27691-52-7

Usage

Appearance

Yellow, crystalline solid

Usage

Intermediate in the synthesis of pharmaceuticals, dyes, and other organic compounds

Functional groups

a. Nitro group (-NO2)
b. Sulfanylidene group (-S)
c. Amino group (-NH2)

Attachment

Nitro, sulfanylidene, and amino groups are attached to a benzene ring

Classification

Hazardous substance

Safety precautions

Must be handled and stored with proper safety measures to avoid health or environmental risks

Upstream product

• 67-68-5 dimethyl sulfoxide 
• 100-01-6 4-nitro-aniline 
• 1516-60-5 4-nitrophenyl azide 
• 75-18-3 dimethylsulfide 

Downstream Products

• 66288-36-6 3-(4-chloro-phenyl)-7-nitro-2⁽⁴⁾H-benzo[1,2,4]oxadiazine 
• 61773-30-6 7-nitro-3-(4-nitro-phenyl)-2⁽⁴⁾H-benzo[1,2,4]oxadiazine 
• 66318-01-2 7-nitro-3-(2,3,5,6-tetramethyl-phenyl)-2⁽⁴⁾H-benzo[1,2,4]oxadiazine 
• 4485-08-9 4-nitrosonitrobenzene 
• 56158-00-0 dimethyl((4-nitrophenyl)imino)-λ6-sulfane 
• 16133-44-1 dimethyl 2-<(4-nitrophenyl)amino>-2-butenedioate 
• 61773-28-2 7-nitro-3-phenyl-2⁽⁴⁾H-benzo[1,2,4]oxadiazine 
• 66288-34-4 3-(2,6-dichloro-phenyl)-7-nitro-2⁽⁴⁾H-benzo[1,2,4]oxadiazine 
• 96307-19-6 N-(4-nitrophenyl)-α-cyano-α-tert-butylacetamide 
• 96307-20-9 N-<2-(methylthio)methyl-4-nitrophenyl>-α-cyano-α-tert-butylacetamide 
• 106086-58-2 2,5-bis(p-nitrophenylamino)-N,N'-bis(phenylsulfonyl)-1,4-benzoquinone diimine 
• 96307-15-2 1-(4-nitrophenyl)-3-phenyl-2-indolinone 
• 404-27-3 2,2,2-trifluoro-N-(4-nitrophenyl)acetamide 
• 100-01-6 4-nitro-aniline 

Relevant academic research and scientific papers

Benzo[c]isothiazole 2-Oxides: Three-Dimensional Heterocycles with Cross-Coupling and Functionalization Potential

A robust method for the synthesis of benzo[c]isothiazole 2-oxides has been developed providing a range of functionalized derivatives starting from anilines and DMSO. The reaction sequence can be performed on a gram scale and leads to products that can easily be modified by standard cross-coupling reactions. (Figure presented.).

Formation of Sommelet-Hauser-Type Products, 2-Aminoarylmethyl Sulphides, and Nitrenium Ion Products, 2- and 4-Aminoaryl Sulphides, via an N-Arylazasulphonium Salt

Reactions of a salt (1) formed at -60 deg C from trifluoroacetic anhydride and dimethyl sulphoxide (DMSO) with primary and secondary arylamines gave 2-aminoarylmethyl sulphides (6), (6') and (12) by a Sommelet-Hauser rearrangement of an ylide (5) formed by loss of a methyl proton of an N-arylazasulphonium salt (3) in the absence of base.The use of ethyl methyl sulphoxide instead of DMSO afforded a similar product (19b) by loss of not the ethyl but the methyl proton.However, the use of diethyl sulphoxide merely caused loss of an ethyl group from the N-arylazasulphonium salt to yield ethanesulphenanilide (20).The reaction of (1) with N-phenyl-1-naphthylamine gave mainly aminoaryl sulphides (13) and (14) via an arylnitrenium ion from the N-arylazasulphonium salt.In fact, the reaction of dimethyl sulphide (DMS) with arylnitrenium ions formed in the acid decomposition of aryl azides gave no Sommelet-Hauser-type products but 2- and 4-aminoaryl sulphides (22), (22') and (23).We also discuss the possibility of the N-arylazasulphonium salt being formed by reaction of the arylnitrenium ion with DMS.