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

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

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

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

Downstream Products

• 855394-48-8 4'-ethoxy-2-nitrobiphenyl 
• 7168-54-9 4,4'-diethoxybiphenyl 
• 445386-74-3 4-dichloroiodanyl-phenetole 
• 846023-26-5 2-iodo-4-nitro-phenetole 
• 116223-44-0 trans-4-ethoxy-4'-stilbazole 
• 102248-81-7 1-ethoxy-4-(2,2,2-trifluoroethoxy)benzene 
• 16029-98-4 trimethylsilyl iodide 
• 107-46-0 Hexamethyldisiloxane 
• 5459-40-5 4-ethoxystyrene 
• 106-99-0 buta-1,3-diene 
• 196599-71-0 3-(4-Ethoxy-phenyl)-prop-2-yn-1-ol 
• 271242-08-1 ethyl 3,5-di[4-(4-ethoxyphenylethynyl)phenyl]-4-hydroxybenzoate 
• 23197-69-5 diethyl (4-ethoxyphenyl)malonate 
• 4345-85-1 1-(4-ethoxy-phenyl)-3-phenyl urea 

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).

Divergent synthesis and biological evaluation of 2-(trifluoromethyl)pyridines as virulence-attenuating inverse agonists targeting PqsR

A short and divergent route towards new derivatives of 2-(trifluoromethyl)pyridines as potent inverse agonists of the bacterial target PqsR against Pseudomonas aeruginosa (PA) infections is described. This Gram-negative pathogen causes severe nosocomial infections and common antibiotic treatment options are rendered ineffective due to resistance issues. Based on an earlier identified optimized hit, we conducted derivatization and rigidification attempts employing two central building blocks. The western part of the molecule is built up via a 2-(trifluoromethyl)pyridine head group equipped with a terminal alkyne. The eastern section is then introduced through aryliode motifs exploiting Sonogashira as well as Suzuki-type chemistry. Subsequent modification provided quick access to an array of compounds, allowed for deep SAR insights, and enabled to optimize the hit scaffold into a lead structure of nanomolar potency combined with favorable in vitro ADME/T features.

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.

Organic hole transport material and preparation method and application thereof

The invention provides an organic hole transport material and a preparation method and application thereof. The structural general formula of the organic hole transport material is shown in the specification, and in the formula, R is ethyl, propyl, isopropyl or butyl. The preparation method is simple and easy to implement, the structure is definite, and the prepared organic hole transport materialhas high photoelectric conversion efficiency and can be applied to perovskite solar cells.

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.).

Carbon Dioxide-Mediated C(sp3)-H Arylation of Amine Substrates

Elaborating amines via C-H functionalization has been an important area of research over the past decade but has generally relied on an added directing group or sterically hindered amine approach. Since free-amine-directed C(sp3)-H activation is still primarily limited to cyclization reactions and to improve the sustainability and reaction scope of amine-based C-H activation, we present a strategy using CO2 in the form of dry ice that facilitates intermolecular C-H arylation. This methodology has been used to enable an operationally simple procedure whereby 1° and 2° aliphatic amines can be arylated selectively at their γ-C-H positions. In addition to potentially serving as a directing group, CO2 has also been demonstrated to curtail the oxidation of sensitive amine substrates.

Effect of alkyl chain length on the properties of triphenylamine-based hole transport materials and their performance in perovskite solar cells

A new series of diacetylide-triphenylamine (DATPA) derivatives with five different alkyl chains in the para position, MeO, EtO, nPrO, iPrO and BuO, were synthesised, fully characterised and their function as hole-transport materials in perovskite solar cells (PSC) studied. Their thermal, optical and electrochemical properties were investigated along with their molecular packing and charge transport properties to analyse the influence of different alkyl chains in the solar cell parameters. The shorter alkyl chain facilitates more compact packing structures which enhanced the hole mobilities and reduced recombination. This work suggests that the molecule with the methoxy substituent (MeO) exhibits the best semiconductive properties with a power conversion efficiency of up to 5.63%, an open circuit voltage (Voc) of 0.83 V, a photocurrent density (Jsc) of 10.84 mA cm-2 and a fill factor of 62.3% in perovskite solar cells. Upon replacing the methoxy group with longer alkyl chain substituents without changing the energy levels, there is a decrease in the charge mobility as well as PCE (e.g. 3.29% for BuO-DATPA). The alkyl chain length of semiconductive molecules plays an important role in achieving high performance perovskite solar cells.

A method of preparing alkoxyl monoiodo-benzene

The invention relates to a method for preparing alkoxy iodobenzene. The method comprises the following steps: adding alkoxy benzene, I2, the catalyst nitrosonium tetrafluoroborate and an organic solvent into a reaction vessel, sealing the reaction vessel, performing a magnetic stirring reaction at the temperature of 20-60 DEG C under an airy condition, cooling to the room temperature after reaction, and performing purification on the mixture after reaction through column chromatography, so as to obtain the alkoxy iodobenzene. According to the method for preparing the alkoxy iodobenzene, any other auxiliary reagent is not added expect the catalyst and the solvent, used auxiliary material is less, the utilization rate of the iodine material under the optimum condition is high, the product purity is good, the reaction can be effectively performed at the room temperature, the production cost is remarkably reduced, and as acid is not added in the reaction system, the cost of production equipment can be lowered.

Synthesis, crystal structures, and two-photon absorption of a series of cyanoacetic acid triphenylamine derivatives

A specific series of chromophores (CN1, CN2, CN3, and CN4) have been synthesized, in which contained a triphenylamine moiety as the electron donor (D), a cyanoacetic acid moiety as the electron acceptor (A), vinylene or phenylethyne as the π-bridge, and ethyoxyl groups as auxiliary electron donor (D′) to construct the D-π-A or D′-D-π-A molecular configuration. Photophysical properties of them were systematically investigated. These results show that the chromophores display a solvatochromism (blue shift) and large Stokes shifts for their absorption bands with increasing polarity of the solvent. Furthermore, the chromophore CN4 shows the strongest intensity of two-photon excited fluorescence and largest two-photon absorption cross section (2783 GM) in the near infrared region. Finally, the connections between the structures and properties are systematically investigated relying on the information from linear and nonlinear optical properties, crytsal structures and quantum chemical calculation.

A series of triphenylamine-based two-photon absorbing materials with AIE property for biological imaging

A specific series of D-π-A (1A-3A) and D-π-A (1B-3B) structural chromophores with various electron donors and π-conjugated bridges were designed, synthesized, and fully characterized. Their crystal structures were determined by single crystal X-ray diffraction analysis. The one/two-photon absorption properties of the chromophores have been successfully tuned by using different electron donors and π-bridges. Interestingly, it was found that chromophore 3B shows quite weak fluorescence in pure DMSO, while a significant AIE (aggregation-induced emission) effect is observed in water-DMSO (v/v 90%) mixtures with a sharp increase in fluorescence intensity of about 11 times. Furthermore, chromophore 3B shows strong two-photon excited fluorescence (TPEF) and has a large 2PA action cross-section (394 GM). The results of live-cell imaging experiments show that 3B can be effectively used as a bio-imaging probe in two-photon fluorescence microscopy towards HepG2 cells in vitro. The TPEF images of 3B not only exhibit cellular cytosol uptake but also exhibit actin regulatory protein uptake which are different from OPEF images.