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CAS No.: | 4612-26-4 |
---|---|
Name: | 1,4-Phenylenebisboronic acid |
Article Data: | 17 |
Molecular Structure: | |
Formula: | C6H8B2O4 |
Molecular Weight: | 165.749 |
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; |
EINECS: | 628-888-0 |
Density: | 1.33 g/cm3 |
Melting Point: | >350 °C(lit.) |
Boiling Point: | 420.1 °C at 760 mmHg |
Flash Point: | 207.9 °C |
Solubility: | Soluble in water 2.5%. |
Appearance: | off-white powder |
Hazard Symbols: | Xi, C, Xn |
Risk Codes: | 22-36/37/38-20/21/22 |
Safety: | 36-26 |
PSA: | 80.92000 |
LogP: | -2.95380 |
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; |
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% |
borane
water
1,4-bis(trimethylstannyl)benzene
A
1,4-Phenyldiboronic acid
B
trimethylstannane
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 |
hydrogenchloride
Trimethyl borate
1.4-dibromobenzene
1,4-Phenyldiboronic acid
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% |
Conditions | Yield |
---|---|
(i) B(OMe)3, (ii) aq. H2SO4; Multistep reaction; |
1,4-bis(dichloroboryl)benzene
1,4-Phenyldiboronic acid
Conditions | Yield |
---|---|
hydrolysis; |
Conditions | Yield |
---|---|
With Na In hexane | |
With Na In hexane |
C10H16B2O4
1,4-Phenyldiboronic acid
Conditions | Yield |
---|---|
With sulfuric acid; water at 0℃; Inert atmosphere; | 3.44 g |
With hydrogenchloride; water at 20℃; for 1h; | 1.6 g |
Conditions | Yield |
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Multi-step reaction with 2 steps 1: tetrachloromethane View Scheme | |
Multi-step reaction with 2 steps 1: tetrachloromethane View Scheme |
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; |
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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