699-08-1

Basic information

• Product Name: 4-Iodophenetole
• Synonyms: 4-ETHOXY-4-IODOBENZENE;4-ETHOXYIODOBENZENE;4-IODOPHENYL ETHYL ETHER;4-IODOPHENETOLE;P-IODOPHENETOLE;4-Ethoxy-4-iodobenzene~Ethyl 4-iodophenyl ether;4-Ethoxyiodobenzene, 4-Iodophenyl ethyl ether;1-Iodo-4-Ethyloxybenzene
• CAS NO: 699-08-1
• Molecular Formula: C₈H₉IO
• Molecular Weight: 248.06
• EINECS: -0
• Product Categories: Phenetole;Anisoles, Alkyloxy Compounds & Phenylacetates;Iodine Compounds
• Mol File: 699-08-1.mol
• Article Data: 28

Chemical Properties

• Melting Point: 25-28 °C(lit.)
• Boiling Point: 133-134°C 19mm
• Flash Point: >230 °F
• Appearance: /
• Density: 1.6502 (estimate)
• Vapor Pressure: 0.0333mmHg at 25°C
• Refractive Index: 1.5970
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• Sensitive: Light Sensitive
• BRN: 2042067
• CAS DataBase Reference: 4-Iodophenetole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Iodophenetole(699-08-1)
• EPA Substance Registry System: 4-Iodophenetole(699-08-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 699-08-1(Hazardous Substances Data)

Usage

Description

4-Iodophenetole is an organic compound characterized by the presence of an iodine atom attached to a phenetole molecule. It is a colorless to pale yellow liquid with a distinctive aromatic odor. Its chemical structure features a phenol group connected to an ethoxy group, with the iodine atom providing unique chemical properties that make it a versatile intermediate in various chemical reactions and synthesis processes.

Uses

Used in Pharmaceutical Industry:
4-Iodophenetole is used as a key intermediate in the synthesis of bis(4-ethoxyphenyl)amine, which is an important compound in the development of pharmaceuticals. Its unique structure allows for the formation of specific chemical bonds that are crucial for the creation of new drug molecules with potential therapeutic applications.
Used in Liquid Crystal Industry:
In the liquid crystal industry, 4-Iodophenetole serves as an intermediate for the production of liquid crystal materials. Its molecular structure contributes to the formation of liquid crystal compounds with specific properties, such as temperature range, dielectric anisotropy, and viscosity, which are essential for various display and optical applications.
Used in Chemical Synthesis:
4-Iodophenetole is utilized as a reactant in the Suzuki reaction, a widely used cross-coupling reaction in organic chemistry. This reaction allows for the formation of carbon-carbon bonds between an aryl or vinyl halide and an organoboron compound, leading to the synthesis of a wide range of organic compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C8H9IO/c1-2-10-8-5-3-7(9)4-6-8/h3-6H,2H2,1H3

Upstream product

• 55476-27-2 hypobromous acid ethyl ester 
• 540-38-5 p-Iodophenol 
• 115764-64-2 bis(p-ethoxyphenyl)(trifluoroacetoxy)thallium 
• 7553-56-2 iodine 
• 64-17-5 ethanol 
• 589-87-7 1,4-bromoiodobenzene 
• 75-03-6 ethyl iodide 
• 87261-58-3 (4-Ethoxy-phenyl)-piperidin-1-yl-diazene 
• 38793-99-6 4-ethoxy-benzenediazonium; chloride 
• 110-86-1 pyridine 
• 7697-37-2 nitric acid 
• 103-73-1 Phenetole 
• 74-96-4 ethyl bromide 
• 156-43-4 4-Ethoxyaniline 

Downstream Products

• 102248-81-7 1-ethoxy-4-(2,2,2-trifluoroethoxy)benzene 
• 613-40-1 4-ethoxy-1,1'-biphenyl 
• 347-36-4 ethyl-(4'-fluoro-biphenyl-4-yl)-ether 
• 449736-97-4 4'-methyl-4-ethoxy-1,1'-biphenyl 

Relevant articles and documents

Synthesis, Crystal Structure, and Photophysical Properties of Nickel Complex from Triphenylamine Schiff Base Ligand

A novel Schiff base ligand L and its mononuclear nickel complex Ni(L)2(SCN)2 were designed, synthesized and characterized by elemental analysis, IR spectra, MS, 1H-NMR spectroscopy, and single-crystal X-ray diffraction analysis. The crystals of L and Ni(L)2(SCN)2 belong to orthorhombic crystal system with the space group of P212121 for L and Pbcn for Ni(L)2(SCN)2, respectively. The center atom Ni(II) is coordinated with six nitrogen atoms in a distorted octahedron coordination environment. The four N atoms of them are from the two independent ligands and the other two nitrogen atoms from two SCN-. Their photophysical properties of the ligand and its Ni(II) complex were investigated and interpreted on the basis of theoretical calculations (TD-DFT).

Carbon Dioxide as a Directing Group for C-H Functionalization Reactions Involving Lewis Basic Amines, Alcohols, Thiols, and Phosphines for the Synthesis of Compounds

Methods of synthesizing compounds using CO2 as a directing group for C—H functionalization, and compounds made thereby, are described.

Photocatalytic Oxidative Iodination of Electron-Rich Arenes

A visible-light-mediated oxidative iodination of electron-rich arenes has been developed. 2.5 mol% of unsubstituted anthraquinone as photocatalyst were used in combination with elementary iodine, trifluoroacetic acid and oxygen as the terminal oxidant. The iodination proceeds upon irradiation in non- or weakly-electron donating solvents (DCM, DCE and benzene) wherein a spectral window in strongly coloured iodine solutions can be observed at around 400 nm. The method provides good to excellent yields (up to 98%) and shows excellent regioselectivity and good functional group tolerance (triple bonds, ketone, ester, amide). Moreover, the photo-iodination was also upscaled to a 5 mmol scale (1.1 g). Mechanistic investigations by intermediate trapping and competition experiments indicate a photocatalytic arene oxidation and the subsequent reaction with iodine as a likely mechanistic pathway. (Figure presented.).