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

Base Information

• Chemical Name: 2-Amino-5-methyl-1,3,4-thiadiazole
• CAS No.: 108-33-8
• Molecular Formula: C3H5N3S
• Molecular Weight: 115.159
• Hs Code.: 29349990
• European Community (EC) Number: 203-573-7
• NSC Number: 526661,137228
• UNII: NC799929EM
• DSSTox Substance ID: DTXSID70148347
• Nikkaji Number: J38.372D
• Wikidata: Q72439731
• ChEMBL ID: CHEMBL1288960
• Mol file: 108-33-8.mol

Synonyms:2-Amino-5-methyl-1,3,4-thiadiazole;108-33-8;5-Methyl-1,3,4-thiadiazol-2-amine;1,3,4-Thiadiazol-2-amine, 5-methyl-;2-Amino-5-methylthiadiazole;MATD;USAF CY-3;5-Methyl-[1,3,4]thiadiazol-2-ylamine;1,3,4-Thiadiazole, 2-amino-5-methyl-;5-Methyl-1,3,4-thiadiazol-2-ylamine;1,4-Thiadiazol-2-amine, 5-methyl-;5-Methyl-1,3,4-thiadiazole-2-amine;AI3-61163;EINECS 203-573-7;MFCD00003110;2-Methyl-5-amino-1,3,4-thiadiazole;NSC 137228;CHEMBL1288960;NC799929EM;5-Amino-2-methyl-1,3,4-thiadiazole;NSC-137228;WLN: T5NN DSJ C1 E1;2-Amino-5-methyl-1,4-thiadiazole;1,4-Thiadiazole, 2-amino-5-methyl-;Amino-5-methyl-1,3,4-thiadiazole;MLS001049227;SCHEMBL282505;UNII-NC799929EM;SCHEMBL21228555;HMPUHXCGUHDVBI-UHFFFAOYSA-;AMY3777;DTXSID70148347;CHEBI:194873;HMS2787M24;amino-5-methyl 1,3,4-thiadiazole;BDBM50331847;NSC137228;NSC526661;STK016821;5-methyl-1,3,4-thiadiazol-2-ylamin;5-methyl-2-amino-1,3,4-thiadiazole;AKOS000100063;NSC-526661;PS-4597;2-amino-5- methyl-1,3,4-thiadiazole;5-methyl-2 -amino-1,3,4-thiadiazole;5-methyl-2-amino-1,3,4 -thiadiazole;NCGC00246452-01;SMR000427775;SY004265;LS-150245;A0874;BB 0217150;CS-0076370;FT-0620585;2-Amino-5-methyl-1,3,4-thiadiazole, 97%;EN300-17271;F13849;W-108723;Z56900928;F1423-2916

Chemical Property of 2-Amino-5-methyl-1,3,4-thiadiazole

Chemical Property:

• Appearance/Colour: White to light beige crystalline powder
• Vapor Pressure: 6.12E-05mmHg at 25°C
• Melting Point: 220-225 °C
• Refractive Index: 1.631
• Boiling Point: 261.2 °C at 760 mmHg
• PKA: 3.84±0.10(Predicted)
• Flash Point: 111.8 °C
• PSA: 80.04000
• Density: 1.372 g/cm³
• LogP: 1.00990
• Storage Temp.: Room temperature.
• Solubility.: DMSO (Sparingly), Methanol (Slightly)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 115.02041835
• Heavy Atom Count: 7
• Complexity: 67.2

Purity/Quality:

2-Amino-5-methyl-1,3,4-thiadiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=NN=C(S1)N
• Uses: 2-Amino-5-methyl-1,3,4-thiadiazole was used as a reagent in the synthesis of substituted 5H-benzo[i][1,3,4]thiadiazolo[3,2-a]quinazoline-6,7-diones which diplayed good cytotoxic activities. Also used in the design of new phenothiazine-thiadiazole hybrids for development of antitubercular agents.

Technology Process of 2-Amino-5-methyl-1,3,4-thiadiazole

There total 23 articles about 2-Amino-5-methyl-1,3,4-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: 96.3%

acetic acid (64-19-7,77671-22-8) + thiosemicarbazide (79-19-6) → 5-methyl-1,3,4-thiadiazol-2-amine (108-33-8)

Guidance literature:

With choline chloride; urea; at 80 ℃; for 1h;

Reference yield: 83.0%

acetaldehyde (75-07-0,9002-91-9) + thiosemicarbazide (79-19-6) → 5-methyl-1,3,4-thiadiazol-2-amine (108-33-8)

Guidance literature:

With tert.-butylhydroperoxide; In ethanol; water; at 20 ℃; for 4h; Green chemistry;

DOI:10.1080/00397911.2017.1398330

Reference yield: 82.6%

thiosemicarbazide (79-19-6) + acetonitrile (75-05-8,26809-02-9) → 5-methyl-1,3,4-thiadiazol-2-amine (108-33-8)

Guidance literature:

With trifluoroacetic acid; at 80 ℃;

DOI:10.1016/j.ejmech.2019.112022

upstream raw materials:

1-acetylthiosemicarbazide

acetaldehyde thiosemicarbazone

1-(1-ethoxy-ethylidene)-thiosemicarbazide

acetic acid

Downstream raw materials:

phenylpropynoic acid 5-methyl-[1,3,4]thiadiazol-2-ylamide

6,8-dibromo-3-(5-methyl-[1,3,4]thiadiazol-2-yl)-2-phenyl-3H-quinazolin-4-one

N-{5-[2-(5-nitro-furan-2-yl)-vinyl]-[1,3,4]thiadiazol-2-yl}-acetamide

3-(5-methyl-[1,3,4]thiadiazol-2-yl)-2-styryl-3H-quinazolin-4-one

Refernces

• 1、 Kidwai, Mazaahir,Misra, Preeti,Bhushan, Kumar Ranjan,Dave, Bhavesh. "A novel route to 1,2,4-triazoles". . p. 3031 - 3040. Retrieved 2000.
• 2、 Bhatt, Priyanka,Deepthi,Ravi Shankar Kumar, Ch,Jha, Anjali. "Facile synthesis, spectral studies, DFT calculations and biological activities of novel NI (II), CU (II), and PD (II) complexes of thiadiazole analogs". . p. 185 - 192. Retrieved 2017.
• 3、 Schüttelkopf, Alexander W.,Gros, Ludovic,Blair, David E.,Frearson, Julie A.,Van Aalten, Daan M.F.,Gilbert, Ian H.. "Acetazolamide-based fungal chitinase inhibitors". . p. 8334 - 8340. Retrieved 2010.
• 4、 Rawat, Ravi,Verma, Saurabh M.. "Pd2(dba)3-catalyzed amination of C5-bromo-imidazo[2,1-b][1,3,4] thiadiazole with substituted anilines at conventional heating in Schlenk tube". . p. 96 - 108. Retrieved 2021.
• 5、 Cao, Lian-Gong,Cao, Zhi-Ling,Chen, Chao,Jiang, Kai-Jun,Liu, Shu-Hao,Liu, Wei-Wei,Ruan, Xin-Chi,Shao, Zhong-Bai,Shi, Da-Hua,Su, Zi-Qin,Wang, You-Xian,Wu, Yu-Ran,Wu, Yu-Yu. "Synthesis of Emodin Amide Derivatives Containing 1,3,4-Thiadiazole and Their Inhibitory Activity on Vibrio harveyi". . p. 281 - 286. Retrieved 2021/08/05.
• 6、 -. "Method for preparing 2-amino-5-substituted-1,3,4-thiadiazole". Paragraph 0038-0044. . Retrieved 2020/02/14.