182490-46-6

Basic information

• Product Name: O-(2-iodo-phenyl)-N,N-diethylcarbamate
• Synonyms: O-(2-iodo-phenyl)-N,N-diethylcarbamate
• CAS NO: 182490-46-6
• Molecular Weight: 319.142
• Mol File: 182490-46-6.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: O-(2-iodo-phenyl)-N,N-diethylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: O-(2-iodo-phenyl)-N,N-diethylcarbamate(182490-46-6)
• EPA Substance Registry System: O-(2-iodo-phenyl)-N,N-diethylcarbamate(182490-46-6)

Safety Data

• Hazardous Substances Data: 182490-46-6(Hazardous Substances Data)

Upstream product

• 65009-00-9 O-phenyl N,N-diethylcarbamate 
• 108-95-2 phenol 
• 88-10-8 N,N-diethylcarbamyl chloride 
• 533-58-4 2-Iodophenol 
• 85630-23-5 N,N-diethyl-O-(2-trimethylsilylphenyl)carbamate 

Downstream Products

• 1225288-49-2 N,N-diethyl-2-hydroxy-3-iodobenzamide 
• 1300713-50-1 N,N-diethyl-2-trimethylsilylbenzofuran-7-carboxamide 
• 1445899-17-1 2-hydroxy-6-iodophenyl diethylcarbamate 
• 1607814-82-3 N,N-diethyl 2-(3-phenylprop-2-ynoyl)phenyl carbamate 
• 1453186-29-2 (E)-methyl 3-(2-((diethylcarbamoyl)oxy)phenyl)acrylate 
• 1453186-30-5 (2E,2'E)-dimethyl 3,3'-(2-((diethylcarbamoyl)oxy)-1,3-phenylene)diacrylate 
• 182489-46-9 Diethyl-carbamic acid 2-(1-diethylcarbamoyloxy-vinyl)-phenyl ester 
• 211449-24-0 diethylcarbamic acid 2-acetylphenyl ester 
• 91731-53-2 2-acetoxy-benzoic acid diethylamide 
• 19311-91-2 N,N-diethylsalicylamide 

Relevant articles and documents

Harnessing [1,4], [1,5], and [1,6] Anionic Fries-type Rearrangements by Reaction-Time Control in Flow

A series of anionic Fries-type rearrangements of carbamoyl-substituted aryllithium intermediates were controlled by using flow microreactor systems. For the [1,4] and [1,5] rearrangements, the aryllithium intermediate formed before carbamoyl migration and

Directed ortho-Metalation of O-Aryl N,N-Dialkylcarbamates: Methodology, Anionic ortho-Fries Rearrangement, and Lateral Metalation

The directed ortho-lithiation reactions of O-aryl N,N-dialkylcarbamates as well as O-1-naphthyl and O-2-naphthyl N,N-dialkylcarbamates with sec-butyllithium/tetramethylethylenediamine (sBuLi/TMEDA) followed by quenching with various electrophiles afford a range of polysubstituted aromatic compounds. If the solutions of the ortho-lithiated carbamates are warmed to room temperature without the addition of external electrophiles, salicylamide and 1- and 2-hydroxynaphthamide derivatives are formed through anionic ortho-Fries rearrangements. The relative stabilities and reactivities of different O-aryl N,N-dialkylcarbamates were investigated. The lateral metalation of 2-tolyl carbamates with lithium diisopropylamide (LDA) provides a route to benzo[b]furan-2(3H)-ones. Previously reported results are used in a comparison of seven O-based directed metalation groups in reactions with several electrophiles. The described methodology is useful for the preparation of 1,2,3-substituted aromatic compounds.

Absolute configuration of anti-HIV-1 agent (-)-concentricolide: Total synthesis of (+)-(R)-concentricolide

The first enantioselective total synthesis of (+)-(R)-concentricolide, the enantiomer of an anti-HIV-1 agent isolated from Daldinia concentrica, from 2-iodophenol in 7 steps reveals the (S)-configuration for the natural form of the furanophthalide. The key features include an anionic ortho-Fries rearrangement to furnish 3-iodosalicylamide, facile construction of the benzofuran system employing the tandem Sonogashira coupling annulation reaction, directed ortho metalation to introduce a propanoyl group, as well as CBS reduction, establishing the stereocenter enantioselectively.