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| | 5-Amino-1,3,4-thiadiazole-2-thiol Basic information |
| Product Name: | 5-Amino-1,3,4-thiadiazole-2-thiol | | Synonyms: | ACETYLAMINE(2-)-5-MERCAPTO-1,3,4-THIADAZOLE;1,3,4-Thiadiazole-2(3H)-thione, 5-amino-;1,3,4-Thiadiazole-2-thiol, 5-amino-;5-Amino-2-mercapto-1,3,4-thiadiazole;5-Amino-2-thiol-1,3,4-thiadiazole;5-Amino-3H-[1,3,4]thiadiazole-2-thione;delta2-1,3,4-Thiadiazoline-2-thiol, 5-imino-;NSC 21402 | | CAS: | 2349-67-9 | | MF: | C2H3N3S2 | | MW: | 133.2 | | EINECS: | 219-078-4 | | Product Categories: | Cephalosporins;Amines;Xanthones;bc0001;2349-67-9;HL00006 | | Mol File: | 2349-67-9.mol |  |
| | 5-Amino-1,3,4-thiadiazole-2-thiol Chemical Properties |
| Melting point | 235 °C (dec.)(lit.) | | Boiling point | 242.3±23.0 °C(Predicted) | | density | 1.503 (estimate) | | refractive index | 1.5800 (estimate) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | 2g/l | | form | Powder | | pka | 7.80±0.20(Predicted) | | color | White or pale yellow to cream | | PH | 3.9 (2g/l, H2O, 20℃) | | Water Solubility | insoluble | | BRN | 81728 | | InChI | 1S/C2H3N3S2/c3-1-4-5-2(6)7-1/h(H2,3,4)(H,5,6) | | InChIKey | GDGIVSREGUOIJZ-UHFFFAOYSA-N | | SMILES | Nc1nnc(S)s1 | | CAS DataBase Reference | 2349-67-9(CAS DataBase Reference) | | NIST Chemistry Reference | 2-Amino-5-mercapto-1,3,4-thiadiazole(2349-67-9) | | EPA Substance Registry System | 1,3,4-Thiadiazole-2(3H)-thione, 5-amino- (2349-67-9) |
| Hazard Codes | Xi,Xn | | Risk Statements | 36/37/38-22-20/21/22 | | Safety Statements | 26-36-36/37 | | WGK Germany | 3 | | RTECS | XI4550000 | | F | 9-13-23 | | Hazard Note | Irritant | | TSCA | TSCA listed | | HS Code | 29349990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 5-Amino-1,3,4-thiadiazole-2-thiol Usage And Synthesis |
| Chemical Properties | White or pale yellow to cream powder | | Uses | 5-Amino-1,3,4-thiadiazole-2-thiol is a thiadiazole derivative with antibacterial acitivity used in the preparation of herbicides as well as carbonic anhydrase inhibitors. | | Uses | 5-amino-1,3,4-thiadiazole-2-thiol was used to prepare new amines exhibiting anti-convulsant activity. | | Synthesis | 2-Amino-5-mercapto-1,3,4-thiadiazole was synthesized as follows: in a three-necked flask equipped with a stirrer, 5.5 g (0.06 mol) of aminothiourea, 20 mL of N,N-dimethylformamide (DMF), and 3 mL (0.1 mol) of carbon disulfide were added sequentially. The reaction mixture was heated to reflux and maintained for 4 hours. After completion of the reaction, the mixture was cooled to room temperature. To the reaction mixture was added 40 mL of 2 mol/L sodium hydroxide solution followed by decolorization. After decolorization, concentrated hydrochloric acid was slowly added to acidic conditions to precipitate the crude product. The crude product was purified by recrystallization from 50% ethanol to give 5.7 g of bright yellow needle-like crystals of 2-amino-5-mercapto-1,3,4-thiadiazole in 67.4% yield. | | References | [1] Journal of Chemical Research, 2010, # 11, p. 619 - 621
[2] Chemical Biology and Drug Design, 2012, vol. 80, # 4, p. 598 - 604
[3] European Journal of Medicinal Chemistry, 2006, vol. 41, # 8, p. 918 - 924
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 2, p. 241 - 246
[5] Chemical Biology and Drug Design, 2013, vol. 81, # 5, p. 666 - 673 |
| | 5-Amino-1,3,4-thiadiazole-2-thiol Preparation Products And Raw materials |
| Raw materials | Ammonium thiocyanate-->Hydrazine sulfate-->Calcium phosphate-->2-Mercapto-5-methyl-1,3,4-thiadiazole-->Hydrazodicarbothioamide-->RHENIUM-->Carbon disulfide-->thiosemicarbazide | | Preparation Products | 2-(ACETAMIDO)-5-(CHLOROSULFONYL)-1,3,4-THIADIAZOLE-->2-Acetylamino-5-mercapto-1,3,4-thiadiazole-->2-Amino-1,3,4-thiadiazole-->2-AMINO-5-(METHYLTHIO)-1,3,4-THIADIAZOLE-->5-{[(4-methylphenyl)methyl]sulfanyl}-1,3,4-thiadiazol-2-amine-->5-(Isopropylthio)-1,3,4-thiadiazol-2-amine-->ethyl N-(5-sulfanyl-1,3,4-thiadiazol-2-yl)carbamate-->ETHYL 2-[(5-AMINO-1,3,4-THIADIAZOL-2-YL)THIO]ACETATE |
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