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| CAS No. : | 2349-67-9 |
| Formula : | C2H3N3S2 |
| M.W : | 133.20 |
| SMILES Code : | SC1=NN=C(N)S1 |
| English Name : | 5-Amino-1,3,4-thiadiazole-2-thiol |
| MDL No. : | MFCD00003108 |
| InChI Key : | GDGIVSREGUOIJZ-UHFFFAOYSA-N |
| Pubchem ID : | 2723847 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With hydrogenchloride by/at 245 degree melting form; | ||
| With hydrogenchloride by/at 234 degree melting form; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With water; iron(III) chloride | ||
| With ethanol; iron(III) chloride | ||
| With water; dihydrogen peroxide |
| With ethanol; dihydrogen peroxide | ||
| With water; iodine; potassium iodide at 30 - 35℃; | ||
| With iodine | ||
| With pyridine; p-toluenesulfonyl chloride | ||
| With sodium hydrogencarbonate; p-toluenesulfonyl chloride; acetone |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; | (2) 2-amino-5-mercapto-1,3,4-thiadiazole (4.0 mmol), potassium carbonate (6.0 mmol), DMF (2 mL) as a solvent, and placed in a 100 mL three-neck bottle. After stirring, the solid was dissolved, and iodomethane (4.0 mmol) was slowly added dropwise, followed by stirring at room temperature for 2-6 h. After the reaction was completed, the solvent was removed under reduced pressure, ice water was added, and then the solid was collected by filtration. Recrystallization from absolute ethanol to give the intermediate 2-amino-5-methylmercapto-1,3,4-thiadiazole. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 91% | With dihydrogen peroxide In methanol; water | 27.1 Example 27; 1 ,2-bis(5-chloro-l ,3,4-thiadiazol-2-yl) disulfane; Step 1 : Aqueous hydrogen peroxide (1.3 g, 30%, 11.25 mmol) was added dropwise to a solution of 5-amino-l,3,4-thiadiazole-2-thiol 1 (100 mg, 0.75 mmol) in MeOH (20 mL) during 5 min. The resulting bright yellow solution was stirred until precipitation of the product was complete. After filtration, 5,5'- disulfanediylbis(l,3,4-thiadiazol-2-amine) 2 was obtained as a yellow solid (900 mg, yield 91%) . The product was used without further purification. |
| 91% | With dihydrogen peroxide In methanol; water | 11.1; 14.1 Step 1: Aqueous hydrogen peroxide (1.3 g, 30%, 11.25 mmol) was added dropwise to a solution of 5 -amino- 1,3, 4-thiadiazole-2 -thiol 1 (100 mg, 0.75 mmol) in MeOH (20 mL) during 5 min. The resulting bright yellow solution was stirred until precipitation of the product was complete. After filtration, 5,5'-disulfanediylbis(l,3,4-thiadiazol-2-amine) 2 was obtained as a yellow solid (900 mg, yield 91%) . The product was used without further purification. |
| 90% | With anhydrous sodium perchlorate In water at 0 - 5℃; for 0.25h; |
| 65% | With pyridine; benzenesulfonyl chloride In dichloromethane Ambient temperature; | |
| 65% | With dihydrogen peroxide In methanol at 20℃; | 4.2.28 Bis(thiazol-2-yl)disulfide (3a) General procedure: H2O2 (1mL) was added dropwise into 2-mercaptothiazole (586mg, 5mmol) was solved in 10mL methanol. After 10min, the mixture was filtrated to generate 3a. |
| 56% | With sulfuric acid; dihydrogen peroxide In ethanol at 20℃; for 1h; | 6 Example 6. 5,5'-disulfanediylbis(1,3,4-thiadiazol-2-amine) (6) Hydrogen peroxide (150 uL) was added dropwise to a suspension of 2-amino- thiadiazine-5-thiol in (290 mg, 2.2 mmol) in ethanol (5 mL), followed by addition of H2SO4 (cone, 2 drops). The mixture was allowed to stir at room temperature for 1 h. The resulting precipitate was then collected and dried (Yield: 56%). LC-MS (ESI+): Calcd. mass for C4H4 6S4 264.37, found m/z 265.64 [M+H]+. (ESI-): Found m/z 263.75. |
| 56% | With sulfuric acid; dihydrogen peroxide In ethanol at 20℃; for 1h; | 6 Example 6 5,5’-disulfanediylbis(l ,3,4-thiadiazol-2-amine) (6) Hydrogen peroxide (150 uL) was added dropwiseto a suspension of 2-amino-thiadiazine-5-thiol in (290 mg, 2.2 mmol) in ethanol (5 mE), followed by addition of H2 504 (conc., 2 drops). The mixture was allowed to stir at room temperature for 1 h. The resulting precipitate was then collected and dried (Yield: 5 6%).LC-MS (ESI+): Calcd. mass for C4H4N6S4 264.37.found mlz 265.64 [M+H]. (ESI-): Found mlz 263.75. |
| 45% | With Porcine Pancreas Lipase In water at 20℃; for 36h; Green chemistry; Enzymatic reaction; | |
| 40% | With bovine serum albumin In water at 20℃; for 30h; Enzymatic reaction; | 2.3.1. General procedure for the synthesis of disulphides (1b-27b) Thiophenol (0.25 mmol), BSA (50 mg) and deionized water(600 L) were stirred at room temperature for 12 h or till com-pletion of reaction (monitored by TLC). Then water (2 mL) wasadded to reaction mixture and extracted with ethyl acetate(3 mL 2), organic part dried over Na2SO4, ltered and then con-centrated under rotary evaporator and chromatographed oversilica gel by hexane/ethyl acetate (99:1). The obtained disulphides(1b-27b) were characterized and conrmed by comparing the1H NMR and 13C NMR data with those reported in the literature[38-51,108-116]. 2.4.25. Bis(benzo[d]oxazol-2-yl)disulphide (25b) [45]White solid, mp: 94-96 C (lit [45] 92-94 C), 1H NMR (DMSO-d6, 400 MHz): 7.77-7.75 (4H, m), 7.44-7.41 (4H, m); 13C NMR(DMSO-d6, 100 MHz): 159.8, 152.0, 141.2, 126.0, 125.3, 119.7,111.0 |
| With anhydrous sodium perchlorate In tetrahydrofuran at 10℃; for 0.25h; | ||
| 88 % | With acetic acid In methanol at 20℃; Electrochemical reaction; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 58% | In tetrahydrofuran at 0 - 20℃; for 17h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In potassium hydroxide; ethanol; water; dimethyl sulfate; | Step 1 5-Amino-1,3,4-thiadiazole-2-thiol (10.1 g) is dissolved in 31 mL of 20% KOH in ethanol and 6.1 mL of water. This solution is cooled in an ice bath and stirred while dimethyl sulfate (7.7 mL) is added dropwise. The reaction is stirred in an ice bath for an additional hour and the filtered. The solid is washed with 50% ethanol/water and dried. Recrystallization from ethanol give 4.8 g of 5-amino-2-methylthio-1,3,4-thiadiazole. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 82.2% | With potassium iodide; sodium hydroxide In ethanol; water at 20℃; for 1h; |