121068-32-4

Basic information

• Product Name: 5-PHENOXYMETHYL-[1,3,4]THIADIAZOL-2-YLAMINE
• Synonyms: TIMTEC-BB SBB007062;2-AMINO-5-PHENOXYMETHYL-1,3,4-THIADIAZOLE;5-(PHENOXYMETHYL)-1,3,4-THIADIAZOL-2-AMINE;5-PHENOXYMETHYL-[1,3,4]THIADIAZOL-2-YLAMINE;AKOS B014676;ART-CHEM-BB B014676;1,3,4-Thiadiazol-2-aMine, 5-(phenoxyMethyl)-;2-Amino-5-(phenoxymethyl)thiadiazole
• CAS NO: 121068-32-4
• Molecular Formula: C₉H₉N₃OS
• Molecular Weight: 207.25
• Mol File: 121068-32-4.mol

Chemical Properties

• Melting Point: 185℃ (ethanol )
• Boiling Point: 408.4°C at 760 mmHg
• Flash Point: 200.8°C
• Appearance: /
• Density: 1.36g/cm³
• Vapor Pressure: 7.01E-07mmHg at 25°C
• Refractive Index: 1.659
• PKA: 2.90±0.10(Predicted)
• CAS DataBase Reference: 5-PHENOXYMETHYL-[1,3,4]THIADIAZOL-2-YLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-PHENOXYMETHYL-[1,3,4]THIADIAZOL-2-YLAMINE(121068-32-4)
• EPA Substance Registry System: 5-PHENOXYMETHYL-[1,3,4]THIADIAZOL-2-YLAMINE(121068-32-4)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 121068-32-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-PhenoxyMethyl-[1,3,4]Thiadiazol-2-Ylamine is used as an antibacterial agent for its potential to combat bacterial infections. Its unique structure allows it to target and disrupt essential cellular processes in bacteria, leading to their inactivation or death.
5-PhenoxyMethyl-[1,3,4]Thiadiazol-2-Ylamine is also used as an antifungal agent, effective against various fungal species that cause infections in humans and animals. Its ability to inhibit fungal growth and proliferation makes it a promising candidate for the development of antifungal drugs.
In addition, 5-PhenoxyMethyl-[1,3,4]Thiadiazol-2-Ylamine has been studied for its antiviral properties, showing potential in inhibiting the replication and spread of viruses. This makes it a valuable compound for the development of antiviral medications, particularly in the face of emerging viral threats.
5-PhenoxyMethyl-[1,3,4]Thiadiazol-2-Ylamine is used as an antidepressant and neuroprotective agent, with research indicating its potential to modulate neurotransmitter levels and protect neurons from damage. This dual action could make it a valuable treatment for mood disorders and neurodegenerative diseases.
Used in Agricultural Industry:
5-PhenoxyMethyl-[1,3,4]Thiadiazol-2-Ylamine is used as an insecticidal agent, with potential to control and eliminate pests that damage crops and reduce agricultural productivity. Its ability to target and disrupt essential biological processes in insects makes it a promising candidate for the development of new insecticides.
Furthermore, 5-PhenoxyMethyl-[1,3,4]Thiadiazol-2-Ylamine has been investigated for its potential herbicidal properties, showing promise in controlling the growth of unwanted plants and weeds. Its ability to selectively target and inhibit the growth of certain plant species could make it a valuable tool in modern agriculture.

InChI:InChI=1/C9H9N3OS/c10-9-12-11-8(14-9)6-13-7-4-2-1-3-5-7/h1-5H,6H2,(H2,10,12)

Upstream product

• 4664-55-5 phenoxyacetyl hydrazine 
• 108-95-2 phenol 
• 35687-21-9 N-phenoxyacetyl-N'-thiocarbamoyl-hydrazine 
• 2555-49-9 phenoxyacetic acid ethyl ester 
• 79-19-6 thiosemicarbazide 
• 122-59-8 2-phenoxyacetic acid 
• 3598-14-9 phenoxyacetonitrile 

Downstream Products

• 1263183-74-9 C₁₃H₁₁N₃O₂S 
• 123306-65-0 2-(Chloroacetamido)-5-(phenoxymethyl)-1,3,4-thiadiazole 
• 141421-54-7 7-Hydroxy-2-phenoxymethyl-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one 
• 123282-34-8 2-(Furylidenimino)-5-(phenoxymethyl)-1,3,4-thiadiazole 
• 1422676-25-2 4-(5-phenoxymethyl-1,3,4-thiadiazole)aminobenzaldehyde 
• 1357853-41-8 C₂₂H₂₂N₄O₂S 
• 1253415-09-6 C₁₇H₁₄N₄OS₂ 

Relevant articles and documents

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

A novel approach to the synthesis of 1,3,4-thiadiazole-2-amine derivatives

The main purpose of the study was the development of a new method for synthesis of 1,3,4-thiadiazol-2-amine derivatives in a one-pot manner using the reaction between a thiosemicarbazide and carboxylic acid without toxic additives such as POCl3 or SOCl2. The reaction was investigated in the presence of polyphosphate ester (PPE). It was found that, in the presence of PPE, the reaction between the thiosemicarbazide and carboxylic acid proceeds in one-pot through three steps with the formation of corresponding 2-amino-1,3,4-thiadiazole. Using the developed approach five, 2-amino-1,3,4-thiadiazoles were synthesized. The structures of all compounds were proven by mass spectrometry, IR, and NMR spectroscopies.

Synthesis, evaluation and in silico molecular modeling of pyrroyl-1,3,4-thiadiazole inhibitors of InhA

Enoyl acyl carrier protein reductase (ENR) is an essential type II fatty acid synthase (FAS-II) pathway enzyme that is an attractive target for designing novel antitubercular agents. Herein, we report sixty-eight novel pyrrolyl substituted aryloxy-1,3,4-thiadiazoles synthesized by three-step optimization processes. Three-dimensional quantitative structure-activity relationships (3D-QSAR) were established for pyrrolyl substituted aryloxy-1,3,4-thiadiazole series of InhA inhibitors using the comparative molecular field analysis (CoMFA). Docking analysis of the crystal structure of ENR performed by using Surflex-Dock in Sybyl-X 2.0 software indicates the occupation of pyrrolyl substituted aryloxy 1,3,4-thiadiazole into hydrophobic pocket of InhA enzyme. Based on docking and database alignment rules, two computational models were established to compare their statistical results. The analysis of 3D contour plots allowed us to investigate the effect of different substituent groups at different positions of the common scaffold. In vitro testing of ligands using biological assays substantiated the efficacy of ligands that were screened through in silico methods.

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

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.

Synthesis and antiallergy activity of [1,3,4]thiadiazolo[3,2-a]-1,2,3-triazolo[4,5-d]pyrimidin-9(3H)-one derivatives. I

A series of 6-substituted [1,3,4]thiadiazolo[3,2-a]-1,2,3-triazolo[4,5-d]pyrimidin-9(3H)-one derivatives 4a-z were synthesized from 5-substituted-1,3,4-thiadiazol-2-amines 5 by the following consecutive reactions: pyrimidine ring closure with bis(2,4,6-trichlorophenyl) malonate, nitration, chlorination, amination, hydrogenation and diazotization. The structure of 4 was confirmed by an alternate synthesis of 4, involving reaction of 5-substituted 2-azido-1,3,4-thiadiazole 13 with ethyl cyanoacetate, followed by the Dimroth rearrangement and ring closure. The antiallergic activities (anti-passive peritoneal anaphylaxis, anti-passive cutaneous anaphylaxis and anti-slow reacting substance of anaphylaxis activities) of the products were evaluated.