117635-33-3

Basic information

• Product Name: Thiophene, 2-(2-nitro-1-phenylethyl)-
• CAS NO: 117635-33-3
• Molecular Formula: C12H11NO2S
• Molecular Weight: 233.291
• Mol File: 117635-33-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Thiophene, 2-(2-nitro-1-phenylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Thiophene, 2-(2-nitro-1-phenylethyl)-(117635-33-3)
• EPA Substance Registry System: Thiophene, 2-(2-nitro-1-phenylethyl)-(117635-33-3)

Safety Data

• Hazardous Substances Data: 117635-33-3(Hazardous Substances Data)

Upstream product

• 874-84-0 2-(2-nitroethenyl)thiophene 
• 34312-77-1 1-(2-thienyl)-2-nitroethene 
• 1135-99-5 diphenyltin(IV) dichloride 
• 143-66-8 sodium tetraphenyl borate 
• 595-90-4 tetraphenyltin(IV) 
• 1003-09-4 2-bromothiophene 
• 5153-67-3 nitrostyrene 

Relevant articles and documents

Boosting Conjugate Addition to Nitroolefins Using Lithium Tetraorganozincates: Synthetic Strategies and Structural Insights

We report the first transition metal catalyst- and ligand-free conjugate addition of lithium tetraorganozincates (R4ZnLi2) to nitroolefins. Displaying enhanced nucleophilicity combined with unique chemoselectivity and functional group tolerance, homoleptic aliphatic and aromatic R4ZnLi2 provide access to valuable nitroalkanes in up to 98 % yield under mild conditions (0 °C) and short reaction time (30 min). This is particularly remarkable when employing β-nitroacrylates and β-nitroenones, where despite the presence of other electrophilic groups, selective 1,4 addition to the C=C is preferred. Structural and spectroscopic studies confirmed the formation of tetraorganozincate species in solution, the nature of which has been a long debated issue, and allowed to unveil the key role played by donor additives on the aggregation and structure of these reagents. Thus, while chelating N,N,N’,N’-tetramethylethylenediamine (TMEDA) and (R,R)-N,N,N’,N’-tetramethyl-1,2-diaminocyclohexane (TMCDA) favour the formation of contacted-ion pair zincates, macrocyclic Lewis donor 12-crown-4 triggers an immediate disproportionation process of Et4ZnLi2 into equimolar amounts of solvent-separated Et3ZnLi and EtLi.

Synthesis of 1,1-Diaryl-2,2-dimethoxyethanes

The 1,4-addition of Grignard reagents to β-nitrostyrene to give 1,1-diaryl-2-nitroethanes and their subsequent conversion via a modified Nef reaction into 1,1-diaryl-2,2-dimethoxyethanes (diarylacetaldehyde dimethyl acetals) is described.The scope of the reaction has been briefly explored and one example demonstrated on a large scale.