Fenipentol

Base Information

• Chemical Name: Fenipentol
• CAS No.: 583-03-9
• Deprecated CAS: 136264-41-0,21632-19-9,21632-19-9
• Molecular Formula: C11H16O
• Molecular Weight: 164.247
• Hs Code.: 2906299090
• European Community (EC) Number: 209-493-9
• NSC Number: 8478
• UNII: X3FZE77O60
• DSSTox Substance ID: DTXSID4046818
• Nikkaji Number: J2.071K
• Wikidata: Q426345
• NCI Thesaurus Code: C65652
• Metabolomics Workbench ID: 126877
• ChEMBL ID: CHEMBL2104321
• Mol file: 583-03-9.mol

Synonyms:1-phenyl-1-hydroxy-n-pentane;1-phenyl-1-hydroxypentane;1-PHNP;Febichol;fenipentol;fenipentol, (R)-isomer;fenipentol, (S)-isomer

Chemical Property of Fenipentol

Chemical Property:

• Vapor Pressure: 0.0156mmHg at 25°C
• Melting Point: <25 °C
• Refractive Index: 1.5080
• Boiling Point: 245.2 °C at 760 mmHg
• PKA: 14.43±0.20(Predicted)
• Flash Point: 110.7 °C
• PSA: 20.23000
• Density: 0,96 g/cm³
• LogP: 2.91020
• Storage Temp.: -20°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 164.120115130
• Heavy Atom Count: 12
• Complexity: 106

Purity/Quality:

97% ^*data from raw suppliers

1-Phenyl-1-pentanol >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCC(C1=CC=CC=C1)O
• Uses: Biliary dyskinesia;Choleretic

Technology Process of Fenipentol

There total 153 articles about Fenipentol 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%

phenyl butyl ketone (1009-14-9) → 1-Phenyl-1-pentanol (583-03-9)

Guidance literature:

With C₂₈H₃₅ClCoN₅⁽¹⁺⁾*Cl^(1-); potassium tert-butylate; hydrogen; In tetrahydrofuran; at 20 ℃; for 16h; under 22502.3 Torr; Autoclave;

DOI:10.1016/j.chempr.2019.03.010

Reference yield: 98.0%

1-bromo-butane (109-65-9) + benzaldehyde (100-52-7) → 1-Phenyl-1-pentanol (583-03-9)

Guidance literature:

1-bromo-butane; With magnesium; lithium chloride; In tetrahydrofuran; at 50 ℃; for 0.125h; Flow reactor;

benzaldehyde; In tetrahydrofuran; at 20 ℃; for 0.333333h; Flow reactor;

DOI:10.1021/acs.orglett.7b01590

Reference yield: 87.0%

2-phenyl-1,3-dioxolane (936-51-6) + lithium di-n-butylcuprate (24406-16-4) → 1-Phenyl-1-pentanol (583-03-9)

Guidance literature:

2-phenyl-1,3-dioxolane; With sodium dodecyl-sulfate; toluene-4-sulfonic acid; In tetrahydrofuran; water; at 25 ℃; for 3.5h;

lithium di-n-butylcuprate; In diethyl ether; hexane; at 25 ℃; for 12h; Further stages.;

DOI:10.1002/anie.200703002

upstream raw materials:

phenyl butyl ketone

n-butyllithium

benzaldehyde

n-butyl magnesium bromide

Downstream raw materials:

benzoic acid-(1-phenyl-pentyl ester)

phenyl butyl ketone

phthalic acid mono-(1-phenyl-pentyl ester)

bis-(1-phenyl-pentyl)-ether

Refernces

ENANTIOSELECTIVE ADDITION OF N-BUTYLLITHIUM TO BENZALDEHYDE IN THE PRESENCE OF CHIRAL LITHIUM AMIDES

10.1016/S0040-4039(01)81559-8

The research aimed to investigate the potential of chiral lithium amides (la-e) as chiral catalysts in the addition of n-butyllithium to benzaldehyde, with the goal of achieving enantioselective synthesis of 1-phenyl-1-pentanol. The study focused on the impact of different ligand structures and reaction conditions on the optical yield of the chiral alcohol. The chemicals used in the process included n-butyllithium, benzaldehyde, and a series of chiral lithium amides (la-e) synthesized from inexpensive S-α-methylbenzylamine. The researchers found that the structure of the ligand and the reaction conditions, such as solvent and temperature, significantly influenced the selectivity of the reaction. The highest optical yield of 90% was achieved using a DMM/Et20 (1:1, v/v) mixture as solvent and a reaction temperature of -120°C with ligand Id. The study concluded that the chiral lithium amides could effectively act as chiral catalysts in this enantioselective addition reaction, with the potential to improve the optical yield through ligand design and optimization of reaction conditions.