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

Base Information

• Chemical Name: 2-(2-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 377780-72-8
• Molecular Formula: C13H18BBrO2
• Molecular Weight: 297
• Hs Code.: 2934999090
• European Community (EC) Number: 687-067-5
• DSSTox Substance ID: DTXSID60397089
• Nikkaji Number: J1.701.439K
• Wikidata: Q72447629
• Mol file: 377780-72-8.mol

Synonyms:377780-72-8;2-(2-(BROMOMETHYL)PHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;2-BROMOMETHYLPHENYLBORONIC ACID, PINACOL ESTER;2-[2-(bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Bromomethylphenylboronic acid pinacol ester;2-(Bromomethyl)benzeneboronic acid, pinacol ester;(2-BROMOMETHYLPHENYL)BORONIC ACID, PINACOL ESTER;2-(BROMOMETHYL)BENZENEBORONIC ACID PINACOL ESTER;2-(Bromomethyl)phenylboronic Acid Pinacol Ester;MFCD01632210;SCHEMBL2586990;(2-(BROMOMETHYL)PHENYL)BORONIC ACID PINACOL ESTER;DTXSID60397089;ROIXSNLOYHDYBP-UHFFFAOYSA-N;AKOS015960316;AB09488;AM90094;AS-2478;CS-W013977;SY047736;2-(bromomethyl)phenylboronic pinacol ester;2-Bromoethylphenylboronic acid pinacol ester;FT-0644532;T3393;2-Bromomethylphenyl boronic acid pinacol ester;EN300-155798;A823868;2-Bromomethylphenylboronic acid pinacol ester, 95%;2-(2-(bromomethylphenyl-4,4,5,5-Tetramethyl-1,3,2-dioxaborolane;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl Bromide;2-[2-(bromomethyl)-phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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

Chemical Property:

• Vapor Pressure: 4.57E-05mmHg at 25°C
• Melting Point: 78-80°C
• Refractive Index: 1.524
• Boiling Point: 360.6 °C at 760 mmHg
• Flash Point: 171.9 °C
• PSA: 18.46000
• Density: 1.26 g/cm³
• LogP: 2.88070
• Storage Temp.: Keep Cold
• Solubility.: Chloroform (Sparingly)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 296.05832
• Heavy Atom Count: 17
• Complexity: 265

Purity/Quality:

98% ^*data from raw suppliers

2-Bromomethylphenylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=CC=C2CBr
• Uses: 2-Bromomethylphenylboronic Acid Pinacol Ester is an intermediate used to prepare [(fluorophenylcarbamoyl)pyridinylsulfanylmethyl]phenylboronic acid and noncompetitive boronic acid antagonist of CXCR1 and CXCR2.

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

There total 16 articles about 2-(2-(Bromomethyl)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: 99.0%

N-Bromosuccinimide (128-08-5) + 2-methylphenylboronic acid pinacol ester (195062-59-0) → 2-(2-(bromomethyl)phenyl)-4,4,5,5,-tetramethyl-1,3,2-dioxaborolane (377780-72-8)

Guidance literature:

In acetonitrile; at 90 ℃; for 4h;

DOI:10.1039/C6CC08534B

Reference yield: 92.0%

2-methylphenylboronic acid pinacol ester (195062-59-0) → 2-(2-(bromomethyl)phenyl)-4,4,5,5,-tetramethyl-1,3,2-dioxaborolane (377780-72-8)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In acetonitrile; at 90 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.dyepig.2019.108000

Reference yield: 80.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 2-Methylphenylboronic acid (16419-60-6) → 2-(2-(bromomethyl)phenyl)-4,4,5,5,-tetramethyl-1,3,2-dioxaborolane (377780-72-8)

Guidance literature:

2,3-dimethyl-2,3-butane diol; 2-Methylphenylboronic acid; In water; toluene; for 2h; Dean-Stark; Reflux; Inert atmosphere;

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In acetonitrile; at 90 ℃; for 2h; Inert atmosphere;

upstream raw materials:

2-methylphenylboronic acid pinacol ester

2-(2,4-bismethylphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

2-(2-methyl-4-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

2-(2-bromomethyl-4-methylphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Downstream raw materials:

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

C₁₀H₁₇BNO₂⁽¹⁺⁾*Br^(1-)

pinacolboronic acid

(2-hydroxybenzyl)trimethylquaternary ammonium bromide