6-carbonyl)phenyl)boronic acid

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 16h;	97%

: 14047-29-1
4-carboxyphenylboronic acid

: 4595-60-2
2-bromopyrimidine

: 199678-12-1
4-(pyrimidine-2-yl)benzoic acid

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; acetonitrile at 140℃; under 9000.9 Torr; for 0.25h; Inert atmosphere; Microwave irradiation;	96%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In acetonitrile at 90℃; for 17h;	89%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In acetonitrile at 90℃; for 4h; Substitution; Suzuki reaction;
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In acetonitrile Inert atmosphere; Reflux;	2 g

: 14047-29-1
4-carboxyphenylboronic acid

Wang resin-bound p-iodobenzoic acid: Wang resin-bound p-iodobenzoic acid

: 103-49-1
dibenzylamine

: 4'-(3-phenyl-propylcarbamoyl)-biphenyl-4-carboxylic acid

Conditions

Conditions	Yield
Multistep reaction.;	96%

...Expand

: 14047-29-1
4-carboxyphenylboronic acid

: 504-63-2
trimethyleneglycol

: 126747-13-5
2-(4-carboxyphenyl)-1,3,2-dioxaborinane

Conditions

Conditions	Yield
In toluene for 2h; Heating;	96%
In toluene byproducts: H2O; mixt. refluxed for 2 h; water removed azeotropically; cooled to 25°C; crystn.; filtration; IR; NMR; mass spectra;	92%
In toluene
In toluene

: 4-(5-bromo-1,3,4-oxadiazol-2-yl)morpholine

: 14047-29-1
4-carboxyphenylboronic acid

: 4-(5-morpholino-1,3,4-oxadiazol-2-yl)benzoic acid

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 120℃; for 0.5h; Suzuki Coupling; Inert atmosphere; Microwave irradiation;	96%

4-Carboxyphenylboronic acid 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.

Product Name

4-Carboxyphenylboronic acid

Synthetic route

4-Carboxyphenylboronic acid Specification

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