4-Hydroxyphenylboronic acid

Base Information

• Chemical Name: 4-Hydroxyphenylboronic acid
• CAS No.: 71597-85-8
• Molecular Formula: C6H7BO3
• Molecular Weight: 137.931
• Hs Code.: 2931 90 00
• DSSTox Substance ID: DTXSID00370250
• Nikkaji Number: J1.751.106H
• Wikidata: Q72480979
• ChEMBL ID: CHEMBL3218996
• Mol file: 71597-85-8.mol

Synonyms:4-Hydroxyphenylboronic acid;71597-85-8;(4-HYDROXYPHENYL)BORONIC ACID;4-Hydroxybenzeneboronic Acid;4-Hydroxyphenylboronicacid;4-hydroxyphenyl boronic acid;MFCD01074628;Boronic acid, (4-hydroxyphenyl)-;(4-hydroxyphenyl)-boronic acid;CHEMBL3218996;p-hydroxyphenylboronic acid;4-Hydroxybenzeneboronicacid;4-hydroxylphenylboronic acid;SCHEMBL8912;4-hydroxy phenylboronic acid;4-hydroxy-phenylboronic acid;4-hydroxyphenyl-boronic acid;4-hydroxy-benzeneboronic acid;4-hydroxybenzene boronic acid;4-hydroxybenzene-boronic acid;4-hydroxylphenyl boronic acid;4-hydroxy phenyl boronic acid;4-hydroxy-phenyl boronic acid;4-hydroxy-phenyl-boronic acid;(4-hydroxyphenyl) boronic acid;4-(hydroxy)benzene boronic acid;DTXSID00370250;COIQUVGFTILYGA-UHFFFAOYSA-N;BCP03521;CS-D1375;(P-HYDROXYPHENYL)BORONIC ACID;BBL100512;BDBM50266954;STL554306;AKOS000285078;AB08076;AC-2399;AS-2661;4-Hydroxyphenylboronic acid, >=95.0%;NCGC00249456-01;AC-24814;BP-11415;SY002870;AM20041070;FT-0618689;H1228;EN300-119268;A837254;J-515526;Z336080006;(p-Hydroxyphenyl)boronic acid, 4-Hydroxybenzeneboronic acid, p-hydroxy-benzeneboronic acid

Chemical Property of 4-Hydroxyphenylboronic acid

Chemical Property:

• Appearance/Colour: off-white to light brown powder
• Melting Point: >230 °C(lit.)
• Boiling Point: 351.4 °C at 760 mmHg
• PKA: 9.09±0.10(Predicted)
• Flash Point: 166.3 °C
• PSA: 60.69000
• Density: 1.32 g/cm³
• LogP: -0.92800
• Storage Temp.: Store below +30°C.
• Water Solubility.: 25 g/L
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 138.0488242
• Heavy Atom Count: 10
• Complexity: 99.2

Purity/Quality:

99% ^*data from raw suppliers

4-Hydroxyphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, C
• Hazard Codes: Xi,C
• Statements: 36/37/38-34
• Safety Statements: 26-36-37/39-45-36/37/39-27

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)O)(O)O
• Uses: suzuki reaction 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. 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.

Technology Process of 4-Hydroxyphenylboronic acid

There total 25 articles about 4-Hydroxyphenylboronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.5%

(4-ethoxyphenyl)boronic acid (22237-13-4) → (p-hydroxyphenyl)boronic acid (71597-85-8)

Guidance literature:

(4-ethoxyphenyl)boronic acid; With aluminum (III) chloride; acetyl chloride; In toluene; at 10 - 80 ℃; for 3.75h; Large scale;

With sulfuric acid; pH=3; Large scale;

Reference yield: 90.6%

4-methoxyphenylboronic acid (5720-07-0) → (p-hydroxyphenyl)boronic acid (71597-85-8)

Guidance literature:

4-methoxyphenylboronic acid; With aluminum (III) chloride; acetyl chloride; In toluene; at 0 - 50 ℃; for 2.25h; Large scale;

With hydrogenchloride; In water; pH=3; Large scale;

Reference yield: 87.0%

[4-(benzyloxy)phenyl]boronic acid (146631-00-7) → (p-hydroxyphenyl)boronic acid (71597-85-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 30 - 35 ℃; for 5h; under 2250.23 Torr;

upstream raw materials:

4-bromo-phenol

boric acid tributyl ester

4-CH₃OC₆H₄BCl₂

2,4,6-tris(4-methoxyphenyl)boroxine

Downstream raw materials:

4-Cyano-4'-hydroxybiphenyl

4-(4-Hydroxyphenyl)-N-(2-morpholin-4-ylethyl)thiophene-2-carboxamide

methyl 2-(4-hydroxyphenyl)-8-isopropoxy-1-(4-isopropoxy-3-methoxyphenyl)-9-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate

4'-fluoro-biphenyl-4-ol

Refernces

• 1、 Han, Min Su,Lim, Taeho,Ryoo, Jeong Yup. "Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source". . p. 10966 - 10972. Retrieved 2020/09/23.
• 2、 Fan, Chenrui,Wu, Qixu,Zhu, Chengfeng,Wu, Xiang,Li, Yougui,Luo, Yunfei,He, Jian-Bo. "Enantioselective Conjugate Addition of Aryl Halides and Triflates to Electron-Deficient Olefins via Nickel- And Rhodium-Catalyzed Sequential Relay Reactions". supporting information. p. 8888 - 8892. Retrieved 2019/10/14.