579-39-5

Basic information

• Product Name: 4,4'-DIFLUOROBENZIL
• Synonyms: 1,2-Bis(4-fluorophenyl)-1,2-ethanedione;BIS(P-FLUOROPHENYL)ETHANEDIONE;4,4'-DIFLUOROBENZIL;4,4'-DIFLUOROBIBENZOYL;4,4'-DIFLUORODIBENZOYL;4,4'-FLUOROBENZIL;4,4'-Difluorobenzil,99%;Ethanedione, bis(4-fluorophenyl)-
• CAS NO: 579-39-5
• Molecular Formula: C₁₄H₈F₂O₂
• Molecular Weight: 246.21
• Product Categories: Aromatic Halides (substituted);C13 to C14;Carbonyl Compounds;Ketones;Aryl Fluorinated Building Blocks;Bioactive Small Molecules;Building Blocks;C13 to C14;C13-C26;Carbonyl Compounds;Cell Biology;Chemical Synthesis;D-DIF;Fluorinated Building Blocks;Organic Building Blocks;Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks
• Mol File: 579-39-5.mol
• Article Data: 46

Chemical Properties

• Melting Point: 120-122 °C(lit.)
• Boiling Point: 370.2 °C at 760 mmHg
• Flash Point: 141.5 °C
• Appearance: pale yellow powder
• Density: 1.3163 (estimate)
• Storage Temp.: Store below +30°C.
• Water Solubility: Soluble in water.
• BRN: 1971736
• CAS DataBase Reference: 4,4'-DIFLUOROBENZIL(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-DIFLUOROBENZIL(579-39-5)
• EPA Substance Registry System: 4,4'-DIFLUOROBENZIL(579-39-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• TSCA: T
• Hazardous Substances Data: 579-39-5(Hazardous Substances Data)

Usage

Description

4,4'-Difluorobenzil is a benzil derivative characterized by its pale yellow powder form. It is known for its chemical reactivity, particularly in condensation reactions with various compounds such as benzylurea, phenethylurea, and Fe2(SH)2(CO)6. 4,4'-DIFLUOROBENZIL has been investigated for its potential applications in the synthesis of various organic compounds and materials.

Uses

Used in Organic Synthesis:
4,4'-Difluorobenzil is used as a key intermediate in the synthesis of various organic compounds, including 2,3-bis(4-fluorophenyl)thieno[3,4-b]pyrazine. Its unique chemical properties make it a valuable component in the creation of complex molecular structures.
Used in Polymer Synthesis:
In the polymer industry, 4,4'-difluorobenzil is used as a reactant in the preparation of poly(ether-α-diketone)s. It undergoes a nucleophilic substitution reaction with bisphenol A, contributing to the formation of these high-performance polymers.
Used in Pharmaceutical Chemistry:
4,4'-Difluorobenzil is utilized in the synthesis of DPPF (4,4′-difluoro-2,3-diphenylpyrazine) and MDPPF (4,4′-difluoro-5-methyl 2,3-diphenylpyrazine), which are compounds that can be used in the development of pharmaceuticals. These compounds are synthesized through direct condensation with ethylenediamine and 1,2-diaminopropane, respectively.
Used in Heterocyclic Chemistry:
4,4'-DIFLUOROBENZIL is also employed in the synthesis of 2,3-bis(4-fluorophenyl)quinoxaline, which is achieved through direct condensation with 1,2-phenylenediamine. The resulting heterocyclic compounds have potential applications in various fields, including materials science and pharmaceuticals.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 2959, 1994 DOI: 10.1016/S0040-4039(00)76671-8

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 1314234-16-6 1,2-bis(3,5-difluorophenyl)acetylene 
• 2265-91-0 1,3-difluoro-5-iodobenzene 
• 5216-31-9 1,2-bis(4-fluorophenyl)acetylene 
• 366-68-7 4,4'-difluorodeoxybenzoin 
• 1493-23-8 (4-fluorophenyl)lithium 
• 106675-70-1 N¹,N²-dimethoxy-N¹,N²-dimethyloxalamide 
• 144461-86-9 2-(4-fluorophenyl)-2-(α-hydroxy-4-fluorobenzyl)-1,3-dithiane 
• 2966-36-1 1-acetoxy-2,2,2-trichloro-1,1-bis-(4-fluoro-phenyl)-ethane 
• 565-04-8 α,α,α',α'-tetrachloro-4,4'-difluoro-bibenzyl 
• 4165-81-5 1,1-diphenyl-1,3-butadiene 
• 588-56-7 1,2-bis(p-fluorophenyl)ethylene 
• 766-98-3 1-ethynyl-4-fluorobenzene 

Downstream Products

• 357-60-8 4,4'-difluoro-benzilic acid 
• 53458-01-8 2-(4-bromophenyl)-4,5-bis(4-fluorophenyl)imidazole 
• 148186-43-0 2,3-bis(4-fluoro-phenyl)quinoxaline 
• 350687-58-0 2,3-bis(4-fluorophenyl)-6-nitroquinoxaline 
• 355397-64-7 2,3-bis(4-fluorophenyl)quinoxaline-6-carboxylic acid 
• 884050-44-6 N,N'-bis(1,1-dimethylethyl)-1,2-bis(4-fluorophenyl)ethane-1,2-diimine 
• 654673-98-0 (α-ethoxy-4-fluorobenzyl)-(4-fluorophenyl)-ketone 
• 654674-03-0 (α-isopropoxy-4-fluorobenzyl)-(4-fluorophenyl)-ketone 
• 61656-00-6 5,6-bis-(4-fluoro-phenyl)-2⁽⁴⁾H-[1,2,4]triazin-3-one 

Relevant articles and documents

Cooperative N-Heterocyclic Carbene/Nickel-Catalyzed Hydroacylation of 1,3-Dienes with Aldehydes in Water

The cooperative N-heterocyclic carbene/nickel-catalyzed redox-neutral hydroacylation of 1,3-dienes with aldehydes in water was reported. A wide range of aliphatic and aromatic aldehydes were directly coupled with 1,3-dienes, providing synthetically useful β,γ-unsaturated ketones or the corresponding ketones after hydrogenation in moderate to high yields and high atom economy. This protocol first demonstrated the compatibility of NHC catalysis with nickel catalysis. Water was used as the sole solvent, which is rarely reported in a cooperative metal/organic catalytic system.

Catalyst-Free and Transition-Metal-Free Approach to 1,2-Diketones via Aerobic Alkyne Oxidation

A catalyst-free and transition-metal-free method for the synthesis of 1,2-diketones from aerobic alkyne oxidation was reported. The oxidation of various internal alkynes, especially more challenging aryl-alkyl acetylenes, proceeded smoothly with inexpensive, easily handled, and commercially available potassium persulfate and an ambient air balloon, achieving the corresponding 1,2-diketones with up to 85% yields. Meanwhile, mechanistic studies indicated a radical process, and the two oxygen atoms in the 1,2-diketons were most likely from persulfate salts and molecular oxygen, respectively, rather than water.

Ring Closing Metathesis Approach for the Synthesis of o-Terphenyl Derivatives

A linear synthesis of o-terphenyl derivatives has been delineated using ring closing metathesis (RCM) as the key step. In this approach, benzil derivatives upon allyl Grignard addition provides diphenyl-1,2-diallyl dihydroxy derivatives which undergo ring closing metathesis to afford tetrahydro terphenyl derivatives. Aromatization-driven dehydration then leads to a diverse set of electron rich and electron deficient o-terphenyls. Furthermore, oxidative coupling of electron rich o-terphenyls provides the corresponding triphenylene derivatives.