29848-57-5

Usage

Uses

1. Used in Pharmaceutical Industry:
1-(Difluoromethyl)-4-nitrobenzene is used as a synthetic intermediate for the production of various pharmaceutical compounds. Its unique structure allows for the creation of molecules with specific biological activities, making it a valuable asset in drug discovery and development.
2. Used in Radiotracer Synthesis:
1-(Difluoromethyl)-4-nitrobenzene is used as a reagent in the preparation of fluorine-18-labeled fluoxetine, which serves as a potential radiotracer for studying reuptake sites in the brain. This application is particularly relevant in the field of neuroscience and psychiatric research, as it can help in understanding the mechanisms underlying various mental health disorders and the effectiveness of treatments.
3. Used in Agrochemical Industry:
In the agrochemical industry, 1-(Difluoromethyl)-4-nitrobenzene is employed as a key intermediate in the synthesis of various pesticides and insecticides. Its incorporation into these compounds can enhance their efficacy and selectivity, leading to improved crop protection and reduced environmental impact.
4. Used in Chemical Research:
Due to its reactivity and unique structural features, 1-(Difluoromethyl)-4-nitrobenzene is also used as a research compound in various chemical studies. It can be employed to explore new reaction pathways, develop innovative synthetic methods, and investigate the properties of related compounds.

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 5315-87-7 4-nitrobenzaldehyde semicarbazone 
• 41159-02-8 2-(4-nitrophenyl)-1,3-dithiolane 
• 619-78-3 1-dichloromethyl-4-nitrobenzene 
• 500-11-8 4-nitrobenzyl fluoride 
• 1309-60-0 lead(IV) oxide 
• 100-14-1 4-nitrobenzyl chloride 
• 636-98-6 p-nitrobenzene iodide 
• 206360-56-7 2,2-difluoro-2-(4-nitrophenyl)acetic acid 
• 243656-25-9 2,2-difluoro-2-(4-nitrophenyl)acetic acid ethyl ester 
• 100-01-6 4-nitro-aniline 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 86340-78-5 2,2-difluoro-1-phenyl-1-trimethylsiloxyethene 
• 6310-10-7 4-nitrobenzaldehyde hydrazone 

Downstream Products

• 29848-60-0 N-[4-(difluoromethyl)phenyl]acetamide 
• 114467-81-1 α,α-difluoro-4-nitrobenzyl phenyl ether 
• 114467-77-5 (difluoro(4-nitrophenyl)methyl)(phenyl)sulfide 
• 114467-86-6 1-(Azido-difluoro-methyl)-4-nitro-benzene 
• 49658-26-6 4-(difluoromethyl)aniline 

Relevant academic research and scientific papers

Synthesis of L-Au(I)-CF2H Complexes and Their Application as Transmetalation Shuttles to the Difluoromethylation of Aryl Iodides

We describe herein two alternative protocols to efficiently prepare difluoromethylgold(I) complexes bearing ancillary ligands with different electronic and steric properties. LAu-OX (X = H andt-Bu) species, formed in the presence of base, have been identified as intermediate complexes involved in these transformations. The application of these compounds as “CF2H transmetalation shuttles” from gold to palladium has been demonstrated in a Pd-catalyzed difluoromethylation reaction of aryl iodides, in which the Au-to-Pd transfer of “CF2H” is feasible under stoichiometric conditions. These findings will pave the way for catalytic manifolds in gold chemistry.

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.

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)

OXALAMIDES AS MODULATORS OF INDOLEAMINE 2,3-DIOXYGENASE

The present invention relates to novel compounds which act as modulators of indoleamine 2,3-dioxygenase (IDOl) and to the use of said compounds in the prophylaxis and/or treatment of diseases or conditions mediated by indoleamine 2,3-dioxygenase. The inve

Controlling the cleavage of carbon-carbon bonds to generate α,α-difluorobenzyl carbanions for the construction of difluoromethylbenzenes

Controlling the cleavage of carbon-carbon bonds during a chemical reaction is a substantial challenge; however, synthetic methods that accomplish this objective produce valuable and often unexplored reactivity. We have designed a mild process to generate α,α-difluorobenzyl carbanions in the presence of potassium carbonate by exploiting the cleavage of C-C bonds during the release of trifluoroacetate. The initiating reagent is potassium carbonate, which represents an improvement over existing protocols that require a strong base. Fragmentation studies across substituted arenes and heteroarenes were conducted along with computational analyses to elucidate reactivity trends. Furthermore, the mildly generated α,α-difluorobenzyl carbanions from electron-deficient aromatics and heteroaromatic rings can react with aldehydes to create derivatives of difluoromethylbenzenes, which are valuable synthetic targets.

Palladium-Catalyzed Decarbonylative Difluoromethylation of Acid Chlorides at Room Temperature

Methods for the direct synthesis of difluoromethylated arenes are sparse, despite the importance of the difluoromethyl group in medical, agro-, and materials chemistry. A palladium-catalyzed decarbonylative cross-coupling reaction of acid chlorides with a difluoromethyl zinc reagent is achieved to access difluoromethylated compounds. The transformation proceeds at room temperature and shows broad functional group tolerance, thus providing a general and efficient method for decarbonylative difluoromethylation of a wide range of aromatic carboxylic acids.

Visible-Light-Driven Oxidative Mono- and Dibromination of Benzylic sp 3 C-H Bonds with Potassium Bromide/Oxone at Room Temperature

Benzylic sp 3 C-H bonds have been successfully brominated with potassium bromide by using Oxone as an oxidant in water/dichloromethane under visible light at room temperature. Toluene, ethylbenzene and other alkylbenzenes bearing an electron-withdrawing group, such as Br, Cl, COMe, CO 2 Et, CO 2 H, CN or NO 2, provide the corresponding benzylic monobromides in good to excellent yields in this reaction. Dibromides can also be produced in the presence of excess potassium bromide in a prolonged reaction time. Control of the illuminance of visible light (~500 lux) is crucial to achieving both high yield and high selectivity in these brominations. Mono- and difluorides can be conveniently prepared through nucleophilic substitutions of the benzylic bromides with potassium fluoride.

Nickel-Catalyzed Aromatic Cross-Coupling Difluoromethylation of Grignard Reagents with Difluoroiodomethane

The nickel-catalyzed cross-coupling difluoromethylation of the Grignard reagents with difluoroiodomethane is shown to provide the corresponding aromatic difluoromethyl products in excellent to moderate yields. The difluoromethylation proceeds smoothly within 1 h at room temperature with 1.5 equiv of the Grignard reagents in the presence of Ni(cod)2/TMEDA (2.5-0.5 mol %). Mechanistic studies clarify that the oxidative addition of the Ni(0) catalyst to difluoroiodomethane provides the TMEDA-Ni(II)(CF2H)I complex. This intermediate is transformed to TMEDA-Ni(II)(CF2H)Ph via transmetalation with PhMgBr. The reductive elimination takes place to give the aromatic cross-coupling difluoromethylation product along with regeneration of the TMEDA-Ni(0) catalyst. Electron paramagnetic resonance (EPR) and radical clock analyses of the nickel-catalyzed reaction provide no EPR active Ni(I) and Ni(III) species at around g = 2 and only a trace amount of the cyclization product.

Synthesis of Aryldihalomethanes by Denitrogenative Dihalogenation of Benzaldehyde Hydrazones

We report a denitrogenative dihalogenation reaction of phenyldiazomethanes in which the hypervalent iodine reagents PhICl2 and TolIF2 act as surrogates for elemental chlorine and fluorine. Halogen transfer from iodane to aryldiazomethane is described, as is a tandem oxidative dihalogenation reaction between iodane and hydrazone. This is the first use of non-α-stabilized diazo compounds in this reaction, which provided an efficient synthesis of aryldifluoromethane (ArCHF2) and aryldichloromethane (ArCHCl2) derivatives. (Figure presented.).

Synthesis, reactivity, and catalytic applications of isolable (NHC)Cu(CHF2) complexes

Difluoromethyl copper complexes have been proposed as key intermediates in a variety of Cu-catalyzed difluoromethylation reactions. However, studies of these putative intermediates have been impeded by the low stability of these [Cu(CHF2)] species. This report describes the synthesis of isolable N-heterocyclic carbene ligated copper(I) difluoromethyl complexes. The stoichiometric reactions of these complexes with aryl electrophiles (i.e., diaryliodonium salts, aryl iodides, and aryl bromides) are described. In addition, Nheterocyclic carbene copper(I) species are demonstrated to serve as catalysts for the cross-coupling of aryl iodides with (difluoromethyl)trimethylsilane to afford difluoromethyl arene products.