53731-26-3

Usage

Uses

Used in Organic Synthesis:
1-(Difluoromethyl)naphthalene is used as a building block in organic synthesis for the creation of more complex molecular structures. Its unique chemical properties and reactivity make it a valuable component in the development of new compounds with specific characteristics.
Used in Pharmaceutical Applications:
In the pharmaceutical industry, 1-(Difluoromethyl)naphthalene is utilized as a precursor for the production of compounds with potential therapeutic applications. Its fluorinated nature may contribute to enhanced bioavailability and pharmacokinetic properties of the resulting molecules.
Used in Agrochemical Applications:
1-(Difluoromethyl)naphthalene also finds use in the agrochemical sector, where it serves as a starting material for the synthesis of compounds with pesticidal or herbicidal activities. The introduction of fluorine atoms can significantly affect the biological activity and environmental fate of these agrochemicals.
Used in Materials Science:
In the field of materials science, 1-(Difluoromethyl)naphthalene is explored for its potential in developing novel materials with improved properties, such as increased stability, reactivity, or selectivity. Its unique structure and fluorination make it an interesting candidate for various applications, including the development of advanced materials for energy storage, sensors, or catalysts.
Overall, 1-(Difluoromethyl)naphthalene is a versatile compound with a wide range of potential applications in different industries, thanks to its unique chemical structure and reactivity. Researchers and industries are continuously exploring its potential to develop new compounds and materials with specific properties for various scientific and industrial applications.

Upstream product

• 66-77-3 1-naphthaldehyde 
• 140135-73-5 1-(chlorodifluoromethyl)naphthalene 
• 86201-62-9 2-(2-naphthalen-1-yl)-1,3-dithiolane 
• 91-20-3 naphthalene 
• 1415126-20-3 C₂₃H₃₄S₂ 
• 57009-77-5 2-(naphthalene-1-yl)-1,3-dithiane 
• 134-32-7 1-amino-naphthalene 
• 90-14-2 1-Iodonaphthalene 
• 420132-02-1 di-(1-naphthalenyl)iodonium triflate 
• 667-27-6 Ethyl bromodifluoroacetate 
• 13922-41-3 1-Naphthylboronic acid 
• 75-45-6 Chlorodifluoromethane 
• 99747-74-7 1-naphthyl triflate 
• 1219454-89-3 2-((difluoromethyl)sulfonyl)pyridine 

Downstream Products

• 90-12-0 1-Methylnaphthalene 

Relevant academic research and scientific papers

Ph2S/selectfluor-promoted deoxydifluorination of aldehydes

The installation of a HCF2 group is a research area that has received increasing attention, and deoxydifluorination of aldehydes have served as an attractive protocol due to the wide availability of aldehydes. Herein we describe a Ph2/sub

Base-Catalyzed H/D Exchange Reaction of Difluoromethylarenes

The budding deuteriodifluoromethyl group (CF2D) is a potentially significant functional group in medicinal chemistry. Herein, we investigated t-BuOK-catalyzed H/D exchange reaction of difluoromethylarenes in DMSO-d6 solution. The method provides excellent

Electrochemical-Promoted Nickel-Catalyzed Oxidative Fluoroalkylation of Aryl Iodides

This work describes a general strategy for metal-catalyzed cross-coupling of fluoroalkyl radicals with aryl halides under electrochemical conditions. The contradiction between anodic oxidation of fluoroalkyl sulfinates and cathodic reduction of low-valent nickel catalysts can be well addressed by paired electrolysis, allowing for direct introduction of fluorinated functionalities into aromatic systems.

Phosphonium Ylide-Mediated Programmable Fluorination to Access Mono- And Difluoromethylarenes

Compounds bearing fluorinated moieties are pervasive in a wide range of pharmaceuticals and agrochemicals. The installation of fluorinated units is a persistently vital task in synthetic chemistry, where facile and manipulable assays are highly demanding.

Deoxyfluorination of (Hetero)aryl Aldehydes Using Tetramethylammonium Fluoride and Perfluorobutanesulfonyl Fluoride or Trifluoromethanesulfonic Anhydride

This Communication describes the conversion of (hetero)aryl aldehydes into the corresponding (hetero)aryl difluoromethyl products using anhydrous NMe4F in combination with perfluorobutanesulfonyl fluoride or trifluoromethanesulfonic anhydride.

Ligand-Less Iron-Catalyzed Aromatic Cross-Coupling Difluoromethylation of Grignard Reagents with Difluoroiodomethane

Iron-catalyzed cross-coupling difluoromethylations of the Grignard reagents with difluoroiodomethane provide various aromatic difluoromethyl products in good yields, not employing sterically demanding ligands. Difluoromethylations proceed within 30 min at -20 °C with 2.0 equiv of the Grignard reagents and FeCl3 or Fe(acac)3 (2.5 mol %). Mechanistic investigations clarify difluoromethyl radical intervention; Fe(0) ate is initially generated. Single-electron transfer from Fe(0) ate to difluoroiodomethane takes place. Recombination with aryl groups gives Ar-CF2Hs. The catalyst can be regenerated by the Grignard reagents.

Synthesis of (difluoromethyl)naphthalenes using the ring construction strategy: C-C bond formation on the central carbon of 1,1-difluoroallenes: Via Pd-catalyzed insertion

The insertion of 1,1-difluoroallenes was carried out to form a C-C bond exclusively on their central carbon. o-Bromophenyl-bearing 1,1-difluoroallenes underwent intramolecular insertion in the presence of a palladium catalyst. Regioselective C-C bond form

Palladium-Catalyzed Difluoromethylation of Aryl Chlorides and Bromides with TMSCF2H

A palladium-catalyzed cross-coupling of aryl chlorides/bromides with TMSCF2H is described. Two different catalysts, Pd(dba)2/BrettPhos and Pd(PtBu3)2, are demonstrated and provide a variety of difluoromethylated arenes in good yields.

Precatalyst Effects on Pd-Catalyzed Cross-Coupling Difluoromethylation of Aryl Boronic Acids

The Pd-catalyzed difluoromethylation of aryl boronic acids with difluoroiodomethane is shown to provide the difluoromethyl compounds in high to moderate yields by Pd(PPh3)2/DPEphos catalyst in H2O/toluene. Mechanistic studies show that the oxidative addition by Pd(PPh3)4 rather than Pd2(dba)3 precatalyst to difluoroiodomethane provides a square-planar trans-(PPh3)2Pd(II)(CF2H)I complex defined by X-ray crystallographic analysis. The trans-(PPh3)2Pd(CF2H)I complex is transformed to cis-(PPh3)2Pd(CF2H)Ph detected by low temperature NMR analysis, via transmetalation with phenylboronic acids. The reductive elimination occurs via ligand exchange to DPEphosPd(CF2H)Ph to give Ph-CF2H (t1/2 = 144.7 min at 20 °C) with formation of the Pd(0)(PPh3)2/DPEphos catalyst.

Difluoromethyl-substituted compound (by machine translation)

[Problem] to provide a, simple and inexpensive manufacturing method is difluoromethyl substituted compounds using a reagent. [Solution] a method for producing a compound using a catalyst [...] difluoromethyl-substituted,(I) the catalyst, a nickel compound and nitrogen in the bidentate ligand, raw Ar a-Z " in the formula, the Ar, substituted or unsubstituted aryl group or a substituted or unsubstituted 5 - 10 membered heteroaryl group C6 a-14, Z is, (OR) B2 Or a group represented by a is represented MgX. " Compound represented, difluoromethyl-substituted compounds, Ar e CF2 A method for producing a compound represented by H, or(II) catalyst, a palladium compound and a diphosphine ligand, raw material is Q-a B (OR1 )2 " In the formula, Q is, substituted or unsubstituted aryl C6 a-10, 5 - 10 membered heteroaryl or substituted or unsubstituted, or Ar1 A group represented by - CH=CH - shown. R1 Is, a hydrogen atom or an alkyl group C1 a-6. " Compounds, a compound represented by Q-a Zn-to-Q or, difluoromethyl-substituted compounds, Q-to-CF2 A method for producing a compound represented by H. [Drawing] no (by machine translation)