799814-30-5

Basic information

• Product Name: 2-difluoromethylbenzonitrile
• Synonyms: 2-difluoromethylbenzonitrile;2-Cyanobenzal fluoride, alpha,alpha-Difluoro-o-tolunitrile
• CAS NO: 799814-30-5
• Molecular Formula: C₈H₅F₂N
• Molecular Weight: 153.1288064
• Mol File: 799814-30-5.mol

Chemical Properties

• Boiling Point: 233.7±35.0 °C(Predicted)
• Appearance: /
• Density: 1.20±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-difluoromethylbenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-difluoromethylbenzonitrile(799814-30-5)
• EPA Substance Registry System: 2-difluoromethylbenzonitrile(799814-30-5)

Safety Data

• Hazardous Substances Data: 799814-30-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-difluoromethylbenzonitrile is used as a building block for the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, 2-difluoromethylbenzonitrile is utilized as a key component in the creation of pesticides and other agrochemical products, enhancing crop protection and yield.
Used in Dye and Pigment Production:
2-difluoromethylbenzonitrile is employed as a raw material in the production of dyes and pigments, offering a wide range of color options for various applications, including textiles, plastics, and printing inks.
Safety Precautions:
Given its flammable nature and potential to cause irritation, 2-difluoromethylbenzonitrile should be handled with care, using appropriate personal protective equipment and following safety guidelines to minimize risks to human health and the environment. Additionally, due to its harmful effects on aquatic organisms, proper disposal and containment measures should be implemented to prevent environmental contamination.

Upstream product

• 1511-62-2 bromodifluoromethane 
• 2042-37-7 o-cyanobromobenzene 
• 4387-36-4 2-iodobenzonitrile 
• 1438388-96-5 tributyl(difluoromethyl)stannane 
• 1335290-31-7 ethyl 2-(2-cyanophenyl)-2,2-difluoroacetate 
• 1824201-60-6 2-cyanobenzenedifluoroacetic acid 
• 7468-67-9 o-formylbenzonitrile 

Downstream Products

• 799814-32-7 2-(difluoromethyl)benzoic acid 

Relevant articles and documents

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)

Metallaphotoredox Difluoromethylation of Aryl Bromides

Herein, we report a convenient and broadly applicable strategy for the difluoromethylation of aryl bromides by metallaphotoredox catalysis. Bromodifluoromethane, a simple and commercially available alkyl halide, is harnessed as an effective source of difluoromethyl radical by silyl-radical-mediated halogen abstraction. The merger of this fluoroalkyl electrophile activation pathway with a dual nickel/photoredox catalytic platform enables the difluoromethylation of a diverse array of aryl and heteroaryl bromides under mild conditions. The utility of this procedure is showcased in the late-stage functionalization of several drug analogues.

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, 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.

Copper-Catalyzed Difluoromethylation of Aryl Iodides with (Difluoromethyl)zinc Reagent

The combination of difluoroiodomethane and zinc dust or diethylzinc can readily lead to (difluoromethyl)zinc reagents. Therefore, the first copper-catalyzed difluoromethylation of aryl iodides with the zinc reagents is accomplished to afford the difluorom

Copper-mediated difluoromethylation of (hetero)aryl iodides and β-styryl halides with tributyl(difluoromethyl)stannane

Owing to their unique properties, molecules containing the difluoromethyl group (CF2H) are of great interest. Tributyl(difluoromethyl)stannane has now been used for the selective and efficient direct ipso difluoromethylation of aryl iodides, he

A new method for aromatic difluoromethylation: Copper-catalyzed cross-coupling and decarboxylation sequence from aryl iodides

A new methodology for aromatic difluoromethylation is described. Aryl iodides reacted with α-silyldifluoroacetates upon treatment with copper catalyst in DMSO or DME to give the corresponding aryldifluoroacetates in moderate to good yields. The subsequent hydrolysis of aryldifluoroacetates and KF-promoted decarboxylation afforded a variety of difluoromethyl aromatics.

DIFLUOROMETHYLBENZANILIDES AND USE THEREOF FOR COMBATING MICRO-ORGANISMS, INTERMEDIATE PRODUCTS AND USE THEREOF

The invention relates to novel difluoromethylbenzanilides of formula (I), wherein R1, R2, R3, R4, R5 and Z have the meanings cited in the description. The invention also relates to several methods for