17467-15-1

Basic information

• Product Name: 5-AMINO-3-PHENYL-1,2,4-THIADIAZOLE
• Synonyms: 4-thiadiazol-5-amine,3-phenyl-2;TIMTEC-BB SBB005511;5-AMINO-3-PHENYL-1,2,4-THIADIAZOLE;3-PHENYL-1,2,4-THIADIAZOL-5-AMINE;1,2,4-THIADIAZOL-5-AMINE, 3-PHENYL-;3-phenyl-1,2,4-thiadiazol-5-ylamine;3-Phenyl-1,2,4-triazol-5-ylamine;5-AMINO-3-PHENYL-1,2,4-THIADIAZOLE 99%
• CAS NO: 17467-15-1
• Molecular Formula: C₈H₇N₃S
• Molecular Weight: 177.23
• EINECS: 241-485-0
• Mol File: 17467-15-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 152-156 °C
• Boiling Point: 359 °C at 760 mmHg
• Flash Point: 170.9 °C
• Appearance: light brownish fine crystalline powder
• Density: 1.2353 (rough estimate)
• Vapor Pressure: 2.45E-05mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-AMINO-3-PHENYL-1,2,4-THIADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-3-PHENYL-1,2,4-THIADIAZOLE(17467-15-1)
• EPA Substance Registry System: 5-AMINO-3-PHENYL-1,2,4-THIADIAZOLE(17467-15-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22-41-22
• Safety Statements: 36/37/39-26-22
• HazardClass: IRRITANT
• Hazardous Substances Data: 17467-15-1(Hazardous Substances Data)

Usage

Chemical Properties

LIGHT BROWNISH FINE CRYSTALLINE POWDER

Uses

3-Phenyl-1,2,4-thiadiazol-5-amine is used as a reactant in the preparation of thiazole and thiadiazole derivatives as potent and selective human adenosine A3 receptor antagonists.

InChI:InChI=1/C8H7N3S/c9-8-10-7(11-12-8)6-4-2-1-3-5-6/h1-5H,(H2,9,10,11)

Upstream product

• 71017-37-3 N-bromo-benzamidine 
• 333-20-0 potassium thioacyanate 
• 1670-14-0 benzamidine monohydrochloride 
• 888-71-1 3,5-diphenyl-1,2,4-oxadiazole 
• 17356-08-0 thiourea 
• 3663-37-4 3-phenyl-1,2,4-oxadiazol-5-amine 
• 683-63-6 O-methyl thiocarbamate 
• 618-39-3 benzamidin 
• 1101173-93-6 3-bromo-5-amino-1,2,4-thiadiazole 
• 98-80-6 phenylboronic acid 
• 825-60-5 benzimidic acid ethyl ester 

Downstream Products

• 17280-75-0 N-(3-phenyl-[1,2,4]thiadiazol-5-yl)-benzamide 
• 331472-36-7 cyclohexanecarboxylic acid (3-phenyl-[1,2,4]thiadiazol-5-yl)-amide 
• 19922-23-7 4-chloro-N-(3-phenyl-[1,2,4]thiadiazol-5-yl)-benzamide 
• 147698-52-0 N-[2,6-Bis(1-methylethyl)phenyl]-N'-(3-phenyl-1,2,4-thiadiazol-5-yl)urea 
• 97879-36-2 (phenyl-piperidin-1-yl-methyl)-(3-phenyl-[1,2,4]thiadiazol-5-yl)-amine 
• 93818-81-6 5-<α-Aethoxy-benzylamino>-3-phenyl-1,2,4-thiadiazol 
• 93567-05-6 4-amino-N-(3-phenyl-[1,2,4]thiadiazol-5-yl)-benzenesulfonamide 
• 108015-80-1 methyl-nitroso-(phenyl-[1,2,4]thiadiazol-5-yl)-amine 
• 106951-15-9 5-(N-methyl-hydrazino)-3-phenyl-[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.

Facile synthesis of substituted 5-amino- And 3-amino-1,2,4-thiadiazoles from a common precursor

[Chemical Equation Presented] A novel approach to the synthesis of substituted 5-amino- and 3-amino-1,2,4-thiadiazoles beginning from a common precursor has been achieved. Derivatization by palladium-catalyzed Suzuki-Miyaura coupling enables the rapid pre

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.