17467-32-2

Basic information

• Product Name: 1,2,4-Thiadiazol-5-amine, N-methyl-3-phenyl-
• CAS NO: 17467-32-2
• Molecular Formula: C9H9N3S
• Molecular Weight: 191.257
• Mol File: 17467-32-2.mol

Chemical Properties

• CAS DataBase Reference: 1,2,4-Thiadiazol-5-amine, N-methyl-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4-Thiadiazol-5-amine, N-methyl-3-phenyl-(17467-32-2)
• EPA Substance Registry System: 1,2,4-Thiadiazol-5-amine, N-methyl-3-phenyl-(17467-32-2)

Safety Data

• Hazardous Substances Data: 17467-32-2(Hazardous Substances Data)

Usage

Chemical Structure

Contains a 1,2,4-thiadiazole ring system with an amine group at the 5-position and a N-methyl-3-phenyl substituent.

Industry Usage

Commonly used in the pharmaceutical industry as a building block for the synthesis of various biologically active compounds.

Therapeutic Potential

Extensively studied for its potential as a therapeutic agent in the treatment of various diseases, including cancer and neurological disorders.

Reactivity

Unique structure and reactivity make it a valuable intermediate in organic synthesis.

Research

Has shown promising results in medicinal chemistry research.

Safety Precautions

Use and handling should be done with caution, following proper safety protocols and regulations.

Upstream product

• 3663-37-4 3-phenyl-1,2,4-oxadiazol-5-amine 
• 14128-35-9 N-methylthiocarbamic acid O-methyl ester 
• 598-52-7 1-(methyl)-thiourea 
• 825-60-5 benzimidic acid ethyl ester 
• 618-39-3 benzamidin 
• 61787-75-5 2-(iminophenylmethyl)-1,1,1-trimethylhydrazinium hydroxide inner salt 
• 103-72-0 phenyl isothiocyanate 
• 556-61-6 methyl thioisocyanate 
• 77509-97-8 C₁₂H₁₈N₄S 
• 79566-38-4 N-methylthiocarbamoyl-benzamidine 
• 24255-23-0 5-chloro-3-phenyl-[1,2,4]thiadiazole 
• 74-89-5 methylamine 

Downstream Products

• 69909-45-1 methyl-(2-methyl-3-phenyl-2H-[1,2,4]thiadiazol-5-ylidene)-amine 
• 108015-80-1 methyl-nitroso-(phenyl-[1,2,4]thiadiazol-5-yl)-amine 
• 95166-41-9 benzhydryl-methyl-(3-phenyl-[1,2,4]thiadiazol-5-yl)-amine 
• 109966-76-9 3,3'-diphenyl-5,5'-(3-methyl-triaz-1-ene-1,3-diyl)-bis-[1,2,4]thiadiazole 

Relevant articles and documents

One-Pot Synthesis of 3-Aryl-5-amino-1,2,4-thiadiazoles from Imidates and Thioureas by I2-Mediated Oxidative Construction of the N–S Bond

A simple and practical method for the one-pot synthesis of 3-aryl-5-amino-1,2,4-thiadiazoles from imidates and thioureas has been developed. The protocol proceeds through sequential base-mediated nucleophilic addition-elimination reactions and an I2-mediated oxidative coupling for the N–S bond formation. The approach employes readily available and nontoxic substrates and a simple workup to provide 3-aryl-5-amino-1,2,4-thiadiazoles that have a free or substituted amino group.

Solid-phase parallel synthesis of 5-amino- and 5-amido-1,2,4-thiadiazole derivatives via cyclization reactions of a carboxamidine thiourea linker

A general method is described for the solid-phase parallel synthesis of 5-amino- and 5-amido-l,2,4-thiadiazoles. The sequence developed for this purpose is based on cyclization reactions of resin-bound carboxamidine thioureas promoted by p-toluenesulfonyl

Photoinduced molecular rearrangements. The photochemistry of 1,2,4-oxadiazoles in the presence of sulphur nucleophiles. Synthesis of 1,2,4-thiadiazoles

The photochemistry of some 1,2,4-oxadiazoles in the presence of sulphur nucleophiles has been investigated. Irradiation of the 5-amino-3-phenyl- and 3,5-diphenyl-1,2,4-oxadiazole at λ = 254 nm in methanol in the presence of sodium hydrogen sulphide or thiols gave a photo-induced redox reaction at the ring O-N bond, leading to the corresponding N-substituted benzamidines. By contrast, irradiation of the 5-amino-3-phenyl-1,2,4-oxadiazole in the presence of thioureas or thiocarbamates, essentially gave 3-phenyl-5-substituted 1,2,4-thiadiazoles, which presume an N-S bond formation between the ring-photolytic species and the sulphur nucleophile. In turn, irradiation of the same 5-amino-3-phenyl-1,2,4-oxadiazole in the presence of thioamides again afforded the redox reaction; in addition, amounts of 3-phenyl-5-substituted-1,2,4-thiadiazoles were also formed. Some mechanistic considerations are reported and synthetic methodologies leading to 1,2,4-thiadiazoles are emphasized.

Amidrazones. 6(1). Synthesis of 1,2,4-Thiadiazoles by Thermolysis of N3-Thiocarbamoylamidrazone Ylides

Reaction of N3-unsubstituted amidrazone ylides (1a and 1b) with alkyl or aryl isothiocyanates gives N3-thiocarbamoylamidrazone ylides (2).Thermolysis of 2 gives 3-alkyl(or aryl)-5-alkyl(or aryl)amino-1,2,4-thiadiazoles (a-i).