2-(1,2,3-Thiadiazol-4-yl)phenol

Base Information

• Chemical Name: 2-(1,2,3-Thiadiazol-4-yl)phenol
• CAS No.: 59834-06-9
• Molecular Formula: C8H6N2OS
• Molecular Weight: 178.214
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID90377617
• Nikkaji Number: J919.120H
• Wikidata: Q82166894
• Mol file: 59834-06-9.mol

Synonyms:2-(1,2,3-thiadiazol-4-yl)phenol;59834-06-9;2-(1,2,3-thiadiazol-4-yl)benzenol;2-(thiadiazol-4-yl)phenol;Bionet2_000823;SCHEMBL1655677;SAEWPOWUMHQORT-UHFFFAOYSA-;DTXSID90377617;SAEWPOWUMHQORT-UHFFFAOYSA-N;HMS1366F09;2-[1,2,3]Thiadiazol-4-ylphenol;MFCD00792963;2-[1,2,3]Thiadiazol-4-yl-phenol;AKOS005069477;4-(2-hydroxyphenyl)-1,2,3-thiadiazole;CS-0358440;11L-004;AO-638/41746397;J-505290;InChI=1/C8H6N2OS/c11-8-4-2-1-3-6(8)7-5-12-10-9-7/h1-5,11H

Chemical Property of 2-(1,2,3-Thiadiazol-4-yl)phenol

Chemical Property:

• Melting Point: 111-113°
• PSA: 74.25000
• LogP: 1.91070
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 178.02008399
• Heavy Atom Count: 12
• Complexity: 156

Purity/Quality:

99% ^*data from raw suppliers

2-(1,2,3-thiadiazol-4-yl)benzenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C2=CSN=N2)O

Technology Process of 2-(1,2,3-Thiadiazol-4-yl)phenol

There total 5 articles about 2-(1,2,3-Thiadiazol-4-yl)phenol 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: 92.0%

N'-[1-(2-hydroxy-phenyl)-ethylidene]-hydrazinecarboxylic acid ethyl ester (59834-04-7) → 4-(2'-hydroxyphenyl)-1,2,3-thiadiazole (59834-06-9)

Guidance literature:

With thionyl chloride; for 1h; Heating;

DOI:10.1016/S0040-4020(00)00315-X

Reference yield: 71.0%

o-hydroxyacetophenone (118-93-4,104809-67-8) → 4-(2'-hydroxyphenyl)-1,2,3-thiadiazole (59834-06-9)

Guidance literature:

With iodine; potassium thioacyanate; toluene-4-sulfonic acid hydrazide; copper dichloride; In dimethyl sulfoxide; at 100 ℃; for 1h; Sealed tube;

DOI:10.1039/c9cc04254g

Reference yield: 69.0%

2'-hydroxyacetophenone p-tosylhydrazone → 4-(2'-hydroxyphenyl)-1,2,3-thiadiazole (59834-06-9)

Guidance literature:

With dipotassium peroxodisulfate; iodine; ammonium thiocyanate; In ethanol; at 20 ℃; for 12h; Sealed tube;

DOI:10.1055/a-1473-7369

upstream raw materials:

[1-(2-hydroxy-phenyl)-ethylidene]-carbazic acid ethyl ester

N'-[1-(2-hydroxy-phenyl)-ethylidene]-hydrazinecarboxylic acid ethyl ester

o-hydroxyacetophenone

Downstream raw materials:

2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzylsulfanyl]benzofuran

2-Benzofuranthiol

n-butylcarbamic acid 2-(1,2,3-thiadiazol-4-yl)phenyl ester

dodecylcarbamic acid 2-(1,2,3-thiadiazol-4-yl)phenyl ester

Refernces

• 1、 Lu, Yuhan,Sun, Yadong,Abdukader, Ablimit,Liu, Chenjiang. "Diiiodine/Potassium Persulfate Mediated Synthesis of 1,2,3-Thiadiazoles from N -Tosylhydrazones and a Thiocyanate Salt as a Sulfur Source under Transition-Metal-Free Conditions". supporting information. p. 1044 - 1048. Retrieved 2021/05/05.
• 2、 Petrov,Iekhlev,Teplyakov,Androsov. "Synthesis of benzo[b]furan-2-thioles from 4-(2-Hydroxyaryl)-1,2,3- thiadiazoles". scheme or table. p. 728 - 735. Retrieved 2012/10/08.