4612-28-6

Basic information

• Product Name: 1,3-Benzenediboronic acid
• Synonyms: 1,3-Phenylenediboronic acid;1,3-BENZENEDIBORONIC ACID;1,3-Benzenediboronicacid,97%;1,3-Benzendibororic Acid;(3-boronophenyl)boronic acid;[3-(dihydroxyboranyl)phenyl]boronic acid;1,3-Benzendiboronic acid;{2-[(hydroxyboranyl)oxy]phenyl}boronic acid
• CAS NO: 4612-28-6
• Molecular Formula: C₆H₈B₂O₄
• Molecular Weight: 165.75
• Mol File: 4612-28-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: >300°C
• Boiling Point: 456.4 °C at 760 mmHg
• Flash Point: 229.8 °C
• Appearance: /
• Density: 1.33g/cm³
• Vapor Pressure: 4.03E-09mmHg at 25°C
• Refractive Index: 1.555
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 8.14±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 1,3-Benzenediboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Benzenediboronic acid(4612-28-6)
• EPA Substance Registry System: 1,3-Benzenediboronic acid(4612-28-6)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36/37/39-36
• Hazardous Substances Data: 4612-28-6(Hazardous Substances Data)

Usage

Chemical Properties

solid

InChI:InChI=1/C6H8B2O4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4,9-12H

Synthetic route

borane (13283-31-3) + water (7732-18-5) + 1,3-bis-(trimethylstannyl)benzene (65844-89-5) → trimethylstannane (1631-73-8) + 1,3-phenylenediboronic acid (4612-28-6)

Conditions	Yield
In tetrahydrofuran (N2); addn. of a soln. of boron compd. in THF to a soln. of tin compd. in THF, stirring at room temp. for 1 h, refluxing for 3 h, addn. of water;	A n/a B 82%

boron tribromide (10294-33-4) + benzene (71-43-2) → 1,3-phenylenediboronic acid (4612-28-6)

Conditions	Yield
With aluminium trichloride first step of react. at 80°C in presence of AlCl3, hydrolysis of bis(dibromoboryl) compound in situ;

1,3-(BCl2)2-C6H4 (116865-44-2) → 1,3-phenylenediboronic acid (4612-28-6)

Conditions	Yield
hydrolysis;

2,2-Dimethyl-1,3-propanediol (126-30-7) + 1,3-phenylenediboronic acid (4612-28-6) → C16H24B2O4

Conditions	Yield
In methanol at 40℃;	100%

dimethyl D/L-tartrate (608-69-5) + 1,3-phenylenediboronic acid (4612-28-6) → C18H20B2O12

Conditions	Yield
In methanol at 20℃; for 0.333333h; Molecular sieve;	100%

(2RS,3RS)-2,3-dihydroxy-3-phenyl-propionic acid methyl ester (81691-59-0) + 1,3-phenylenediboronic acid (4612-28-6) → dimethyl 2,2′-(1,3-phenylene)bis(5-phenyl-1,3,2-dioxaborolane-4-carboxylate)

Conditions	Yield
In methanol at 20℃; for 0.333333h; Molecular sieve;	100%

1-phenyl-1,3-propanediol (4850-49-1) + 1,3-phenylenediboronic acid (4612-28-6) → 1,3-bis(4-phenyl-1,3,2-dioxaborinan-2-yl)benzene

Conditions	Yield
In methanol at 20℃; for 0.333333h; Molecular sieve;	100%

syn-1-phenylpropane-1,2-diol (88196-06-9) + 1,3-phenylenediboronic acid (4612-28-6) → 1,3-bis(4-methyl-5-phenyl-1,3,2-dioxaborolan-2-yl)benzene

Conditions	Yield
In methanol at 20℃; for 0.333333h; Molecular sieve;	100%

DL-1,2-diphenylethane-1,2-diol (655-48-1) + 1,3-phenylenediboronic acid (4612-28-6) → 1,3-bis(4,5-diphenyl-1,3,2-dioxaborolan-2-yl)benzene

Conditions	Yield
In methanol at 20℃; for 0.333333h; Molecular sieve;	100%

dibenzyl DL-tartrate + 1,3-phenylenediboronic acid (4612-28-6) → tetrabenzyl 2,2′-(1,3-phenylene)bis(1,3,2-dioxaborolane-4,5-dicarboxylate)

Conditions	Yield
In methanol at 20℃; for 0.333333h; Molecular sieve;	100%

3-(3-bromophenyl)propanenitrile + 1,3-phenylenediboronic acid (4612-28-6) → C24H20N2 (1654738-10-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 120℃; for 0.25h; Inert atmosphere; Microwave irradiation;	95%

N-(4-chlorophenyl)-N-cyano-4-nitrobenzenesulfonamide + 1,3-phenylenediboronic acid (4612-28-6) → benzene-1,3-dicarbonitrile (626-17-5) + 4-nitro-N-(4-chlorophenyl)benzenesulfonamide (16937-03-4)

Conditions	Yield
With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 14h; Catalytic behavior; Reflux;	A 95% B n/a

4-bromo-N-(4-chlorophenyl)-N-cyanobenzenesulfonamide + 1,3-phenylenediboronic acid (4612-28-6) → benzene-1,3-dicarbonitrile (626-17-5) + 4-bromo-benzenesulfonic acid-(4-chloro-anilide) (6295-97-2)

Conditions	Yield
With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 15h; Catalytic behavior; Reflux;	A 93% B n/a

N-(4-chlorophenyl)-N-cyano-4-methylbenzenesulfonamide (119986-58-2) + 1,3-phenylenediboronic acid (4612-28-6) → benzene-1,3-dicarbonitrile (626-17-5) + 4-methyl-N-(4-chlorophenyl)benzenesulfonamide (2903-34-6)

Conditions	Yield
With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 16h; Catalytic behavior; Reflux;	A 92% B n/a

ethyl 3,5-dimethyl-4-(trifluoromethylsulfonyloxy)benzoate + 1,3-phenylenediboronic acid (4612-28-6) → C28H30O4

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 100℃; for 72h; Sealed tube; Inert atmosphere; Schlenk technique;	92%

9-(4-chloro-6-phenyl-1,3,5-triazine-2-yl)-9H-carbazole (1268244-56-9) + 1,3-phenylenediboronic acid (4612-28-6) → C48H30N8

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 24h; Reflux;	90%

1,3-phenylenediboronic acid (4612-28-6) → recorcinol (108-46-3)

Conditions	Yield
With Fe2O3-SiO2 nanoparticles; air In water at 50℃; for 3h; Green chemistry;	89%
With [Cu6I2(μ4-I)2(μ4-5-phpymt)2]; triethylamine In water; acetonitrile for 48h; Catalytic behavior; Solvent; Time; UV-irradiation;	74%

6-bromo-pyridin-3-ol (55717-45-8) + 1,3-phenylenediboronic acid (4612-28-6) → 1,3-di(5-hydroxy-2-pyridyl)benzene

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In 1,4-dioxane; water at 101℃; for 24h; Inert atmosphere;	89%

1,4-Phenyldiboronic acid (4612-26-4) + 1,3-phenylenediboronic acid (4612-28-6) + 2,7-dibromo-9,9-bis(6-bromohexyl)fluorene (570414-33-4) → polymer, Mw 29000 g/mol, Mn 14720 g/mol; monomer(s): 2,7-dibromo-9,9-bis(6\-bromohexyl)fluorene; 1,4-phenyldiboronic acid; 1,3-diphenylboronic acid

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In tetrahydrofuran at 85℃; for 24h; Suzuki copolymerization;	88%

2-bromoaniline (615-36-1) + 1,3-phenylenediboronic acid (4612-28-6) → 2,2''-diamino-[1,1';3',1'']terphenyl (95919-19-0)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In tetrahydrofuran; water at 70℃;	88%

C18H16Br2 + 1,3-phenylenediboronic acid (4612-28-6) → C24H22BBrO2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 110℃; Inert atmosphere;	88%

2-bromo-N-(tert-butoxycarbonyl)aniline (78839-75-5) + 1,3-phenylenediboronic acid (4612-28-6) → C28H32N2O4

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In water; N,N-dimethyl-formamide at 20 - 90℃; Suzuki-Miyaura cross-coupling; Inert atmosphere;	87%

methyl 2-(2-bromothiophene-3-yl)acetate (683251-61-8) + 1,3-phenylenediboronic acid (4612-28-6) → methyl 2-(2-{3-[3-(2-methoxy-2-oxoethyl)thiophen-2-yl]phenyl}thiophen-3-yl)acetate (1419171-74-6)

Conditions	Yield
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium carbonate In methanol; toluene at 60℃; for 1h; Suzuki Coupling; Inert atmosphere;	87%
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium carbonate In methanol; toluene at 60℃; for 1h; Suzuki Coupling; Inert atmosphere;	87%

C14H7BrN4 + 1,3-phenylenediboronic acid (4612-28-6) → C34H18N8

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol for 12h; Inert atmosphere; Reflux;	86%

(1S,2R,5S,6R)-3,3,7,7-Tetramethyl-1,2,3,5,6,7-hexahydro-s-indacene-1,2,5,6-tetraol + 1,3-phenylenediboronic acid (4612-28-6) → C44H44B4O8

Conditions	Yield
In methanol at 20℃; for 24h;	85%

C16H14BrF2NO + 1,3-phenylenediboronic acid (4612-28-6) → N1,N1,N3,N3-tetrabenzylisophthalamide (104560-41-0)

Conditions	Yield
With potassium fluoride; 5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene; copper(ll) bromide; magnesium chloride for 8h; Inert atmosphere; Heating;	85%

C33H24ClN3Si + 1,3-phenylenediboronic acid (4612-28-6) → C72H52N6Si2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 24h; Reflux;	84%

1-chloroisoquinoline (19493-44-8) + 1,3-phenylenediboronic acid (4612-28-6) → 1,3-bis(1-isoquinolyl)benzene

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 72h; Suzuki Coupling; Inert atmosphere; Reflux;	82%

2-bromobenzoic acid methyl ester (610-94-6) + 1,3-phenylenediboronic acid (4612-28-6) → dimethyl [1,1':3',1''-terphenyl]-2,2''-dicarboxylate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 70℃; Suzuki-Miyaura Coupling;	80%

C30H17BrN2 + 1,3-phenylenediboronic acid (4612-28-6) → C36H23BN2O2

Conditions	Yield
Stage #1: C30H17BrN2; 1,3-phenylenediboronic acid With sodium carbonate In ethanol; water; toluene for 1h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene for 15h; Inert atmosphere; Reflux;	79.31%

1,4-Phenyldiboronic acid (4612-26-4) + 1,3-phenylenediboronic acid (4612-28-6) + 2,7-dibromo-9,9-bis(6-bromohexyl)fluorene (570414-33-4) → polymer, Mw 17340 g/mol, Mn 10080 g/mol; monomer(s): 2,7-dibromo-9,9-bis(6\-bromohexyl)fluorene; 1,4-phenyldiboronic acid; 1,3-diphenylboronic acid

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In tetrahydrofuran at 85℃; for 24h; Suzuki copolymerization;	78%

1-(3-bromophenyl)-1H-imidazole (25372-02-5) + 1,3-phenylenediboronic acid (4612-28-6) → 3,3’‘-di(1H-imidazol-1-yl)-1,1′:3′,1’‘-terphenyl

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; tetrabutyl ammonium fluoride In tetrahydrofuran; N,N-dimethyl-formamide at 90℃; for 72h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	78%

Upstream product

• 13283-31-3 borane 
• 7732-18-5 water 
• 65844-89-5 1,3-bis-(trimethylstannyl)benzene 
• 10294-33-4 boron tribromide 
• 71-43-2 benzene 
• 116865-44-2 1,3-(BCl₂)2-C₆H₄ 

Downstream Products

• 883738-23-6 3-(3-methyl-3H-imidazol-4-yl)-phenylboronic acid 
• 7330-44-1 1,3-bis(di-n-butoxy)-boryl-phenylene 
• 1071444-88-6 C₂₃H₁₉NO₄ 
• 1071444-89-7 C₂₃H₁₉NO₄ 
• 912844-37-2 C₂₄H₂₁NO₃S 
• 912844-36-1 C₂₂H₁₈N₂O₃S 
• 912844-39-4 C₂₄H₂₀N₂O₃ 
• 912844-38-3 C₂₄H₂₁NO₃S 
• 1071444-96-6 C₂₃H₁₉N₃O₃ 
• 912844-35-0 C₂₄H₂₁NO₃S 
• 1071444-92-2 C₂₃H₂₁N₃O₃ 
• 503468-73-3 C₂₅H₂₁NO₃ 
• 1071444-85-3 C₂₄H₂₁NO₃S 
• 912844-32-7 C₂₄H₂₀N₂O₃ 

Relevant articles and documents

Synthesis of benzene- and pyridinediboronic acids via organotin compounds

The synthesis of benzene- and pyridinediboronic acids via the organotin compounds was discussed. The organotin compound was dissolved in dry tetrahydrofuran (THF) and treated with a solution of borane in the same solvent under dry nitrogen. The physical characteristics of the compounds formed were found to be in agreement with those found in the literature.