5728-14-3

Basic information

• Product Name: 3-CHLORO-4-PHENYL-1,2,5-THIADIAZOLE
• Synonyms: 3-CHLORO-4-PHENYL-1,2,5-THIADIAZOLE;3-chloro-4-phenyl-1,2,5-thiadiazole(WXC08480)
• CAS NO: 5728-14-3
• Molecular Formula: C₈H₅ClN₂S
• Molecular Weight: 196.66
• Mol File: 5728-14-3.mol

Chemical Properties

• Melting Point: 139-144°C
• Boiling Point: 94-96°/0.1mm
• Flash Point: 235.8°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 7.13E-09mmHg at 25°C
• Refractive Index: 1.627
• CAS DataBase Reference: 3-CHLORO-4-PHENYL-1,2,5-THIADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-4-PHENYL-1,2,5-THIADIAZOLE(5728-14-3)
• EPA Substance Registry System: 3-CHLORO-4-PHENYL-1,2,5-THIADIAZOLE(5728-14-3)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• HazardClass: IRRITANT
• Hazardous Substances Data: 5728-14-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Chloro-4-phenyl-1,2,5-thiadiazole is used as a pharmaceutical agent for its antitumor properties. It has been studied for its potential to inhibit the growth of cancer cells, making it a promising candidate for the development of new anticancer drugs.
Used in Agrochemical Industry:
In the agrochemical industry, 3-chloro-4-phenyl-1,2,5-thiadiazole is used as an antimicrobial agent. Its ability to combat microbial infections in crops can contribute to improved crop yields and reduced losses due to diseases.
Used in Materials Science:
3-Chloro-4-phenyl-1,2,5-thiadiazole is utilized as a building block in the synthesis of various organic materials. Its unique structure and properties make it a valuable component in the development of new materials with specific characteristics for various applications in materials science.
Used in Organic Synthesis:
As a key intermediate in organic synthesis, 3-chloro-4-phenyl-1,2,5-thiadiazole is used to construct a wide range of organic compounds. Its reactivity and structural features allow for the synthesis of diverse molecules with potential applications in various industries.

InChI:InChI=1/C18H24N2OS/c1-2-12-22-18-19-16-11-7-6-10-15(16)17(21)20(18)13-14-8-4-3-5-9-14/h6-7,10-11,14H,2-5,8-9,12-13H2,1H3

Upstream product

• 53641-60-4 2-phenylglycinonitrile hydrochloride 
• 4589-97-3 phenylglyoxime 
• 140-29-4 phenylacetonitrile 
• 537706-14-2 3-chloro-4-iodo-1,2,5-thiadiazole 
• 98-80-6 phenylboronic acid 
• 537706-13-1 3-bromo-4-chloro-1,2,5-thiadiazole 
• 5728-20-1 3,4-dichloro-1,2,5-thiadiazole 
• 960-16-7 tributylphenylstannane 
• 825-52-5 2-(hydroxyimino)-2-phenylacetonitrile 

Downstream Products

• 33710-57-5 4-amino-N-(4-phenyl-[1,2,5]thiadiazol-3-yl)-benzenesulfonamide 
• 1048980-26-2 1-hydroxy-4-(4-phenyl-1,2,5-thiadiazol-3-yloxy)-2,2,6,6-tetramethylpiperidine hydrochloride 
• 33710-58-6 3-amino-4-phenyl-1,2,5-thiadiazole 

Relevant articles and documents

The preparation and characterization of 5-substituted-4-chloro-1,2,3- dithiazolium salts and their conversion into 4-substituted-3-chloro-1,2,5- thiadiazoles

A series of monosubstituted acetonitriles were treated with disulfur dichloride at room temperature in CH2Cl2 to afford 5-substituted-4-chloro-1,2,3-dithiazolium chlorides 1. Where the 5-substituent was not a good leaving group the chloride salts were converted into the corresponding perchlorate salts 2 which were sufficiently stable and soluble to provide both 1H- and 13C-NMR and cyclic voltammetry data. Several of the dithiazolium chlorides were converted into their corresponding 4-substituted-3-chloro-1,2,5-thiadiazoles 13 on treatment with aqueous ammonia. Mechanisms for all reactions are proposed.

Synthesis of 4-substituted 3-chloro-1,2,5-thiadiazoles from monosubstituted glyoximes

One-pot synthesis of 3-chloro-1,2,5-thiadiazoles from monosubstituted glyoximes and sulfur monochloride was developed.

HETEROCYCLIC DERIVATIVES AS IAP BINDING COMPOUNDS

The present invention relates to compounds of formula (I), or pharmaceutically acceptable salts, solvates thereof, that bind to Inhibitor of Apoptosis Proteins (IAPs). The compounds of the invention may be used as diagnostic and therapeutic agents in the

HYDROXYLAMINE COMPOUNDS AND METHODS OF THEIR USE

The present disclosure provides compounds that include hydroxylamines of formula (I) or (II), pharmaceutical compositions, and methods for their use. The methods utilize hydroxylamine compounds and/or their pharmaceutical compositions for the treatment of angiogenesis, hepatitis, complement-mediated pathologies, drusen-mediated pathologies, macular degeneration and certain other ophthalmic conditions, inflammation, arthritis, and related diseases and for the inhibition of complement activation.

Drug Resistance Reversal In Neoplastic Disease

The present invention is directed to compounds, compositions, and methods for halting or reversing the effects of chemoresistance in neoplastic diseases. In particular the use of hydroxylamines is described.

Inhibitors of IAP

The invention provides novel inhibitors of IAP that are useful as therapeutic agents for treating malignancies where the compounds have the general formula I: wherein X, Y, A, R1, R2, R3, R4, R4′, R5, R5′, R6 and R6′ are as described herein.

Palladium-catalyzed cross-coupling chemistry on 3-chloro-4-halo-1,2,5-thiadiazole

The present invention relates to 3-chloro-4-halo-1,2,5-thiadiazole compounds, a method of producing novel mono- and di-substituted-1,2,5-thiadiazoles therefrom, as well as mono- and di-substituted -1,2,5-thiadiazoles.

The palladium-catalyzed cross-coupling reactions of 3-chloro-4-halogeno-1,2,5-thiadiazoles

3,4-Dichloro- and 3-chloro-4-halogeno-1,2,5-thiadiazoles (halogeno-: bromo- and iodo-) are involved in Pd-catalyzed cross-coupling reactions under Stille and Suzuki conditions. As a result, by using the commercially available 3,4-dichloro-1,2,5-thiadiazole as substrate, several 3-alkyl-, 3-alkenyl-, 3-alkynyl-and 3-aryl-4-chloro-1,2,5-thiadiazoles can easily be prepared. However, these reactions through direct desymmetrization of the 3,4-dichloro-1,2,5-thiadiazole always occur with side-reactions resulting from the concurrent decomposition of the heterocyclic ring of the starting material. These problems are resolved by involving, in these Pd-catalyzed cross-coupling reactions, the more reactive and selective 3-bromo-4-chloro- and 3-chloro-4-iodo-1,2,5-thiadiazole. These new dihalogeno-1,2,5-thiadiazoles can easily be prepared, via diazotization reaction followed by halogen substitution, from the 3-amino-4-chloro-1,2,5-thiadiazole.

Reactions of 1-aryl-2,2-dihalogenoethanone oximes with tetrasulfur tetranitride (S4N4): A general method for the synthesis of 3-aryl-4-halogeno-1,2,5-thiadiazoles

1-Aryl-2,2-dichloro-7, 1-aryl-2,2-dibromo-8, 1-aryl-2-bromo-2-fluoro-9 and 1-aryl-2-chloro-2-fluoroethanone oximes 10 have been prepared by allowing the corresponding ketones to react with hydroxylamine hydrochloride in EtOH at room temperature. Stereoche