331818-28-1

Basic information

• Product Name: 1,3,4-Thiadiazol-2-aMine, 5-[(4-nitrophenoxy)Methyl]-
• Synonyms: 1,3,4-Thiadiazol-2-aMine, 5-[(4-nitrophenoxy)Methyl]-;5-[(4-Nitrophenoxy)methyl]-1,3,4-thiadiazol-2-amine
• CAS NO: 331818-28-1
• Molecular Formula: C₉H₈N₄O₃S
• Molecular Weight: 252.24982
• Mol File: 331818-28-1.mol

Chemical Properties

• Melting Point: 198℃ (tetrahydrofuran )
• Boiling Point: 519.6±56.0 °C(Predicted)
• Appearance: /
• Density: 1.536±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 2.60±0.10(Predicted)
• CAS DataBase Reference: 1,3,4-Thiadiazol-2-aMine, 5-[(4-nitrophenoxy)Methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4-Thiadiazol-2-aMine, 5-[(4-nitrophenoxy)Methyl]-(331818-28-1)
• EPA Substance Registry System: 1,3,4-Thiadiazol-2-aMine, 5-[(4-nitrophenoxy)Methyl]-(331818-28-1)

Safety Data

• Hazardous Substances Data: 331818-28-1(Hazardous Substances Data)

Usage

Chemical family

Thiadiazole and amine

Structure

Contains a 1,3,4-thiadiazole ring with an amino group attached at the 2-position

Substituent

5-[(4-nitrophenoxy)methyl] group attached to the amine nitrogen

Components of substituent

4-nitrophenoxy and methyl group

Common use

Synthesis of pharmaceutical and agrochemical products

Applications

Potential use in medicinal chemistry and drug discovery

Functional groups

Thiadiazole ring, amine group, nitro group, and phenoxy group

Molecular weight

Approximately 252.25 g/mol

Appearance

Likely a solid or crystalline substance, though specific appearance may vary depending on the conditions

Stability

May be sensitive to light, heat, or moisture, but specific stability information is not provided in the material

Reactivity

Potential to react with strong acids, strong bases, or other reactive chemicals, but specific reactivity information is not provided in the material

Hazards

Information on potential hazards, such as toxicity or flammability, is not provided in the material

Storage

Appropriate storage conditions are not specified in the material, but it is generally recommended to store chemicals away from heat, light, and moisture, and in a well-sealed container

Disposal

Information on proper disposal methods is not provided in the material, but it is generally recommended to follow local regulations and guidelines for chemical waste disposal.

Upstream product

• 19076-89-2 ethyl 4-nitrophenoxyacetate 
• 75129-74-7 (4-nitro-phenoxy)-acetic acid hydrazide 
• 100-02-7 4-nitro-phenol 
• 1263183-95-4 C₉H₁₀N₄O₄S 
• 1798-11-4 4-nitrophenoxyacetic acid 
• 79-19-6 thiosemicarbazide 

Downstream Products

• 1018474-92-4 C₁₁H₉ClN₄O₄S 
• 1263183-65-8 C₁₃H₁₀N₄O₄S 
• 1252594-20-9 2-(1,3-benzothiazol-2-ylsulfanyl)-N-{5-[(4-nitrophenoxy)methyl]-1,3,4-thiadiazol-2-yl} acetamide 
• 1357853-58-7 C₂₂H₂₁N₅O₄S 
• 1357853-74-7 C₁₇H₁₂N₄O₃S 
• 1227624-49-8 C₁₀H₈N₄O₄S 
• 1240041-00-2 C₁₉H₁₃N₅O₆S 

Relevant articles and documents

Synthesis and xanthine oxidase inhibitory activity of 7-methyl-2- (phenoxymethyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one derivatives

An elevated level of blood uric acid (hyperuricemia) is the underlying cause of gout. Xanthine oxidase is the key enzyme that catalyzes the oxidation of hypoxanthine to xanthine and then to uric acid. Allopurinol, a widely used xanthine oxidase inhibitor is the most commonly used drug to treat gout. However, a small but significant portion of the population suffers from adverse effects of allopurinol that includes gastrointestinal upset, skin rashes and hypersensitivity reactions. Moreover, an elevated level of uric acid is considered as an independent risk factor for cardiovascular diseases. Therefore use of allopurinol-like drugs with minimum side effects is the ideal drug of choice against gout. In this study, we report the synthesis of a series of pyrimidin-5-one analogues as effective and a new class of xanthine oxidase inhibitors. All the synthesized pyrimidin-5-one analogues are characterized by spectroscopic techniques and elemental analysis. Four (6a, 6b, 6d and 6f) out of 20 synthesized molecules in this class showed good inhibition against three different sources of xanthine oxidase, which were more potent than allopurinol based on their respective IC50 values. Molecular modeling and docking studies revealed that the molecule 6a has very good interactions with the Molybdenum-Oxygen-Sulfur (MOS) complex a key component in xanthine oxidase. These results highlight the identification of a new class of xanthine oxidase inhibitors that have potential to be more efficacious, than allopurinol, to treat gout and possibly against cardiovascular diseases.

Synthesis and biological evaluation of some novel 2-mercaptobenzothiazoles carrying 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole moieties

Several 2-mercaptobenzothiazole derivatives containing 1,3,4-oxadiazoles, 1,2,4-triazoles and 1,3,4-thiadiazoles at the second position were synthesized. Some of these synthesized compounds were evaluated for their in vivo analgesic, anti-inflammatory, acute toxicity and ulcerogenic actions. Some of the tested compounds showed significant analgesic and anti-inflammatory activities. Two of the compounds showed significant gastrointestinal protection compared to the standard drug diclofenac sodium. The compounds were also tested for their in vitro antimicrobial activity with most displaying selective activity against the Gram-negative bacteria Pseudomonas aeruginosa. In the present investigation the tested compounds did not possess antifungal activity.

Synthesis of 2-(N-formyl)-5-aryl/aryloxymethyl-1,3,4-thiadiazoles with potential bioactivity in PEG-400

An environmental benign procedure for synthesis of 2-(N-formyl)-5-aryl/aryloxymethyl-1,3,4-thiadiazoles has been developed by reaction of 2-amino-5-aryl/aryloxymethyl-1,3,4-thiadiazoles with formic acid in PEG-400. The key advantages of this protocol are

Solvent-free synthesis of 2-amino-5-aryloxymenthyl-1,3,4-thiadiazoles and their coumarin or benzofuran bis-heterocyclic derivatives

2-amino-5-aryloxymethyl-1,3,4-thiadiazoles were synthesized rapidly by a microwave-accelerated solvent-free procedure in high yield via the condensation of thiosemicarbazide with aryloxyacetic acids using poly(ethylene glycol)-supported dichlorophosphate

Polymer-supported dichlorophosphate: A recoverable new reagent for synthesis of 2-amino-1,3,4-thiadiazoles

Poly(ethylene glycol) (PEG) supported dichlorophosphate was efficiently used as a recoverable new dehydration reagent for rapid synthesis of 2-amino-5-substituted-1,3,4-thiadiazoles under microwave irradiation and solvent-free condition by reactions of thiosemicarbazide with aliphatic acids, benzoic acid, aryloxyacetic acids or furan-2-carboxylic acids.