66938-86-1

Basic information

• Product Name: (3,4-DIAMINOPHENYL)(4-FLUORO PHENYL)METHANONE
• Synonyms: (3,4-DIAMINOPHENYL)(4-FLUORO PHENYL)METHANONE;(3,4-diaminophenyl) (4-fluorophenyl) ketone;Methanone, (3,4-diaminophenyl)(4-fluorophenyl)-
• CAS NO: 66938-86-1
• Molecular Formula: C₁₃H₁₁FN₂O
• Molecular Weight: 230.24
• EINECS: 266-522-8
• Mol File: 66938-86-1.mol

Chemical Properties

• Melting Point: 113-114℃ (methanol )
• Boiling Point: 447.4 °C at 760 mmHg
• Flash Point: 224.4 °C
• Appearance: /
• Density: 1.305±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 3.38E-08mmHg at 25°C
• Refractive Index: 1.652
• PKA: 2.76±0.10(Predicted)
• CAS DataBase Reference: (3,4-DIAMINOPHENYL)(4-FLUORO PHENYL)METHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: (3,4-DIAMINOPHENYL)(4-FLUORO PHENYL)METHANONE(66938-86-1)
• EPA Substance Registry System: (3,4-DIAMINOPHENYL)(4-FLUORO PHENYL)METHANONE(66938-86-1)

Safety Data

• Hazardous Substances Data: 66938-86-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(3,4-Diaminophenyl)(4-fluorophenyl)methanone is used as a building block in organic synthesis for the creation of various complex organic molecules. Its unique structure, including amine groups and a fluorine atom, allows for versatile chemical reactions and the formation of diverse compounds.
Used in Chemical Research:
In the field of chemical research, (3,4-Diaminophenyl)(4-fluorophenyl)methanone serves as a valuable compound for studying the properties and reactivity of benzoyl derivatives. Its aromatic nature and the presence of amine and fluorine groups make it an interesting subject for investigations into chemical bonding, reaction mechanisms, and the development of new synthetic methods.
Used in Pharmaceutical Industry:
(3,4-Diaminophenyl)(4-fluorophenyl)methanone is utilized as a starting material or intermediate in the synthesis of pharmaceutical compounds. Its unique structural features, including the amine groups and fluorine atom, can be exploited to design and develop new drugs with specific therapeutic properties. (3,4-DIAMINOPHENYL)(4-FLUORO PHENYL)METHANONE's potential applications in drug discovery and development may include the creation of novel therapeutic agents, as well as the improvement of existing medications through structural modifications.

InChI:InChI=1/C13H11FN2O/c14-10-4-1-8(2-5-10)13(17)9-3-6-11(15)12(16)7-9/h1-7H,15-16H2

Upstream product

• 31431-26-2 (4-amino-3-nitrophenyl)(4-fluorophenyl)ketone 
• 180601-52-9 3-Amino-4-nitro-4'-fluorobenzophenone 
• 96-99-1 4-chloro-3-nitrobenzoate 
• 31431-16-0 4-chloro-4'-fluoro-3-nitrobenzophenone 
• 462-06-6 fluorobenzene 
• 24376-18-9 3,4-dinitrobenzoyl chloride 
• 528-45-0 3,4-dinitrobenzoic acid 
• 1635-61-6 5-chloro-2-nitroaniline 
• 459-22-3 4-fluorophenylacetonitrile 
• 97183-75-0 3,4-dinitro-4'-fluorobenzophenone 

Downstream Products

• 180601-53-0 4-Amino-3-isopropylsulfonamido-4'-fluorobenzophenone 
• 31430-15-6 flubendazole 
• 1026173-27-2 1-[2-Amino-3-(propane-2-sulfonyl)-3H-benzoimidazol-5-yl]-1-(4-fluoro-phenyl)-but-3-yn-1-ol 
• 186092-72-8 6-[(E)-1-(4-Methylsulfanyl-phenyl)-but-1-en-3-ynyl]-1-(propane-2-sulfonyl)-1H-benzoimidazol-2-ylamine 
• 180601-45-0 [2-Amino-3-(propane-2-sulfonyl)-3H-benzoimidazol-5-yl]-(4-methylsulfanyl-phenyl)-methanone 
• 189061-08-3 Propane-2-sulfonic acid [2-amino-5-(4-methylsulfanyl-benzoyl)-phenyl]-amide 
• 186093-19-6 6-[(E)-1-(4-Fluoro-phenyl)-4-trimethylsilanyl-but-1-en-3-ynyl]-1-(propane-2-sulfonyl)-1H-benzoimidazol-2-ylamine 

Relevant articles and documents

A catalytic hydrogenation preparing high-purity (3,4-diamino-phenyl) (4-fluoro phenyl) ketone method

The invention relates to a method for preparing high-purity (3,4-diaminophenyl)(4-fluorophenyl) ketone by virtue of catalytic hydrogenation, belonging to the technical field of pharmaceutical and chemical engineering. The method comprises the following steps: adding (4-amino-3-nitrophenyl)(4-fluorophenyl) ketone (I) and a catalyst into an organic solvent, introducing hydrogen, and performing hydrogenation reduction reaction to obtain a flubendazole intermediate namely (3,4-diaminophenyl)(4-fluorophenyl) ketone (II). The method disclosed by the invention has the advantages that compared with a reduction method using sodium hydrosulfide, the method is simple in process, small in solvent dosage and short in reaction time, can be used for solving the problem that a large amount of sulfide-containing wastewater is difficult to be treated, and is beneficial for industrial production; meanwhile, a novel catalyst preparation method is simple, and has the characteristics of high reaction activity, good selectivity and recycled catalyst; compared with a pure Pt/C catalyst, the novel catalyst can be used for effectively inhibiting the phenomenon that carbanyl groups are reduced into methylene and inhibiting the occurrence of the defluorination phenomenon, and is relatively high in product yield and purity.

Anti-viral compounds

The present application provides a series of benzimidazole compounds of formula I: which inhibit the growth of picornaviruses, such as rhinoviruses (bovine and human), enteroviruses such as polioviruses, coxsackieviruses of the A and B groups, or echo virus, cardioviruses such as encephalomyocarditis (EMC), apthoviruses such as foot and mouth disease virus, and flaviviruses such as hepatitis C virus and bovine viral diarrhea virus. Such compounds are also useful as intermediates for preparing additional benzimidazole antiviral compounds.

Anti-viral compounds

The present application provides a series of benzimidazole compounds which inhibit the growth of picornaviruses, such as rhinoviruses, enteroviruses, polioviruses, coxsackieviruses of the A and B groups, echo virus and Mengo virus and flaviviruses such as hepatitis C and bovine diarrheal virus.

Synthesis, antiviral activity, and biological properties of vinylacetylene analogs of enviroxime

A series of vinylacetylene analogs of Enviroxime (1) was synthesized. The new compounds are potent inhibitors of poliovirus in tissue culture. Cross-sensitivity with Enviroxime-derived mutants shows that the new compounds have the same mechanism of action as Enviroxime, which involves the viral 3A protein. In studies with Rhesus monkeys, the p-fluoro derivative 12 was found to be unique in providing oral bioavailability. Metabolism studies using hepatic microsomes suggest that this procedure would be a useful in vitro method for selecting the appropriate animal model for testing oral absorption. Compound 12 was found to be efficacious by oral administration in treating a Coxsackie A21 infection in CD-1 mice.

Antirhino/enteroviral vinylacetylene benzimidazoles: A study of their activity and oral plasma levels in mice

In an effort to find an orally bioavailable antiviral for the treatment of rhino/enteroviral infections, a series of vinylacetylene benzimidazoles (11a-o, 12, and 18a) was made. Initial studies of this class of antivirals showed that fluorine substitution on the left-hand phenyl ring in combination with the vinylacetylene moiety gave the requisite mix of physical properties to achieve good in vitro antiviral activity as well as respectable oral bioavailability in rhesus monkeys. To ascertain the generality of this finding and to broaden the scope of the structure-activity relationship (SAR), the present study concentrated on fluoro substitution of this class of molecules. The initial antiviral activity for each analogue was measured using human rhinovirus 14 (HRV-14). This served as an indicator of general antiviral activity for SAR purposes. Subsequently, the spectrum of antirhino/enteroviral activity of the more interesting analogues was evaluated through testing against a panel of seven additional rhino/enteroviruses. Broad-spectrum activity was present and consistent for all analogues tested, and it tracked closely with the antiviral activity observed against HRV-14. A simple screening protocol for oral bioavailability was established whereby compounds were administered orally to mice and plasma levels were measured. This procedure facilitated the evaluation of numerous analogues in a rapid manner. The C(max) was used as a measure of oral bioavailability to allow relative ranking of compounds. In general, fluorine substitution directly on the left-hand aromatic ring does give good oral blood levels. However, fluorine incorporation at other positions in the molecule was not as effective at maintaining either the activity or the oral plasma levels. The constructive combination of activity and oral plasma levels was maximized in three derivatives: 11a,e,g.

Anti-viral compounds

Certain vinyl acetylene benzimidazole compounds which inhibit the growth of picornaviruses, such as rhinoviruses, enteroviruses, cardioviruses, polioviruses, coxsackieviruses of the A and B groups, echo virus and Mengo virus.

Anti-viral compounds

The present application provides a series of benzimidazole compounds which inhibit the growth of picornaviruses, such as rhinoviruses, enteroviruses, cardioviruses, polioviruses, coxsackieviruses of the A and B groups, echo virus and Mengo virus. Such compounds are also useful as intermediates for preparing additional benzimidazole antiviral compounds.

Synthesis and anthelminthic acitivity of alkyl-(5-acyl-1-benzimidazol-2-yl) carbamates

A series of alkyl-(5-acyl-l-H-benzimidazol-2-yl)-carbamates were prepared and screened for anthelminthic activity. Some of them were found to be fully active at low, atoxic oral dose levels against gastro-intestinal nematodes. The activity against Syphacia muris and Strongyloides ratta is indicated. From these studies methyl (5-benzoyl-1-H-benzimidazol-2-yl) carbamate (mebendazole) and methyl [5-(4-fluorobenzoyl)-1-H-benzimidazol-2-yl]carbamate (flubendazole) were selected for detailed investigation.