20651-66-5

Basic information

• Product Name: 1-butyl-3-fluoro-benzene
• Synonyms: 1-butyl-3-fluoro-benzene
• CAS NO: 20651-66-5
• Molecular Formula: C₁₀H₁₃F
• Molecular Weight: 152.21
• Mol File: 20651-66-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 181.3°C at 760 mmHg
• Flash Point: 55.2°C
• Appearance: /
• Density: 0.954g/cm³
• Vapor Pressure: 1.17mmHg at 25°C
• Refractive Index: 1.477
• CAS DataBase Reference: 1-butyl-3-fluoro-benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-butyl-3-fluoro-benzene(20651-66-5)
• EPA Substance Registry System: 1-butyl-3-fluoro-benzene(20651-66-5)

Safety Data

• Hazardous Substances Data: 20651-66-5(Hazardous Substances Data)

Usage

Physical state

Colorless liquid

Odor

Faint aromatic

Uses

a. Manufacturing of pharmaceuticals
b. Dyes
c. Perfumes

Primary role

Intermediate in the production of other organic chemicals

Application

Solvent in various industrial processes

Known for

a. Precursor in the synthesis of different fluorinated organic compounds
b. Potential biological and pharmaceutical applications
c. Building block for drug molecules due to its unique structure and functional groups

Safety

Handle with care and follow proper safety procedures due to potential health hazards

InChI:InChI=1/C10H13F/c1-2-3-5-9-6-4-7-10(11)8-9/h4,6-8H,2-3,5H2,1H3

Upstream product

• 84648-67-9 C₁₂H₁₃FO₄ 
• 1215100-19-8 4-n-butylphenyl trifluoromethanesulfonate 
• 66107-29-7 4-methoxyphenyl triflate 
• 41492-05-1 p-bromobutylbenzene 
• 1073-06-9 3-fluorobromobenzene 
• 693-04-9 butyl magnesium bromide 
• 5369-17-5 m-(n-butyl)-aniline 

Downstream Products

• 1312574-01-8 (4-butyl-2-fluorophenyl)boronic acid 

Relevant articles and documents

Oxidative Addition Complexes as Precatalysts for Cross-Coupling Reactions Requiring Extremely Bulky Biarylphosphine Ligands

In this report, we describe the application of palladium-based oxidative addition complexes (OACs) as effective precatalysts for C-N, C-O, and C-F cross-coupling reactions with a variety of (hetero)arenes. These complexes offer a convenient alternative to previously developed classes of precatalysts, particularly in the case of the bulkiest biarylphosphine ligands, for which palladacycle-based precatalysts do not readily form. The precatalysts described herein are easily prepared and stable to long-term storage under air.

A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides

A new biaryl monophosphine ligand (AlPhos, L1) allows for the room-temperature Pd-catalyzed fluorination of a variety of activated (hetero)aryl triflates. Furthermore, aryl triflates and bromides that are prone to give mixtures of regioisomeric aryl fluorides with Pd-catalysis can now be converted to the desired aryl fluorides with high regioselectivity. Analysis of the solid-state structures of several Pd(II) complexes, as well as density functional theory (DFT) calculations, shed light on the origin of the enhanced reactivity observed with L1.

Studying regioisomer formation in the pd-catalyzed fluorination of aryl triflates by deuterium labeling

Isotopic labeling has been used to determine that a portion of the desired product in the Pd-catalyzed fluorination of electron-rich, non-ortho-substituted aryl triflates results from direct C-F cross-coupling. In some cases, formation of a Pd-aryne intermediate is responsible for producing undesired regioisomers. The generation of the Pd-aryne intermediate occurs primarily via ortho-deprotonation of a L·Pd(Ar)OTf (L = biaryl monophosphine) species by CsF and thus competes directly with the transmetalation step of the catalytic cycle. Deuterium labeling studies were conducted with a variety of aryl triflates.