45534-08-5

Basic information

• Product Name: 3-AMINO-5-METHYLTHIO-1H-1,2,4-TRIAZOLE
• Synonyms: ART-CHEM-BB B028585;3-AMINO-5-METHYLTHIO-1,2,4-TRIAZOLE;3-AMINO-5-METHYLTHIO-1H-1,2,4-TRIAZOLE;3-AMINO-5-(METHYLMERCAPTO)-1H-1,2,4-TRIAZOLE;5-METHYLSULFANYL-1 H-[1,2,4]TRIAZOL-3-YLAMINE;5-(METHYLTHIO)-1H-1,2,4-TRIAZOL-3-AMINE;AMTT;AKOS B028585
• CAS NO: 45534-08-5
• Molecular Formula: C₃H₆N₄S
• Molecular Weight: 130.17
• EINECS: 256-242-4
• Product Categories: THIOL;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Triazoles
• Mol File: 45534-08-5.mol

Chemical Properties

• Melting Point: 130-133 °C(lit.)
• Boiling Point: 393.7 °C at 760 mmHg
• Flash Point: 191.9 °C
• Appearance: /solid
• Density: 1.326 (estimate)
• Vapor Pressure: 2.08E-06mmHg at 25°C
• Refractive Index: 1.5605 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: 10.24±0.40(Predicted)
• Water Solubility: very faint turbidity
• CAS DataBase Reference: 3-AMINO-5-METHYLTHIO-1H-1,2,4-TRIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-5-METHYLTHIO-1H-1,2,4-TRIAZOLE(45534-08-5)
• EPA Substance Registry System: 3-AMINO-5-METHYLTHIO-1H-1,2,4-TRIAZOLE(45534-08-5)

Safety Data

• Hazard Codes: Xn-F
• Statements: 40-11
• Safety Statements: 36/37-16
• RIDADR: 2811
• WGK Germany: 3
• Hazardous Substances Data: 45534-08-5(Hazardous Substances Data)

Usage

Uses

Used in Research Chemicals:
3-AMINO-5-METHYLTHIO-1H-1,2,4-TRIAZOLE is used as a research chemical for various scientific studies and experiments due to its unique chemical properties and reactivity.
Used in Dye Synthesis:
In the Dye Industry, 3-AMINO-5-METHYLTHIO-1H-1,2,4-TRIAZOLE is used as a key component in the synthesis of heterocyclic disperse azo dyes based on 8-hydroxyquinoline, contributing to the development of new and improved dyes with specific properties.
Used in Solar Cell Technology:
3-AMINO-5-METHYLTHIO-1H-1,2,4-TRIAZOLE is used as an efficient electrolyte additive in the Solar Energy Industry, specifically in dye-sensitized solar cells, where it enhances the performance and efficiency of these renewable energy devices.
Used in Schiff Base Ligand Synthesis:
In the field of Coordination Chemistry, 3-AMINO-5-METHYLTHIO-1H-1,2,4-TRIAZOLE is used as a precursor to synthesize triazole-derived Schiff base ligands, which are important for the development of new coordination compounds and catalysts.

InChI:InChI=1/C3H6N4S/c1-8-3-5-2(4)6-7-3/h1H3,(H3,4,5,6,7)

Upstream product

• 77-78-1 dimethyl sulfate 
• 74-83-9 methyl bromide 
• 118025-46-0 3-amino-1H-1,2,4-triazole-5-thiol 
• 27798-35-2 S-methyl thioformate 
• 79-17-4 aminoguanidine 
• 104667-67-6 methyl N'-cyano-N-[(4-methylphenyl)sulfonyl]imidothiocarbamate 
• 104692-80-0 methyl N'-cyano-N-(phenylsulfonyl)imidothiocarbamate 
• 16691-43-3 3-amino-5-thioxo-1,2,4-triazole 
• 10191-60-3 dimethyl N-cyanodithioiminocarbonate 
• 92945-30-7 methyl (5-amino-3-methylthio-1,2,4-triazol-1-yl)dithiocarbonate 
• 60-34-4 methylhydrazine 
• 103-72-0 phenyl isothiocyanate 
• 135857-21-5 1-(5-amino-3-methylthio-1H-1,2,4-triazol-1-yl)-N-methylcarbothiohydrazide 
• 74586-16-6 S,S'-dimethyl-dithiodiisobiurea 

Downstream Products

• 90674-13-8 ethyl 2-methylthio-1,2,4-triazolo<1,5-α>pyrimidin-7(4H)-one-6-carboxylate 
• 1020167-03-6 C₁₂H₁₄N₄O₂S 
• 110984-36-6 (5-Amino-3-methylsulfanyl-[1,2,4]triazol-1-yl)-(5-methyl-3-phenyl-isoxazol-4-yl)-methanone 
• 121079-72-9 7,8-dihydro-2-methylthio-7-phenyl-6H-pyrrolo<3,4-d>-1,2,4-triazolo<1,5-a>pyrimidine-5(9H)-one 
• 121079-73-0 butyl 1-phenyl-4-(3-methylthio-1H-1,2,4-triazol-5-yl)imino-3-pyrrolidinecarboxylate 
• 92945-31-8 benzyl (5-amino-3-methylthio-1,2,4-triazol-1-yl)dithiocarbonate 
• 90666-81-2 (5-Amino-3-methylsulfanyl-[1,2,4]triazol-1-yl)-phenyl-methanone 
• 116986-62-0 1-(5-Methylsulfanyl-2H-[1,2,4]triazol-3-yl)-3-phenyl-thiourea 
• 82118-02-3 5-Amino-3-methylsulfanyl-[1,2,4]triazole-1-carbothioic acid phenylamide 
• 90666-79-8 1-(4-chlorobenzoyl)-3-methylsulfanyl-5-amino-1,2,4-triazole 
• 51646-19-6 5,7-dimethyl-2-methylthio-1,2,4-triazolo<1,5-a>pyrimidine 

Relevant articles and documents

Preparation method of 3-amino-5-methylmercapto-1,2,4-triazole

The invention discloses a preparation method of 3-amino-5-methylmercapto-1,2,4-triazole. The preparation method comprises the following steps of carrying out nitrogen replacement on a reactor, and then using dimethyl cyanimino dithiocarbonate and a hydrazine hydrate as raw materials, wherein a solvent is an alcohol organic solvent; adding the dimethyl cyanimino dithiocarbonate into the solvent, agitating an obtained first mixture to dissolve the dimethyl cyanimino dithiocarbonate, and then slowly dropwise adding the hydrazine hydrate into the first mixture in a condition of 25 to 28 DEG C, wherein the mole ratio of the dimethyl cyanimino dithiocarbonate to the hydrazine hydrate is (1 to 1.1) to (1 to 15); dropwise adding the hydrazine hydrate for 1.5 to 2 hours, subsequently raising a temperature to 65 to 70 DEG C, in a refluxing condition, carrying out a reaction for 2 to 3 hours, preparing and synthesizing a similarly white solid through a one-step reaction, and confirming the similarly white solid to be the target product 3-amino-5-methylmercapto-1,2,4-triazole through nuclear magnetic resonance. The target product is prepared and synthesized through the one-step reaction; the costs of the raw materials are low; iodine-containing wastewater which pollutes an environment is not generated; operation steps are simple; further, the purity of the product can reach 98 percent or above; the preparation method has a quite good commercial application prospect, and is worthy to popularized in a large range.

ANTI-VIRAL DRUG

An antiviral compound for use in the treatment of positive-sense, single-stranded RNA (herein after ssRNA] virus infections different from the West Nile Fever virus infections wherein said antiviral compound is of general formula (I) [compound (A), herein after] or a pharmaceutically acceptable salt thereof (I) formula (I) wherein - R1 is selected from an alkyl group having 1 to 12 carbon atoms which is optionally substituted by a halogen atom or hydroxyl group, a cycloalkyl group having 3 to 12 carbon atoms which is optionally substituted by a halogen atom or hydroxyl group, an aryl group, an alkylaryl group, or a cycloheteroalkyl group having 3 to 12 carbon atoms, preferably an alkyl group having 1 to 8 carbon atoms optionally substituted by a halogen atom or hydroxyl group, a cycloalkyl group having 3 to 6 carbon atoms which is optionally substituted by a halogen atom or hydroxyl group, a phenyl, a benzyl, a morpholine, or an imidazolyl, more preferably an alkyl group having 1 to 4 carbon atoms, a cyclohexyl, a phenyl or a benzyl.

ANTI-VIRAL DRUG

An antiviral compound for use in the treatment of negative-sense, single-stranded RNA [herein after ssRNA] virus infections different from the Influenza A and Influenza B virus infections wherein said antiviral compound is of general formula (I) ) [compound (A), herein after] or a pharmaceutically acceptable salt thereof wherein - R1 is selected from an alkyl group having 1 to 12 carbon atoms which is optionally substituted by a halogen atom or hydroxyl group, a cycloalkyl group having 3 to 12 carbon atoms which is optionally substituted by a halogen atom or hydroxyl group, an aryl group, an alkylaryl group, or a cycloheteroalkyl group having 3 to 12 carbon atoms, preferably an alkyl group having 1 to 8 carbon atoms optionally substituted by a halogen atom or hydroxyl group, a cycloalkyl group having 3 to 6 carbon atoms which is optionally substituted by a halogen atom or hydroxyl group, a phenyl, a benzyl, a morpholine, or an imidazolyl, more preferably an alkyl group having 1 to 4 carbon atoms, a cyclohexyl, a phenyl or a benzyl.

Synthesis and structure activity relationship investigation of triazolo[1,5-a]pyrimidines as CB2 cannabinoid receptor inverse agonists

CB2 cannabinoid receptor ligands are known to be therapeutically important for the treatment of numerous diseases. Recently, we have identified the heteroaryl-4-oxopyridine/7-oxopyrimidine derivatives as highly potent and selective CB2 receptor ligands, showing that the pharmakodynamics of the new compounds was controlled by the nature of the heterocycle core. In this paper we describe the synthesis and biological evaluation of 7-oxo-4-pentyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxamide derivatives that led to the identification of novel CB2 receptor inverse agonists. Cyclic AMP experiments on CB2 receptors expressed in CHO cells revealed that introduction of structural modifications at position 2 of triazolopyrimidine template changes the functional activity from partial to inverse agonism. The molecular docking analysis of the novel structures is reported.

Synthesis and evaluation of 1,2,4-triazolo[1,5- a ]pyrimidines as antibacterial agents against Enterococcus faecium

Rapid emergence of antibiotic resistance is one of the most challenging global public health concerns. In particular, vancomycin-resistant Enterococcus faecium infections have been increasing in frequency, representing 25% of enterococci infections in intensive care units. A novel class of 1,2,4-triazolo[1,5-a]pyrimidines active against E. faecium is reported herein. We used a three-component Biginelli-like heterocyclization reaction for the synthesis of a series of these derivatives based on reactions of aldehydes, β-dicarbonyl compounds, and 3-alkylthio-5-amino-1,2,4-triazoles. The resulting compounds were assayed for antimicrobial activity against the ESKAPE panel of bacteria, followed by investigation of their in vitro activities. These analyses identified a subset of 1,2,4-triazolo[1,5-a]pyrimidines that had good narrow-spectrum antibacterial activity against E. faecium and exhibited metabolic stability with low intrinsic clearance. Macromolecular synthesis assays revealed cell-wall biosynthesis as the target of these antibiotics.

A one-pot, three-component, microwave-promoted synthesis of 2-amino-substituted 7-amino-1,2,4-triazolo[1,5-a][1,3,5]triazines

A new, efficient, catalyst-free, one-pot, three-component method for the synthesis of 2-amino-substituted 7-amino-1,2,4-triazolo[1,5-a][1,3,5]triazines using 3,5-diamino-1,2,4-triazoles, cyanamide, and triethyl orthoformate is developed. The reaction proceeds smoothly under microwave-assisted heating. Advantages of the method include using easily available reagents, short reaction times, and operational simplicity.

Synthesis of 5,7-diamino1,2,4 triazolo[1,2-a1,3,5 triazines via annulation of 1,3,5-triazine ring onto 3(5)-amino-1,2,4-triazoles

The 5,7-diamino[1,2,4]triazoeo[1,5-a][1,3,5]triazines were synthesized by cyclocondensation of 3(5)-amino-1,2,4-triazoles with cyanoguanidine. The substituted 3(5)-amino-1,2,4-triazoles were prepared from corresponding hydrazides and S-methylisothiourea via ring closure of the intermediate acylaminoguanidines. The 3,5-diamino-1,2,4-triazoles were prepared using partial aminolysis of dimethyl N-cyanodithiocarbonimidate followed by cyclization of the obtained N-substituted N′-cyano-S-methylisothioureas with hydrazine. The structures of the prepared compound were confirmed using NMR spectral data.

A novel and efficient regiospecific preparation of arenesulfonamide derivatives of 3,5-diamino-1,2,4-triazole

A new simple and efficient procedure was designed for the regiospecific preparation of arenesulfonamide derivatives of 3,5-diamino-1,2,4-triazole 1 which are precursors of N-([1,2,4] triazolo [1,5-a]pyrimidin-2-yl)arenesulfonamides 2, an important family of herbicidal and antibacterial agents. The key feature of this procedure is the preparation of a wide range of compounds 1 on a large scale, in pure form and high yield without the need for any workup or the use of the highly hazardous hydrazine. This was made possible by a novel tandem reaction promoted by sulfuryl chloride to effect the formation of the triazole ring.

Synthesis of novel derivatives of 3(5)-alkylsulfonyl-1,2,4-triazoles

The feasibility of preparing novel 1,2,4-triazole derivatives bearing alkylsulfonyl and other functional groups on the ring carbon atom has been demonstrated. The syntheses are carried out via transformation of the amino group of 3(5)-alkylsulfonyl-5(3)-amino-1,2,4-triazoles into other functional groups.

On Triazoles. XXIX. The Reaction of Triazolyl Thiohydrazides with Isocyanates and Isothiocyanates

Different N-methylsubstituted, N'-methylsubstituted and N,N'-unsubstituted triazol-1-ylcarbothiohydrazides were reacted with isocyanates and isothiocyanates to yield the corresponding carbamoyl and thiocarbamoyl derivatives 4.The thiocarbamoyl derivatives could be cyclised by heating in dimethylformamide or 10percent sodium hydroxide solution, reacting them with dicyclohexylcarbodiimide or thier alkylation to the corresponding 1,3,4-thiadiazoles 12 and 16, and derivatives 5 formed by splitting the triazole moiety.Cleaved derivatives 9 and 11 were also formed in the reaction of thiocarbamoyl derivatives 4 with carbon disulfide in the absence or presence of methyl iodide, respectively.Spectroscopic evidence is given for the structure of products obtained.