149113-41-7

Basic information

• Product Name: [4-(4-Hydroxy-3,5-diiodo-phenoxy)-3,5-diiodo-phenyl]-acetic acid ethyl ester
• Synonyms: [4-(4-Hydroxy-3,5-diiodo-phenoxy)-3,5-diiodo-phenyl]-acetic acid ethyl ester
• CAS NO: 149113-41-7
• Molecular Weight: 775.887
• Mol File: 149113-41-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: [4-(4-Hydroxy-3,5-diiodo-phenoxy)-3,5-diiodo-phenyl]-acetic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [4-(4-Hydroxy-3,5-diiodo-phenoxy)-3,5-diiodo-phenyl]-acetic acid ethyl ester(149113-41-7)
• EPA Substance Registry System: [4-(4-Hydroxy-3,5-diiodo-phenoxy)-3,5-diiodo-phenyl]-acetic acid ethyl ester(149113-41-7)

Safety Data

• Hazardous Substances Data: 149113-41-7(Hazardous Substances Data)

Upstream product

• 17138-28-2 (4-hydroxy-phenyl)-acetic acid ethyl ester 
• 90917-49-0 ethyl 4-hydroxy-3,5-diiodophenylacetate 

Relevant articles and documents

Synthesis of thyroxine: Biomimetic studies

The biomimetic oxidative coupling of the ethyl ester of N-acetyl-3,5- diiodotyrosine (1) to yield the ethyl ester of N-acetylthyroxine (2) has been investigated. A putative mechanism involving phenolic coupling to yield an intermediate aryloxydienone (7) followed by an E2 elimination for loss of the side chain has been proposed. Oxidative couplings with analogous 4- substituted 3,5-diiodophenols indicate that a number of mechanisms are possible; these include quinone methide intermediates and S(N)2 substitutions in the intermediate aryloxydienones. Rearomatization of the intermediate aryloxydienones is a strong driving force for the loss of the side chains. The results indicate that 3,5-diiodo-4-aryloxydienones are good leaving groups in E2 and S(N)2 mechanisms. The synthetic method provides a facile synthesis of thyroxine analogues from readily available 4-substituted 3,5- diiodophenols. The biomimetic oxidative coupling of the ethyl ester of N-acetyl-3,5-diiodotyrosine (1) to yield the ethyl ester of N-acetylthyroxine (2) has been investigated. A putative mechanism involving phenolic coupling to yield an intermediate aryloxydienone (7) followed by an E2 elimination for loss of the side chain has been proposed. Oxidative couplings with analogous 4-substituted 3,5-diiodophenols indicate that a number of mechanisms are possible; these include quinone methide intermediates and SN2 substitutions in the intermediate aryloxydienones. Rearomatization of the intermediate aryloxydienones is a strong driving force for the loss of the side chains. The results indicate that 3,5-diiodo-4-aryloxydienones are good leaving groups in E2 and SN2 mechanisms. The synthetic method provides a facile synthesis of thyroxine analogues from readily available 4-substituted 3,5-diiodophenols.