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

Base Information

• Chemical Name: 2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
• CAS No.: 760990-08-7
• Molecular Formula: C12H16BFO3
• Molecular Weight: 238.067
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID50468772
• Nikkaji Number: J2.346.000I
• Wikidata: Q82296162
• Mol file: 760990-08-7.mol

Synonyms:760990-08-7;2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol;3-Fluoro-4-hydroxyphenylboronic acid, pinacol ester;SCHEMBL2130844;DTXSID50468772;LMLXGCAZONOZKO-UHFFFAOYSA-N;AMY29882;AKOS022172820;PHENOL, 2-FLUORO-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-;MB09892;DS-18086;CS-0041658;FT-0761227;W17228;EN300-1860014;A865551;Z2049761342;2-FLUORO-4-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENOL

Chemical Property of 2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Chemical Property:

• Melting Point: 99.3-100.2 °C
• Boiling Point: 324.9±32.0 °C(Predicted)
• PKA: 8.39±0.35(Predicted)
• PSA: 38.69000
• Density: 1.15±0.1 g/cm3(Predicted)
• LogP: 1.83050
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 238.1176527
• Heavy Atom Count: 17
• Complexity: 280

Purity/Quality:

97% ^*data from raw suppliers

3-Fluoro-4-hydroxyphenylboronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=C(C=C2)O)F
• Uses: 3-Fluoro-4-hydroxyphenylboronic acid, pinacol ester

Technology Process of 2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

There total 5 articles about 2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 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: 93.0%

4-bromo-2-fluorophenol (2105-94-4) + bis(pinacol)diborane (73183-34-3) → 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (760990-08-7)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; for 4h; Inert atmosphere; Reflux;

Reference yield: 52.0%

4-bromo-2-fluorophenol (2105-94-4) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (760990-08-7)

Guidance literature:

4-bromo-2-fluorophenol; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 0.5h;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In diethyl ether; pentane; at -78 - 20 ℃; Further stages.;

DOI:10.1039/b603574d

Reference yield:

tetrapropylammonium 2-fluorophenylsulfate + bis(pinacol)diborane (73183-34-3) → 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (760990-08-7) + 2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol + C18H27B2FO5

Guidance literature:

tetrapropylammonium 2-fluorophenylsulfate; bis(pinacol)diborane; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-Dimethoxy-2,2'-bipyridin; In 1,4-dioxane; at 60 ℃; for 36h; Glovebox;

With hydrogenchloride; In 1,4-dioxane; water; for 1h; pH=1 - 2; Overall yield = 56 percent; Overall yield = 67 mg; regioselective reaction; Glovebox;

DOI:10.1021/jacs.9b08464

upstream raw materials:

4-bromo-2-fluorophenol

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

bis(pinacol)diborane

2-fluorophenol

Downstream raw materials:

2-((2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenoxy)methyl)pyridine