1,4-Phenylenebisboronic acid supplier

Name
1,4-Phenylenebisboronic acid
EINECS 628-888-0
CAS No. 4612-26-4
Article Data17
CAS DataBase
Density 1.33 g/cm³
Solubility Soluble in water 2.5%.
Melting Point >350 °C(lit.)
Formula C₆H₈B₂O₄
Boiling Point 420.1 °C at 760 mmHg
Molecular Weight 165.749
Flash Point 207.9 °C
Transport Information
Appearance off-white powder
Safety 36-26
Risk Codes 22-36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xi, C, Xn
Synonyms Boronicacid, 1,4-phenylenebis- (9CI);p-Benzenediboronic acid (6CI,7CI,8CI);1,4-Phenylenediboronic acid;Benzene-1,4-diboronic acid;NSC 25410;p-Phenylenebis(boric acid);p-Phenylenediboronic acid;
PSA 80.92000
LogP -2.95380

Synthetic route

: 106-37-6
1.4-dibromobenzene

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

Conditions

Conditions	Yield
Stage #1: 1.4-dibromobenzene With magnesium In tetrahydrofuran Reflux; Stage #2: With Trimethyl borate In tetrahydrofuran; diethyl ether at -70℃; Stage #3: With sulfuric acid; water In tetrahydrofuran; diethyl ether at 20℃;	88%
Stage #1: 1.4-dibromobenzene With magnesium In tetrahydrofuran Heating; Stage #2: With Trimethyl borate In tetrahydrofuran at -70℃; for 2h; Stage #3: With hydrogenchloride In tetrahydrofuran pH=3;	35%
Stage #1: 1.4-dibromobenzene With magnesium In tetrahydrofuran Metallation; Stage #2: With Trimethyl borate In tetrahydrofuran at -78℃; Substitution; Stage #3: With hydrogen cation at 0℃; Substitution;

: 121-43-7
Trimethyl borate

: 106-37-6
1.4-dibromobenzene

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

Conditions

Conditions	Yield
Stage #1: 1.4-dibromobenzene With iodine; magnesium In tetrahydrofuran at 30℃; for 3h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at -70℃; for 1h; Temperature; Concentration;	84.6%
Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: Trimethyl borate In tetrahydrofuran; hexane for 2h;	47%

: 13283-31-3
borane

: 7732-18-5
water

: 1012-73-3
1,4-bis(trimethylstannyl)benzene

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

B: 1631-73-8
trimethylstannane

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 83% B n/a

...Expand

: 7647-01-0
hydrogenchloride

: 121-43-7
Trimethyl borate

: 106-37-6
1.4-dibromobenzene

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

Conditions

Conditions	Yield
Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: Trimethyl borate In tetrahydrofuran; hexane for 2h; Stage #3: hydrogenchloride In tetrahydrofuran; hexane; water	47%

...Expand

: 2425-81-2
phen-1,4-ylenbis(magnesiumbromid)

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

Conditions

Conditions	Yield
(i) B(OMe)3, (ii) aq. H2SO4; Multistep reaction;

: 71258-12-3
1,4-bis(dichloroboryl)benzene

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

Conditions

Conditions	Yield
hydrolysis;

: 121-43-7
Trimethyl borate

: (4-ClC6H4)BF2

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

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

Conditions

Conditions	Yield
With Na In hexane
With Na In hexane

...Expand

: 93687-09-3
C10H16B2O4

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

Conditions

Conditions	Yield
With sulfuric acid; water at 0℃; Inert atmosphere;	3.44 g
With hydrogenchloride; water at 20℃; for 1h;	1.6 g

: 2449-19-6
1,4-bis(di-n-butoxy)-boryl-phenylene

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrachloromethane View Scheme
Multi-step reaction with 2 steps 1: tetrachloromethane View Scheme

: 121-43-7
Trimethyl borate

: 106-37-6
1.4-dibromobenzene

: 7732-18-5
water

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

Conditions

Conditions	Yield
With HCl In tetrahydrofuran (inert atm.); addn. of THF soln. of dibromobenzene to Mg in dry THF, refluxing for 24-48 h, addn. of trimethylborate in dry THF, refluxing for 2h, addn. into aq. HCl, stirring at room temp. for 1 h; extn. (diethyl ether), drying over Na2SO4, filtration, evapn., NMR and MS;

...Expand

: C18H32B2O4

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

Conditions

Conditions	Yield
With water In water Inert atmosphere;

: 13675-18-8
tetrahydroxydiboron

: 637-87-6
1-Chloro-4-iodobenzene

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

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

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

: 5565-36-6
1,4-bis-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzene

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 12h; Inert atmosphere; Reflux;	100%
With toluene-4-sulfonic acid In benzene for 24h; Reflux; Dean-Stark;	90%
In toluene for 24h; Reflux;	80%
With toluene-4-sulfonic acid In benzene at 70℃; for 12h;

: 5034-74-2
5-bromo-3-methoxysalicylaldehyde

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

: 4,4''-dihydroxy-5,5''-dimethoxy-[1,1':4',1''-terphenyl]-3,3''-dicarbaldehyde

Conditions

Conditions	Yield
With palladium diacetate; potassium carbonate; triphenylphosphine In 1,2-dimethoxyethane; water for 24h; Reflux;	100%

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

: 586-78-7
para-nitrophenyl bromide

: 3282-11-9
p,p-dinitro-p-terphenyl

Conditions

Conditions	Yield
With [PdCl2(2-pyridin-2-yl-benzo[b]thiophen-3-ol)]; potassium carbonate In water; N,N-dimethyl-formamide at 90℃; for 6h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Suzuki-Miyaura Coupling;	99%
With palladium; potassium carbonate In methanol; acetonitrile at 20℃; for 2h; Suzuki Coupling;	88%
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 18h; Suzuki cross-coupling; Heating;	76%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 65h;	54%

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

: 695150-26-6
7,8,13,14-tetrahydro-6-(3'-bromophenyl)chino[8,7-k][1,8]phenanthroline

: 3,3''-di-(7,8,13,14-tetrahydroquino[8,7-k][1,8]phenanthrolin-6-yl)-[1,1';4',1'']terphenyl

Conditions

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In methanol; toluene for 24h; Suzuki cross-coupling reaction; Heating;	99%

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

: 120-80-9
benzene-1,2-diol

: 98494-81-6
2,2'-(1,4-phenylene)bis-1,3,2-benzodioxaborole

Conditions

Conditions	Yield
In toluene for 48h; Heating;	99%
In dichloromethane; ethyl acetate at 20℃;	36%
In water; toluene byproducts: H2O; bisdioxaborole synthesized from mixt. of diboronic acid and excess catechol through azeotropic removal of water with toluene; unreacted catechol sublimited under reduced pressure; (1)H NMR, MS;
Stage #1: 1,4-Phenyldiboronic acid; benzene-1,2-diol With 4,4'-bipyridine In tetrahydrofuran; toluene for 4h; Inert atmosphere; Dean-Stark; Reflux; Stage #2: In chloroform-d1 Heating; Inert atmosphere;

: 623-00-7
4-bromobenzenecarbonitrile

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

: 17788-93-1
[1,1′:4′,1”‐terphenyl]‐4,4″‐dicarbonitrile

Conditions

Conditions	Yield
With C37H28N8O2Cl(1-)Pd(2+); potassium carbonate In ethanol at 70℃; for 2h; Suzuki-Miyaura Coupling;	99%
With [PdCl2(2-pyridin-2-yl-benzo[b]thiophen-3-ol)]; potassium carbonate In water; N,N-dimethyl-formamide at 90℃; for 6h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Suzuki-Miyaura Coupling;	95%
With palladium; potassium carbonate In methanol; acetonitrile at 20℃; for 2h; Suzuki Coupling;	86%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In methanol; toluene at 80℃; for 12h; Suzuki coupling;	73%

: 2446-83-5
di-isopropyl azodicarboxylate

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

: 1,2-bis(isopropoxycarbonyl)-1-(4-(1,2-bis(isopropoxycarbonyl)hydrazinyl)phenyl)hydrazine

Conditions

Conditions	Yield
2,9-dimethyl-1,10-phenanthroline-based palladium(II) complex In N,N-dimethyl-formamide at 60℃; for 12h;	99%

: 108-86-1
bromobenzene

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

: 92-94-4
[1,1';4',1'']terphenyl

Conditions

Conditions	Yield
With C37H28N8O2Cl(1-)Pd(2+); potassium carbonate In ethanol at 70℃; for 2h; Suzuki-Miyaura Coupling;	99%
With 1,3-bis[3-(3-phenylpropyl)-1-ylbenzimidazolium]propane dibromide; palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 0.0833333h; Reagent/catalyst; Suzuki-Miyaura Coupling; Microwave irradiation;	94%
With palladium diacetate; 3,3'-(propane-1,3-diyl)bis(1-pentyl-1,3-dihydro-2H-benzo[d]imidazole-2-tellurone); potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 0.166667h; Reagent/catalyst; Suzuki-Miyaura Coupling; Microwave irradiation;	73%
With palladium diacetate; potassium carbonate In 2-methoxy-ethanol; water at 21℃; for 0.25h; Suzuki coupling;	98 %Chromat.

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

: 99-90-1
para-bromoacetophenone

: 4191-07-5
1,1'-(1,1':4',1''-terphenyl-4,4''-diyl)diethanone

Conditions

Conditions	Yield
With C37H28N8O2Cl(1-)Pd(2+); potassium carbonate In ethanol at 70℃; for 2h; Suzuki-Miyaura Coupling;	99%
With palladium; potassium carbonate In methanol; acetonitrile at 20℃; for 2h; Suzuki Coupling;	87%

: 1444011-04-4
C34H38O6

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

: 1444011-06-6
C80H76B4O12

Conditions

Conditions	Yield
In chloroform-d1; d(4)-methanol at 50℃; Inert atmosphere;	99%

: C76H102O12

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

: C164H204B4O24

Conditions

Conditions	Yield
In methanol; chloroform at 50℃; Molecular sieve;	99%

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

: 599575-85-6
2,5-dibromo-N,N'-bis-(4-octyl-phenyl)-benzene-1,4-diamine

polymer, product of polymerization by Suzuki coupling, Mw 7900 Da, PDI 1.8; monomer(s): benzene-1,4-diboronic acid; 2,5-dibromo-N,N\-bis(4-octylphenyl)-1,4-phenylenediamine: polymer, product of polymerization by Suzuki coupling, Mw 7900 Da, PDI 1.8; monomer(s): benzene-1,4-diboronic acid; 2,5-dibromo-N,N\-bis(4-octylphenyl)-1,4-phenylenediamine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 80℃; Suzuki coupling;	98%

: 908015-73-6
2-(2-bromo-6-fluoro-1H-indol-3-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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

: 1,4-bis-[2-(6-fluoro-1H-indol-3-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester]benzene

Conditions

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 100℃; for 5h;	98%

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

: 1122-91-4
4-bromo-benzaldehyde

: 62940-38-9
[1,1′:4′,1″-terphenyl]-4,4″-dicarbaldehyde

Conditions

Conditions	Yield
With [PdCl2(2-pyridin-2-yl-benzo[b]thiophen-3-ol)]; potassium carbonate In water; N,N-dimethyl-formamide at 90℃; for 8h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Suzuki-Miyaura Coupling;	98%
With palladium; potassium carbonate In methanol; acetonitrile at 20℃; for 2h; Suzuki Coupling;	82%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 80℃; for 8.5h; Suzuki-Miyaura Coupling; Inert atmosphere;	72.5%
With tetrakis(triphenylphosphine) palladium(0); water; sodium carbonate In tetrahydrofuran; toluene at 80℃; for 48h; Suzuki coupling; Inert atmosphere;	34%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; toluene at 80℃; for 7h; Suzuki-Miyaura cross-coupling;	32%

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

: 143444-51-3
N-<1(S)-methyl-2(R)-phenyl-2-hydroxyethyl>sarcosine

: (+)-(N->B)(N'->B')-1,4-phenylenebis{N-methyl-N-(1-(S)-methyl-2-(R)-phenyl-2-oxyethyl)aminoacetate-O,O',N}bisboron

Conditions

Conditions	Yield
In ethanol; benzene addn. of boronic acid to a soln. of glycine derivate in C2H5OH/C6H6, reflux for 8 h; evapn. (vac.);	98%

p-nitrobenzene iodide: p-nitrobenzene iodide

: 1591-31-7
4-iodo-biphenyl

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

: 25627-14-9
4-nitro-1,1':4',1'':4'',1'''-quaterphenyl

Conditions

Conditions	Yield
Stage #1: p-nitrobenzene iodide; 1,4-Phenyldiboronic acid With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol; water; toluene Suzuki cross-coupling; Stage #2: 4-iodo-biphenyl With tetrakis(triphenylphosphine) palladium(0) In methanol; water; toluene for 32h; Reflux;	98%

...Expand

: 1007375-07-6
1-bromo-2-methoxy-3-tert-butylbenzene

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

: 1205536-15-7
3,3"-di-tert-butyl-2,2"-dimethoxy[1,1';4',1"]terphenyl

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 20h; Suzuki coupling; Inert atmosphere;	98%

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

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

: 99770-93-1
benzene-1,4-diboronic acid bispinacol ester

Conditions

Conditions	Yield
With magnesium sulfate In methanol at 30℃;	97%
In diethyl ether at 20℃; for 12h;	95%
In N,N-dimethyl-formamide at 20℃; for 12h;	93%

: 41939-99-5
1-phenyl-1,2-propanedione 2-oxime 1-hydrazone

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

: iron(II) bromide

: {{Fe(PMXY)3}2B2C6H4}Br2

Conditions

Conditions	Yield
In ethanol Dissolving/suspending of PMXY in absolute EtOH, outgassing of mixt. with N2, and then addn. of FeBr2. B-compd. is added to resulting orange-brown suspn., and mixt. is stirred (2 h, N2).; Filtn. of pptd. solid via suction and washing with EtOH followed by ethyl ether.;	97%

...Expand

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

: 112776-83-7
diethyl 4-bromo-2,6-pyridinedicarboxylate

: C28H28N2O8

Conditions

Conditions	Yield
Stage #1: 1,4-Phenyldiboronic acid; diethyl 4-bromo-2,6-pyridinedicarboxylate With potassium carbonate In water; toluene at 60℃; for 1h; Suzuki Coupling; Inert atmosphere; Stage #2: With tris(dibenzylideneacetone)dipalladium; tri-tert-butyl phosphine In water; toluene at 80℃; for 0.25h;	97%

: C42H42O6

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

: C96H84B4O12

Conditions

Conditions	Yield
In methanol; chloroform at 50℃; Molecular sieve;	97%

: 591-50-4
iodobenzene

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

: 92-94-4
[1,1';4',1'']terphenyl

Conditions

Conditions	Yield
With potassium carbonate In water; N,N-dimethyl-formamide at 20℃; for 2h; Catalytic behavior; Suzuki Coupling; Inert atmosphere; Irradiation;	97%
With potassium phosphate In ethanol; water at 80℃; for 1h; Suzuki-Miyaura Coupling; Inert atmosphere;	99 %Chromat.

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

: 5-bromo-2-methoxybenzoate

: methyl 4,4′′-dimethoxy-[1,1′:4′,1′′-terphenyl]-3,3′′-dicarboxylate

Conditions

Conditions	Yield
With C45H58ClNPPd; potassium carbonate In tetrahydrofuran; water for 20h; Reflux;	96.4%

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

: 107-21-1
ethylene glycol

: 94934-64-2
1,4-bis(1,3,2-dioxaborolanyl)benzene

Conditions

Conditions	Yield
In toluene for 2h; Heating;	96%

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

: (1S,2R,5S,6R)-3,3,7,7-Tetramethyl-1,2,3,5,6,7-hexahydro-s-indacene-1,2,5,6-tetraol

polymer; monomer(s): 1,4-benzenedi(boronic acid): polymer; monomer(s): 1,4-benzenedi(boronic acid)

Conditions

Conditions	Yield
In methanol at 20℃; for 3h;	96%

: 853577-63-6
3-iodo-8-isobutyl-5,6,7-trimethoxy-2-methyl-4H-chromen-4-one

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

: 943027-57-4
C40H46O10

Conditions

Conditions	Yield
With sodium carbonate; Pd2(dpf)2Cl2*CH2Cl2 In ethanol; water; N,N-dimethyl-formamide at 90℃; for 10h; Suzuki coupling;	96%

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

: (1S,2R,5S,6R)-3,3,7,7-Tetramethyl-1,2,3,5,6,7-hexahydro-s-indacene-1,2,5,6-tetraol

: BC6H4BO2C12H6(CH3)4O2

Conditions

Conditions	Yield
In methanol react. tetrol and 1,4-benzenedi(boronic acid) in 1:1 ratio in MeOH at room temp. for 3 h; elem. anal.;	96%

1,4-Phenylenebisboronic acid Specification

This chemical is called Boronic acid, B,B'-1,4-phenylenebis-, and its systematic name is benzene-1,4-diyldiboronic acid. With the molecular formula of C₆H₈B₂O₄, its product categories are Blocks; Boronic Acids; B (Classes of Boron Compounds). The CAS registry number of this chemical is 4612-26-4. In addition, this chemical should be sealed in the cool and dry place, with the temperature 0-6 °C.

Other characteristics of the Boronic acid, B,B'-1,4-phenylenebis- can be summarised as followings: (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)Density: 1.33 g/cm³; (13)Flash Point: 207.9 °C; (14)Enthalpy of Vaporization: 71.05 kJ/mol; (15)Boiling Point: 420.1 °C at 760 mmHg; (16)Vapour Pressure: 8.27E-08 mmHg at 25°C.

Uses of this chemical: The Boronic acid, B,B'-1,4-phenylenebis- could react with 5-bromo-1,3-di-(2'-pyridyl)benzene, and obtain the C₃₈H₂₆N₄. This reaction needs the reagent of aq. Na₂CO₃, and the solvent of toluene, ethanol. The yield is 78 %. In addition, this reaction should be taken for 16 hours with the heating.

When you are using this chemical, please be cautious about it as the following: This chemical is irritating / harmful to eyes, respiratory system and skin. You should wear suitable protective clothing if you use it. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1.SMILES: OB(O)c1ccc(B(O)O)cc1
2.InChI: InChI=1/C6H8B2O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4,9-12H
3.InChIKey: BODYVHJTUHHINQ-UHFFFAOYAQ

Product Name

1,4-Phenylenebisboronic acid

Synthetic route

1,4-Phenylenebisboronic acid Specification

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