159613-21-5

Basic information

• Product Name: 3-CYCLOPENTYLOXY-4-METHOXYBENZENEBORONIC ACID
• Synonyms: AKOS BRN-0166;3-CYCLOPENTYLOXY-4-METHOXYPHENYLBORONIC ACID;3-CYCLOPENTYLOXY-4-METHOXYBENZENEBORONIC ACID
• CAS NO: 159613-21-5
• Molecular Formula: C₁₂H₁₇BO₄
• Molecular Weight: 236.07
• Mol File: 159613-21-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 404.9 °C at 760 mmHg
• Flash Point: 198.7 °C
• Appearance: /
• Density: 1.18 g/cm³
• Vapor Pressure: 2.78E-07mmHg at 25°C
• Refractive Index: 1.539
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-CYCLOPENTYLOXY-4-METHOXYBENZENEBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CYCLOPENTYLOXY-4-METHOXYBENZENEBORONIC ACID(159613-21-5)
• EPA Substance Registry System: 3-CYCLOPENTYLOXY-4-METHOXYBENZENEBORONIC ACID(159613-21-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• Hazardous Substances Data: 159613-21-5(Hazardous Substances Data)

Usage

Uses

3-(Cyclopentyloxy)-4-methoxyphenylboronic acid

InChI:InChI=1/C12H17BO4/c1-16-11-7-6-9(13(14)15)8-12(11)17-10-4-2-3-5-10/h6-8,10,14-15H,2-5H2,1H3

Upstream product

• 613-70-7 2-methoxyphenyl acetate 
• 90-05-1 2-methoxy-phenol 
• 137-43-9 Cyclopentyl bromide 
• 60-29-7 diethyl ether 
• 108-95-2 phenol 
• 109-72-8 n-butyllithium 
• 121-43-7 Trimethyl borate 
• 138509-45-2 4-bromo-2-cyclopentyloxyanisole 
• 5419-55-6 Triisopropyl borate 
• 37942-01-1 5-bromo-2-methoxyphenol 
• 66037-04-5 1-acetoxy-5-bromo-2-methoxybenzene 
• 658081-58-4 2-(3-(cyclopentyloxy)-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 61413-54-5 Rolipram 
• 959799-63-4 ethyl (S)-3-[3-(cyclopentyloxy)-4-methoxyphenyl]-4-phthalimidobutanoate 
• 1002760-95-3 tert-butyl (R)-3-(3-(cyclopentyloxy)-4-methoxy-phenyl)-3-phenyl-propanoate 
• 171808-25-6 6-(3-Cyclopentyloxy-4-methoxy-phenyl)-3,4-dihydro-2H-naphthalen-1-one 
• 158427-69-1 3'-cyclopentyloxy-4'-methoxy-biphenyl-4-carboxylic acid 
• 222840-53-1 5-(4-Carboxyphenyl)-2,3-bis((3-cyclopentyloxy-4-methoxy)phenyl)thiophene 
• 85416-73-5 (S)-rolipram 
• 85416-75-7 (R)-4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one 
• 894421-61-5 (Z)-ethyl 4-azido-3-(3-(cyclopentyloxy)-4-methoxyphenyl)but-2-enoate 
• 894421-55-7 (Z)-ethyl 4-bromo-3-(3-(cyclopentyloxy)-4-methoxyphenyl)but-2-enoate 
• 162542-90-7 R-(+)-4-(2-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethyl)pyridine 
• 1027203-75-3 C₂₈H₃₀F₃NO₆S 

Relevant articles and documents

Solid phase parallel synthesis of highly substituted thiophene derivatives and identification of novel phosphodiesterase-4 (PDE-4) inhibitors

A versatile protocol for solid phase synthesis of highly substituted thiophene derivatives and their activity against the PDE-4 enzyme are discussed. This protocol employs 3-hydroxymethylthiophene-2-boronic acid (5) as the scaffold and sequential palladium catalyzed cross-coupling reactions as the C-C bond forming step. This methodology allows convenient modification of the thiophene core from three directions, giving rise to structurally diverse derivatives with overall high chemical purity and yield. A novel series of potent PDE-4 inhibitors have been identified from these compounds.

Enantioselective Syntheses of (-)-(R)-Rolipram, (-)-(R)-Baclofen and Other GABA Analogues via Rhodium-Catalyzed Conjugate Addition of Arylboronic Acids

Highly enantioselective syntheses of two important γ-aminobutyric acid (GABA) analogues, the antispastic drug (-)-(R)-Baclofen and the antidepressant agent (-)-(R)-Rolipram, are reported. Key-steps in both syntheses are the Rh-catalyzed asymmetric 1,4-additions of arylboronic acids to 4-aminobut-2,3-enoic acid derivatives.

Substituted biphenyl derivatives

A compound of the following structure: STR1 wherein R8 =H: R1 =alkyl, cycloalkyl, arylalkyl, aryl; R2 =cycloalkyl, aryl, C3 -C10 alkyl; X,Y=O, S(O)n, NH; Z=CO2 R3, C(O