2974-94-9

Basic information

• Product Name: 4-IODODIPHENYL ETHER
• Synonyms: 4-IODODIPHENYL ETHER;1-IODO-4-PHENOXY-BENZENE;4-Iodophenyl phenylether;4-Phenoxyphenyl iodide;4-Phenoxyiodobenzene;Phenyl iodophenyl ether;p-Phenoxyiodobenzene
• CAS NO: 2974-94-9
• Molecular Formula: C₁₂H₉IO
• Molecular Weight: 296.10373
• Product Categories: API intermediates
• Mol File: 2974-94-9.mol
• Article Data: 21

Chemical Properties

• Melting Point: 43～45℃
• Boiling Point: 317.6 °C at 760 mmHg
• Flash Point: 145.9 °C
• Appearance: /
• Density: 1.626 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.65
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 4-IODODIPHENYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-IODODIPHENYL ETHER(2974-94-9)
• EPA Substance Registry System: 4-IODODIPHENYL ETHER(2974-94-9)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• Hazardous Substances Data: 2974-94-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Iododiphenyl ether is used as a reactant for the synthesis of pharmaceuticals, leveraging its ability to participate in cross-coupling reactions and serve as a precursor for the development of new medicinal compounds.
Used in Dye Industry:
In the dye industry, 4-Iododiphenyl ether is utilized as a reactant for the production of various dyes, capitalizing on its chemical structure to create a range of colorants for different applications.
Used in Polymer Industry:
4-Iododiphenyl ether is employed as a building block in the synthesis of polymers, where its unique structure contributes to the development of materials with specific properties for various uses.
Used in Organic Synthesis:
4-Iododiphenyl ether is used as a reactant in organic synthesis for the creation of a wide array of organic compounds, taking advantage of its reactivity and the presence of iodine atoms for cross-coupling reactions.
Used in Material Science:
As a precursor for the synthesis of functional materials, 4-Iododiphenyl ether is instrumental in material science, where its properties can be harnessed to develop new materials with specialized functions.

InChI:InChI=1/C18H13IO/c19-15-12-10-14(11-13-15)17-8-4-5-9-18(17)20-16-6-2-1-3-7-16/h1-13H

Upstream product

• 696-62-8 para-iodoanisole 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 540-38-5 p-Iodophenol 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 639-58-7 triphenyltin chloride 
• 98-95-3 nitrobenzene 
• 624-38-4 para-diiodobenzene 
• 108-95-2 phenol 
• 106-37-6 1.4-dibromobenzene 
• 66003-76-7 Diphenyliodonium triflate 
• 591-50-4 iodobenzene 
• 620-88-2 4-nitrophenyl phenyl ether 
• 1483-73-4 diphenyliodonium bromide 
• 101-84-8 diphenylether 

Downstream Products

• 28896-49-3 bis(4-iodophenyl) ether 
• 21969-05-1 1-(4-nitrophenoxy)-4-iodobenzene 
• 854257-01-5 1-chloro-4-(4-iodophenoxy)benzene 
• 220025-13-8 1-bromo-4-(4-iodophenoxy)benzene 
• 69199-91-3 5-iodo-2-phenoxy-benzoic acid 
• 77384-56-6 1,2-bis(4-phenoxyphenyl)ethyne 
• 153984-74-8 1,7-bis(4-phenoxyphenyl)-1,7-dicarba-closo-dodecaborane⁽¹²⁾ 
• 153984-73-7 1-(4-phenoxyphenyl)-1,7-dicarba-closo-dodecaborane⁽¹²⁾ 
• 1069045-77-7 ethyl 3-[1-(4-phenoxyphenyl)-3-(2-phenylethyl)-1H-indol-5-yl]propanoate 
• 1199939-46-2 1-methyl-5-(4-phenoxyphenyl)-1H-1,2,4-triazole 
• 2367-02-4 1-phenoxy-4-(trifluoromethyl)benzene 

Relevant articles and documents

Competing Pathways in O-Arylations with Diaryliodonium Salts: Mechanistic Insights

A mechanistic study of arylations of aliphatic alcohols and hydroxide with diaryliodonium salts, to give alkyl aryl ethers and diaryl ethers, has been performed using experimental techniques and DFT calculations. Aryne intermediates have been trapped, and additives to avoid by-product formation originating from arynes have been found. An alcohol oxidation pathway was observed in parallel to arylation; this is suggested to proceed by an intramolecular mechanism. Product formation pathways via ligand coupling and arynes have been compared, and 4-coordinated transition states were found to be favored in reactions with alcohols. Furthermore, a novel, direct nucleophilic substitution pathway has been identified in reactions with electron-deficient diaryliodonium salts.

One-Pot, Metal-Free Conversion of Anilines to Aryl Bromides and Iodides

A metal-free synthesis of aryl bromides and iodides from anilines via halogen abstraction from bromotrichloromethane and diiodomethane is described. This one-pot reaction affords aryl halides from the corresponding anilines in moderate to excellent yields without isolation of diazonium salts. The transformation has short reaction times, a simple workup, and insensitivity to moisture and air and avoids excess halogenation. DFT calculations support a SRN1 mechanism. This method represents a convenient alternative to the classic Sandmeyer reaction.

Synthesis of copper nanoparticles supported on a microporous covalent triazine polymer: An efficient and reusable catalyst for O-arylation reaction

Copper nanoparticles were supported on a microporous covalent triazine polymer prepared by the Friedel-Crafts reaction (Cu@MCTP-1). The resulting material was characterized by powder X-ray diffraction, thermogravimetric analysis, N2 adsorption-desorption isotherms at 77 K, transmission electron microscopy, X-ray photoelectron spectroscopy, and inductively coupled plasma optical emission spectroscopy, and Cu particles with an average size of 3.0 nm and a BET total surface area of ca. 1002 m2 g-1 were obtained. Cu@MCTP-1 was evaluated as a heterogeneous catalyst for the Ullmann coupling of O-arylation over a series of aryl halides and phenols without employing expensive ligands or inert atmosphere, which produced an excellent yield of the corresponding diaryl ethers. The catalyst could be recovered by simple centrifugation and was reusable at least five times with only a slight decrease in catalytic activity.

An in situ acidic carbon dioxide/glycol system for aerobic oxidative iodination of electron-rich aromatics catalyzed by Fe(NO3)3·9H2O

An environmentally benign CO2/glycol reversible acidic system was developed for the iron(iii)-catalyzed aerobic oxidative iodination of electron-rich aromatics without the need for any conventional acid additive or organic solvent. Notably, moderate to high isolated yields (up to 97%) of the aryl iodides were attained with comparable regioselectivity when ferric nitrate nonahydrate was used as the catalyst with molecular iodine under 1 MPa of CO2.

Greener iodination of arenes using sulphated ceria-zirconia catalysts in polyethylene glycol

An environmentally benign method for the selective monoiodination of diverse aromatic compounds has been developed using reusable sulphated ceria-zirconia under mild conditions. The protocol provides moderate to good yields and selectively introduces iodine at the para/ortho position in monosubstituted arenes. SO42-/Ce0.07Zr 0.93O2 was found to be the best choice for the synthesis of aryl iodides in high yield, presumably due to the maximum number of acid sites (4.23 mmol g-1) among the various compositions of the catalyst system.

Triphenyltin chloride as a new source of phenyl group for C-heteroatom and C-C bond formation

Ph3SnCl is introduced as a very suitable source of phenyl group for coupling with phenols, amines, and thiols in the presence of Cu(OAc)2 in Et3N at room temperature to give aryl ethers, amines, and arylthio ethers in high yields. In addition, the application of Ph3SnCl in the Stille coupling of aryl halides in the presence of Pd(0) catalyst in PEG 400 at 110C is discussed.

Microwave-assisted synthesis of nonsymmetrical aryl ethers using nitro-arenes

An efficient, microwave-assisted ligand-free, catalyst-free synthetic method for nonsymmetrical diaryl ethers has been developed by using nitroarenes. A variety of phenols and nitroarenes was scanned by using this method to produce nonsymmetrical aryl ethers. The newly developed method is an ecofriendly and cost-effective approach to synthesize nonsymmetrical aryl ethers.

Metal-free arylation of oxygen nucleophiles with diaryliodonium salts

Phenols and carboxylic acids are efficiently arylated with diaryliodonium salts. The reaction conditions are mild, metal free, and avoid the use of halogenated solvents, additives, and excess reagents. The products are obtained in good-to-excellent yields after short reaction times. Steric hindrance is very well tolerated, both in the nucleophile and diaryliodonium salt. The scope includes ortho- and halo-substituted products, which are difficult to obtain by metal-catalyzed protocols. Many functional groups are tolerated, including carbonyl groups, heteroatoms, and alkenes. Unsymmetric salts can be chemoselectively utilized to obtain products with hitherto unreported levels of steric congestion. The arylation has been extended to sulfonic acids, which can be converted to sulfonate esters by two different approaches. With recent advances in efficient synthetic procedures for diaryliodonium salts the reagents are now inexpensive and readily available. The iodoarene byproduct formed from the iodonium reagent can be recovered quantitatively and used to regenerate the diaryliodonium salt, which improves the atom economy. Copyright

Ligand-free highly effective iron/copper co-catalyzed formation of dimeric aryl ethers or sulfides

Highly selective coupling of diiodoarenes with phenols or phenthiols can be performed by using a low-cost, benign character and readily available Fe/Cu catalytic system in the absence of ligands. It is noteworthy that the desired dimeric aryl ethers or sulfides could be obtained in high yields by coupling between diiodoarenes and phenols, or diphenols with aryl iodides. The Royal Society of Chemistry 2011.

Room temperature, metal-free synthesis of diaryl ethers with use of diaryliodonium salts

A fast, high-yielding synthesis of diaryl ethers with use of mild and metal-free conditions has been developed. The scope includes bulky ortho-substituted diaryl ethers, which are difficult to obtain by metal-catalyzed protocols. Halo-substituents, racemization-prone amino acid derivatives, and heteroaromatics are also tolerated. The methodology is expected to be of high utility in the synthesis of complex molecules and in the pharmaceutical industry.