Basic information
- CAS
71597-85-8- Standard SMILES
OB(O)c1ccc(O)cc1- InChIKey
COIQUVGFTILYGA-UHFFFAOYSA-N- Molecular formula
- C6H7BO3
- Average molar mass
- 137.93 g/mol
- Monoisotopic mass
- 138.04882448
Names & identifiers
- Preferred name
- 4-Hydroxyphenylboronic acid
- IUPAC
- (4-hydroxyphenyl)boronic acid
- English name
- 4-Hydroxyphenylboronic acid
- Molecular formula
- C6H7BO3
- Molecular weight
- 137.93
Names & synonyms
4-Hydroxyphenylboronic acid71597-85-8(4-HYDROXYPHENYL)BORONIC ACIDDTXSID00370250RefChem:524064DTXCID40321286615-307-04-Hydroxybenzeneboronic Acid4-HydroxyphenylboronicacidMFCD01074628(P-HYDROXYPHENYL)BORONIC ACIDSCHEMBL8912
Show more names
ACF2AKOS BRN-0188RARECHEM AH PB 02224-Hydroxybenzeneboronic4-DIHYDROXYBORANYL-PHENOL4-Hydroxyphenylboronicaci
4-hydroxy phenyl boronic acid(4-hydroxyphenyl) boronic acid(4-hydroxyphenyl)-boronic acidCHEMBL3218996AKOS000285078Z3360800064-BoronophenolBoronic acid, (4-hydroxyphenyl)-
Database identifiers
- CAS
71597-85-8- PubChem CID
- 2734360
- DTXSID
DTXSID00370250- ChEMBL
CHEMBL3218996- UNII
- U8AX2ASL53
- EC Number
- 615-307-0
- Nikkaji
- J1.751.106H
Properties
Computed structural properties
- Topological polar surface area
- 60.7 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 99.2
Physicochemical properties
- Melting point
- 230 °C · >230 °C (lit.)
- Boiling point
- 351.4 · 351.4±44.0 °C(Predicted)
- Density
- 1.32 · 1.32±0.1 g/cm3(Predicted)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- soluble in Acetonitrile, DMSO, Methanol
- form
- Powder
- pka
- 9.09 · 9.09±0.10(Predicted)
- color
- Off-white to light brown
- Water Solubility
- 25 g/L · 25 g/L
- BRN
- 2963491 · 2963491
- InChI
- InChI=1S/C6H7BO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8-10H
- InChIKey
- COIQUVGFTILYGA-UHFFFAOYSA-N
- SMILES
- B(C1=CC=C(O)C=C1)(O)O
- CAS DataBase Reference
- 71597 · 71597-85-8(CAS DataBase Reference)
- UNSPSC Code
- 12352301 · 12352301
- NACRES
- 22 · NA.22
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (96.2%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 52 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (96.2%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- No
- hs_code
- 2931 90 00
- risk_code
- 36/37/38-34
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,C
- safety_code
- 26-36-37/39-45-36/37/39-27
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2
- Precautionary statements
- P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
Chemistry & industry
Applications
Uses4-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.
Uses4-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.
Upstream & downstream products
Upstream raw materials
Related reactions
282 records
Compound notes
Loading…