4-Methyl-1,2,3-thiadiazole-5-carboxylic acid

Base Information

• Chemical Name: 4-Methyl-1,2,3-thiadiazole-5-carboxylic acid
• CAS No.: 18212-21-0
• Molecular Formula: C4H4N2O2S
• Molecular Weight: 144.154
• Hs Code.: 29349990
• European Community (EC) Number: 672-573-0
• DSSTox Substance ID: DTXSID40362538
• Nikkaji Number: J2.358.866H
• Wikidata: Q72491140
• Mol file: 18212-21-0.mol

Synonyms:4-methyl-1,2,3-thiadiazole-5-carboxylic acid;18212-21-0;4-methylthiadiazole-5-carboxylic acid;1,2,3-Thiadiazole-5-carboxylic acid, 4-methyl-;4-Methyl-[1,2,3]thiadiazole-5-carboxylic acid;4-Methyl-1,2,3-Thiadiazole-5-CarboxylicAcid;MFCD00173830;4-methyl-5-hydroxycarbonyl-1,2,3-thiadiazole;SCHEMBL452517;(R)-2-Hydroxymethylpropanoicacid;DTXSID40362538;AMY24728;CS-B1141;CX1010;LT0133;STK711191;AKOS000104176;SDCCGMLS-0065716.P001;10J-524S;BP-10765;A4029;BB 0218315;FT-0618980;M3081;EN300-13420;4-methyl-[1,2,3]thiadiazol-5-carboxylic acid;4Methyl-[1,2,3]thiadiazole-5-carboxylic acid;A26564;4-methyl-[l,2,3]thiadiazole-5-carboxylic acid;W-206298;4-Methyl-1,2,3-thiadiazole-5-carboxylic acid, 97%;Z90121760;F2630-0005

Chemical Property of 4-Methyl-1,2,3-thiadiazole-5-carboxylic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.000188mmHg at 25°C
• Melting Point: 166 °C
• Boiling Point: 315.173 °C at 760 mmHg
• PKA: 1.33±0.37(Predicted)
• Flash Point: 144.412 °C
• PSA: 91.32000
• Density: 1.531 g/cm³
• LogP: 0.54470
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Aqueous Base (Slightly), DMSO
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 143.99934855
• Heavy Atom Count: 9
• Complexity: 130

Purity/Quality:

99% ^*data from raw suppliers

4-Methyl-1,2,3-thiadiazole-5-carboxylic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(SN=N1)C(=O)O
• General Description: 4-Methyl-1,2,3-thiadiazole-5-carboxylic acid is a key intermediate in the synthesis of bioactive 4-methyl-1,2,3-thiadiazole derivatives, which exhibit promising fungicidal and antiviral properties, particularly against tobacco mosaic virus (TMV). Its incorporation into Ugi reaction-derived compounds highlights its utility in generating structurally diverse agrochemical candidates with potential broad-spectrum activity. The presence of specific substituents on the phenyl rings of these derivatives further modulates their biological efficacy.

Technology Process of 4-Methyl-1,2,3-thiadiazole-5-carboxylic acid

There total 7 articles about 4-Methyl-1,2,3-thiadiazole-5-carboxylic acid 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: 96.0%

4-methyl-1,2,3-thiadiazole-5-carboxylic acid ethyl ester (18212-20-9) → 4-methyl-[1,2,3]thiadiazole-5-carboxylic acid (18212-21-0)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 16h;

DOI:10.1021/jf8031364

Reference yield: 93.01%

4-methyl-1,2,3-thiadiazole-5-carboxylic acid-(N-benzoyl-N-cyclohexyl)-amide (175136-67-1) → 4-methyl-[1,2,3]thiadiazole-5-carboxylic acid (18212-21-0)

Guidance literature:

With bromine; sodium hydroxide; In water; at 70 ℃; Cooling with ice;

Reference yield: 71.75%

4-methyl-[1,2,3]thiadiazole-5-carbonyl chloride (59944-65-9) + N'-tert-butyl-3-methoxybenzohydrazide (1047997-69-2) → C16H20N4O3S (1202365-86-3) + N'-tert-butyl-N-(3-methoxybenzoyl)-N-(4-methyl-1,2,3-thiadiazole-5-carbonyl)hydrazine (1202365-99-8) + 4-methyl-[1,2,3]thiadiazole-5-carboxylic acid (18212-21-0)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 6h; Cooling with ice;

DOI:10.1007/s10870-011-0189-1

upstream raw materials:

4-methyl-1,2,3-thiadiazole-5-carboxylic acid ethyl ester

methyl 4-methyl-1,2,3-thiadiazole-5-carboxylate

4-butyl-1-(4-methyl-1,2,3-thiadiazol-5-yl-carbonyl)-thiosemicarbazide

4-ethyl-1-(4-methyl-1,2,3-thiadiazol-5-yl-carbonyl)-thiosemicarbazide

Downstream raw materials:

4-methyl-[1,2,3]thiadiazole-5-carbonyl chloride

4-methyl-1,2,3-thiadiazole

(4-methyl-1,2,3-thiadiazol-5-yl)(phenyl)methanone

methyl 4-methyl-1,2,3-thiadiazole-5-carboxylate

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.