(Z)-5-[(Dichlorophosphinyl)amino]-alpha-(ethoxyimino)-1,2,4-thiadiazole-3-acetyl chloride
[CAS# 90211-01-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Acid halide
• Name: (Z)-5-[(Dichlorophosphinyl)amino]-alpha-(ethoxyimino)-1,2,4-thiadiazole-3-acetyl chloride
• Synonyms: (2Z)-2-[5-(dichlorophosphorylamino)-1,2,4-thiadiazol-3-yl]-2-ethoxyiminoacetyl chloride
• Molecular Formula: C₆H₆Cl₃N₄O₃PS
• Molecular Weight: 351.53
• CAS Registry Number: 90211-01-1
• EC Number: 448-000-3
• SMILES: CCO/N=C(/C1=NSC(=N1)NP(=O)(Cl)Cl)C(=O)Cl

Properties

• Solubility: Very slightly soluble (0.31 g/L) (25 $degree$C), Calc.^*
• Density: 1.92$+/-$0.1 g/cm³ (20 $degree$C 760 Torr), Calc.^*
• Boiling point: 457.1$+/-$28.0 $degree$C 760 mmHg (Calc.)^*
• Flash point: 230.2$+/-$24.0 $degree$C (Calc.)^*
• Index of refraction: 1.708 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05 Danger
• Risk Statements: H314
• Safety Statements: P260-P264-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P363-P405-P501

Discovery and Applications

(Z)-5-[(Dichlorophosphinyl)amino]-α-(ethoxyimino)-1,2,4-thiadiazole-3-acetyl chloride is a highly functionalized heterocyclic compound containing a 1,2,4-thiadiazole core substituted with multiple reactive groups. The molecule features a dichlorophosphinylamino substituent at the 5-position, an ethoxyimino group at the α-position, and an acetyl chloride at the 3-position of the thiadiazole ring. The (Z)-configuration of the ethoxyimino moiety provides defined geometry around the C=N double bond, which can influence both chemical reactivity and interactions in biological systems. This compound is primarily of interest in agrochemical synthesis, heterocyclic chemistry, and as a reactive intermediate in organophosphorus chemistry. Structurally, the molecule combines a planar aromatic 1,2,4-thiadiazole ring with a range of electrophilic and nucleophilic functional groups. The dichlorophosphinylamino group introduces a phosphorus center bonded to two chlorine atoms and a nitrogen, providing both electron-withdrawing character and potential reactivity toward nucleophiles. The ethoxyimino group attached to the α-carbon forms a conjugated C=N–OEt system, capable of acting as a Michael acceptor or coordinating site, while the acetyl chloride provides a highly reactive acyl group suitable for amide formation or acylation reactions. The combination of these functionalities within a heterocyclic scaffold enables diverse chemical transformations. The synthesis of (Z)-5-[(dichlorophosphinyl)amino]-α-(ethoxyimino)-1,2,4-thiadiazole-3-acetyl chloride generally involves stepwise functionalization of a pre-formed 1,2,4-thiadiazole ring. Introduction of the dichlorophosphinylamino group is achieved via reaction with phosphorus chlorides under controlled low-temperature conditions. The ethoxyimino group is installed through condensation of the corresponding aldehyde or ketone derivative with ethoxyamine, ensuring the (Z)-configuration. The acetyl chloride is formed by acylation using thionyl chloride or oxalyl chloride in an anhydrous environment to prevent hydrolysis. Careful control of reaction conditions is necessary to preserve the integrity of the reactive functional groups and avoid decomposition of the heterocycle. In agrochemical and medicinal chemistry research, compounds containing thiadiazole cores with phosphorus and oxime functionalities are investigated for their potential bioactivity. The dichlorophosphinylamino group can confer activity against pests or pathogens, while the ethoxyimino moiety and acetyl chloride allow further derivatization to optimize efficacy and selectivity. The electrophilic centers in the molecule can interact with nucleophilic residues in target proteins, enabling the design of inhibitors or functionalized derivatives with improved stability and solubility. Beyond bioactivity, this compound serves as a versatile intermediate in synthetic organic chemistry. The phosphorus center allows for cross-coupling and substitution reactions, the ethoxyimino group can participate in cycloaddition or condensation chemistry, and the acetyl chloride provides a reactive site for forming amides or esters. These combined features make it valuable for the preparation of heterocyclic libraries, phosphorus-containing scaffolds, or functionalized thiadiazoles for chemical research. Overall, (Z)-5-[(dichlorophosphinyl)amino]-α-(ethoxyimino)-1,2,4-thiadiazole-3-acetyl chloride is a multifunctional heterocyclic compound featuring a 1,2,4-thiadiazole core with phosphorus, oxime, and acyl chloride substituents. Its combination of electrophilic, nucleophilic, and heteroaromatic properties makes it a highly reactive intermediate suitable for agrochemical synthesis, heterocyclic chemistry, and the development of bioactive or functionalized compounds.

References

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