(4-pentylphenyl)boronic Acid

Base Information

• Chemical Name: (4-pentylphenyl)boronic Acid
• CAS No.: 121219-12-3
• Molecular Formula: C11H17BO2
• Molecular Weight: 192.066
• Hs Code.: 29319090
• European Community (EC) Number: 681-163-0
• ChEMBL ID: CHEMBL1952296
• DSSTox Substance ID: DTXSID50404610
• Nikkaji Number: J1.102.040B
• Pharos Ligand ID: ZR7Y666HH5CF
• Wikidata: Q72500114
• Mol file: 121219-12-3.mol

Synonyms:121219-12-3;(4-pentylphenyl)boronic Acid;4-n-Pentylphenylboronic acid;4-Pentylphenylboronic Acid;4-Pentylbenzeneboronic acid;4-N-PENTYLBENZENEBORONIC ACID;4-Amylbenzeneboronic Acid;MFCD00995151;CHEMBL1952296;Boronic acid, (4-pentylphenyl)-;4-Amylphenylboronic Acid;4-n-pentylphenyl boronic acid;AKOS BRN-0130;4-n-pentylbenzene boronic acid;SCHEMBL1509988;DTXSID50404610;UZRMPSOGFATLJE-UHFFFAOYSA-N;BCP22757;BDBM50364283;AKOS004116473;AB07922;BCP9000264;CS-W002722;GS-6717;4-N-Pentylphenylboronic acid, AldrichCPR;AC-24820;SY015715;AM20050555;FT-0619317;A804694;J-515894;(4-pentylphenyl)boronic acid

Chemical Property of (4-pentylphenyl)boronic Acid

Chemical Property:

• Appearance/Colour: tan powder
• Vapor Pressure: 7.85E-05mmHg at 25°C
• Melting Point: 290-295 °C(lit.)
• Refractive Index: 1.509
• Boiling Point: 328 °C at 760 mmHg
• PKA: 8.87±0.10(Predicted)
• Flash Point: 152.2 °C
• PSA: 40.46000
• Density: 1.01 g/cm³
• LogP: 1.09910
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 192.1321599
• Heavy Atom Count: 14
• Complexity: 142

Purity/Quality:

99%, ^*data from raw suppliers

4-PentylphenylboronicAcid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)CCCCC)(O)O
• Uses: 4-Pentylphenylboronic Acid can be used for aryl coupling (in the presence of palladium) and Cannabinol (C175350)?synthesis. Intermediates of Liquid Crystals suzuki reaction

Technology Process of (4-pentylphenyl)boronic Acid

There total 7 articles about (4-pentylphenyl)boronic 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:

4,4,5,5-tetramethyl-2-(4-pentylphenyl)-1,3,2-dioxaborolane (1359844-02-2) → (4-pentylphenyl)boronic acid (121219-12-3)

Guidance literature:

4,4,5,5-tetramethyl-2-(4-pentylphenyl)-1,3,2-dioxaborolane; With potassium hydrogen fluoride; In methanol; water; for 0.5h;

With chloro-trimethyl-silane; water; In acetonitrile; for 1h;

DOI:10.1016/j.bmcl.2011.12.043

Reference yield:

tetrahydroxydiboron (13675-18-8) + 4-pentylaniline (33228-44-3) → (4-pentylphenyl)boronic acid (121219-12-3)

Guidance literature:

4-pentylaniline; With hydrogenchloride; sodium nitrite; In water; at 0 ℃; for 0.25h;

tetrahydroxydiboron; With potassium carbonate; In water; at 20 ℃; for 0.333333h;

DOI:10.1021/jo501665e

Reference yield:

n-pentylboronic acid (4737-50-2) → (4-pentylphenyl)boronic acid (121219-12-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate monohydrate; palladium diacetate / toluene

2.1: palladium on activated charcoal; hydrogen / ethanol

3.1: hydrogenchloride; sodium nitrite / water / Cooling with ice

4.1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; triethylamine / 1,4-dioxane / 80 °C

5.1: potassium hydrogen fluoride / methanol; water / 0.5 h

5.2: 1 h

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; hydrogenchloride; potassium phosphate monohydrate; potassium hydrogen fluoride; palladium on activated charcoal; hydrogen; palladium diacetate; triethylamine; sodium nitrite; In 1,4-dioxane; methanol; ethanol; water; toluene; 1.1: Suzuki coupling;

DOI:10.1016/j.bmcl.2011.12.043

upstream raw materials:

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

n-pentylboronic acid

para-nitrophenyl triflate

4-pentylaniline

Downstream raw materials:

1-pentyl-4-phenylbenzene

4-amino-4'-n-pentylbiphenyl

1-(4-pentylphenyl)-2,6,1-dioxaborinane

2-(4-pentylphenyl)-4-methylbenzoic acid

Refernces

• 1、 O'Connell, Daniel P.,Leblanc, Daniel F.,Cromley, Debra,Billheimer, Jeffrey,Rader, Daniel J.,Bachovchin, William W.. "Design and synthesis of boronic acid inhibitors of endothelial lipase". supporting information; experimental part. p. 1397 - 1401. Retrieved 2012/03/26.