51249-08-2

Basic information

• Product Name: N-(3,5-dinitrothiophen-2-yl)acetamide
• CAS NO: 51249-08-2
• Molecular Formula: C₆H₅N₃O₅S
• Molecular Weight: 231.186
• Mol File: 51249-08-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 467.1°C at 760 mmHg
• Flash Point: 236.3°C
• Density: 1.703g/cm³
• Vapor Pressure: 6.72E-09mmHg at 25°C
• Refractive Index: 1.692
• CAS DataBase Reference: N-(3,5-dinitrothiophen-2-yl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3,5-dinitrothiophen-2-yl)acetamide(51249-08-2)
• EPA Substance Registry System: N-(3,5-dinitrothiophen-2-yl)acetamide(51249-08-2)

Safety Data

• Hazardous Substances Data: 51249-08-2(Hazardous Substances Data)

Upstream product

• 13053-81-1 2-acetylaminothiophene 
• 2045-70-7 3,5-dinitro-2-amino thiophene 
• 108-24-7 acetic anhydride 

Downstream Products

• 2045-70-7 3,5-dinitro-2-amino thiophene 

Relevant articles and documents

Studies on the biological activity of some nitrothiophenes

The biological activity of nineteen substituted thiophenes (3) have been assessed by evaluating the minimum inhibitory concentration required to inhibit the growth of E. coli, M. luteus and A. niger. The series displays a wide range of activities with 2-chloro-3,5-dinitrothiophene (3a) or 2-bromo-3,5- dinitrothiophene (3c) showing the highest activity against all three organisms, while the simplest compound of the series, 2-nitrothiophene (3s) shows the smallest activity in each case. The mode of action of 3a and 3c is thought to involve nucleophilic attack by intracellular thiols at the 2-position of the heterocyclic ring leading to displacement of halogen, but other active derivatives, such as 2,4-dinitrothiophene (3h) and 5-nitrothiophene-2- carbaldehyde (3d) which have no displaceable halogen or leaving group are thought to act by forming Meisenheimer complexes. The Royal Society of Chemistry 2006.

Azoles. Part 7. A Convenient Synthesis of Thienoimidazoles

A number of 1-mono- and 1,2-di-protected 4-bromoimidazole-5-carbaldehydes, (7), (8), (11), and (13)-(15), reacted with ethyl thioglycollate in ethanol in the presence of sodium ethoxide to give the corresponding title compound, (16), (17), or (19)-(22), respectively (65-70percent yield).Shorter reaction times allowed intermediates to be isolated, e.g. (13) gave (20) (69percent) and (23) (12percent).Several attempts to obtain the parent system, 1H- or 3H-thienoimidazole, failed.Attempts to prepare the title compounds from imidazoles by several classical syntheses used for annelated thiophene systems (due to Tilak, Campaigne, and Krollpfeiffer) failed as did attempts to prepare imidazolethiols through chlorosulphonation or thiocyanation of imidazoles or via their reaction with 2,4-dinitrobenzenesulphenyl chloride.Several unsuccesful approaches to the title compounds from thiophenes are also described.