| Identification | More | [Name]
4-Hydroxyphenylboronic acid | [CAS]
71597-85-8 | [Synonyms]
4-BORONOPHENOL
4-HYDROXYBENZENEBORONIC ACID
4-HYDROXYPHENYLBORONIC ACID
AKOS BRN-0188
BORONIC ACID, (4-HYDROXYPHENYL)-
(P-HYDROXYPHENYL)BORONIC ACID
RARECHEM AH PB 0222
4-Boronophenol~4-Hydroxyphenylboronic acid
4-Hydroxybenzeneboronic
4-DIHYDROXYBORANYL-PHENOL
4-Hydroxyphenylboronic Acid (contains varying amounts of Anhydride) | [EINECS(EC#)]
615-307-0 | [Molecular Formula]
C6H7BO3 | [MDL Number]
MFCD01074628 | [Molecular Weight]
137.93 | [MOL File]
71597-85-8.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white to light brown powder | [Melting point ]
>230 °C (lit.) | [Boiling point ]
351.4±44.0 °C(Predicted) | [density ]
1.32±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
Powder | [pka]
9.09±0.10(Predicted) | [color ]
Off-white to light brown | [Water Solubility ]
25 g/L | [BRN ]
2963491 | [InChIKey]
COIQUVGFTILYGA-UHFFFAOYSA-N | [CAS DataBase Reference]
71597-85-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,C | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S27:Take off immediately all contaminated clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [TSCA ]
No | [HazardClass ]
IRRITANT | [HS Code ]
29319099 |
| Hazard Information | Back Directory | [Chemical Properties]
off-white to light brown powder | [Uses]
4-Hydroxyphenylboronic acid can be used as a reactant in:
- Suzuki-Miyaura coupling and Stille coupling reactions.
- Palladium-catalyzed aminocarbonylation and cross-coupling reactions.
- Suzuki reaction for preparation of bio-supported palladium nanoparticles as phosphine-free catalysts.
- Cu2O-catalyzed aerobic oxidative cross-coupling of tetrazoles.
It can also be used to prepare/promote:
- PDK1 inhibitory activity (cancer cell growth, survival, and tumorigenesis inhibitor).
- Rod-like dendronized polymers containing G4 and G5 ester dendrons via macromonomer approach by living ROMP.
- Estrone-derived cyclopamine analogs as Sonic Hedgehog signaling inhibitors for anti-cancer chemotherapeutics.
- Enzymatic inhibitors for the treatment of Gram-negative bacterial infections.
- Oligoarenes by Suzuki-Miyaura palladium-catalyzed cross-coupling.
| [Uses]
4-Hydroxybenzeneboronic acid is used for Suzuki-Miyaura coupling and Stille coupling and potential for introducing different alkyl groups, palladium-catalyzed aminocarbonylation and cross-coupling reactions, bio-supported palladium nanoparticles as phosphine-free catalyst for Suzuki reaction in water and Cu2O-catalyzed aerobic oxidative cross-coupling of tetrazoles. It is also used in preparation of rod-like dendronized polymers. | [Uses]
suzuki reaction | [Synthesis Reference(s)]
Tetrahedron Letters, 37, p. 6705, 1996 DOI: 10.1016/S0040-4039(96)01468-2 |
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