| Identification | More | [Name]
1,4-Phenylenebisboronic acid | [CAS]
4612-26-4 | [Synonyms]
1,4-BENZENEDIBORONIC ACID
1,4-PHENYLENEBIS(BORONIC ACID)
1,4-PHENYLENEDIBORONIC ACID
4-(DIHYDROXYBORYL)PHENYLBORONIC ACID
AKOS BRN-0002
BENZENE-1,4-DIBORONIC ACID
P-PHENYLENEDIBORONIC ACID
1,4-Phenyldiboronic acid
1,4-Benzenediboronicacid,96%
1,4-Phenylenebisboronic
1,4-benzeendiboronic acid
1,4-Phenylenediboronic Acid (contains varying amounts of Anhydride)
1,4-Benzendiboronic acid
1,4-Phenylenebisboronic acid, p-Phenylenediboronic acid, Benzene-1,4-diboronic acid | [EINECS(EC#)]
628-888-0 | [Molecular Formula]
C6H8B2O4 | [MDL Number]
MFCD00236018 | [Molecular Weight]
165.75 | [MOL File]
4612-26-4.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white powder | [Melting point ]
>350 °C(lit.)
| [Boiling point ]
420.1±55.0 °C(Predicted) | [density ]
1.33±0.1 g/cm3(Predicted) | [storage temp. ]
0-6°C | [solubility ]
soluble in Methanol | [form ]
liquid | [pka]
8.30±0.17(Predicted) | [color ]
white to off-white | [Water Solubility ]
Soluble in water 2.5%. | [BRN ]
2836921 | [InChI]
InChI=1S/C6H8B2O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4,9-12H | [InChIKey]
BODYVHJTUHHINQ-UHFFFAOYSA-N | [SMILES]
C1(B(O)O)=CC=C(B(O)O)C=C1 | [CAS DataBase Reference]
4612-26-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,C,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [Hazard Note ]
Corrosive | [TSCA ]
No | [HazardClass ]
IRRITANT | [HS Code ]
29319090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Chemical Properties]
1,4-Phenylenebisboronic acid is off-white powder
| [Uses]
Reagent used for
. Externally initiated Kumada catalyst-transfer polycondensation
. Suzuki-Miyaura cross-coupling reactions
. Energy transfer processes in optoelectronic devices
. Palladium-catalyzed sequential alkenylation and conjugate addition reactions
. Scholl cyclizations
| [Uses]
suzuki reaction | [Synthesis]
Under the protection of nitrogen atmosphere, 200 mL of tetrahydrofuran (THF) was added to the reaction flask and cooled to 15°C. 0 g (0.62 mmol) of magnesium and 1.0 g (0.004 mol) of iodine were slowly added followed by the dropwise addition of 300 mL of THF solution containing 68.4 g (0.29 mol) of 1,4-dibromobenzene at a controlled titration rate maintaining the reaction temperature at 30°C. The reaction was continued for 3 hours. After completion, the reaction was continued for 3 hours. After completion of the reaction, the reaction mixture was cooled to -70°C and a mixed solution consisting of trimethyl borate (78.5 mL, 0.72 mol) and 300 mL of THF was slowly added dropwise. After the dropwise addition was completed, the reaction was continued at -70°C for 1 hour, then slowly warmed to room temperature and stirred for 12 hours. To the reaction mixture was added 950 mL of 2.5 M hydrochloric acid, stirred rapidly for 15 minutes and the solid product was collected by filtration. The solid was washed 3 times with 300 mL of hexane and finally dried under vacuum to give 40.7 g of white solid 1,4-phenylenediboronic acid in 84.6% yield. | [References]
[1] Patent: CN103570530, 2016, B. Location in patent: Paragraph 0042; 0043 |
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