153446-72-1

Basic information

• Product Name: 3-iodo-7-methoxy-2-phenyl-chromen-4-one
• Synonyms: 3-Iodo-7-methoxy-2-phenyl-4H-chromen-4-one; 3-Iodo-7-methoxy-2-phenylchromen-4-one; 3-Iodo-7-methoxy-2-phenyl-chromen-4-one; 4H-1-benzopyran-4-one, 3-iodo-7-methoxy-2-phenyl-
• CAS NO: 153446-72-1
• Molecular Formula: C₁₆H₁₁IO₃
• Molecular Weight: 378.1612
• Mol File: 153446-72-1.mol

Chemical Properties

• Boiling Point: 452.7°C at 760 mmHg
• Flash Point: 227.6°C
• Density: 1.72g/cm³
• Vapor Pressure: 2.19E-08mmHg at 25°C
• Refractive Index: 1.693
• CAS DataBase Reference: 3-iodo-7-methoxy-2-phenyl-chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-iodo-7-methoxy-2-phenyl-chromen-4-one(153446-72-1)
• EPA Substance Registry System: 3-iodo-7-methoxy-2-phenyl-chromen-4-one(153446-72-1)

Safety Data

• Hazardous Substances Data: 153446-72-1(Hazardous Substances Data)

Upstream product

• 878199-35-0 1-(2,4-dimethoxyphenyl)-3-phenylprop-2-yn-1-one 
• 21785-09-1 7-methoxyflavanone 
• 4440-01-1 lithium phenylacetylide 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 22395-22-8 7-methoxoyflavone 

Downstream Products

• 59208-57-0 7-methoxy-3-(4-methylphenyl)-2-phenylchromone 

Relevant articles and documents

Photo-induced tandem cyclization of 3-iodoflavones with electron rich five-membered heteroarenes

Vinyl radicals were generated from 3-iodoflavones under a mercury lamp and tandem cyclization reactions occurred with five-membered heteroarenes entailing two consecutive C-C bond formations to synthesize benzo[e]chromeno[2,3-g]indol-13(1H)-one derivatives. The tandem cyclization reactions worked in acetonitrile without any additives such as transition metals, ligands and oxidants, giving rise to a broad variety of novel polycyclic xanthone frameworks in good yield under mild and environmentally friendly reaction conditions.

Metal-free oxidative nitration of α-carbon of carbonyls leads to one-pot synthesis of thiohydroximic acids from acetophenones

A metal-free nitration of the α-C-H to carbonyl in propiophenones was achieved with I2/NaNO2 in the presence of an oxidant in dimethyl sulfoxide (DMSO) as the medium. Conversely under similar conditions, reaction of acetophenones produced thiohydroximic acids via a radical-based cascade event which involves oxidative nitration of the α-carbon to a carbonyl followed by Michael addition of the thiomethyl group from DMSO and subsequent rearrangement. Besides DMSO, the scope of the reaction encompasses other symmetrical and unsymmetrical dialkylsulfoxides.

Multi-Step synthesis by using modular flow reactors: The preparation of Yne-Ones and their use in heterocycle synthesis

"Chemical Equation Presented" Multi-step in flow: The palladium-catalysed acylation of terminal alkynes for the synthesis of yne-ones as well as their further transformation to various heterocycles in a continuous-flow mode is presented. Furthermore, an extension of the simple flow configuration that allows for easy batch splitting and the generation of a heterocyclic library is described (see scheme).

Diversity-oriented synthesis of 3-iodochromones and heteroatom analogues via ICl-induced cyclization

The ICl-induced cyclization of heteroatom-substituted alkynones provides a simple, highly efficient approach to various 3-iodochromones and analogues. This process is run under mild conditions, tolerates various functional groups, and generally provides chromones in good to excellent yields. Subsequent palladium-catalyzed transformations afford a rapid increase in molecular complexity and a convenient preparation of a wide range of functionally substituted chromones, furans, and polycyclic compounds. Iodothiochromenones and iodoquinolinones are also prepared by similar ICl-induced cyclizations.

Synthesis of 3-iodo derivatives of flavones, thioflavones and thiochromones

The title compounds, 2-aryl-3-iodo-4H-1-benzopyrans and 2-alkyl or 2-aryl-3-iodo-4H-1-benzothiopyrans, were prepared by reaction of the corresponding heterocyclic derivatives with the iodine-cerium(IV) ammonium nitrate system under mild conditions. The scope and proposed mechanism of the reaction were also demonstrated.