(3-(Cyclopentyloxy)-4-methoxyphenyl)boronic acid

Base Information

• Chemical Name: (3-(Cyclopentyloxy)-4-methoxyphenyl)boronic acid
• CAS No.: 159613-21-5
• Molecular Formula: C12H17BO4
• Molecular Weight: 236.076
• Hs Code.: 2931900090
• European Community (EC) Number: 810-870-0
• DSSTox Substance ID: DTXSID10400719
• Nikkaji Number: J1.989.198D
• Wikidata: Q82203737
• Mol file: 159613-21-5.mol

Synonyms:159613-21-5;(3-(Cyclopentyloxy)-4-methoxyphenyl)boronic acid;3-(Cyclopentyloxy)-4-methoxyphenylboronic acid;(3-cyclopentyloxy-4-methoxyphenyl)boronic acid;[3-(Cyclopentyloxy)-4-methoxyphenyl]boronic acid;QUININEHYDROBROMIDE;Boronic acid,B-[3-(cyclopentyloxy)-4-methoxyphenyl]-;SCHEMBL2889886;DTXSID10400719;PTXMXVNPZGJCAA-UHFFFAOYSA-N;MFCD04039013;AKOS004116176;AB17252;BS-21606;CS-0176117;FT-0763614;3-cyclopentyloxy-4-methoxy-phenylboronic acid;3-(Cyclopentyloxy)-4-methoxybenzeneboronic acid;F75670;(3-(Cyclopentyloxy)-4-methoxyphenyl)boronicacid;A883295;3-(cyclopentyloxy)-4-methoxybenzeneboronic acid, AldrichCPR

Chemical Property of (3-(Cyclopentyloxy)-4-methoxyphenyl)boronic acid

Chemical Property:

• Vapor Pressure: 2.78E-07mmHg at 25°C
• Refractive Index: 1.539
• Boiling Point: 404.9 °C at 760 mmHg
• Flash Point: 198.7 °C
• PSA: 58.92000
• Density: 1.18 g/cm³
• LogP: 0.69640
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 236.1219892
• Heavy Atom Count: 17
• Complexity: 231

Purity/Quality:

98%min ^*data from raw suppliers

(3-(Cyclopentyloxy)-4-methoxyphenyl)boronic acid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=C(C=C1)OC)OC2CCCC2)(O)O
• Uses: 3-(Cyclopentyloxy)-4-methoxyphenylboronic acid

Technology Process of (3-(Cyclopentyloxy)-4-methoxyphenyl)boronic acid

There total 11 articles about (3-(Cyclopentyloxy)-4-methoxyphenyl)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: 89.0%

Triisopropyl borate (5419-55-6) + 4-bromo-2-cyclopentyloxyanisole (138509-45-2) → 3-cyclopentyloxy-4-methoxyphenylboronic acid (159613-21-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran;

Reference yield: 89.0%

4-bromo-2-cyclopentyloxyanisole (138509-45-2) → 3-cyclopentyloxy-4-methoxyphenylboronic acid (159613-21-5)

Guidance literature:

4-bromo-2-cyclopentyloxyanisole; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 5h;

With Triisopropyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃;

With acetic acid; In tetrahydrofuran; hexane; water;

DOI:10.1016/S0040-4020(99)00686-9

Reference yield:

5-bromo-2-methoxyphenol (37942-01-1) → 3-cyclopentyloxy-4-methoxyphenylboronic acid (159613-21-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 89 percent / K₂CO₃ / dimethylformamide / 12 h / 50 °C

2.1: n-BuLi / diethyl ether; hexane / 1 h / -78 °C

2.2: diethyl ether; hexane / 1 h / -78 °C

With n-butyllithium; potassium carbonate; In diethyl ether; hexane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.03.017

upstream raw materials:

4-bromo-2-cyclopentyloxyanisole

2-(3-(cyclopentyloxy)-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Trimethyl borate

Cyclopentyl bromide

Downstream raw materials:

3'-cyclopentyloxy-4'-methoxy-biphenyl-4-carboxylic acid

Rolipram

Refernces

• 1、 Paraskar, Abhimanyu S.,Sudalai, Arumugam. "Co-catalyzed reductive cyclization of azido and cyano substituted α,β-unsaturated esters with NaBH4: enantioselective synthesis of (R)-baclofen and (R)-rolipram". . p. 4907 - 4916. Retrieved 2007/10/03.
• 2、 -. "Aryl thiophene derivatives as PDE IV inhibitors". . . Retrieved 2008/06/13.