1,3-Benzenediboronic acid supplier

Name
1,3-Benzenediboronic acid
EINECS
CAS No. 4612-28-6
Article Data5
CAS DataBase
Density 1.33g/cm³
Solubility Slightly soluble in water.
Melting Point >300°C
Formula C₆H₈B₂O₄
Boiling Point 456.4 °C at 760 mmHg
Molecular Weight 165.749
Flash Point 229.8 °C
Transport Information
Appearance
Safety 26-36/37/39
Risk Codes 36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xn
Synonyms Boronicacid, 1,3-phenylenebis- (9CI);m-Benzenediboronic acid (6CI,7CI,8CI);Benzene-1,3-diboronic acid;NSC 25409;m-Phenylenediboronic acid;
PSA 80.92000
LogP -2.95380

Synthetic route

: 13283-31-3
borane

: 7732-18-5
water

: 65844-89-5
1,3-bis-(trimethylstannyl)benzene

A: 1631-73-8
trimethylstannane

B: 4612-28-6
1,3-phenylenediboronic acid

Conditions

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%

...Expand

: 10294-33-4
boron tribromide

: 71-43-2
benzene

: 4612-28-6
1,3-phenylenediboronic acid

Conditions

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

: 116865-44-2
1,3-(BCl2)2-C6H4

: 4612-28-6
1,3-phenylenediboronic acid

Conditions

Conditions	Yield
hydrolysis;

: 126-30-7
2,2-Dimethyl-1,3-propanediol

: 4612-28-6
1,3-phenylenediboronic acid

: C16H24B2O4

Conditions

Conditions	Yield
In methanol at 40℃;	100%

: 608-69-5
dimethyl D/L-tartrate

: 4612-28-6
1,3-phenylenediboronic acid

: C18H20B2O12

Conditions

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

: 81691-59-0
(2RS,3RS)-2,3-dihydroxy-3-phenyl-propionic acid methyl ester

: 4612-28-6
1,3-phenylenediboronic acid

: dimethyl 2,2′-(1,3-phenylene)bis(5-phenyl-1,3,2-dioxaborolane-4-carboxylate)

Conditions

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

: 4850-49-1
1-phenyl-1,3-propanediol

: 4612-28-6
1,3-phenylenediboronic acid

: 1,3-bis(4-phenyl-1,3,2-dioxaborinan-2-yl)benzene

Conditions

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

: 88196-06-9
syn-1-phenylpropane-1,2-diol

: 4612-28-6
1,3-phenylenediboronic acid

: 1,3-bis(4-methyl-5-phenyl-1,3,2-dioxaborolan-2-yl)benzene

Conditions

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

: 655-48-1
DL-1,2-diphenylethane-1,2-diol

: 4612-28-6
1,3-phenylenediboronic acid

: 1,3-bis(4,5-diphenyl-1,3,2-dioxaborolan-2-yl)benzene

Conditions

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

: dibenzyl DL-tartrate

: 4612-28-6
1,3-phenylenediboronic acid

: tetrabenzyl 2,2′-(1,3-phenylene)bis(1,3,2-dioxaborolane-4,5-dicarboxylate)

Conditions

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

: 3-(3-bromophenyl)propanenitrile

: 4612-28-6
1,3-phenylenediboronic acid

: 1654738-10-9
C24H20N2

Conditions

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

: 4612-28-6
1,3-phenylenediboronic acid

A: 626-17-5
benzene-1,3-dicarbonitrile

B: 16937-03-4
4-nitro-N-(4-chlorophenyl)benzenesulfonamide

Conditions

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

...Expand

: 4-bromo-N-(4-chlorophenyl)-N-cyanobenzenesulfonamide

: 4612-28-6
1,3-phenylenediboronic acid

A: 626-17-5
benzene-1,3-dicarbonitrile

B: 6295-97-2
4-bromo-benzenesulfonic acid-(4-chloro-anilide)

Conditions

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

...Expand

: 119986-58-2
N-(4-chlorophenyl)-N-cyano-4-methylbenzenesulfonamide

: 4612-28-6
1,3-phenylenediboronic acid

A: 626-17-5
benzene-1,3-dicarbonitrile

B: 2903-34-6
4-methyl-N-(4-chlorophenyl)benzenesulfonamide

Conditions

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

...Expand

: ethyl 3,5-dimethyl-4-(trifluoromethylsulfonyloxy)benzoate

: 4612-28-6
1,3-phenylenediboronic acid

: C28H30O4

Conditions

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

: 1268244-56-9
9-(4-chloro-6-phenyl-1,3,5-triazine-2-yl)-9H-carbazole

: 4612-28-6
1,3-phenylenediboronic acid

: C48H30N8

Conditions

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

: 4612-28-6
1,3-phenylenediboronic acid

: 108-46-3
recorcinol

Conditions

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%

: 55717-45-8
6-bromo-pyridin-3-ol

: 4612-28-6
1,3-phenylenediboronic acid

: 1,3-di(5-hydroxy-2-pyridyl)benzene

Conditions

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

: 4612-26-4
1,4-Phenyldiboronic acid

: 4612-28-6
1,3-phenylenediboronic acid

: 570414-33-4
2,7-dibromo-9,9-bis(6-bromohexyl)fluorene

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: 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

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

...Expand

: 615-36-1
2-bromoaniline

: 4612-28-6
1,3-phenylenediboronic acid

: 95919-19-0
2,2''-diamino-[1,1';3',1'']terphenyl

Conditions

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

: C18H16Br2

: 4612-28-6
1,3-phenylenediboronic acid

: C24H22BBrO2

Conditions

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

: 78839-75-5
2-bromo-N-(tert-butoxycarbonyl)aniline

: 4612-28-6
1,3-phenylenediboronic acid

: C28H32N2O4

Conditions

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%

: 683251-61-8
methyl 2-(2-bromothiophene-3-yl)acetate

: 4612-28-6
1,3-phenylenediboronic acid

: 1419171-74-6
methyl 2-(2-{3-[3-(2-methoxy-2-oxoethyl)thiophen-2-yl]phenyl}thiophen-3-yl)acetate

Conditions

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

: 4612-28-6
1,3-phenylenediboronic acid

: C34H18N8

Conditions

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

: 4612-28-6
1,3-phenylenediboronic acid

: C44H44B4O8

Conditions

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

: C16H14BrF2NO

: 4612-28-6
1,3-phenylenediboronic acid

: 104560-41-0
N1,N1,N3,N3-tetrabenzylisophthalamide

Conditions

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

: 4612-28-6
1,3-phenylenediboronic acid

: C72H52N6Si2

Conditions

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

: 19493-44-8
1-chloroisoquinoline

: 4612-28-6
1,3-phenylenediboronic acid

: 1,3-bis(1-isoquinolyl)benzene

Conditions

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

: 610-94-6
2-bromobenzoic acid methyl ester

: 4612-28-6
1,3-phenylenediboronic acid

: dimethyl [1,1':3',1''-terphenyl]-2,2''-dicarboxylate

Conditions

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

: C30H17BrN2

: 4612-28-6
1,3-phenylenediboronic acid

: C36H23BN2O2

Conditions

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%

: 4612-26-4
1,4-Phenyldiboronic acid

: 4612-28-6
1,3-phenylenediboronic acid

: 570414-33-4
2,7-dibromo-9,9-bis(6-bromohexyl)fluorene

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: 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

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

...Expand

: 25372-02-5
1-(3-bromophenyl)-1H-imidazole

: 4612-28-6
1,3-phenylenediboronic acid

: 3,3’‘-di(1H-imidazol-1-yl)-1,1′:3′,1’‘-terphenyl

Conditions

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%

1,3-Benzenediboronic acid Specification

The 1,3-Benzenediboronic acid with the CAS number 4612-28-6 is also called Boronic acid,B,B'-1,3-phenylenebis-. The systematic name is benzene-1,3-diyldiboronic acid. Its molecular formula is C₆H₈B₂O₄. This chemical should be stored in dry and cool environment.

The properties of the 1,3-Benzenediboronic acid are: (1)ACD/LogP: 0.96; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 4; (4)#H bond donors: 4; (5)#Freely Rotating Bonds: 6; (6)Polar Surface Area: 36.92 Å²; (7)Index of Refraction: 1.555; (8)Molar Refractivity: 39.82 cm³; (9)Molar Volume: 124 cm³; (10)Polarizability: 15.78×10^-24cm³; (11)Surface Tension: 55.1 dyne/cm; (12)Enthalpy of Vaporization: 75.48 kJ/mol; (13)Vapour Pressure: 4.03×10^-9 mmHg at 25°C.

While using this chemical, you should be very cautious. This chemical is harmful by inhalation, in contact with skin and if swallowed. It is not only irritating to skin, but also irritating to eyes and respiratory system. Therefore, you should take the following instructions. Firstly, you should wear suitable protective clothing, gloves and eye/face protection. Then in case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: OB(O)c1cccc(B(O)O)c1
(2)InChI: InChI=1/C6H8B2O4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4,9-12H
(3)InChIKey: UXPAASVRXBULRG-UHFFFAOYAZ

Product Name

1,3-Benzenediboronic acid

Synthetic route

1,3-Benzenediboronic acid Specification

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