Acute and Cutaneous Toxicity of β-Chlorovinyl Ketones and Aldehydes in Rodents

Vinylogous Acyl Compounds. XX. Reactivity and Toxicity of Aryl‐substituted β‐Chlorovinyl Ketones, β‐Chlorovinyl Aldehydes, and β‐Chlorovinyl Methyleniminium Salts Based on kinetic measurements, the nucleophilic replaceability of the chlorine in aromatic β‐chlorovinyl ketones ArCO‐CH  CH‐Cl (1), isomeric β‐chlorovinyl aldehydes OCHCHC(Cl)Ar(2), and corresponding β‐chlorovinyl methyleniminium salts Me2N⊕;CHCHC(Cl)Ar X⊖ (3) is compared and related to toxicological findings. The chemical reactivity of these important synthetic building blocks increases in the order 2<1<3, the acute toxicity (24 h LD50 i. p. in the mouse) shows the graduation 2<3<1. Compounds of type 1 prove to be relatively toxic (LD50 24–42 mg/kg) and display a marked necrotic action after percutaneous absorption, whereas the aldehydes 2 have not only a minor acute toxicity (LD50 158–298 mg/kg) but also a somewhat less marked skin damaging activity. In addition, the LD50 values of selected β‐chlorovinyl carbonyl compounds are compared with those of corresponding halogen‐free compounds as well as of vinylogous carbonamidium salts ArCOCHCHN⊕R3X⊖. The latter, which can be used as synthetic equivalents of 1, differ in both the reduced acute toxicity and missing skin damaging properties.

show abstract

Vinyloge Acylverbindungen. XX. Reaktivität und Toxizität arylsubstituierter β‐Chlorvinylketone, β‐Chlorvinylaldehyde und β‐Chlorvinylmethyleniminiumsalze

Fischer

Jentzsch

Riemer

1983

J. Prakt. Chem.

View full text Add to dashboard Cite

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Acute and Cutaneous Toxicity of β-Chlorovinyl Ketones and Aldehydes in Rodents

Cited by 1 publication

References 2 publications

Vinyloge Acylverbindungen. XX. Reaktivität und Toxizität arylsubstituierter β‐Chlorvinylketone, β‐Chlorvinylaldehyde und β‐Chlorvinylmethyleniminiumsalze

Vinyloge Acylverbindungen. XX. Reaktivität und Toxizität arylsubstituierter β‐Chlorvinylketone, β‐Chlorvinylaldehyde und β‐Chlorvinylmethyleniminiumsalze

Contact Info

Product

Resources

About