2-(2-(Benzyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(2-(Benzyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 1027757-13-6
• Molecular Formula: C19H23BO3
• Molecular Weight: 310.201
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID40393307
• Wikidata: Q82192044
• Mol file: 1027757-13-6.mol

Synonyms:1027757-13-6;2-(2-(Benzyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Benzyloxyphenylboronic acid pinacol ester;2-BENZYLOXYPHENYLBORONIC ACID, PINACOL ESTER;4,4,5,5-tetramethyl-2-(2-phenylmethoxyphenyl)-1,3,2-dioxaborolane;2-[2-(benzyloxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;MFCD03001334;SCHEMBL9946168;DTXSID40393307;CS-M0703;AKOS004114853;AB12797;AS-2617;1,3,2-DIOXABOROLANE, 4,4,5,5-TETRAMETHYL-2-[2-(PHENYLMETHOXY)PHENYL]-;FT-0685808;EN300-1706468;2-(Benzyloxy)phenylboronic acid pinacol ester, 97%;J-508129;Z1336745489;2-(2-Benzyloxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of 2-(2-(Benzyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Melting Point: 100-104 °C(lit.)
• Boiling Point: 435.2±28.0 °C(Predicted)
• PSA: 27.69000
• Density: 1.08±0.1 g/cm3(Predicted)
• LogP: 3.56480
• Storage Temp.: Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 310.1740248
• Heavy Atom Count: 23
• Complexity: 374

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-BenzyloxyphenylboronicAcidPinacolEster ^*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=CC=C2OCC3=CC=CC=C3
• Uses: 2-Benzyloxyphenylboronic acid, pinacol ester

Technology Process of 2-(2-(Benzyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 2 articles about 2-(2-(Benzyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 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: 55.0%

2-(benzyloxy)-N,N,N-trimethylbenzenaminium trifluoromethanesulfonate + bis(pinacol)diborane (73183-34-3) → 2-(2-(benzyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1027757-13-6)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel⁽⁰⁾; potassium tert-butylate; 1,3-dicyclohexyl-1H-imidazol-3-ium chloride; In 2-ethoxy-ethanol; toluene; at 50 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.joc.5b02557

Reference yield:

o-(benzyloxy)aniline (20012-63-9) → 2-(2-(benzyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1027757-13-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: formic acid; sodium cyanoborohydride / methanol / 16 h / 0 - 20 °C / pH 3 - 4 / Inert atmosphere

1.2: 0 °C / Inert atmosphere

2.1: bis(1,5-cyclooctadiene)nickel⁽⁰⁾; 1,3-dicyclohexyl-1H-imidazol-3-ium chloride; potassium tert-butylate / toluene; 2-ethoxy-ethanol / 24 h / 50 °C / Schlenk technique; Inert atmosphere

With bis(1,5-cyclooctadiene)nickel⁽⁰⁾; formic acid; potassium tert-butylate; sodium cyanoborohydride; 1,3-dicyclohexyl-1H-imidazol-3-ium chloride; In methanol; 2-ethoxy-ethanol; toluene;

DOI:10.1021/acs.joc.5b02557

Reference yield: 98.0%

2-(2-(benzyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1027757-13-6) + [hydroxy(tosyloxy)iodo]benzene (27126-76-7) → (4-(benzyloxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)(phenyl)iodonium tosylate (1417417-98-1)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 3h;

DOI:10.1002/anie.201206917

upstream raw materials:

o-(benzyloxy)aniline

bis(pinacol)diborane

Downstream raw materials:

C₂₅H₂₄O₅

(4-(benzyloxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)(phenyl)iodonium tosylate

7-(2-(benzyloxy)phenyl)-5-methyl-2-((4-(methylsulphonyl)piperazin-1-yl)methyl)thieno[3,2-c]pyridin-4(5H)-one

Refernces