Triafur

Base Information

• Chemical Name: Triafur
• CAS No.: 712-68-5
• Molecular Formula: C6H4 N4 O3 S
• Molecular Weight: 212.189
• Hs Code.: 2934999090
• European Community (EC) Number: 211-925-6
• NSC Number: 78274,53279
• UNII: 4JJ4COI21V
• DSSTox Substance ID: DTXSID7020059
• Wikidata: Q27155857
• ChEMBL ID: CHEMBL139005
• Mol file: 712-68-5.mol

Synonyms:TRIAFUR;712-68-5;Furidiazine;Thiafur;Tiafur;Furidazina;Furidiazina;5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amine;2-Amino-5-(5-nitro-2-furyl)-1,3,4-thiadiazole;ASA-140;Ph/778;NF-475;NSC 53279;CCRIS 35;NSC 78274;1,3,4-Thiadiazol-2-amine, 5-(5-nitro-2-furanyl)-;EINECS 211-925-6;UNII-4JJ4COI21V;2-(5-Nitro-2-furyl)-5-amino-1,3,4-thiadiazole;5-(5-Nitro-2-furyl)-1,3,4-thiadiazol-2-ylamine;5-(5-Nitro-2-furyl)-2-amino-1,3,4-thiadiazole;5-Amino-2-(5-nitro-2-furyl)-1,3,4-thiadiazole;BRN 0616834;4JJ4COI21V;1,3,4-Thiadiazole, 2-amino-5-(5-nitro-2-furyl)-;1,3,4-Thiadiazole, 5-amino-2-(5-nitro-2-furyl)-;MLS002667577;CHEBI:82286;NSC-53279;NSC-78274;5-(5-nitro-2-furyl)-1,3,4-thiadiazol-2-amine;5-(5-Nitro-2-furanyl)-1,3,4-thiadiazol-2-amine;WLN: T5OTJ BNW E- ET5NN DSJ CZ;2-(5-Nitro-2-furyl)-5-amino-1,4-thiadiazole;2-Amino-5-(5-nitro-2-furyl)-1,4-thiadiazole;5-(5-Nitro-2-furyl)-2-amino-1,4-thiadiazole;5-Amino-2-(5-nitro-2-furyl)-1,4-thiadiazole;1,4-Thiadiazol-2-amine, 5-(5-nitro-2-furanyl)-;1,4-Thiadiazole, 2-amino-5-(5-nitro-2-furyl)-;1,4-Thiadiazole, 5-amino-2-(5-nitro-2-furyl)-;TRIAFUR [MI];Maybridge1_002122;NCIOpen2_004401;Oprea1_523685;C6H4N4O3S;CHEMBL139005;SCHEMBL1997012;DTXSID7020059;HMS547I10;HMS3079O04;NSC53279;NSC78274;CCG-55397;AKOS000224930;LS-7186;SMR000684791;C19189;2-Amino-5-(5-nitro-2-furyl)-1 ,3,4-thiadiazol;SR-01000644423-1;Q27155857

Chemical Property of Triafur

Chemical Property:

• Vapor Pressure: 7.18E-08mmHg at 25°C
• Melting Point: 280°
• Refractive Index: 1.6200 (estimate)
• Boiling Point: 437.9°C at 760 mmHg
• Flash Point: 218.7°C
• PSA: 139.00000
• Density: 1.663g/cm³
• LogP: 2.39290
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 212.00041118
• Heavy Atom Count: 14
• Complexity: 236

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(OC(=C1)[N+](=O)[O-])C2=NN=C(S2)N
• Uses: 5-?(5-?Nitrofuran-?2-?yl)?-?1,?3,?4-?thiadiazol-?2-?amine is a fungicide that provides anti-Heliicobacter pylori activity. Pesticide component.

Technology Process of Triafur

There total 10 articles about Triafur 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%

5-nitro-furfural thiosemicarbazone (831-71-0,146827-83-0) → 2-amino-5-(5-nitro-2-furyl)-1,3,4-thiadiazole (712-68-5)

Guidance literature:

With iron(III) chloride hexahydrate; In water; for 12h; Reflux;

DOI:10.1016/j.ejmech.2020.112178

Reference yield: 65.0%

2-[(E)-1-(5-nitro-2-furyl)methylidene]-1-hydrazinecarbothioamide (146827-83-0) → 2-amino-5-(5-nitro-2-furyl)-1,3,4-thiadiazole (712-68-5)

Guidance literature:

With iron(III) chloride; In water; for 4h; Heating;

DOI:10.1021/jm021030a

Reference yield: 63.0%

4-methylbenzenesulfonyl N'-(5-nitrofuran-2-ylmethylene)hydrazide (13777-58-7) + potassium thioacyanate (333-20-0) → 2-amino-5-(5-nitro-2-furyl)-1,3,4-thiadiazole (712-68-5)

Guidance literature:

With N-chloro-succinimide; boron trifluoride diethyl etherate; In tert-butyl alcohol; Inert atmosphere; Reflux;

DOI:10.1021/acs.orglett.1c01379

upstream raw materials:

1-(5-nitro-furan-2-carbonyl)-thiosemicarbazide

5-nitro-furfural thiosemicarbazone

2-[(E)-1-(5-nitro-2-furyl)methylidene]-1-hydrazinecarbothioamide

5-nitrofurane-2-carboxaldehyde

Downstream raw materials:

N-(2-butyl)-4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)benzamidine hydrochloride

N-benzyl-4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)benzamidine hydrochloride

N-(4-methoxybenzyl)-4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)benzamidine hydrochloride

N-((tetrahydrofuran-2-yl)methyl)-4-(4-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl)piperazin-1-yl)benzamidine hydrochloride

Refernces

• 1、 George, Shilpa E.,Guddat, Luke W.,Krishna, Vagolu Siva,Nallangi, Radhika,Rekha, Estharla Madhu,Sai Prasad, D. V.,Sriram, Dharmarajan,Zheng, Shan. "Design and development of ((4-methoxyphenyl)carbamoyl) (5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-yl)amide analogues as Mycobacterium tuberculosis ketol-acid reductoisomerase inhibitors". . . Retrieved 2020/03/19.
• 2、 Moshafi, Mohammad Hassan,Yahya-Meymandi, Azadeh,Sadat-Ebrahimi, Seyed Esmaeil,Emami, Saeed,Nakhjiri, Maryam,Siavoshi, Farideh,Omrani, Maryam,Vosooghi, Mohsen,Alipour, Eskandar,Shafiee, Abbas,Foroumadi, Alireza. "Synthesis and biological activity of 5-nitrofuran-containing (1,3,4-thiadiazol-2-yl)piperazine moieties as a new type of anti-Helicobacter pylori heterocycles". scheme or table. p. 201 - 210. Retrieved 2012/01/14.