5533-31-3

Basic information

• Product Name: 4-tert-butyl-N-(4-methyl-2-nitrophenyl)benzamide
• Synonyms: 4-tert-Butyl-N-(4-methyl-2-nitrophenyl)benzamide; benzamide, 4-(1,1-dimethylethyl)-N-(4-methyl-2-nitrophenyl)-
• CAS NO: 5533-31-3
• Molecular Formula: C₁₃H₁₁ClO₂S
• Molecular Weight: 312.363
• Mol File: 5533-31-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 391.8°C at 760 mmHg
• Flash Point: 190.8°C
• Density: 1.187g/cm³
• Vapor Pressure: 2.4E-06mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: 4-tert-butyl-N-(4-methyl-2-nitrophenyl)benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-tert-butyl-N-(4-methyl-2-nitrophenyl)benzamide(5533-31-3)
• EPA Substance Registry System: 4-tert-butyl-N-(4-methyl-2-nitrophenyl)benzamide(5533-31-3)

Safety Data

• Hazardous Substances Data: 5533-31-3(Hazardous Substances Data)

Upstream product

• 98-87-3 benzylidene dichloride 
• 873-55-2 sodium benzenesulfonate 
• 831-91-4 Benzyl phenyl sulfide 
• 21128-89-2 α-Chlorobenzyl phenyl sulfoxide 
• 591-51-5 phenyllithium 
• 1939-99-7 benzenesulfonyl chloride 
• 3112-88-7 Benzyl phenyl sulfone 
• 5533-32-4 α,α-dichlorobenzyl phenyl sulfone 

Downstream Products

• 89303-57-1 1-(Benzenesulfonyl-phenyl-methyl)-2,4-dinitro-benzene 
• 119657-09-9 5-nitro-2-benzophenone 
• 119657-02-2 4-benzophenone 
• 119656-98-3 2-nitro-5-benzophenone 
• 116971-88-1 chloro(7-cycloheptatrienyl)phenyl(phenylsulfonyl)methane 
• 69709-36-0 4-nitrobenzhydryl phenyl sulfone 
• 3112-88-7 Benzyl phenyl sulfone 
• 71376-61-9 C₁₅H₁₅ClO₂S 
• 116971-94-9 7--1,3,5-cycloheptatriene 

Relevant articles and documents

Unexpected differences in the α-halogenation and related reactivity of sulfones with perhaloalkanes in KOH-t-BuOH

Most alkyl phenyl sulfones are readily α-chlorinated with CCl4 and α-brominated with CBrCl3 in KOH-t-BuOH via radical-anion radical pair (RARP) reactions. While isopropyl mesityl sulfone (4) is easily α-chlorinated with CCl4, it was completely recovered when treated with the more reactive CBrCl3. Subsequent investigations showed the latter result to be due to the poor acidity of 4 together with the rapid depletion of CBrCl3 and KOH by their reaction with each other, and led to a variety of other important results. 4-Hydroxyphenyl isopropyl sulfone (6) is unreactive with either CCl4 or CBrCl3 in KOH-t-BuOH, its phenoxide anion strongly reducing the electronegativity of the sulfonyl group, thereby inhibiting α-anion formation. This effect is reversed by the electron-withdrawing influence of two α-phenyls, so that benzhydryl 4-hydroxyphenyl sulfone (8) is readily α-halogenated in KOH-t-BuOH with CCl4 or CBrCl3. On further contact with KOH-t-BuOH the α-halogenated sulfones from 8 are decomposed into benzophenone and phenol. While the α-halogenated derivatives of 4-methoxyphenyl benzhydryl sulfone (9) are stable to base, they are decomposed even under mildly acidic conditions into 4-methoxyphenyl 4-methoxybenzenethiolsulfonate (9c), phenol, and benzophenone. Mono-α-halogenation of benzyl phenyl sulfone (10) enhances the rate of the subsequent halogenation, so that α,α-dihalogenation is attained while much substrate is still present and the mono-α-halogenated product is not detected. The ease of reductive debromination of α-bromo sulfones with Cl3C- was correlated with the stability of the formed α-anions, explaining the success with α-bromobenzylic sulfones but failure with α-bromoalkyl sulfones. In the presence of air and the absence of competing halogenation, formation of the α-anions of alkyl aryl sulfones is quickly accompanied by oxidative cleavage by atmospheric O2, leading to the formation of arenesulfonyl alcohols, arenesulfonyl halides, and haloarenes.