4-METHYL-1,2,3-THIADIAZOLE

Base Information

• Chemical Name: 4-METHYL-1,2,3-THIADIAZOLE
• CAS No.: 18212-62-9
• Molecular Formula: C3H4N2S
• Molecular Weight: 100.14
• Hs Code.: 2934999090
• Mol file: 18212-62-9.mol

Synonyms:4-METHYL-1,2,3-THIADIAZOLE

Chemical Property of 4-METHYL-1,2,3-THIADIAZOLE

Chemical Property:

• Vapor Pressure: 8.33mmHg at 25°C
• Boiling Point: 138.5°C at 760 mmHg
• Flash Point: 43°C
• PSA: 54.02000
• Density: 1.226g/cm³
• LogP: 0.84650

Purity/Quality:

98%Min ^*data from raw suppliers

4-Methyl-1,2,3-thiadiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 4-METHYL-1,2,3-THIADIAZOLE is a heterocyclic compound that serves as a key scaffold in the synthesis of biologically active derivatives, particularly in the development of novel pesticides. Its derivatives, synthesized via the Ugi reaction, exhibit promising fungicidal and antiviral properties, including activity against tobacco mosaic virus (TMV). The structural incorporation of substituents like 3-chloro-4-methylphenyl or 3-fluoro-4-methylphenyl enhances these biological activities, highlighting its potential as a versatile agrochemical intermediate.

Technology Process of 4-METHYL-1,2,3-THIADIAZOLE

There total 5 articles about 4-METHYL-1,2,3-THIADIAZOLE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 43.0%

N'-isopropylidenehydrazinecarboxylic acid ethyl ester (6637-60-1) → 4-methyl-1,2,3-thiadiazole (18212-62-9) + 5-chloro-4-methyl-1,2,3-thiadiazole (53645-99-1)

Guidance literature:

With thionyl chloride;

DOI:10.1055/s-2006-951552

Reference yield:

acetone (67-64-1) → 4-methyl-1,2,3-thiadiazole (18212-62-9)

Guidance literature:

acetone; With acetic acid; ethylhydrazine carboxylate; for 3h; Reflux;

With thionyl chloride; In 1,2-dichloro-ethane; at 20 ℃; for 24h;

DOI:10.1039/c7ob01214d

Reference yield:

C11H13N2O2Pol → 4-methyl-1,2,3-thiadiazole (18212-62-9)

Guidance literature:

With thionyl chloride; In dichloromethane; at 20 ℃; for 20h; solid phase reaction;

DOI:10.1080/00397910802369521

upstream raw materials:

4-methyl-[1,2,3]thiadiazole-5-carboxylic acid

N'-isopropylidenehydrazinecarboxylic acid ethyl ester

acetone

Downstream raw materials:

N-benzylpropionthioamide

Refernces

Synthesis of 4-Methyl-1,2,3-thiadiazole derivatives via ugi reaction and their biological activities

10.1021/jf902863z

The research focuses on the synthesis and biological evaluation of 4-methyl-1,2,3-thiadiazole derivatives, which are potential candidates for novel pesticides with diverse biological activities. The study employs the Ugi four-component condensation reaction (U-4CR), a green and rapid one-pot process, to synthesize two series of these derivatives, incorporating active substructures of 3-chloro-4-methylphenyl or 3-fluoro-4-methylphenyl. The reactants used in the Ugi reaction include amines, carbonyl compounds (aldehydes or ketones), isocyanides, and carboxylic acids, with specific mention of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid, cyclohexyl isocyanide, and various substituted benzaldehyde derivatives. The synthesized compounds were characterized using proton nuclear magnetic resonance (1H NMR) and high-resolution mass spectrometry (HRMS). The biological activities of the target compounds, including fungicide activity, antivirus activity in vitro and in vivo, and systemic acquired resistance, were systematically evaluated. The experiments involved the use of different fungi strains for fungicide screening and tobacco plants for antivirus and systemic acquired resistance assessments. The results indicated that certain derivatives showed potential broad-spectrum fungicidal activity and direct antivirus activities against tobacco mosaic virus (TMV), with the structure-activity relationship suggesting that the presence of specific substituents on the phenyl rings influenced the biological activities.