188595-72-4

Usage

Type of compound

Nitrophenyl derivative of N-methyl-1,2-diaminoethane

Usage

Intermediate in the synthesis of pharmaceuticals and other organic compounds

Physical state

Yellow crystalline solid

Melting point

149-150°C

Solubility

Soluble in water and organic solvents

Applications

Production of dyes, pharmaceuticals, and other organic compounds

Role in chemical synthesis

Reagent in chemical synthesis

Importance

Important compound in the field of organic chemistry

Biological application

Inhibitor of polyamine oxidase, an enzyme involved in the metabolism of polyamines in the body

Upstream product

• 13624-01-6 N-[1-(methylthio)-2-nitroethenyl]benzenamine 
• 74-89-5 methylamine 

Downstream Products

• 188595-77-9 (Z)-3-Methylamino-2-nitro-N-phenyl-3-phenylamino-thioacrylamide 
• 188595-78-0 (Z)-N-(4-Methoxy-phenyl)-3-methylamino-2-nitro-3-phenylamino-thioacrylamide 

Relevant academic research and scientific papers

An unexpected isomerization of N-aryl-3-amino-4-nitroisothiazol-5(2H)-imines to 2-(benzothiazol-2-yl)-2-nitroethene-1,1-diamines

The syntheses of several N-aryl-3-amino-4-nitroisothiazol-5(2H)-imines 12 from 3,3-diamino-2-nitrothioacrylamides 11 are reported. In polar solvents, a spontaneous isomerization of some of the prepared isothiazol-5(2H)-imines 12 yielded benzothiazoles 13. In the case of 2-alkyl-substituted derivatives of type 12, the isomerization occurred only at higher temperatures. Electronic influences of different substituents on the rate of the isomerization were studied, and a polar reaction mechanism is proposed. The structures of 12e and 13e were established by X-ray crystallography. Conformational analyses of 3-(methylamino)-2-nitro-N-phenyl-3-(pyrrolidin-1-yl)thioacrylamide (111) by NMR and X-ray methods were performed with the aim of explaining the distinct behavior of this amide towards Br2 or diethyl azodicarboxylate.