103697-17-2

Basic information

• Product Name: Phosphonic acid, (4-iodophenyl)-, diethyl ester
• CAS NO: 103697-17-2
• Molecular Formula: C10H14IO3P
• Molecular Weight: 340.098
• Mol File: 103697-17-2.mol

Chemical Properties

• CAS DataBase Reference: Phosphonic acid, (4-iodophenyl)-, diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphonic acid, (4-iodophenyl)-, diethyl ester(103697-17-2)
• EPA Substance Registry System: Phosphonic acid, (4-iodophenyl)-, diethyl ester(103697-17-2)

Safety Data

• Hazardous Substances Data: 103697-17-2(Hazardous Substances Data)

Upstream product

• 42822-57-1 diethyl (4-aminophenyl)phosphonate 
• 540-37-4 p-aminoiodobenzene 
• 78-40-0 triethyl phosphate 
• 624-38-4 para-diiodobenzene 
• 122-52-1 triethyl phosphite 

Downstream Products

• 21267-14-1 tetraethyl 1,4-phenylbis(phosphonate) 
• 1443991-68-1 3,4-bis(4-methoxyphenyl)-1-ethoxy-6-iodobenz[c-1,2]oxaphosphinine 1-oxide 
• 1443991-44-3 4-iodophenyl phosphonic acid monoethyl ester 

Relevant articles and documents

Synthesis and characterization of two bifunctional pyrazole-phosphonic acid ligands

The bifunctional compounds 3,5-dimethyl-4-(4-phosphonophenyl)-1H-pyrazole 1 and 4-(4-phosphonophenyl)-1H-pyrazole 2 were synthesized via Suzuki-Miyaura coupling, starting from a Boc-protected pyrazolylboronic acid ester and the iodoarylphosphonate. The ta

A Pd complex of a NNN pincer ligand supported on γ-Fe2O3@SiO2 as the first magnetically recoverable heterogeneous catalyst for C-P bond forming reactions

A Pd complex of a NNN pincer ligand supported on γ-Fe2O3@SiO2 as a new phosphine-free Pd catalyst was synthesized and characterized by different methods such as SEM, TEM, FT-IR, TGA, ICP, XRD, XPS and elemental analysis. The synthesized catalyst was successfully used as the first magnetically recoverable heterogeneous catalyst for the synthesis of arylphosphonates via C-P bond formation by a cross-coupling reaction of different electrophilic benzenes with phosphite esters under solvent-free conditions.

P-arylation of aryl halides by an environmentally compatible method

In this paper, palladium-DABCO complex supported on magnetic nanoparticles was successfully used as a new magnetically recoverable heterogeneous catalyst for the synthesis of arylphosphonates via P-arylation of different types of aryl halides (aryl iodides/bromides/chlorides and benzene boronic acid/sulfonate), with phosphite esters (triethyl/triphenyl/tri-iso-propyl/diethyl/diphenyl/di-iso-propyl phosphite) in neat water without using any additive. The heterogeneous catalyst was easily isolated from the reaction mixture by an external magnet and reused five times without significant degradation in its activity.

Variable-gap conjugated oligomers grafted to CdSe nanocrystals

Three linear asymmetrically functionalized conjugated molecules composed of five or six aromatic rings were synthesized, bearing a terminal phosphonic acid group, with the objective of enabling their grafting onto inorganic CdSe nanocrystals. These chromo

A new magnetically recoverable heterogeneous palladium catalyst for phosphonation reactions in aqueous micellar solution

A new heterogeneous palladium complex of 2-aminothiophenol supported on nanomagnetic γ-Fe2O3 was synthesized and characterized using various methods. The catalyst was used as a magnetically recoverable heterogeneous palladium catalyst for phosphonation reactions via C-P bond formation. Using this method, a wide range of electrophilic benzenes was coupled successfully with phosphite esters (triethyl/tri-isopropyl/triphenylphosphite and diethyl/di-isopropyl/diphenylphosphite) in aqueous micellar solution to generate the corresponding arylphosphonates in good to high yields. The catalyst was separated using an external magnet and reused for six consecutive cycles without any significant loss of its reactivity.

Fe-MIL-101 modified by isatin-Schiff-base-Co: a heterogeneous catalyst for C-C, C-O, C-N, and C-P cross coupling reactions

A metal-organic framework functionalized with a cobalt-complex is preparedviapost-synthetic modification of Fe-MIL-101-NH2. Initially, Fe-MIL-101-NH2reacted with isatin to produce Fe-MIL-101-isatin-Schiff-base, which can anchor the cobalt by the addition of cobalt acetate. The resulting MOF-Co catalyst is characterized by employing multiple techniques. This new modified MOF acts as a heterogeneous and recyclable catalyst for efficient Ullmann, Buchwald-Hartwig, Hirao, Hiyama and Mizoroki-Heck cross-coupling reactions of several aryl halides/phenylboronic acid/phenyltosylate with phenols, anilines/heterocyclic amines, triethyl phosphite, triethoxyphenylsilane and alkenes and generates the expected coupling products in good to high yields.

A hydrophilic heterogeneous cobalt catalyst for fluoride-free Hiyama, Suzuki, Heck and Hirao cross-coupling reactions in water

A hydrophilic heterogeneous cobalt catalyst of chitosan, denoted as mTEG-CS-Co-Schiff-base, has been successfully prepared. This newly synthesized catalyst was characterized by different methods such as XRD, FE-SEM, TEM, TGA, FT-IR, 13C{1H} CP/MAS NMR, XPS and ICP analyses. The catalyst displayed excellent activity for the palladium and fluoride-free Hiyama, Suzuki, Heck and Hirao reactions of various aryl iodides, bromides and chlorides (i.e., the most challenging aryl halides which are cheaper and more widely available than aryl iodides and bromides) in water. The presence of triethylene glycol tags with hydrophilic character on the Co-complex supported on chitosan provides dispersion of the catalyst particles in water, which leads to higher catalytic performance and also facile catalyst recovery by successive extraction. It was reused for at least six successive runs without any discernible decrease in its catalytic activity or any remarkable changes in catalyst structure. The use of water as a green solvent, without requiring any additive or organic solvent, as well as use of a low cost and abundant cobalt catalyst instead of expensive Pd catalysts along with the catalyst recovery and scalability, make this method favorable from environmental and economic points of view for the C-C and C(sp2)-P coupling reactions. Notably, this is the first report on the application of a cobalt catalyst in Hiyama reactions.

Synthesis of arylphosphonates catalyzed by Pd-imino-Py-γ-Fe2O3 as a new magnetically recyclable heterogeneous catalyst in pure water without requiring any additive

A palladium-Schiff base complex immobilized covalently on γ-Fe2O3 (Pd-imino-Py-γ-Fe2O3) was synthesized and characterized by different methods such as XRD (X-ray diffraction), SEM (scanning electron microscopy), TEM (transmission electron microscopy), FT-IR (Fourier transform infrared spectroscopy), TGA (thermogravimetric analysis), ICP (inductively coupled plasma), XPS (X-ray photoelectron spectroscopy), VSM (vibrating sample magnetometer) and elemental analysis. It was used as a new magnetically recyclable heterogeneous Pd catalyst for the synthesis of arylphosphinates via Csp2-P coupling reactions. A wide range of electrophilic benzenes were coupled successfully with triethylphosphite to generate the corresponding products in good to high yields in pure water without using any additive. The true heterogeneous Pd-imino-Py-γ-Fe2O3 could be reused simply with the aid of a magnetic bar for eight consecutive cycles without any drastic loss of its reactivity.

A copper-catalyzed variant of the Michaelis-Arbuzov reaction

As part of our studies on copper-catalyzed arylation of nucleophiles, we report on Michaelis-Arbuzov reactions with a novel catalytic system, featuring a copper(I) salt as precatalyst without any additional ligand. This procedure is an interesting alternative to the use of expensive and toxic transition metals (nickel, palladium) traditionally used as catalysts in Michaelis-Arbuzov reactions. Our approach allows the synthesis from triethylphosphite, diethyl aryl phosphonite, and diaryl ethylphosphinite of various aryl phosphonates, aryl phosphinates, and aryl phosphine oxides, respectively. These families of compounds are essential owing to their respective importance in bioorganic and medical chemistry, their applicability as flame retardants, and their usability in coordination chemistry and catalysis. Copper load of this! The first copper-catalyzed Michaelis-Arbuzov reactions are described. The methodology is ligand-free and allows the direct synthesis of various aryl phosphonates, aryl phosphinates, and aryl phosphine oxides from aryl iodides.

Aromatic nucleophilic polysubstitution by sequential SRN1 reactions

Substitution of aromatics (benzene, naphthalene and pyridine) by two or three distinct nucleophiles derived from phosphonates and/or thiolates can be performed by sequential photosimulated SRN1 reactions whose radical chain mechanism is compatible with the successively introduced substituents. aromatic polysubstitution / SRN1 mechanism / disubstituted aromatic / trisubstituted aromatic / distinct substituent