37566-39-5

Basic information

• Product Name: 2-AMINO-5-BROMO-[1,3,4]THIADIAZOLE
• Synonyms: 5-BROMO-1,3,4-THIADIAZOL-2-AMINE;5-Bromo-1,3,4-thiadiazol-2-ylamine;2-AMINO-5-BROMO-[1,3,4]THIADIAZOLE;TOSLAB 5874;2-amino-4-bromo-1,3,4-thiadiazole;5-bromo-1,3,4-thiadiazol-2-amine(SALTDATA: FREE);1,3,4-Thiadiazol-2-aMine, 5-broMo-;2-Amino-5-bromo-1,3,4-thiadiazole 95% (HPLC)
• CAS NO: 37566-39-5
• Molecular Formula: C₂H₂BrN₃S
• Molecular Weight: 180.03
• EINECS: 231-484-3
• Mol File: 37566-39-5.mol
• Article Data: 33

Chemical Properties

• Melting Point: 168 °C
• Boiling Point: 314.1 °C at 760 mmHg
• Flash Point: 143.7 °C
• Appearance: /
• Density: 2.147
• Vapor Pressure: 0.000477mmHg at 25°C
• Refractive Index: 1.709
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 1.76±0.10(Predicted)
• CAS DataBase Reference: 2-AMINO-5-BROMO-[1,3,4]THIADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5-BROMO-[1,3,4]THIADIAZOLE(37566-39-5)
• EPA Substance Registry System: 2-AMINO-5-BROMO-[1,3,4]THIADIAZOLE(37566-39-5)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36
• Safety Statements: 22-36/37/39
• WGK Germany: 2
• HazardClass: IRRITANT
• Hazardous Substances Data: 37566-39-5(Hazardous Substances Data)

Usage

Chemical Properties

Yellow powder

Uses

2-Amino-5-bromo-1,3,4-thiadiazole can be used:As the key building block for the synthesis of myriad of thiadiazolo[3,2-α]pyrimidin-7-ones which have diverse biological activities.For the synthesis of 2-bromoimidazo[2,1-b][1,3,4]thiadiazoles by reacting with α-bromo ketones.

InChI:InChI=1/C2H2BrN3S/c3-1-5-6-2(4)7-1/h(H2,4,6)

Upstream product

• 4005-51-0 [1,3,4]Thiadiazol-2-ylamin 
• 64-18-6 formic acid 
• 79-19-6 thiosemicarbazide 

Downstream Products

• 55114-97-1 N-(5-bromo-1,3,4-thiadiazol-2-yl)-acetamide 
• 98159-68-3 N-<3-<3-(1-Piperidinylmethyl)phenoxy>propyl>-1,3,4-thiadiazol-2,5-diamin 
• 129579-74-4 N-(5-Bromo-[1,3,4]thiadiazol-2-yl)-succinamic acid (3S,8S,9S,10R,13R,14S,17R)-17-((1R,4R)-4-ethyl-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 868946-34-3 N-(5-bromo-1,3,4-thiadiazol-2-yl)acetoacetamideb 
• 857265-81-7 N-(5-bromo-1,3,4-thiadiazol-2-yl)-N'-[2-fluoro-5-(trifluoromethyl)phenyl]urea 
• 88013-14-3 2-methylamino-6-phenylimidazo[2,1-b]-1,3,4-thiadiazole 
• 916889-37-7 5-bromo-1,3,4-thiadiazole-2-carbonitrile 
• 1097016-59-5 2-bromo-6-(4-isopropylphenyl)imidazo[2,1-b][1,3,4]thiadiazole 
• 1241538-21-5 C₁₃H₂₄N₆S 

Relevant articles and documents

Synthesis of new 2,5-disubstituted-1,3,4-thiadiazole derivatives and their in vivo anticonvulsant activity

A series of 2,5-disubstituted-1,3,4-thiadiazole derivatives were synthesized by the reaction of 3-(2-cyanopropan-2-yl)-N-(5-(piperazine-1-yl)-1, 3,4-thiadiazol-2-yl)benzamide with various sulfonyl chlorides and evaluated for their anticonvulsant activity in MES test. Rotorod method was employed to determine the neurotoxicity. The purity of the compounds is confirmed on the basis of their elemental analysis. The structures of all the new compounds are established on the basis of 1H NMR and mass spectral data. Out of fifteen compounds, three were found to be potent anticolvunstants. The same compounds showed no neurotoxicity at the maximum dose administered (100 mg/kg).

PPAR gamma targeted molecular docking and synthesis of some new amide and urea substituted 1, 3, 4-thiadiazole derivative as antidiabetic compound

The PPAR-γ agonist enhances the insulin sensitivity and avoids the disorganized hyperglycemic by promoting the insulin guided cellular uptake of blood glucose. Therefore, in the present work PPAR-γ has chosen as the target for the molecular docking study to design an effective agonist of the same. By this research work an effort has been made to prepare amide and urea series of 1, 3, 4-thiadiazole derivatives as 4-substituted-N-(5-(4-(1-piperidino)1-piperidinyl)-1,3,4-(2-thiadiazolyl)benzamide (4a-f) and 1-(4-substitutedphenyl)-3-(5-(4-(1-piperidino)1-piperidinyl)-1,3,4-(2-thiadiazolyl)urea (6a-f). Both the docking score as well as the pharmacological animal study data has been suggested that the electron donating group containing compound 4f and 6f are most potent molecules for the antidiabetic activity close to the standard drug pioglitazone. It was further observed that the unsubstituted aromatic ring containing derivatives have also considerable effect (4a and 6a) than the electron withdrawing containing derivatives. After the comparison of biological data for amide and urea series, it was concluded that the urea (6a-f) series is more effective than the amide series.

Discovery of potent and novel smoothened antagonists via structure-based virtual screening and biological assays

The Hedgehog (Hh) signaling pathway plays a critical role in controlling patterning, growth and cell migration during embryonic development. Aberrant activation of Hh signaling has been linked to tumorigenesis in various cancers, such as basal cell carcinoma (BCC) and medulloblastoma. As a key member of the Hh pathway, the Smoothened (Smo) receptor, a member of the G protein-coupled receptor (GPCR) family, has emerged as an attractive therapeutic target for the treatment and prevention of human cancers. The recent determination of several crystal structures of Smo in complex with different antagonists offers the possibility to perform structure-based virtual screening for discovering potent Smo antagonists with distinct chemical scaffolds. In this study, based on the two Smo crystal complexes with the best capacity to distinguish the known Smo antagonists from decoys, the molecular docking-based virtual screening was conducted to identify promising Smo antagonists from ChemDiv library. A total of 21 structurally novel and diverse compounds were selected for experimental testing, and six of them exhibited significant inhibitory activity against the Hh pathway activation (IC50 50 lower than 1 μM. The important residues uncovered by binding free energy calculation (MM/GBSA) and binding free energy decomposition were highlighted and discussed. These findings suggest that the novel scaffold afforded by compound 20 can be used as a good starting point for further modification/optimization and the clarified interaction patterns may also guide us to find more potent Smo antagonists.

1,3,4-thiadiazole heterocyclic compound having hedgehog pathway antagonist activity

The present invention discloses a 1,3,4-thiadiazole heterocyclic compound having hedgehog pathway antagonist activity, wherein the compound has a structure represented by a general formula I defined in the specification. According to the present invention, the 1,3,4-thiadiazole heterocyclic compound having hedgehog pathway antagonist activity can block tumor cell metastasis regeneration by antagonizing hedgehog pathway so as to achieve significant antitumor effect.