52755-34-7

Basic information

• Product Name: Benzene, 1-chloro-4-[(1-methyl-1-nitroethyl)thio]-
• CAS NO: 52755-34-7
• Molecular Formula: C9H10ClNO2S
• Molecular Weight: 231.703
• Mol File: 52755-34-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzene, 1-chloro-4-[(1-methyl-1-nitroethyl)thio]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-chloro-4-[(1-methyl-1-nitroethyl)thio]-(52755-34-7)
• EPA Substance Registry System: Benzene, 1-chloro-4-[(1-methyl-1-nitroethyl)thio]-(52755-34-7)

Safety Data

• Hazardous Substances Data: 52755-34-7(Hazardous Substances Data)

Upstream product

• 1142-19-4 4,4'-dichlorodiphenyl disulfide 
• 594-71-8 2-chloro-2-nitro-propane 
• 18803-44-6 sodium p-chlorothiophenolate 
• 595-49-3 2,2-dinitropropane 
• 41774-06-5 α-nitroisopropyl phenyl sulfone 
• 74974-44-0 2-nitro-2-thiocyanatopropane 
• 75376-74-8 1-methyl-1-nitroethyl 1,3-benzothiazol-2-yl sulphide 
• 95106-82-4 1-methylimidazol-2-yl 1-methyl-1-nitroethyl sulphide 
• 95106-83-5 1-methyl-1-nitroethylpyrimidin-2-yl sulphide 
• 95106-85-7 1-methyl-1-nitroethyl 2-pyridyl sulphide 
• 35337-68-9 4-Chloro-benzenethiol anion 
• 79-46-9 2-nitropropane 
• 24163-39-1 sodium 2-nitropropane 
• 21272-86-6 α-nitroisopropyl p-tolyl sulfone 

Downstream Products

• 77-76-9 2,2-dimethoxy-propane 
• 75376-78-2 1-methyl-1-nitroethyl p-chlorophenyl sulphoxide 
• 3964-18-9 2,3-dimethyl-2,3-dinitrobutane 
• 1142-19-4 4,4'-dichlorodiphenyl disulfide 

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.

EFFECTS OF METHANOL SOLVATION ON THE NUCLEOPHILIC REACTIONS OF THIOLATES WITH 2-SUBSTITUTED-2-NITROPROPANES

Methanol solvation prevents SRN1 substitution in the reaction of Me2C(X)NO2 with thiolates and favours an alternative redox reaction to yield disulphide and nitronate.

REACTIONS OF THIOLATE ANIONS WITH 2-SUBSTITUTED-2-NITROPROPANES

Thiolates undergo substitution reactions with 2-substituted-2-nitropropanes by an SRN1 mechanism or are oxidised to disulphides by an ionic mechanism.