28177-54-0

Basic information

• Product Name: Phenol, 2,6-diiodo-
• CAS NO: 28177-54-0
• Molecular Formula: C6H4I2O
• Molecular Weight: 345.906
• Mol File: 28177-54-0.mol

Chemical Properties

• CAS DataBase Reference: Phenol, 2,6-diiodo-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, 2,6-diiodo-(28177-54-0)
• EPA Substance Registry System: Phenol, 2,6-diiodo-(28177-54-0)

Safety Data

• Hazardous Substances Data: 28177-54-0(Hazardous Substances Data)

Upstream product

• 2297-82-7 2,6-diiodo-4-aminophenol 
• 7553-56-2 iodine 
• 108-95-2 phenol 
• 609-23-4 2,4,6-Triiodophenol 
• 99-09-2 3-nitro-aniline 
• 146512-89-2 2,4-diiodo-3-nitroaniline 
• 861606-52-2 1,3-diiodo-2-nitro-benzene 
• 305-85-1 2,6-diiodo-4-nitrophenol 
• 100-02-7 4-nitro-phenol 
• 17614-10-7 phenyl N-isopropylcarbamate 
• 899427-44-2 2,6-bis(trimethylsilyl)phenyl isopropylcarbamate 
• 899427-47-5 2,6-diiodophenyl isopropylcarbamate 
• 139-02-6 sodium phenoxide 
• 49865-78-3 2,6-diiodoaniline 

Downstream Products

• 1948-40-9 4-hydroxy-3,5-diiodobenzaldehyde 
• 609-23-4 2,4,6-Triiodophenol 
• 20389-01-9 2,6-diiodo-p-benzoquinone 
• 76469-12-0 3,3',5,5'-tetraiodo-4,4'-diphenol 
• 784210-33-9 4-chloro-benzenesulfonic acid 2,6-diiodophenyl ester 
• 784210-28-2 4-chloro-benzenesulfonic acid 2-allyl-6-iodophenyl ester 

Relevant articles and documents

Synthesis of Stannylated Aryl Imines and Amines via Aryne Insertion Reactions into Sn?N Bonds

The reaction of in situ generated arynes with stannylated imines to provide ortho-stannyl-aniline derivatives is reported. The readily prepared trimethylstannyl benzophenone imine is introduced as an efficient reagent to realize the aryne σ-insertion reaction. The imine functionality is an established N-protecting group and insertions proceed with good yields and good to excellent regioselectivities. The product anilines are valuable starting materials for follow-up chemistry thanks to the rich chemistry offered by the trimethylstannyl moiety.

A dinuclear rhenium complex in the electrochemically driven homogeneous and heterogeneous H+/CO2-reduction

A dinculear Re(CO)3 complex with a proton responsive phenol unit and a pyrene anchor in the ligand backbone was investigated in the electrochemical CO2/H+ conversion in solution and adsorbed on multi walled carbon nanotubes (MWCNT) on an GC electrode surface. The pyrene group unit is introduced at the end of the ligand synthesis via a coupling reaction, which allows for a versatile ligand modification in order to tune the electronic properties or to introduce various anchor groups for heterogenisation at a late stage. The redox chemistry of the pyrene-α-diimine-Re(CO)3 complex, 1, was investigated in N,N-dimethylformamide (dmf), including IR-spectroelectrochemical (IR-SEC) characterisation of the short lived, reduced species. Subsequently, the electrochemical H+/CO2-reduction catalysis in dmf/water was investigated. The complex catalyses syngas formation yielding CO and H2 with similar rates, namely in Faraday yields of 45% and 35%, respectively. Since the similar complex without the pyrene anchor in the backbone, I, prefers CO2 over H+ reduction, the formation of syngas was rationalised by the small differences in the redox properties and pKa values of the phenol-pyrene unit in regard to phenol unit as in I. Subsequently, the complex was adsorbed on multi walled carbon nanotubes (MWCNT) on a GC electrode surface. Scanning electron microscopy (SEM) and X-ray photoelectron spectroscopy (XPS) confirmed coating of the electrode. The immobilised complex was utilised in the electrochemical CO2/H+ reduction in dmf/water, however, the complex quickly desorbed under reductive conditions, likely due to the good solubility of the reduced species. Water as a solvent prevents desorption as confirmed by XPS, however, then a preference for H2 formation over syngas formation was observed under electrocatalytic conditions. Thus, these experiments show, that the results obtained in aqueous organic solution are not easily transferable to the heterogeneous systems operating in water due to changes in the reaction rates for competing pathways.

Two-stage metal ion sensing by through-space and through-bond charge transfer

A highly selective colorimetric and ratiometric "two-stage"/"off-on"type fluorescent probe with an ability to exclude other heavy and transition metal ions has been designed and synthesized. Low concentrations of Fe3+ cause through-space charge transfer which leads to fluorescence quenching exceeds 96%, and a further increase of Fe3+ concentration results in the formation of a complex with the maximum emission peak of 1,3-bis((E)-2-(pyridin-4-yl)vinyl)-2-methoxy benzene (BPVMB) being shifted largely by 100 nm (from 416 to 516 nm), which was examined by fluorescence, absorption detection and femtosecond transient absorption measurements on the basis of intramolecular charge transfer (ICT).

Aryne Trifunctionalization Enabled by 3-Silylaryne as a 1,2-Benzdiyne Equivalent

An unprecedented aryne 1,2,3-trifunctionalization protocol from 2,6-bis(silyl)aryl triflates was developed under transition-metal-free conditions. The reaction of generated 3-silylaryne with both pyridine N-oxide and N-hydroxylamide afforded o-silyl triflate/tosylate in a one-pot transformation, allowing the formation of 2,3-aryne precursors with various vicinal pyridinyl/amido substituents. These pyridinyl-substituted 2,3-aryne intermediates exhibit a broad scope of reactivity with diverse arynophiles in good yields and high selectivity.

Synthesis of Silylbiaryl Triflates by Chemoselective Suzuki Reaction

A modular approach for the synthesis of functionalized silylbiaryl triflates has been developed. Iodinated silylaryl triflates were prepared via a gram-scale diiodination reaction, followed by a one-flask transformation, in 42-52% overall yield. The iodin

Regiocomplementary cycloaddition reactions of boryl- and silylbenzynes with 1,3-dipoles: Selective synthesis of benzo-fused azole derivatives

Benzo-fused nitrogen-containing heterocycles are abundant in biologically active compounds. One of the most important methods for preparing such heterocycles is the (3 + 2) cycloaddition reaction of benzynes with 1,3-dipolar compounds. However, the reacti

A Green protocol for the bromination and iodination of the aromatic compounds using H5IO6/NaBr and H5IO 6/NaI in the water

Bromination and iodination of the aromatic compounds have efficiently been carried out at room temperature and 70 °C, respectively, in short reaction times using orthoperiodic acid/sodium bromide (1:2) and orthoperiodic acid/sodium iodide (1:2) in water to prepare the corresponding halo compounds with excellent yields.

1,3-Phenylene bis(ketoacid) derivatives as inhibitors of Escherichia coli dihydrodipicolinate synthase

Dihydrodipicolinate synthase is a key enzyme in the lysine biosynthesis pathway that catalyzes the condensation of pyruvate and aspartate semi-aldehyde. A series of phenolic ketoacid derivatives that mimic the proposed enzymatic intermediate were designed

Gas-Chromatographic identifi cation of products formed in iodination of methyl phenols by retention indices

Iodination reaction followed by conversion of iodine-substituted methylphenols to the corresponding trifl uoroacetates was suggested for improving the sensitivity of the gas-chromatographic determination of phenol and its methyl-substituted derivatives (al isomers of mono- and diethylphenols, 2,3,5-, 2,3,6-, and 3,4,5-trimethylphenols) in aqueous media. Acylation products of iodo methylphenols (104 compounds) were identifi ed by linear-logarithmic retention indices on a standard nonpolar polydimethylsiloxane stationary phase, and the pattern of their variation with the number and nature of substituents were characterized. A procedure for identifi cation of methyl-substituted phenols in water in their gas-chromatographic determination with an electron-capture detector was developed. Pleiades Publishing, Ltd., 2012.

Direct green iodination of phenol over solid acids

Examination of several solid acid catalysts of different nature (acid resins, zeolites, mixed oxides, Nb-oxide, and Nb-phosphate) was performed for the direct iodination reaction of phenol by using molecular iodine. The experiments were carried out in mil