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

Base Information

• Chemical Name: 2-(4-(Benzyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 754226-40-9
• Molecular Formula: C₁₉H₂₃BO₃
• Molecular Weight: 310.201
• Hs Code.: 2931900090
• European Community (EC) Number: 805-456-1
• DSSTox Substance ID: DTXSID50407868
• Nikkaji Number: J3.028.135G
• Wikidata: Q82213214
• Mol file: 754226-40-9.mol

Synonyms:754226-40-9;2-(4-(Benzyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-BENZYLOXYPHENYLBORONIC ACID, PINACOL ESTER;4-Benzyloxyphenylboronic acid pinacol ester;4,4,5,5-tetramethyl-2-(4-phenylmethoxyphenyl)-1,3,2-dioxaborolane;MFCD04974107;2-(4-Benzyloxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-[4-(benzyloxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;1,3,2-DIOXABOROLANE, 4,4,5,5-TETRAMETHYL-2-[4-(PHENYLMETHOXY)PHENYL]-;4-Benzyloxybenzeneboronic acid, pinacol ester;SCHEMBL298401;(4-(BENZYLOXY)PHENYL)BORONIC ACID PINACOL ESTER;DTXSID50407868;KMKOKPUXZWBMEI-UHFFFAOYSA-N;AKOS004114822;AB21474;AS-2398;SY004814;AM20041117;CS-0089501;FT-0678865;O10095;EN300-1706441;A865687;4-(Benzyloxy)phenylboronic acid pinacol ester, 97%;Z1336746165;2-(4-(Benzyloxy)phenyl)-4 pound not4 pound not5 pound not5-tetramethyl-1 pound not3 pound not2-dioxaborolane

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

Chemical Property:

• Vapor Pressure: 3.76E-07mmHg at 25°C
• Melting Point: 81-85 °C(lit.)
• Refractive Index: 1.544
• Boiling Point: 428.5 °C at 760 mmHg
• Flash Point: 213 °C
• Density: 1.08 g/cm³
• Storage Temp.: Keep Cold
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 310.1740248
• Heavy Atom Count: 23
• Complexity: 366

Purity/Quality:

97% ^*data from raw suppliers

4-(Benzyloxy)phenylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)OCC3=CC=CC=C3

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

There total 24 articles about 2-(4-(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: 78.0%

p-benzyloxyphenylbromide (6793-92-6) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 4,4,5,5,-tetramethyl-2-[4-(phenylmethoxy)phenyl]-1,3,2-dioxaborolane (754226-40-9)

Guidance literature:

p-benzyloxyphenylbromide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h; Schlenk technique; Inert atmosphere;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.joc.0c00998

Reference yield: 73.3%

S-ethyl 4-benzyloxybenzothioate (1067665-48-8) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5,-tetramethyl-2-[4-(phenylmethoxy)phenyl]-1,3,2-dioxaborolane (754226-40-9)

Guidance literature:

With [Rh(OH)(cod)]2; tributylphosphine; potassium acetate; at 80 ℃; for 24h; Inert atmosphere; Glovebox;

DOI:10.1002/anie.201611974

Reference yield: 70.0%

4-(4-benzyloxyphenyl) iodide (19578-68-8) + 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane (78782-17-9) → 4,4,5,5,-tetramethyl-2-[4-(phenylmethoxy)phenyl]-1,3,2-dioxaborolane (754226-40-9)

Guidance literature:

With sodium t-butanolate; In tetrahydrofuran; toluene; at 120 ℃; for 6h; chemoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.6b11757

upstream raw materials:

2,3-dimethyl-2,3-butane diol

p-benzyloxyphenylbromide

[4-(benzyloxy)phenyl]boronic acid

benzyl bromide

Downstream raw materials:

(R)-4-(4-(benzyloxy)phenyl)-4-methyl-1,2,3-oxathiazolidine 2,2-dioxide