2-(2,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(2,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 1073339-07-7
• Molecular Formula: C14H21BO4
• Molecular Weight: 264.129
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID80682207
• Nikkaji Number: J2.845.909B
• Wikidata: Q82606511
• Mol file: 1073339-07-7.mol

Synonyms:1073339-07-7;2-(2,5-DIMETHOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;2,5-Dimethoxyphenylboronic acid pinacol ester;2,5-Dimethoxyphenylboronic acid, pinacol ester;(2,5-DIMETHOXYPHENYL)BORONIC ACID PINACOL ESTER;DTXSID80682207;MFCD12405521;AKOS015851751;DS-2018;CS-0153875;FT-0727284;EN300-1425778;A895504

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

Chemical Property:

• Melting Point: 58-60 °C
• Boiling Point: 376.3±32.0 °C(Predicted)
• PSA: 36.92000
• Density: 1.05±0.1 g/cm3(Predicted)
• LogP: 2.00300
• Storage Temp.: Room temperature.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 264.1532893
• Heavy Atom Count: 19
• Complexity: 303

Purity/Quality:

98% ^*data from raw suppliers

2,5-Dimethoxyphenylboronicacid,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=C(C=CC(=C2)OC)OC

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

There total 5 articles about 2-(2,5-Dimethoxyphenyl)-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: 32.0%

bis(pinacol)diborane (73183-34-3) + 1,4-dimethoxybezene (150-78-7) → 2-(2,5-dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1073339-07-7)

Guidance literature:

With tert-butyl peroxide; K₂CO₃; iron oxide; In octane; under air, (t-BuO)2 2.0 equiv., K2CO3 2.0 equiv., Fe2O3 0.2 equiv.; 80 °C, 5 d;

DOI:10.1039/b926945b

Reference yield:

2,3-dimethyl-2,3-butane diol (76-09-5) + 2,5-dimethoxyphenyl-N,N-diisopropylaminoborane → 2-(2,5-dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1073339-07-7)

Guidance literature:

2,5-dimethoxyphenyl-N,N-diisopropylaminoborane; With methanol; In ethyl acetate; at -5 - 20 ℃; for 1h; Inert atmosphere; Schlenk technique;

2,3-dimethyl-2,3-butane diol; In diethyl ether; at 20 ℃; for 4h; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.201304861

Reference yield:

1,4-dimethoxybezene (150-78-7) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(2,5-dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1073339-07-7) + 2,2'-(2,5-dimethoxy-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (1338777-82-4)

Guidance literature:

With C₂₆H₄₅OSiY; In hexane; at 100 ℃; for 24h; regioselective reaction;

DOI:10.1021/acscatal.8b01364

upstream raw materials:

bis(pinacol)diborane

1,4-dimethoxybezene

2-chloro-1,4-dimethoxybenzene

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

Refernces

• 1、 -. "METHOD FOR PREPARING AMINOARYLBORANE COMPOUNDS OR DERIVATIVES THEREOF". . . Retrieved 2015/06/18.
• 2、 Guerrand, Helene D. S.,Marciasini, Ludovic D.,Jousseaume, Melissa,Vaultier, Michel,Pucheault, Mathieu. "Borylation of unactivated aryl chlorides under mild conditions by using diisopropylaminoborane as a borylating reagent". . p. 5573 - 5579. Retrieved 2014/05/20.