3,5-Dimethylphenylboronic acid

Base Information

• Chemical Name: 3,5-Dimethylphenylboronic acid
• CAS No.: 172975-69-8
• Molecular Formula: C8H11BO2
• Molecular Weight: 149.985
• Hs Code.: 29319090
• DSSTox Substance ID: DTXSID50370240
• Nikkaji Number: J806.558F
• Wikidata: Q72471230
• Mol file: 172975-69-8.mol

Synonyms:3,5-Dimethylphenylboronic acid;172975-69-8;(3,5-dimethylphenyl)boronic Acid;3,5-Dimethylbenzeneboronic Acid;MFCD00185689;Boronic acid, (3,5-dimethylphenyl)-;(3,5-Dimethylphenyl)Boranediol;3,5-dimethylphenyl boronic acid;m-Xylene-5-boronic Acid;3,5-Dimethylphenylboronicacid;AKOS BRN-0067;SCHEMBL364635;3.5-Dimethylphenylboronic acid;DTXSID50370240;3, 5-dimethylphenyl boronic acid;3,5-dimethyl phenyl boronic acid;3,5-dimethyl-phenyl boronic acid;DJGHSJBYKIQHIK-UHFFFAOYSA-N;BCP22767;CS-D1028;AKOS000285069;AB04450;AS-3151;BCP9000260;AC-24810;SY005165;3,5-Dimethylphenylboronic acid, >=95.0%;AM20050277;D3396;FT-0614688;EN300-117674;A811474;J-507519;J-511361;Z336079698;(3,5-dimethylphenyl)boronic acid

Chemical Property of 3,5-Dimethylphenylboronic acid

Chemical Property:

• Appearance/Colour: off-white to light yellow crystalline powder
• Melting Point: 261-265 °C(lit.)
• Boiling Point: 312.7 °C at 760 mmHg
• PKA: 8.72±0.10(Predicted)
• Flash Point: 142.9 °C
• PSA: 40.46000
• Density: 1.07 g/cm³
• LogP: -0.01680
• Storage Temp.: 0-6°C
• Water Solubility.: Slightly soluble in water
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 150.0852098
• Heavy Atom Count: 11
• Complexity: 117

Purity/Quality:

≥98.0% ^*data from raw suppliers

3,5-Dimethylphenylboronic Acid (contains varying amounts of Anhydride) ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=CC(=C1)C)C)(O)O
• Uses: suzuki reaction 3,5-Dimethylphenylboronic Acid is a useful research intermediate for organic synthesis 3,5-Dimethylphenylboronic acid (DMPBA) can be used as: A reactant in the palladium-catalyzed Suzuki coupling reactions. A co-extractant in the combination with modified Aliquat 336 for the extraction of xylose, glucose, and fructose from aqueous solutions. A reactant to prepare penultimate methyl ester.

Technology Process of 3,5-Dimethylphenylboronic acid

There total 21 articles about 3,5-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: 89.0%

methanol (67-56-1) + diisopropylamine borane (55124-35-1) + 5-bromo-1,3-xylene (556-96-7) → 3,5-dimethylphenyl boronic acid (172975-69-8)

Guidance literature:

diisopropylamine borane; With magnesium; phenylmagnesium bromide; In tetrahydrofuran; at 20 ℃; for 0.166667h;

5-bromo-1,3-xylene; In tetrahydrofuran; at 70 ℃;

methanol; Further stages;

DOI:10.1016/j.tet.2018.11.036

Reference yield: 85.6%

Trimethyl borate (121-43-7,63156-11-6) + 5-bromo-1,3-xylene (556-96-7) → 3,5-dimethylphenyl boronic acid (172975-69-8)

Guidance literature:

With Mg; H₂SO₄; In tetrahydrofuran; diethyl ether; aryl bromide in THF was added to Mg turnings, filtered, added dropwise with stirring to trimethyl borate in ether at -70°C, the suspn. was allowed to warm to room temp. overnight, added with stirring to ice, concd. H2SO4, stirred for 30 min (Ar); shaken with ether, dried over Na2SO4, evapd., filtered, dried in vac.; elem. anal.;

DOI:10.1021/om010001f

Reference yield: 74.0%

Trimethyl borate (121-43-7,63156-11-6) + water (7732-18-5) + 3,5-dimethyphenylmagnesium bromide (34696-73-6) → 3,5-dimethylphenyl boronic acid (172975-69-8)

Guidance literature:

Trimethyl borate; 3,5-dimethyphenylmagnesium bromide; In tetrahydrofuran; at 20 ℃;

water; With hydrogenchloride; In tetrahydrofuran; diethyl ether;

upstream raw materials:

5-bromo-1,3-xylene

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

m-xylene

Triisopropyl borate

Downstream raw materials:

4-(3,5-dimethylphenyl)-2H-chromen-2-one

4-(3,5-dimethyl-phenyl)-5H-furan-2-one

3,5-Dimethylphenol

C₃₆H₃₈O₂

Refernces

• 1、 Liu, Hao,Su, Huan,Chen, Zhiyuan,Zhu, Senqiang,Liu, Rui,Zhu, Hongjun. "Meso-substituted boron-dipyrromethene compounds: synthesis, tunable solid-state emission, and application in blue-driven LEDs". . p. 1697 - 1705. Retrieved 2021/07/10.
• 2、 -. "PROCESS FOR PREPARING PROPYLENE COPOLYMERS COMPRISING C4-C12-ALPHA OLEFIN COMONOMER UNITS". Page/Page column 60-61. . Retrieved 2020/01/10.