1-Fluoro-4-phenyl-2-butanone

Base Information

• Chemical Name: 1-Fluoro-4-phenyl-2-butanone
• CAS No.: 772-67-8
• Molecular Formula: C10H11FO
• Molecular Weight: 166.195
• DSSTox Substance ID: DTXSID101309066
• Nikkaji Number: J1.731.687G
• Mol file: 772-67-8.mol

Synonyms:1-Fluoro-4-phenyl-2-butanone;772-67-8;1-Fluoro-4-phenyl-butan-2-one;DTXSID101309066

Chemical Property of 1-Fluoro-4-phenyl-2-butanone

Chemical Property:

• Boiling Point: 112 - 116 °C (10 mmHg)
• PSA: 17.07000
• LogP: 2.15780
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 166.079393132
• Heavy Atom Count: 12
• Complexity: 139

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCC(=O)CF

Technology Process of 1-Fluoro-4-phenyl-2-butanone

There total 12 articles about 1-Fluoro-4-phenyl-2-butanone 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: 72.0%

fluoroacetonitrile (503-20-8) + 1-phenyl-2-bromoethane (103-63-9) → 1-fluoro-4-phenyl-butan-2-one (772-67-8)

Guidance literature:

1-phenyl-2-bromoethane; With magnesium; In diethyl ether; at 20 ℃; for 1h; Inert atmosphere;

fluoroacetonitrile; In diethyl ether; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.joc.5b01240

Reference yield: 70.0%

fluoroiodomethane (373-53-5) + N-methoxy-N-methyl-3-phenylpropionamide (170646-96-5) → 1-fluoro-4-phenyl-butan-2-one (772-67-8)

Guidance literature:

fluoroiodomethane; With methyllithium; In tetrahydrofuran; diethyl ether; at -60 ℃; for 3.61111E-06h; Flow reactor;

N-methoxy-N-methyl-3-phenylpropionamide; In tetrahydrofuran; diethyl ether; at -60 ℃; for 0.00218056h; chemoselective reaction; Flow reactor;

DOI:10.1002/anie.202003831

Reference yield: 63.0%

1-fluoro-4-phenylbutan-2-ol (1035814-78-8) → 1-fluoro-4-phenyl-butan-2-one (772-67-8)

Guidance literature:

With 2,6-dimethylpyridine; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate; In dichloromethane; for 6h;

DOI:10.1021/acs.joc.5b01240

upstream raw materials:

phenethylmagnesium bromide

ethyl 2-fluoroacetate

benzyl bromide

fluoroacetone cyclohexylimine

Downstream raw materials:

Acetic acid 1-fluoromethyl-3-phenyl-propyl ester

C₁₄H₁₉F

C₁₂H₁₅FO

C₁₄H₁₇FO₂

Refernces

• 1、 Parisi, Giovanna,Colella, Marco,Monticelli, Serena,Romanazzi, Giuseppe,Holzer, Wolfgang,Langer, Thierry,Degennaro, Leonardo,Pace, Vittorio,Luisi, Renzo. "Exploiting a beast in carbenoid chemistry: Development of a straightforward direct nucleophilic fluoromethylation strategy". supporting information. p. 13648 - 13651. Retrieved 2017/11/06.
• 2、 Grassi, David,Li, Hailing,Alexakis, Alexandre. "Formation of chiral fluoroalkyl products through copper-free enantioselective allylic alkylation catalyzed by an NHC ligand". supporting information. p. 11404 - 11406. Retrieved 2013/01/15.