66463-89-6

Basic information

• Product Name: Benzene, 1-[(1-methyl-1-nitroethyl)thio]-4-nitro-
• CAS NO: 66463-89-6
• Molecular Formula: C9H10N2O4S
• Molecular Weight: 242.255
• Mol File: 66463-89-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Benzene, 1-[(1-methyl-1-nitroethyl)thio]-4-nitro-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-[(1-methyl-1-nitroethyl)thio]-4-nitro-(66463-89-6)
• EPA Substance Registry System: Benzene, 1-[(1-methyl-1-nitroethyl)thio]-4-nitro-(66463-89-6)

Safety Data

• Hazardous Substances Data: 66463-89-6(Hazardous Substances Data)

Upstream product

• 100-32-3 di(p-nitrophenyl) disulfide 
• 24163-39-1 sodium 2-nitropropane 
• 5447-97-2 2-bromo-2-nitropropane 
• 45797-13-5 4-nitrophenylthiolate 
• 13113-79-6 sodium 4-nitrobenzenethiolate 
• 74974-44-0 2-nitro-2-thiocyanatopropane 

Downstream Products

• 75376-79-3 1-methyl-1-nitroethyl p-nitrophenyl sulphoxide 
• 3964-18-9 2,3-dimethyl-2,3-dinitrobutane 
• 75376-77-1 diethyl 2-(1-nitro-1-methylethyl)-2-ethylmalonate 
• 1636-28-8 1-(1-methyl-1-nitroethyl)-1-nitrocyclohexane 
• 1636-37-9 1,1'-dinitro-bicyclohexyl 
• 41774-06-5 α-nitroisopropyl phenyl sulfone 

Relevant articles and documents

Radical-nucleophilic substitution (SRN1) reactions. Part 7. Reactions of aliphatic α-substituted nitro compounds

α-Nitrothiocyanates R2C(SCN)NO2 have been prepared by oxidative addition of thiocyanate anion to nitronate anions and undergo SRN1 substitution reactions by loss of thiocyanate with nitronate anions, phenylsulfinate, azide and p-nitro- and p-chloro-benzenethiolates in dipolar aprotic solvents. 2-Nitro-2-thiocyanatopropane and other 2-substituted-2-nitropropanes [Me2C(X)NO2 with X = I, Br, Cl, NO2, PhSO2] react with thiolates by SRN1 reactions and/or redox reactions to give disulfides by a polar abstraction or chain SET (SET2) mechanisms. The products are dependent on the nucleophilicity of the thiolates, the polarisability of the α-substituent, the solvent and the presence of light catalysis, radical traps or strong electron acceptors. 2-Substituted-2-nitropropanes [Me2C(X)NO2 with X = N3, NO2, CN, p-NO2-C6H4-N=N] undergo SRN1 substitutions with thiolates by loss of nitrite. 2-Substituted-2-nitropropanes Me2C(X)NO2 and thiolates only yield disulfides in methanol due to solvation of the nitro groups.

RADICAL-NUCLEOPHILIC SUBSTITUTION (SRN1) REACTIONS OF α-NITRO-THIOCYANATES

α-Nitro-thiocyanates undergo substitution by a SRN1 mechanism with a range of anions to give loss of thiocyanate, corroborating behaviour observed for the intermediate α-nitro-thiocyanato radical-anions by e.s.r. spectroscopy.

Radical-Nucleophilic Substitution (SRN1) Reactions: Preparation and Reactions of α-Nitrosulphides

α-Nitrosulphides were prepared by SRN1 reaction of 2-bromo-2-nitropropane with thiolate anions, and by SN2 attack of sodium 2-nitropropan-2-ide on symmetrical disulphides.The α-nitrosulphides undergo radical-nucleophilic substitution (SRN1) by nitronate, sulphinate, and malonate anions, but not by thiolate anions.