5-AMINO-1,3,4-THIADIAZOLE-2-SULFONAMIDE

Base Information

• Chemical Name: 5-AMINO-1,3,4-THIADIAZOLE-2-SULFONAMIDE
• CAS No.: 14949-00-9
• Molecular Formula: C2H4 N4 O2 S2
• Molecular Weight: 180.211
• Hs Code.: 2935909550
• Mol file: 14949-00-9.mol

Synonyms:2-Amino-1,3,4-thiadazole-5-sulfonamide;2-Amino-1,3,4-thiadiazole-5-sulfonamide; 5-Amino-1,3,4-thiadiazol-2-sulfonamide;5-Amino-1,3,4-thiadiazole-2-sulfonamide; CL 5343; NSC 22979; Tio-urasin

Chemical Property of 5-AMINO-1,3,4-THIADIAZOLE-2-SULFONAMIDE

Chemical Property:

• Vapor Pressure: 1.57E-09mmHg at 25°C
• Melting Point: 188-190°C
• Refractive Index: 1.6440 (estimate)
• Boiling Point: 484.2°C at 760 mmHg
• PKA: 7.76±0.60(Predicted)
• Flash Point: 246.6°C
• PSA: 148.58000
• Density: 1.865g/cm³
• LogP: 1.13000
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 4.739g/L(15 oC)

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Amino-1,3,4-thiadiazol-2-sulfonamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Acetazolamide intermediate.

Technology Process of 5-AMINO-1,3,4-THIADIAZOLE-2-SULFONAMIDE

There total 5 articles about 5-AMINO-1,3,4-THIADIAZOLE-2-SULFONAMIDE 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: 100.0%

acetazolamide (59-66-5,8017-69-4) → 5-amino-1, 3, 4-thiadiazole-2-sulfonamide (14949-00-9)

Guidance literature:

With hydrogenchloride; In ethanol; for 4h; Reflux;

DOI:10.1016/j.bmcl.2018.01.060

Reference yield:

5-amino-2-sulfamoyl-1,3,4-thiadiazole monohydrochloride (120208-98-2) → 5-amino-1, 3, 4-thiadiazole-2-sulfonamide (14949-00-9)

Guidance literature:

With sodium hydrogencarbonate; In water; pH=7;

Reference yield:

acetazolamide (59-66-5,8017-69-4) → 5-amino-1, 3, 4-thiadiazole-2-sulfonamide (14949-00-9) + acetic acid (64-19-7,77671-22-8)

Guidance literature:

With water; at 25 ℃; Thermodynamic data; effect of pH (1.68 - 8.17), two buffer species (phosphate and citrate), ionic strength and temperature on stability of title compound; E_a;

DOI:10.1002/jps.2600781015

upstream raw materials:

acetazolamide

5-amino-2-sulfamoyl-1,3,4-thiadiazole monohydrochloride

Downstream raw materials:

N-(sulfamoyl-[1,3,4]thiadiazol-2-yl)-phthalamic acid

glycine-(5-sulfamoyl-[1,3,4]thiadiazol-2-ylamide)

N-(2-sulfamoyl-1,3,4-thiadiazol-5-yl)benzamide

N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)propionamide

Refernces

• 1、 Zhou, Wen,Zhang, Bin,Fan, Keyu,Yin, Xiaojian,Liu, Jinfeng,Gou, Shaohua. "An Original Aspirin-Containing Carbonic Anhydrase 9 Inhibitor Overcomes Hypoxia-Induced Drug Resistance to Enhance the Efficacy of Myocardial Protection". . . Retrieved 2021.
• 2、 Dilworth, Jonathan R.,Pascu, Sofia I.,Waghorn, Philip A.,Vullo, Daniela,Bayly, Simon R.,Christlieb, Martin,Sun, Xin,Supuran, Claudiu T.. "Synthesis of sulfonamide conjugates of Cu(ii), Ga(iii), In(iii), Re(v) and Zn(ii) complexes: Carbonic anhydrase inhibition studies and cellular imaging investigations". . p. 4859 - 4873. Retrieved 2015.
• 3、 Andring, Jacob T.,Fouch, Mallorie,Akocak, Suleyman,Angeli, Andrea,Supuran, Claudiu T.,Ilies, Marc A.,McKenna, Robert. "Structural Basis of Nanomolar Inhibition of Tumor-Associated Carbonic Anhydrase IX: X-Ray Crystallographic and Inhibition Study of Lipophilic Inhibitors with Acetazolamide Backbone". . p. 13064 - 13075. Retrieved 2020.
• 4、 El-Gohary, Nadia S.,Shaaban, Mona I.. "Antimicrobial and Antiquorum-Sensing Studies. Part 3: Synthesis and Biological Evaluation of New Series of [1,3,4]Thiadiazoles and Fused [1,3,4]Thiadiazoles". . p. 283 - 297. Retrieved 2015.
• 5、 Tanpure, Rajendra P.,Ren, Bin,Peat, Thomas S.,Bornaghi, Laurent F.,Vullo, Daniela,Supuran, Claudiu T.,Poulsen, Sally-Ann. "Carbonic anhydrase inhibitors with dual-tail moieties to match the hydrophobic and hydrophilic halves of the carbonic anhydrase active site". . p. 1494 - 1501. Retrieved 2015.
• 6、 Tatiparti, Katyayani,Sau, Samaresh,Gawde, Kaustubh A.,Iyer, Arun K.. "Copper-free ‘click’ chemistry-based synthesis and characterization of carbonic anhydrase-IX anchored albumin-paclitaxel nanoparticles for targeting tumor hypoxia". . . Retrieved 2018.
• 7、 More, Kunal N.,Lee, Jun Young,Kim, Dong-Yeon,Cho, Nam-Chul,Pyo, Ayoung,Yun, Misun,Kim, Hyeon Sik,Kim, Hangun,Ko, Kwangseok,Park, Jeong-Hoon,Chang, Dong-Jo. "Acetazolamide-based [18F]-PET tracer: In vivo validation of carbonic anhydrase IX as a sole target for imaging of CA-IX expressing hypoxic solid tumors". . p. 915 - 921. Retrieved 2018.
• 8、 Arslan, Oktay,Kuefrevioglu, Oe. Irfan,Nalbantoglu, Barbaros. "Synthesis and investigation of inhibition effects of new carbonic anhydrase inhibitors". . p. 515 - 518. Retrieved 1997.
• 9、 -. "N-aryl sulfanilamide-N-beta-D-glucopyranose diamide compound and application thereof". Paragraph 0029; 0036. . Retrieved 2021/06/26.