2-Hydroxyphenylboronic acid

Base Information

• Chemical Name: 2-Hydroxyphenylboronic acid
• CAS No.: 89466-08-0
• Molecular Formula: C6H7BO3
• Molecular Weight: 137.931
• Hs Code.: 29319000
• European Community (EC) Number: 677-277-5
• DSSTox Substance ID: DTXSID20378470
• Nikkaji Number: J1.197.346I
• Wikidata: Q72480982
• ChEMBL ID: CHEMBL4093004
• Mol file: 89466-08-0.mol

Synonyms:Benzeneboronicacid, o-hydroxy- (6CI,7CI);Boronic acid, (2-hydroxyphenyl)- (9CI);2-Hydroxybenzeneboronic acid;Phenol-2-ylboronicacid;

Chemical Property of 2-Hydroxyphenylboronic acid

Chemical Property:

• Appearance/Colour: Off-white powder
• Vapor Pressure: 8.28E-05mmHg at 25°C
• Melting Point: 178-182 °C
• Refractive Index: 1.582
• Boiling Point: 327.3 °C at 760 mmHg
• PKA: 8.61±0.58(Predicted)
• Flash Point: 151.7 °C
• PSA: 60.69000
• Density: 1.32 g/cm³
• LogP: -0.92800
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Acetonitrle (Slightly), DMSO (Slightly)
• Water Solubility.: Insoluble in water.
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 138.0488242
• Heavy Atom Count: 10
• Complexity: 107

Purity/Quality:

98% ^*data from raw suppliers

2-Hydroxyphenylboronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-41-22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=CC=C1O)(O)O
• Uses: suzuki reaction 2-Hydroxybenzeneboronic acid is used as a pharmaceutical intermediate.

Technology Process of 2-Hydroxyphenylboronic acid

There total 18 articles about 2-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: 95.0%

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (269409-97-4) → 2-hydroxyphenyl boronic acid (89466-08-0)

Guidance literature:

With hydrogenchloride; polystyrene boronic acid; In acetonitrile; at 20 ℃; for 18h;

DOI:10.1016/j.tetlet.2004.07.014

Reference yield: 94.9%

(2-ethoxyphenyl)boronic acid (213211-69-9) → 2-hydroxyphenyl boronic acid (89466-08-0)

Guidance literature:

(2-ethoxyphenyl)boronic acid; With aluminum (III) chloride; acetyl chloride; In 5,5-dimethyl-1,3-cyclohexadiene; at 10 - 100 ℃; for 4.25h; Large scale;

With hydrogenchloride; In water; pH=4; Large scale;

Reference yield: 93.0%

dihydroxy-methyl-borane (13061-96-6) + 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (269409-97-4) → 2-hydroxyphenyl boronic acid (89466-08-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃;

DOI:10.1021/acs.orglett.9b00584

upstream raw materials:

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

2-hydroxybromobenzene

2-monochlorophenol

Triisopropyl borate

Downstream raw materials:

(5‐chloro‐2‐hydroxyphenyl)boronic acid

(5-bromo-2-hydroxyphenyl)boronic acid

3-cyclohexyl-2-(2-hydroxy-phenyl)-1H-indole-6-carboxylic acid methyl ester

C₈H₉BO₄

Refernces

• 1、 -. "Method for preparing boric acid derivative (by machine translation)". Paragraph 0042-0043; 0048-0049. . Retrieved 2020/12/29.
• 2、 -. "Metal complex and OLED (Organic Light Emitting Device) thereof". Paragraph 0072; 0073; 0074; 0075. . Retrieved 2018/10/19.