10349-14-1

Basic information

• Product Name: 4-Phenylfurazanamine
• Synonyms: 4-Phenylfurazanamine
• CAS NO: 10349-14-1
• Molecular Formula: C₈H₇N₃O
• Molecular Weight: 161.16
• Mol File: 10349-14-1.mol

Chemical Properties

• Boiling Point: 313.9°Cat760mmHg
• Flash Point: 143.7°C
• Appearance: /
• Density: 1.276g/cm³
• Vapor Pressure: 0.000481mmHg at 25°C
• Refractive Index: 1.606
• CAS DataBase Reference: 4-Phenylfurazanamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Phenylfurazanamine(10349-14-1)
• EPA Substance Registry System: 4-Phenylfurazanamine(10349-14-1)

Safety Data

• Hazardous Substances Data: 10349-14-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H7N3O/c9-8-7(10-12-11-8)6-4-2-1-3-5-6/h1-5H,(H2,9,11)

Upstream product

• 623-11-0 1-methyl-4-nitrosobenzene 
• 532-54-7 oxo-phenyl-acetaldehyde oxime 
• 114930-63-1 N-(phenyl-furazan-3-yl)-diacetamide 
• 7647-01-0 hydrogenchloride 
• 99285-90-2 3-benzoyl-5-methyl-1,2,4-oxadiazole (E)-oxime 
• 10349-15-2 3-(Acetylamino)-4-phenylfurazan 
• 96798-97-9 N-(4-phenyl-1,2,5-oxadiazol-3-yl)benzamide 
• 7732-18-5 water 
• 64-17-5 ethanol 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 613-90-1 benzoyl cyanide 
• 140-29-4 phenylacetonitrile 
• 825-52-5 2-(hydroxyimino)-2-phenylacetonitrile 
• 29939-70-6 N-hydroxy-2-(Z)-hydroxyimino-2-phenyl-acetamidine 

Downstream Products

• 10349-15-2 3-(Acetylamino)-4-phenylfurazan 
• 114930-63-1 N-(phenyl-furazan-3-yl)-diacetamide 
• 96798-97-9 N-(4-phenyl-1,2,5-oxadiazol-3-yl)benzamide 
• 30016-23-0 3-formylamino-4-phenylfurazan 
• 49615-83-0 N,N'-bis-(4-phenyl-furazan-3-yl)-oxalamide 
• 49615-84-1 1-phenyl-3-(4-phenyl-furazan-3-yl)-urea 
• 64821-99-4 1-phenyl-3-(4-phenyl-furazan-3-yl)-thiourea 
• 64822-03-3 (5-anilino-[1,2,4]thiadiazol-3-yl)-phenyl-methanone (Z)-oxime 
• 64822-04-4 (5-anilino-[1,2,4]thiadiazol-3-yl)-phenyl-methanone (E)-oxime 
• 63558-50-9 N-(4-phenyl-furazan-3-yl)-formimidic acid ethyl ester 
• 32545-23-6 2-chloro-N-(4-phenyl-furazan-3-yl)-acetamide 
• 49615-78-3 2-cyano-3-(4-phenyl-furazan-3-ylamino)-acrylic acid ethyl ester 
• 49615-77-2 [(4-phenyl-furazan-3-ylamino)-methylene]-malonic acid diethyl ester 
• 130137-90-5 Phenanthridin-6-yl-(4-phenyl-furazan-3-yl)-amine 

Relevant articles and documents

Synthesis of novel 1,2,5-oxadiazoles and evaluation of action against Acinetobacter baumannii

With multidrug resistant bacteria on the rise, novel antibiotics are becoming highly sought after. In 2008, eleven compounds were identified by high throughput screening as inhibitors of BasE, a key enzyme of the non-ribosomal peptide synthetase pathway found in Acinetobacter baumannii. Herein, we describe the preparation of four structurally similar heterocyclic lead compounds from that study, including one 1,2,5-oxadiazole. A further library of 30 analogues containing the oxadiazole moiety was then generated. All compounds were screened against Acinetobacter baumannii and their minimum inhibitory concentration data is reported, with (E)-3-(2-hydroxyphenyl)-N-(4-methyl-1,2,5-oxadiazol-3-yl)acrylamide 32 found to have an MIC of 0.5 mM. This work provides the foundation for further investigation of 1,2,5-oxadizoles as novel inhibitors of A. baumannii.

New acyl derivatives of 3-aminofurazanes and their antiplasmodial activities

An N-acylated furazan-3-amine of a Medicines for Malaria Venture (MMV) project has shown activity against different strains of Plasmodium falciparum. Seventeen new derivatives were prepared and tested in vitro for their activities against blood stages of two strains of Plasmodium falciparum. Several structure–activity relationships were revealed. The activity strongly depended on the nature of the acyl moiety. Only benzamides showed promising activity. The substitution pattern of their phenyl ring affected the activity and the cytotoxicity of compounds. In addition, physicochemical parameters were calculated (log P, log D, ligand efficiency) or determined experimentally (permeability) via a PAMPA. The N-(4-(3,4-diethoxyphenyl)-1,2,5-oxadiazol-3-yl)-3(trifluoromethyl)benzamide possessed good physicochemical properties and showed high antiplasmodial activity against a chloroquine-sensitive strain (IC50 (NF54) = 0.019 μM) and even higher antiplasmodial activity against a multiresistant strain (IC50 (K1 ) = 0.007 μM). Compared to the MMV compound, the permeability and the activity against the multiresistant strain were improved.

Straightforward Access to the Nitric Oxide Donor Azasydnone Scaffold by Cascade Reactions of Amines

A novel one-pot cascade method for the assembly of valuable NO-donor azasydnone scaffold has been developed. The construction strategy involves a diazotization/azo coupling/elimination/double rearrangement cascade sequence of readily available amines. The

N -Oxide-Controlled Chemoselective Reduction of Nitrofuroxans

A facile and chemoselective SnCl 2 -mediated mild reduction of regioisomeric 3- and 4-nitrofuroxans for the synthesis of aminofurazans and aminofuroxans in good yields is developed. Reduction of 4-nitrofuroxans results in the selective formation of 4-aminofuroxans, while analogous reduction of 3-nitrofuroxans affords 3-aminofurazans as a result of simultaneous reduction of the nitro group and exocyclic N-O bond.

Mild Synthesis of Substituted 1,2,5-Oxadiazoles Using 1,1′-Carbonyldiimidazole as a Dehydrating Agent

1,1′-Carbonyldiimidazole was found to induce the formation of a variety of 3,4-disubstituted 1,2,5-oxadiazoles (furazans) from the corresponding bisoximes at ambient temperature. This method enables these inherently energetic compounds to be prepared at t

Generation of oxodiazonium ions 1. Synthesis of [1,2,5]oxadiazolo[3,4-c] cinnoline 5-oxides

Methods for the synthesis of [1,2,5]oxadiazolo[3,4-c]cinnoline 5-oxides, which include the reaction of 3-nitramino-4-(R-phenyl)furazans or their O-methyl derivatives with electrophilic agents, have been developed. Unsubstituted [1,2,5]oxadiazolo[3,4-c]cin

One-pot synthesis of 3-amino-4-aryl- and 3-amino-4-hetarylfurazans

A "one pot" method for the synthesis of 3-amino-4-aryl- and 3-amino-4-hetarylfurazans from β-aryl- and 4-β-hetaryl-β-oxo acid esters was developed.

Nucleophilic substitution in the furazan series. Reactions of nitrofurazans with ammonia

The reactions of 3-nitro-4-R-furazans with ammonia were studied. The effect of the substituent R on the specific features of the nucleophilic substitution reaction observed was considered. The nitro group attached to the furazan ring can act as both the l

Novel Syntheses of Heterocycles from α-Ketonitriles: Part II - 3-Amino-4-aryl-1,2,5-oxadiazoles

A general synthesis is described for 3-amino-4-aryl-1,2,5-oxadiazoles (3) by treatment of aroyl cyanides (1) with hydroxylamine hydrochloride in the presence of anhyd. sodium acetate.A plausible reaction mechanism involving the intermediacy of α-amino-α'-

Heterocyclic Rearrangements. Rearrangement of the Oximes of Some 3-Acyl-1,2,4-oxadiazoles into 1,2,5-Oxadiazoles. A Revision

The oximation reaction of some 3-acyl-1,2,4-oxadiazoles and the geometry of the product oximes were reinvestigated. 3-Benzoyl-1,2,4-oxadiazoles gave mixtures of (E)-oximes and 1,2,5-oxadiazoles (furazans), these latter deriving from unisolated (Z)-oximes,