2,5-Dimethylphenylboronic acid

Base Information

• Chemical Name: 2,5-Dimethylphenylboronic acid
• CAS No.: 85199-06-0
• Molecular Formula: C8H11BO2
• Molecular Weight: 149.985
• Hs Code.: 29163990
• European Community (EC) Number: 677-065-2
• DSSTox Substance ID: DTXSID80370238
• Nikkaji Number: J1.762.499G
• Wikidata: Q72471217
• Mol file: 85199-06-0.mol

Synonyms:2,5-Dimethylphenylboronic acid;85199-06-0;(2,5-dimethylphenyl)boronic Acid;2,5-Dimethylbenzeneboronic Acid;p-Xylene-2-boronic Acid;MFCD01863525;Boronic acid, (2,5-dimethylphenyl)-;2,5-Dimethylphenylboronicacid;(2,5-Dimethylphenyl)Boranediol;2,5-DIMETHYLBENZENEBORONICACID;2,5-dimehylphenylboronic acid;SCHEMBL513136;2,5-Dimethylbenzenboronic acid;2,5-Dimethylphenylboranic acid;2,5-dimethyl-phenylboronic acid;2,5-dimethylphenyl boronic acid;2,5-Dimethyl phenylboronic acid;2,5-dimethylbenzene boronic acid;DTXSID80370238;OOMZKLJLVGQZGV-UHFFFAOYSA-N;CS-D1026;AKOS000285071;GS-6906;AC-24789;SY014621;AM20060967;D3517;FT-0610456;EN300-117672;J-507365;F0001-2144;Z381540980

Chemical Property of 2,5-Dimethylphenylboronic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.000367mmHg at 25°C
• Melting Point: 186-191 °C(lit.)
• Refractive Index: 1.523
• Boiling Point: 305.1 °C at 760 mmHg
• PKA: 8.70±0.58(Predicted)
• Flash Point: 138.3 °C
• PSA: 40.46000
• Density: 1.07 g/cm³
• LogP: -0.01680
• Storage Temp.: 0-6°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 150.0852098
• Heavy Atom Count: 11
• Complexity: 127

Purity/Quality:

99% ^*data from raw suppliers

2,5-Dimethylphenylboronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(C=CC(=C1)C)C)(O)O
• Uses: Reactant for:? ;Friedel-Crafts alkylation1? ;Suzuki-Miyaura coupling2 suzuki reaction Reactant for:Friedel-Crafts alkylationSuzuki-Miyaura coupling

Technology Process of 2,5-Dimethylphenylboronic acid

There total 10 articles about 2,5-Dimethylphenylboronic 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: 69.0%

4-bromo-m-xylene (553-94-6) + boric acid (11113-50-1,14635-83-7) → 2,5-dimethylphenyl boronic acid (85199-06-0)

Guidance literature:

4-bromo-m-xylene; With magnesium; In tetrahydrofuran; for 3.5h; Inert atmosphere; Reflux;

boric acid; In water; at -78 - 20 ℃; for 60h; Inert atmosphere;

DOI:10.1021/jacs.8b02443

Reference yield: 62.0%

Trimethyl borate (121-43-7,63156-11-6) + 4-bromo-m-xylene (553-94-6) + water (7732-18-5) → 2,5-dimethylphenyl boronic acid (85199-06-0)

Guidance literature:

4-bromo-m-xylene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 2h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

water; With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;

Reference yield: 55.0%

Trimethyl borate (121-43-7,63156-11-6) + 4-bromo-m-xylene (553-94-6) → 2,5-dimethylphenyl boronic acid (85199-06-0)

Guidance literature:

With Mg; In tetrahydrofuran; 1) Mg/THF; 2) B(OCH3)3; 3) H3O(1+); according to Chen, Z., Lee, N.H.S. &Huang, W. (2003). Macromolecules, 36, 1009-1020;

DOI:10.1107/S0108270111008195

upstream raw materials:

(2,5-dimethylphenyl)dichloroborane

water

2,5-dimethylphenylmagnesium bromide

bis-(2,5-dimethyl-phenyl)-mercury

Downstream raw materials:

2',5'-Bis-(4-dodecyloxy-phenylethynyl)-2,5,2'',5''-tetramethyl-[1,1';4',1'']terphenyl

2',5'-bis(4-(N,N-dibutylamino)phenyl)ethynyl-2,2,5,5-tetramethyl[1,1':4',1]terphenyl

(+/-)-{[7-(2,5-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine

Refernces

• 1、 Nomrowski, Julia,Guo, Xingwei,Wenger, Oliver S.. "Charge Accumulation and Multi-Electron Photoredox Chemistry with a Sensitizer–Catalyst–Sensitizer Triad". supporting information. p. 14084 - 14087. Retrieved 2018/09/11.
• 2、 Simmons, Scott,Fratini, Albert,Benin, Vladimir. "A sodium salt of the dimer of boronoterephthalic acid anhydride". scheme or table. p. m123-m125. Retrieved 2011/06/26.