4-tert-Butylphenylboronic acid

Base Information

• Chemical Name: 4-tert-Butylphenylboronic acid
• CAS No.: 123324-71-0
• Molecular Formula: C10H15BO2
• Molecular Weight: 178.039
• Hs Code.: 29163990
• DSSTox Substance ID: DTXSID60370211
• Nikkaji Number: J732.736F
• Wikidata: Q72504020
• Mol file: 123324-71-0.mol

Synonyms:4-tert-Butylphenylboronic acid;123324-71-0;4-t-butylphenylboronic acid;(4-(tert-Butyl)phenyl)boronic acid;4-tert-Butylbenzeneboronic Acid;(4-tert-butylphenyl)boronic Acid;4-tert-Butylphenyl boronic acid;MFCD01009697;4-(tert-butyl)phenylboronic acid;4-tert-butyl-phenyl boronic acid;4-tertbutylphenylboronic acid;Boronic acid, [4-(1,1-dimethylethyl)phenyl]-;p-t-butylphenylboronic acid;SCHEMBL27736;4-t-butylphenyl boronic acid;4-t-butylphenyl-boronic acid;4-t-butyl phenyl boronic acid;4-t-butyl-phenyl boronic acid;4-tert-butyl-phenylboronic acid;4-tert-butyl-benzeneboronic acid;(4-tert-butyl)phenylboronic acid;4-(tertbutyl)-phenylboronic acid;4-tert-butyl phenyl boronic acid;4-tert-butyl-phenyl-boronic acid;DTXSID60370211;4-(tert-butyl)benzeneboronic acid;4-tert-butyl benzene boronic acid;4-tert-butyl-benzene boronic acid;MNJYZNVROSZZQC-UHFFFAOYSA-N;4-(tert-butyl)-phenylboronic acid;BCP22766;STR03834;4-(tert butyl)-phenyl boronic acid;AKOS003585337;AB07967;AC-5365;BCP9000169;CS-W007389;NCGC00249512-01;SY001215;4-tert-Butylphenylboronic acid, >=95.0%;AM20060223;B2251;FT-0619493;EN300-49217;A805046;Boronic acid, B-[4-(1,1-dimethylethyl)phenyl]-;[4-(1,1-DIMETHYLETHYL)PHENYL]BORONIC ACID;J-004912;J-513870;Z330828692

Chemical Property of 4-tert-Butylphenylboronic acid

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 193-199 ºC
• Refractive Index: 1.59
• Boiling Point: 296.7 ºC at 760 mmHg
• PKA: 8.79±0.10(Predicted)
• Flash Point: 133.2 ºC
• PSA: 40.46000
• Density: 1.02 g/cm²
• LogP: 0.66390
• Storage Temp.: 0-6°C
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 178.1165099
• Heavy Atom Count: 13
• Complexity: 155

Purity/Quality:

99% ^*data from raw suppliers

4-tert-Butylphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22-20/21/22-R36/37/38
• Safety Statements: 37/39-26-36-S37/39-S26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)C(C)(C)C)(O)O
• Uses: suzuki reaction 4-t-Butylphenylboronic acid is a cross-coupling building block used in the preparation of tetracyclnes and tetracycline derivatives. Cross-coupling building block used in synthesis of tetracycline derivatives.

Technology Process of 4-tert-Butylphenylboronic acid

There total 10 articles about 4-tert-Butylphenylboronic 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: 90.0%

1-bromo-4-tert-butylbenzene (3972-65-4) → p-tert-butylphenylboronic acid (123324-71-0)

Guidance literature:

1-bromo-4-tert-butylbenzene; With n-butyllithium; In tetrahydrofuran; at -78 - -45 ℃; for 3h;

With boric acid tributyl ester; In tetrahydrofuran; at -78 - 20 ℃;

Acid hydrolysis;

DOI:10.1016/S0040-4039(03)01300-5

Reference yield: 85.0%

water (7732-18-5) + potassium (4-tert-butyl)phenyltrifluoroborate → p-tert-butylphenylboronic acid (123324-71-0)

Guidance literature:

With 1H-imidazole; iron(III) chloride; at 20 ℃; for 0.25h; Inert atmosphere;

DOI:10.1055/s-0033-1340500

Reference yield: 83.4%

Trimethyl borate (121-43-7,63156-11-6) + 1-bromo-4-tert-butylbenzene (3972-65-4) → p-tert-butylphenylboronic acid (123324-71-0)

Guidance literature:

1-bromo-4-tert-butylbenzene; With magnesium; In tetrahydrofuran;

Trimethyl borate; In tetrahydrofuran; diethyl ether; at -70 - 20 ℃;

DOI:10.1515/znb-2002-1011

upstream raw materials:

1-bromo-4-tert-butylbenzene

Trimethyl borate

boric acid tributyl ester

tert-butylbenzene

Downstream raw materials:

4-(4-tert-butyl-phenyl)-2,3-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

5-(4-tert-butylphenyl)furan-2-carbaldehyde

3,6-bis-(4-tert-butyl-phenyl)-9-(4-vinyl-phenyl)-9H-carbazole

2-(4'-tert-butyl-biphenyl-4-ylmethyl)-1,1-dioxo-1λ⁶-[1,2]thiazinane-3-carboxylic acid tert-butyl ester

Refernces

• 1、 Schmid, Markus,Eberhardt, Robert,Klinga, Martti,Leskel?, Markku,Rieger, Bernhard. "New C2v- and chiral C2-symmetric olefin polymerization catalysts based on nickel(II) and palladium(II) diimine complexes bearing 2,6-diphenyl aniline moieties: Synthesis, structural characterization, and first insight into polymerization properties". . p. 2321 - 2330. Retrieved 2001.
• 2、 Han, Min Su,Lim, Taeho,Ryoo, Jeong Yup. "Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source". . p. 10966 - 10972. Retrieved 2020/09/23.
• 3、 Guan, Yong,Ding, Zhensheng,Wulff, William D.. "Vaulted biaryls in catalysis: A structure-activity relationship guided tour of the immanent domain of the VANOL ligand". . p. 15565 - 15571. Retrieved 2013/11/19.