458-11-7

Basic information

• Product Name: 3',4'-DIFLUOROACETANILIDE
• Synonyms: 3',4'-DIFLUOROACETANILIDE;3,4-DIFLUOROACETANILIDE;BUTTPARK 144\07-35;N-(3,4-Difluorophenyl)acetamide
• CAS NO: 458-11-7
• Molecular Formula: C₈H₇F₂NO
• Molecular Weight: 171.14
• Product Categories: Anilines, Amides & Amines;Fluorine Compounds
• Mol File: 458-11-7.mol

Chemical Properties

• Melting Point: 127-127.5 °C
• Boiling Point: 291.2 °C at 760 mmHg
• Flash Point: 129.9 °C
• Appearance: /
• Density: 1.307 g/cm³
• Vapor Pressure: 0.00198mmHg at 25°C
• Refractive Index: 1.531
• PKA: 13.32±0.70(Predicted)
• CAS DataBase Reference: 3',4'-DIFLUOROACETANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3',4'-DIFLUOROACETANILIDE(458-11-7)
• EPA Substance Registry System: 3',4'-DIFLUOROACETANILIDE(458-11-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 458-11-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Manufacturing:
3',4'-Difluoroacetanilide is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure allows for the selective modification of functional groups, which is essential in the development of new drugs with specific therapeutic properties.
Used in Chemical Synthesis:
In the field of chemical synthesis, 3',4'-Difluoroacetanilide serves as a building block for the creation of a wide range of organic compounds. Its solubility in organic solvents and reactivity make it a valuable component in the synthesis of various chemical products.
Used in Medicinal Chemistry Research:
3',4'-Difluoroacetanilide is utilized as a reagent in medicinal chemistry research, where it aids in the exploration and development of novel drug candidates. Its potential application in this field is attributed to its ability to selectively modify molecular structures, which can lead to the discovery of new therapeutic agents.
Used in Organic Synthesis as a Reagent:
3',4'-Difluoroacetanilide is employed as a reagent in organic synthesis due to its capacity to selectively modify specific functional groups in a molecule. This selective modification is crucial for the synthesis of complex organic compounds with desired properties.

InChI:InChI=1/C8H7F2NO/c1-5(12)11-6-2-3-7(9)8(10)4-6/h2-4H,1H3,(H,11,12)

Upstream product

• 108-24-7 acetic anhydride 
• 3863-11-4 3,4-difluoroaniline 
• 103-84-4 Acetanilid 
• 75-36-5 acetyl chloride 
• 372-39-4 3,5-difluoroaniline 
• 141-32-2 acrylic acid n-butyl ester 
• 1182601-99-5 N-(3,4-difluoro-2-(trimethylsilyl)phenyl)acetamide 
• 653-22-5 1-Acetylamino-2,3,4,5,6-pentafluorobenzen 
• 771-60-8 2,3,4,5,6-pentafluoroaniline 

Downstream Products

• 330-48-3 3,4-difluoro-N-(3,4-difluorophenyl)benzenamine 
• 1662-21-1 N-(3,4-difluoro-2-nitrophenyl)acetamide 
• 209909-13-7 2-chloro-6,7-difluoro-3-quinoline-3-carbaldehyde 
• 78056-39-0 4,5-difluoro-2-nitroaniline 
• 173029-85-1 5⁽⁶⁾-fluoro-6⁽⁵⁾-(4-methyl-1-piperazinyl)benzofuroxan 
• 76179-40-3 2-amino-4,5-difluoroaniline 
• 125163-15-7 4-Fluoro-5-methoxy-1,2-phenylenediamine 
• 125163-14-6 4-Ethoxy-5-fluoro-1,2-phenylenediamine 
• 123470-47-3 5,6-difluoro-1H-benzo[d]imidazole-2-thiol 
• 125163-12-4 4-Fluoro-5-methoxy-2-nitroaniline 
• 125163-13-5 5-Ethoxy-4-fluoro-2-nitroaniline 
• 329939-78-8 4,5-difluoro-2-nitro-phenylacetamide 
• 1182601-93-9 (C₆H₂F₂NHCCH₃OPdCH₃C₆H₄SO₃)2 
• 1182602-19-2 butyl (E)-3-(2-acetamido-4,5-difluorophenyl)acrylate 

Relevant articles and documents

A comprehensive assessment of a new series of 5′,6′-difluorobenzotriazole-acrylonitrile derivatives as microtubule targeting agents (MTAs)

Microtubules (MTs) are the principal target for drugs acting against mitosis. These compounds, called microtubule targeting agents (MTAs), cause a mitotic arrest during G2/M phase, subsequently inducing cell apoptosis. MTAs could be classified in two groups: microtubule stabilising agents (MSAs) and microtubule destabilising agents (MDAs). In this paper we present a new series of (E) (Z)-2-(5,6-difluoro-(1H)2H-benzo[d] [1,2,3]triazol-1(2)-yl)-3-(R)acrylonitrile (9a-j, 10e, 11a,b) and (E)-2-(1H-benzo[d] [1,2,3]triazol-1-yl)-3-(R)acrylonitrile derivatives (13d,j), which were recognised to act as MTAs agents. They were rationally designed, synthesised, characterised and subjected to different biological assessments. Computational docking was carried out in order to investigate the potential binding to the colchicine-binding site on tubulin. From this first prediction, the di-fluoro substitution seemed to be beneficial for the binding affinity with tubulin. The new fluorine derivatives, here presented, showed an improved antiproliferative activity when compared to the previously reported compounds. The biological evaluation included a preliminary antiproliferative screening on NCI60 cancer cells panel (1–10 μM). Compound 9a was selected as lead compound of the new series of derivatives. The in vitro XTT assay, flow cytometry analysis and immunostaining performed on HeLa cells treated with 9a showed a considerable antiproliferative effect, (IC50 = 3.2 μM), an increased number of cells in G2/M-phase, followed by an enhancement in cell division defects. Moreover, β-tubulin staining confirmed 9a as a MDA triggering tubulin disassembly, whereas colchicine-9a competition assay suggested that compound 9a compete with colchicine for the binding site on tubulin. Then, the co-administration of compound 9a and an extrusion pump inhibitor (EPI) was investigated: the association resulted beneficial for the antiproliferative activity and compound 9a showed to be client of extrusion pumps. Finally, structural superimposition of different colchicine binding site inhibitors (CBIs) in clinical trial and our MDA, provided an additional confirmation of the targeting to the predicted binding site. Physicochemical, pharmacokinetic and druglikeness predictions were also conducted and all the newly synthesised derivatives showed to be drug-like molecules.

Direct para-Selective C-H Amination of Iodobenzenes: Highly Efficient Approach for the Synthesis of Diarylamines

Iodine(III)-mediated synthesis of 4-iodo-N-phenylaniline from iodobenzene has been achieved, and the reaction can proceed under mild conditions. A variety of functional groups were well tolerated, providing the corresponding products in moderate to good yields. The remaining iodine group provides an effective platform for converting the products into several valuable asymmetric diphenylamines. Most importantly, this reaction can be easily scaled up to the ten-gram scale, highlighting its synthetic utility. The mechanistic study revealed that the in situ generated aryl hypervalent iodine intermediate is the key factor to realize this para-selective C-H amination reaction.

Vinylene-bridged difluorobenzo[: C] [1,2,5]-thiadiazole (FBTzE): A new electron-deficient building block for high-performance semiconducting polymers in organic electronics

A new class of an acceptor unit, vinylene-bridged 5,6-difluorobenzothiadiazole FBTzE, has been developed. Palladium-catalyzed Migita-Kosugi-Stille coupling reactions of 1 with 2, yielding 3 and its sequential dehydrogenative coupling with 4, readily affor

Synthesis, antibacterial activities, mode of action and acute toxicity studies of new oxazolidinone-fluoroquinolone hybrids

To combat bacterial resistance, a series of new oxazolidinone-fluoroquinolone hybrids have been synthesized and characterized. All synthetic hybrids were preliminarily evaluated for their in vitro antibacterial activities against 6 standard strains and 3 clinical isolates. The majority of hybrids displayed excellent activities against Gram-positive bacteria, but limited activities against Gram-negative bacteria. Hybrids OBP-4 and OBP-5 were found to be the most promising compounds. Further, in vitro antibacterial activities, mode of action and acute toxicity in mice of hybrids OBP-4 and OBP-5 were investigated. Hybrids OBP-4 and OBP-5 exhibited potent activities against Gram-positive bacteria, including drug-resistant strains. Correspondingly, studies on the mode of action of hybrids OBP-4 and OBP-5 indicated a strong inhibitory activity on protein synthesis by binding the active site of 50S subunit, but a weak inhibitory action on DNA synthesis. In addition, LD50 values of hybrids OBP-4 and OBP-5 in the acute oral toxicity were larger than 2000 mg/kg, suggesting a good safety profile.

Activation of C-F bonds in ionic liquids catalyzed by nickel complex compounds

A nickel complex-catalyzed hydrodefluorination of acet(pentafluoroanilide) with zinc in ionic liquids resulted in the corresponding 2,3,4,5-tetrafluoro, 3,4,5-trifluoro, and 3,4-difluoro derivatives. The influence of the ionic liquid nature and the reaction conditions on its selectivity were studied, a possibility of the multiple reuse of the ionic liquids as the reaction media was demonstrated.

Air oxidation of N-cyclopropylanilines

Air oxidation of N-cyclopropylanilines was shown to occur under either ambient conditions or accelerated conditions (warming or shining light) in an open container. A subsequent fragmentation resulted in formation of the corresponding acetamide. While potential mechanisms have been previously proposed, simple aerobic oxidation to β-hydroxy-propionamides in the absence of a radical promoter has not been previously reported. Copyright Taylor & Francis Group, LLC.

The ionic liquid [bmim]Br as an alternative medium for the catalytic cleavage of aromatic C-F and C-Cl bonds

The potential of [bmim]Br as an alternative to aprotic dipolar solvents in nickel-catalyzed hydrodehalogenation reactions is demonstrated. Hydrodechlorination of pentafluorochlorobenzene proceeds under the action of zinc in aqueous [bmim]Br. Under the above conditions aromatic C-F bonds also undergo slow cleavage. The reaction is significantly accelerated in the presence of nickel complexes with 2,2′-bipyridine or 1,10-phenanthroline. In the case of pentafluoroacetanilide highly regioselective ortho-hydrodefluorination leading to the formation of 3,4,5-trifluoroacetanilide is observed.

Reaction of pentafluoroacetanilide with zinc catalyzed by nickel complexes

The reaction of pentafluoroacetanilide hydrodefluorination under the action of zinc in the presence of catalytic amounts of complexes, generated in situ from nickel chloride and 2,2′-bipyridine or 1,10-phenanthroline, was studied. The influence of the sol

Comparative catalytic C-H vs. C-Si activation of arenes with Pd complexes directed by urea or amide groups

Analysis of regiocontrol in Pd-catalysed C-H activation leads to observations of aryltrimethylsilyl activation and to superior results with urea-based substrates.

Exploration of the diketoacid integrase inhibitor chemotype leading to the discovery of the anilide-ketoacids chemotype

Integrase is one of three enzymes expressed by HIV and represents a validated target for therapy. A previous study of the diketoacid-based chemotype suggested that there are two aryl-binding domains on integrase. In this study, modifications to the indole-based diketoacid chemotype are explored. It is demonstrated that the indole group can be replaced with secondary but not tertiary (e.g., N-methyl) aniline-based amides without sacrificing in vitro inhibitory activity. The difference in activity between the secondary and tertiary amides is most likely due to the opposite conformational preferences of the amide bonds, s-trans for the secondary-amide and s-cis for the tertiary-amide. However, it was found that the conformational preference of the tertiary amide can be reversed by incorporating the amide nitrogen atom into an indoline heterocycle, resulting in very potent integrase inhibitors.