25487-66-5

Basic information

• Product Name: 3-Carboxyphenylboronic acid
• Synonyms: 3-(dihydroxyboranyl)benzoic acid;3 - carboxyl benzene boric acid;RARECHEM AH PB 0148;3-borono-benzoicaci;m-borono-benzoicaci;m-carboxy-benzeneboronicaci;m-carboxybenzeneboronicacid;M-CARBOXYPHENYLBORONIC ACID
• CAS NO: 25487-66-5
• Molecular Formula: C₇H₇BO₄
• Molecular Weight: 165.94
• EINECS: -0
• Product Categories: Boronate Ester;Potassium Trifluoroborate;Boric Acid| Boric Acid Ester| Potassium Trifluoroborate| carboxylic acid;Eltrombopag/Lumacaftor;Thiophenes;blocks;BoronicAcids;Carboxes;Boronic Acid series;Acids and Derivatives;Boron, Nitrile, Thio,& TM-Cpds;Substituted Boronic Acids;Boronic Acids & Esters;Phenyls & Phenyl-Het;Boronic acids;Boronic Acid;Aryl;Organoborons;B (Classes of Boron Compounds);CHIRAL CHEMICALS;Boronic Acids & Esters;Phenyls & Phenyl-Het;Boronic Acids;Boronic Acids and Derivatives;organic or inorganic borate;Aryl Boronic Acids;Boronic Acids and Derivatives;Chemical Synthesis;Monosubstituted Aryl Boronic Acids;Organometallic Reagents
• Mol File: 25487-66-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 243-247 °C(lit.)
• Boiling Point: 434.512 °C at 760 mmHg
• Flash Point: 216.585 °C
• Appearance: Off-white/Crystalline Powder
• Density: 1.406 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.585
• Storage Temp.: 0-6°C
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 4.21±0.10(Predicted)
• Water Solubility: 2.5 g/100 mL
• BRN: 2967400
• CAS DataBase Reference: 3-Carboxyphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Carboxyphenylboronic acid(25487-66-5)
• EPA Substance Registry System: 3-Carboxyphenylboronic acid(25487-66-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 37/39-26-36
• WGK Germany: 2
• RTECS: CY8750000
• HazardClass: IRRITANT
• Hazardous Substances Data: 25487-66-5(Hazardous Substances Data)

Usage

Chemical Properties

3-Carboxyphenylboronic acid is off-white crystalline powder

Uses

Different sources of media describe the Uses of 25487-66-5 differently. You can refer to the following data:
1. 3-Carboxyphenylboronic acid is used in Suzuki coupling chemistry.1,2,3
2. suzuki reaction
3. 3-Carboxyphenylboronic acid can be used as a substrate in the preparation of:Biaryl derivatives by reacting with bromoaniline through the Suzuki-Miyaura coupling reaction.Boronic acid-functionalized block copolymer.1H-Imidazo[1,2-a]quinoxaline derivatives.

InChI:InChI=1/C7H7BO4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4,11-12H,(H,9,10)

Synthetic route

3-carboxyphenylboronic acid pinacol ester (269409-73-6) + dihydroxy-methyl-borane (13061-96-6) → 3-Carboxyphenylboronic acid (25487-66-5)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃;	99%

(3‐cyanophenyl)boronic acid (150255-96-2) → 3-Carboxyphenylboronic acid (25487-66-5)

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%

potassium permanganate (7722-64-7) + m-tolylboronic acid (17933-03-8) → 3-Carboxyphenylboronic acid (25487-66-5)

Conditions	Yield
With sodium hydroxide In water at 30 - 40℃; Temperature;	61.2%

tetrahydroxydiboron (13675-18-8) + meta-aminobenzoic acid (99-05-8) → 3-Carboxyphenylboronic acid (25487-66-5)

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;

carbon dioxide (124-38-9) + 1,3-Diiodobenzene (626-00-6) → 3-Carboxyphenylboronic acid (25487-66-5)

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 (13675-18-8) + 3-carboxybenzenediazonium tetrafluoroborate → 3-Carboxyphenylboronic acid (25487-66-5)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 0.25h;	39%

m-tolylboronic acid (17933-03-8) → 3-Carboxyphenylboronic acid (25487-66-5)

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 (535-80-8) → 3-Carboxyphenylboronic acid (25487-66-5)

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 (99-05-8) → 3-Carboxyphenylboronic acid (25487-66-5)

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

carbon dioxide (124-38-9) + tris(3-bromo phenyl)boroxine (98527-70-9) → 3-Carboxyphenylboronic acid (25487-66-5)

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

5-bromo-2-furancarboxaldehyde (1899-24-7) + 3-Carboxyphenylboronic acid (25487-66-5) → 5-(3-carboxyphenyl)furane-2-carbaldehyde (304884-54-6)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene at 90℃; for 7h; Suzuki-Miyaura coupling;	100%
With C11H8Cl4N2O3Pd; potassium carbonate In methanol; water; N,N-dimethyl-formamide at 100℃; for 0.0833333h; Suzuki Coupling;	98%
With ethylenediaminetetraacetic acid; tetrabutylammomium bromide; potassium carbonate; palladium dichloride at 50℃; for 0.166667h; Suzuki-Miyaura reaction;	92%

3-Carboxyphenylboronic acid (25487-66-5) + para-nitrophenyl bromide (586-78-7) → 4'-nitrobiphenyl-3-carboxylic acid (729-01-1)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene for 48h; Suzuki Coupling; Heating / reflux;	100%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 48h; Suzuki Coupling; Reflux; Inert atmosphere;	96.1%
Stage #1: 3-Carboxyphenylboronic acid; para-nitrophenyl bromide With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 48h; Suzuki coupling; Inert atmosphere; Reflux; Stage #2: With hydrogenchloride In water pH=3;	89%

3-Carboxyphenylboronic acid (25487-66-5) + C41H89N17O6 → C69H109B4N17O18

Conditions	Yield
With diisopropyl-carbodiimide In methanol at 0 - 20℃; for 24.5h;	100%
With diisopropyl-carbodiimide In methanol at 0 - 20℃; for 24.5h;

3-Carboxyphenylboronic acid (25487-66-5) + para-chlorobenzoic acid (74-11-3) → biphenyl-3,4′-dicarboxylic acid

Conditions	Yield
With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate; palladium diacetate; potassium carbonate In water at 50℃; for 8h; Suzuki-Miyaura coupling;	99%

1,1-dimethylethyl 1-[(5-bromo-2-methylphenyl)methyl]-3-[4-(1,1-dimethylethyl)phenyl]-1H-indole-2-carboxylate (1010413-06-5) + 3-Carboxyphenylboronic acid (25487-66-5) → 3'-({2-{[(1,1-dimethylethyl)oxy]carbonyl}-3-[4-(1,1-dimethylethyl)phenyl]-1H-indol-1-yl}methyl)-4'-methyl-3-biphenylcarboxylic acid (1010413-07-6)

Conditions	Yield
Stage #1: 1,1-dimethylethyl 1-[(5-bromo-2-methylphenyl)methyl]-3-[4-(1,1-dimethylethyl)phenyl]-1H-indole-2-carboxylate; 3-Carboxyphenylboronic acid With sodium hydrogencarbonate; palladium 10% on activated carbon In water; N,N-dimethyl-formamide at 90℃; for 36h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide	99%

5-chloro-2-nitrotoluene (5367-28-2) + 3-Carboxyphenylboronic acid (25487-66-5) → 3'-methyl-4'-nitrobiphenyl-3-carboxylic acid (1303573-22-9)

Conditions	Yield
With palladium diacetate; sodium carbonate; triphenylphosphine In ethanol; water; toluene at 100℃; for 24h; Suzuki coupling; Inert atmosphere; Sealed vessel;	99%

6-bromo-1-methyl-3-trityl-1H-imidazo[4,5-b]pyridin-2(3H)-one (1355152-77-0) + 3-Carboxyphenylboronic acid (25487-66-5) → 3-(1-methyl-2-oxo-3-trityl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-6-yl)benzoic acid (1355152-95-2)

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In 1,4-dioxane at 100℃; for 1h; Microwave irradiation;	99%

3-Carboxyphenylboronic acid (25487-66-5) + 5-bromo-1-(4-methoxyphenyl)-3-(4-(trifluoromethyl)phenyl)-1H-pyrrolo[2,3-b]pyridine → 3-(1-(4-methoxyphenyl)-3-(4-(trifluoromethyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzoic acid

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In water; acetonitrile at 100℃; Suzuki Coupling; Inert atmosphere;	98%

methanol (67-56-1) + 3-Carboxyphenylboronic acid (25487-66-5) → [3-(methoxycarbonyl)phenyl]boronic acid (99769-19-4)

Conditions	Yield
With thionyl chloride at 55 - 65℃; Autoclave; Industrial scale;	97.1%
With sulfuric acid at 80℃; for 20h; Temperature;

3-Carboxyphenylboronic acid (25487-66-5) + dihydrogen peroxide (7722-84-1) → 3-Carboxyphenol (99-06-9)

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

3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-5-(((trifluoromethyl)sulfonyl)oxy)benzofuran-6-yl)propyl benzoate + 3-Carboxyphenylboronic acid (25487-66-5) → 3-(6-(3-(benzoyloxy)propyl)-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)benzoic acid

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 90℃; for 4h;	96%

3-Carboxyphenylboronic acid (25487-66-5) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → 2-(3-carboxyphenyl)-5,5-dimethyl-1,3,2-dioxaborinane

Conditions	Yield
In chloroform at 25℃; for 12h;	96%
In diethyl ether at 20℃; Inert atmosphere; Molecular sieve;

2-bromo-4-chlorophenol (695-96-5) + 3-Carboxyphenylboronic acid (25487-66-5) → 5'-chloro-2'-hydroxybiphenyl-3-carboxylic acid (376592-57-3)

Conditions	Yield
With palladium diacetate; sodium carbonate In water at 50℃; for 4h; Inert atmosphere;	95%
With palladium diacetate; sodium carbonate In water at 50℃; for 19h; Inert atmosphere;

3-Carboxyphenylboronic acid (25487-66-5) + 2-bromo-8-(trifluoromethoxy)-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one → 3-(11-oxo-8-(trifluoromethoxy)-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)benzoic acid

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; acetonitrile at 160℃; for 1h; Inert atmosphere; Microwave irradiation;	95%

3,5-dibromopyridine (625-92-3) + 3-Carboxyphenylboronic acid (25487-66-5) → 3,3’-(pyridine-3,5-diyl)dibenzoic acid (1429436-06-5)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In acetonitrile at 90℃; for 36h; Suzuki Coupling; Inert atmosphere;	93%

p-bromobenzamide (698-67-9) + 3-Carboxyphenylboronic acid (25487-66-5) → 3-(4'-aminocarbonylphenyl)benzoic acid

Conditions	Yield
With tetrabutylammomium bromide; sodium carbonate In water at 100℃; for 4h; Suzuki Coupling;	93%

2,3-dimethyl-2,3-butane diol (76-09-5) + 3-Carboxyphenylboronic acid (25487-66-5) → 3-carboxyphenylboronic acid pinacol ester (269409-73-6)

Conditions	Yield
In toluene for 12h; Reflux; Inert atmosphere;	92%
In ethyl acetate for 4h;	91%
With 1H-imidazole; iron(III) chloride In water; acetonitrile at 20℃; for 0.5h;	21.5%
In ethyl acetate for 4h; Inert atmosphere;

3-Carboxyphenylboronic acid (25487-66-5) → 3-Carboxyphenol (99-06-9)

Conditions	Yield
With copper(II) ferrite; water; sodium hydroxide at 40℃; for 24h; Green chemistry;	92%
With oxygen; triethylamine In water; acetonitrile at 25℃; for 8h; UV-irradiation;	86%
With oxygen; N-ethyl-N,N-diisopropylamine; [5,6]fullerene-C70 In chloroform; toluene at 20℃; for 12h; Irradiation;	66%

3-Carboxyphenylboronic acid (25487-66-5) + 1,3-bis(5-chloro-3-bromo-2-benzyloxyphenyl)urea → 1,3-bis(5-chloro-3-(m-carboxyphenyl)-2-benzyloxyphenyl)urea

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 75 - 80℃; for 2h; Suzuki Coupling; Inert atmosphere;	92%

2-bromo-6-nitro-phenol (13073-25-1) + 3-Carboxyphenylboronic acid (25487-66-5) → 2'-hydroxy-3'-nitro-biphenyl-3-carboxylic acid (376591-95-6)

Conditions	Yield
With palladium on activated charcoal; potassium carbonate In methanol; water for 6h; Inert atmosphere; Reflux;	92%

3-Carboxyphenylboronic acid (25487-66-5) + 2-bromopyrimidine (4595-60-2) → 3-(pyrimidin-2-yl)benzoic acid (579476-26-9)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In acetonitrile at 90℃; for 4h; Substitution; Suzuki reaction;	91%

2-bromo-5-nitropyridine (4487-59-6) + 3-Carboxyphenylboronic acid (25487-66-5) → 3-(5-nitropyridin-2-yl)benzoic acid (864075-95-6)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene for 48h; Suzuki Coupling; Heating / reflux;	91%

2-bromo-4-chlorophenol (695-96-5) + 3-Carboxyphenylboronic acid (25487-66-5) → potassium 5'-chloro-2'-hydroxybiphenyl-3-carboxylate

Conditions	Yield
Stage #1: 2-bromo-4-chlorophenol With potassium hydroxide In 1,2-dimethoxyethane; water Inert atmosphere; Stage #2: 3-Carboxyphenylboronic acid With 5%-palladium/activated carbon; potassium carbonate In 1,2-dimethoxyethane; water at 18 - 40℃; Inert atmosphere;	90.7%

(6-chloro-2-methoxy-pyrimidin-4-yl)-[2-(4-methoxy-phenyl)-ethyl]-amine (885066-04-6) + 3-Carboxyphenylboronic acid (25487-66-5) → 3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzoic acid

Conditions	Yield
Stage #1: (6-chloro-2-methoxy-pyrimidin-4-yl)-[2-(4-methoxy-phenyl)-ethyl]-amine; 3-Carboxyphenylboronic acid With caesium carbonate In 1,2-dimethoxyethane; water for 0.0833333h; Stage #2: tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 90℃; for 17h;	90.4%
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 90℃; for 17.0833h;	90.4%

1-bromo-2-naphthylamine (20191-75-7) + 3-Carboxyphenylboronic acid (25487-66-5) → 3-(2-aminonaphthalen-1-yl)benzoic acid

Conditions	Yield
With tetrabutylammomium bromide; palladium diacetate; sodium carbonate; potassium carbonate; disodium ethylenediamine tetraacetic acid In water for 16h; Reflux; Inert atmosphere;	90.4%

3-Carboxyphenylboronic acid (25487-66-5) + 5-bromosalicyclaldehyde (1761-61-1) → 3-(3-nitro-2-(2,4,5-trifluorophenyl)-2H-chromen-6-yl)benzoic acid

Conditions	Yield
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; caesium carbonate In water; N,N-dimethyl-formamide at 100℃; for 4h;	90.2%

3-Bromopyridine (626-55-1) + 3-Carboxyphenylboronic acid (25487-66-5) → 3-(pyridine-3-yl)benzoic acid (4385-77-7)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In acetonitrile at 90℃; for 16h; Substitution; Suzuki reaction;	90%
With potassium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; acetonitrile Reflux;	83%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,2-dimethoxyethane; water at 100℃; for 4h; Suzuki Coupling; Inert atmosphere;	70%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In acetonitrile at 90℃; for 36h; Suzuki Coupling; Inert atmosphere;	22%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In acetonitrile at 90℃; for 14h;

cyclopentyl 2-amino-2-methylpropanoate hydrochloride + 3-Carboxyphenylboronic acid (25487-66-5) → cyclopentyl N-[3-(dihydroxyboryl)benzoyl]-2-methylalaninate (1192471-48-9)

Conditions	Yield
Stage #1: 3-Carboxyphenylboronic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.333333h; Stage #2: cyclopentyl 2-amino-2-methylpropanoate hydrochloride In dichloromethane at 20℃; for 4h;	90%

3-bromobenzamide (22726-00-7) + 3-Carboxyphenylboronic acid (25487-66-5) → 3'-carbamoylbiphenyl-3-carboxylic acid

Conditions	Yield
With tetrabutylammomium bromide; sodium carbonate In water at 100℃; for 4h; Suzuki Coupling;	90%

Upstream product

• 17933-03-8 m-tolylboronic acid 
• 124-38-9 carbon dioxide 
• 626-00-6 1,3-Diiodobenzene 
• 150255-96-2 (3‐cyanophenyl)boronic acid 
• 535-80-8 3-chlorobenzoate 
• 98527-70-9 tris(3-bromo phenyl)boroxine 
• 269409-73-6 3-carboxyphenylboronic acid pinacol ester 
• 13061-96-6 dihydroxy-methyl-borane 
• 7722-64-7 potassium permanganate 
• 99-05-8 meta-aminobenzoic acid 
• 13675-18-8 tetrahydroxydiboron 

Downstream Products

• 397843-69-5 3-iso-propylaminocarbonylphenylboronic acid 
• 397843-71-9 3-phenylaminocarbonylphenylboronic acid 
• 1064458-00-9 methyl 5-(3-carboxyphenyl)-2-[(2,4-dichlorobenzoyl)amino]benzoate 
• 635757-61-8 4'-acetylbiphenyl-3-carboxylic acid 
• 460345-72-6 C₂₀H₁₉ClN₂O₃ 
• 304884-54-6 5-(3-carboxyphenyl)furane-2-carbaldehyde 
• 177171-15-2 2-amino-3'-biphenylcarboxylic acid 
• 868394-58-5 4'-carboxymethyl-biphenyl-3-carboxylic acid 
• 605683-57-6 3-[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-benzoic acid 
• 92152-01-7 biphenyl-3,4′-dicarboxylic acid 
• 874288-15-0 C₁₅H₁₆BNO₄ 
• 729-01-1 4'-nitrobiphenyl-3-carboxylic acid 
• 727396-17-0 3-(2,4-dimethoxyphenylmethylaminocarbonyl)-benzeneboronic acid 
• 877059-18-2 3-(7-benzyl-4-oxo-3-phenyl-4,7-dihydrofuro[2,3-b]pyridin-2-yl)benzoic acid 

Relevant articles and documents

Virtues of Volatility: A Facile Transesterification Approach to Boronic Acids

Boronic acids are an increasingly important compound class for many applications, including C-C bond formation reactions, medicinal chemistry, and diagnostics. The deprotection of boronic ester intermediates is frequently a problematic and inefficient step in boronic acid syntheses. We describe an approach that highly facilitates this transformation by leveraging the volatility of methylboronic acid and its diol esters. The method is performed under mild conditions, provides high yields, and eliminates cumbersome and problematic purification steps.

Preparation method for 3-carboxyphenylboronic acid

The invention discloses a preparation method for 3-carboxyphenylboronic acid, relating to the technical field of organic synthesis. The preparation method comprises the steps of performing Grignard reaction on m-bromomethyl benzene, magnesium scraps and iodine by using the m-bromomethyl benzene as a starting material, so as to generate a Grignard reagent, performing boronated reaction on the Grignard reagent and trimethyl borate so as to prepare 3-Tolylboronic acid, and oxidizing the 3-Tolylboronic acid with potassium permanganate in an alkaline condition so as to prepare 3-carboxyphenylboronic acid. According to the preparation method, cheap m-bromomethyl benzene easy to obtain is used as the starting material, the 3-carboxyphenylboronic acid is prepared through Grignard reaction, boronated reaction and oxidization reaction, the operations are simple, the average purity of the product 3-carboxyphenylboronic acid reaches 99.3%, and the average total yield reaches 50%. The product yield and purity are ensured at low cost, so that the preparation method is applicable to industrial production.

Sequential one-pot access to molecular diversity through aniline aqueous borylation

On the basis of our recently reported aniline aqueous borylation, molecular diversity was achieved in a one-pot process by combining other reactions such as esterification, Suzuki-Miyaura coupling, hydrogenolysis, or Petasis borono-Mannich.