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

Base Information

• Chemical Name: 2-Amino-5-trifluoromethyl-1,3,4-thiadiazole
• CAS No.: 10444-89-0
• Molecular Formula: C3H2F3N3S
• Molecular Weight: 169.13
• Hs Code.: 29349990
• European Community (EC) Number: 233-930-2
• NSC Number: 231655
• DSSTox Substance ID: DTXSID4065078
• Nikkaji Number: J212.400I
• Wikidata: Q72442885
• ChEMBL ID: CHEMBL1311331
• Mol file: 10444-89-0.mol

Synonyms:10444-89-0;2-Amino-5-trifluoromethyl-1,3,4-thiadiazole;5-(Trifluoromethyl)-1,3,4-thiadiazol-2-amine;2-Amino-5-(trifluoromethyl)-1,3,4-thiadiazole;1,3,4-Thiadiazol-2-amine, 5-(trifluoromethyl)-;MFCD00003109;5-Trifluoromethyl-[1,3,4]thiadiazol-2-ylamine;1,3,4-Thiadiazole, 2-amino-5-(trifluoromethyl)-;EINECS 233-930-2;NSC 231655;NSC231655;Maybridge1_003448;MLS001004764;SCHEMBL294025;CHEMBL1311331;DTXSID4065078;HMS551E16;AMY3762;HMS2666K05;CS-D0490;GEO-00205;STK347897;AKOS000225115;6K-633S;NSC-231655;SDCCGMLS-0065806.P001;NCGC00246021-01;SMR000348329;SY048743;Methyl2-(4-aminophenoxy)benzenecarboxylate;2-Amino-5-trifluoromethyl-1,3,4-triazole;5-trifluoromethyl2-amino-1,3,4-thiadiazole;FT-0602605;2-Amino-5-(trifluoromethyl)-1,4-thiadiazole;2-amino-5-trifluoromethyl[1,3,4]thiadiazole;2-trifluoromethyl-5-amino-1,3,4-thiadiazole;5-trifluoromethyl-2-amino-1,3,4-thiadiazole;EN300-31423;VU0301508-3;1,4-Thiadiazol-2-amine, 5-(trifluoromethyl)-;2-amino-5-(trifluormethyl)-1,3,4-thiadiazole;5-trifluoromethyl- 2-amino-1,3,4-thiadiazole;5-trifluoromethyl-1,3,4-thiadiazole-2-ylamine;F50734;1,3,4-Thiadiazole, 2-amino-5-trifluoromethyl-;1,4-Thiadiazole, 2-amino-5-(trifluoromethyl)-;5-(trifluoromethyl)-1,3,4-thiadiazole-2-amine;AB00590159-02;5-(Trifluoromethyl)-1,3,4-thiadiazol-2-amine #;AG-389/00757061;2-Amino-5-trifluoromethyl-1,3,4-thiadiazole, 97%;W-200075;2-AMINO-5-TRIFLUOROMETHYL-1,3,4-THIADIAZ OLE;Z56791151;F3143-0097;5-(trifluoromethyl)-1,3,4-thiadiazol-2-amine

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

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 0.0473mmHg at 25°C
• Melting Point: 220-225 °C
• Refractive Index: 1.491
• Boiling Point: 182.2±50.0 °C at 760 mmHg
• PKA: 0.30±0.10(Predicted)
• Flash Point: 64.0±30.1 °C
• PSA: 80.04000
• Density: 1.7±0.1 g/cm³
• LogP: 1.72030
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: methanol: soluble0.25g/10 mL, clear, colorless
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 0
• Exact Mass: 168.99215274
• Heavy Atom Count: 10
• Complexity: 127

Purity/Quality:

97% ^*data from raw suppliers

5-(Trifluoromethyl)-1,3,4-thiadiazol-2-amine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1(=NN=C(S1)N)C(F)(F)F

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

There total 8 articles about 2-Amino-5-trifluoromethyl-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: 85.0%

thiosemicarbazide (79-19-6) + trifluoroacetic acid (76-05-1) → 2-amino-5-trifluoromethyl-1,3,4-thiadiazole (10444-89-0)

Guidance literature:

With sulfuric acid; at 99.85 ℃; for 7h;

DOI:10.1107/S0108270105040126

Reference yield: 83.0%

2,2,2-Trifluoroacetaldehyde (75-90-1) + thiosemicarbazide (79-19-6) → 2-amino-5-trifluoromethyl-1,3,4-thiadiazole (10444-89-0)

Guidance literature:

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

DOI:10.1080/00397911.2017.1398330

Reference yield: 81.0%

thiosemicarbazide (79-19-6) + trifluoroacetic anhydride (407-25-0) → 2-amino-5-trifluoromethyl-1,3,4-thiadiazole (10444-89-0)

Guidance literature:

at -5 - 40 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.bmcl.2012.01.052

upstream raw materials:

thiosemicarbazide

trifluoroacetic acid

trifluoroacetic anhydride

trifluoracetyl chloride

Downstream raw materials:

1-phenyl-3-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-urea

2-(trifluoromethyl)-6-(4-fluorophenyl)imidazo[2,1-b][1,3,4]-thiadiazole

phenyl 5-(trifluoromethyl)-1,3,4-thiadiazol-2-ylcarbamate

2-bromo-N-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-acetamide

Refernces

Novel imidazo[2,1-b][1,3,4]thiadiazole carrying rhodanine-3-acetic acid as potential antitubercular agents

10.1016/j.bmcl.2012.01.052

The research is focused on the synthesis and evaluation of a new class of 2-(trifluoromethyl)-6-arylimidazo[2,1-b][1,3,4]thiadiazole derivatives as potential antitubercular agents. The researchers synthesized these compounds using both conventional and microwave-assisted methods, and evaluated their in vitro antitubercular activity against M. tuberculosis H37Rv. The chemicals that played a role in the research include 5-(trifluoromethyl)-1,3,4-thiadiazol-2-amine, various substituted α-haloaryl ketones, thiazolidine-2,4-dione, 2-thioxothiazolidin-4-one (rhodanine), and 2-(4-oxo-2-thioxothiazolidin-3-yl)acetic acid (rhodanine acetic acid). The synthesized compounds were characterized by IR, NMR, mass spectra, and elemental analysis. The study found that several compounds exhibited good antitubercular activity, with some showing promising potential as lead scaffolds for the development of new anti-TB agents.