4 iodoanisole

Manufactured by Merck Group

4-iodoanisole is a laboratory chemical compound used as a building block in organic synthesis. It is a crystalline solid with the molecular formula C₇H₇IO. 4-iodoanisole serves as a precursor for the preparation of other organic compounds, but a detailed description of its core function without extrapolation on intended use cannot be provided in a concise and unbiased manner.

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4 protocols using 4 iodoanisole

Polymer-Mediated Synthesis of Substituted Aromatics

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Poly(methyl
vinyl ether-alt-maleic anhydride) (PMVEMA) (average M_w ∼ 216 kDa, average M_n ∼
80 kDa), polyethyleneimine (PEI)–branched (average M_w ∼ 800 Da, average M_n ∼ 600 Da), 4-iodotoluene (99%), 4-iodoanisole
(99%), 4-bromoanisole (99%), and bromobenzene (99%) were used as received
from Sigma-Aldrich. Ethanol (200 proof, 100%, bioreagent grade), potassium
carbonate (99%), sodium borohydride (98%; granules ca. 3 mm), potassium
tetrachloropalladate(II) (99.99% metals basis), 4-bromotoluene (99%),
phenyl boronic acid (98%+), dimethyl sulfoxide (DMSO) (99.7%+), 4-bromophenol
(98 + %), 4-bromobenzotrifluoride (98%+), 4-bromobenzonitrile (97%+),
4-methylbenzeneboronic acid (98%), 4-(trifluoromethoxy)phenylboronic
acid (98%), 4-nitrophenol (99%), 4-chloronitrobenzene (98%+), 2,6-dimethylnitrobenzene
(99%+), 4-nitrobenzonitrile (97%), 4-(2-fluoro-4-nitrophenyl)morpholine
(98%), 3-fluoro-4-morpholinoaniline (98%+), 2,6-dimethylaniline (99%),
4-aminobenzonitrile (98%+), 4-aminophenol (98%), 4-chloroaniline (98%),
4-methylbiphenyl (98%+), 4-methoxybiphenyl (98%+), 4-phenylphenol
(97%), 4-cyanobiphenyl (95%), 4,4′-dimethylbiphenyl (99%),
4,4′-biphenol (97%), and biphenyl-4,4′-dicarbonitrile
(98%) were used as received from Fisher Scientific. Water (18.2 MΩ)
was filtered, purified, and deionized using a PURELAB Flex 3.

Davis B.A., Genzer J., Efimenko K, & Abolhasani M. (2023). Continuous Ligand-Free Catalysis Using a Hybrid Polymer Network Support. JACS Au, 3(8), 2226-2236.

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Synthesis of Organic Compounds via Palladium Catalysis

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All
the chemical precursors,
namely, 4-iodoanisole, 4-nitroaniline, Cu powder, K₂CO₃, 18-Crown-6, Pd/C (10%), KOH, 1,10-phenanthroline, CuI, and
phenothiazine, as well as the solvents, were purchased form Sigma-Aldrich
and used without further purification. Compound 3 and 4 were synthesized according to previously reported methods.^{56 (link),57 (link)} All the reactions were carried out under an inert environment in
Schleck tube. ¹H and ¹³C NMR spectra were recorded
with 500 MHz JEOL spectrometer in CDCl₃ against tetramethylsilane
as reference. Mass spectroscopy was carried out using a high-resolution
ESI-TOF LCT Premier XE mass spectrometer (Waters Corp.). The analyte
was dissolved in chloroform/methanol (c ≈
0.01 mg/mL). More details on the synthesis are in the Supporting Information.

Salunke J., Guo X., Liu M., Lin Z., Candeias N.R., Priimagi A., Chang J, & Vivo P. (2020). N-Substituted Phenothiazines as Environmentally Friendly Hole-Transporting Materials for Low-Cost and Highly Stable Halide Perovskite Solar Cells. ACS Omega, 5(36), 23334-23342.

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Comprehensive Synthesis of Quinoline and Isoquinoline Derivatives

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Chemicals and solvents were used without further purification as they were of the highest commercial grade, unless otherwise stated. 1,2,3,4-Tetrahydroquinoline, 1,2,3,4-Tetrahydroisoquinoline, Tris(2,2-bipyridyl)dichlororuthenium(II)hexahydrate, (Ru(bpy)3Cl2.6H2O), Tris(dibenzylideneacetone)dipalladium(0) (Pd₂(dba)₃), 2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene (BINAP), Bromobenzene, 4-Iodoanisole, 4-IodoToluene, 4-Fluroiodobenzene, Methyliodide, Sodium tert-butoxide, Pyridine chloride, Ammonium hydroxide, Magnesium sulfate, Formic acid, triethylamine, Pottasium carbonate, (1Z,5Z)-cycloocta-1,5-diene and all the solvents (Acetonitrile, trideuteroAcetonitrile, Toluene, Dichloromethane, Cyclohexane, Tetrahydrofuran, Ethyl acetate, Ethanol, Chloroform) were purchased from Sigma-Aldrich. Decahydroquinoline and Decahydroisoquinoline were purchased from Ark Pharm, Inc. All the N-derivatives of Tetrahydroquinoline and Tetrahydroisoquinoline were synthesized in-house under N₂ environment (see supporting information for synthetic details).

Jayaraj S, & Badu-Tawiah A.K. (2019). N-Substituted Auxiliaries for Aerobic Dehydrogenation of Tetrahydro-isoquinoline: A Theory-Guided Photo-Catalytic Design. Scientific Reports, 9, 11280.

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Synthesis of Biaryl Compounds

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2,2′-Dinitrobiphenyl
and 2,2′-diiodo-1,1′-biphenyl
were purchased from TCI Chemicals. Iodobenzene, 4-iodothioanisole,
and boron tribromide were purchased from Acros Organics. 4-Iodotoluene
was purchased from Alfa Aesar. 4-Iodo anisole and trifluoromethane
sulfonate were purchased from Sigma-Aldrich. Dry dimethyl sulfoxide-d₆ (99.96% D) was purchased from Cambridge Isotope
Laboratories. 4–5a,^{32 (link)}4–5b,^{34 (link)} and 4–5g(34 (link)) were prepared as
previously described. NMR tubes (Wilmad-LabGlass) with a septum were
used for the kinetic studies. All materials, unless otherwise stated,
were used without additional purification. Schlenk glassware was dried
in an oven at 120 °C prior to use. Xylenes were passed through
alumina and deoxygenated by argon bubbling for 10 min, followed by
three freeze–thaw–pump cycles. Flash column chromatography
was performed with silica gel 60 (230–400 mesh) from Merck.
TLC was performed on silica gel 60 F254 plates from Merck.

Gjineci N., Aharonovich S., Dekel D.R, & Diesendruck C.E. (2020). Increasing the Alkaline Stability of N,N-Diaryl Carbazolium Salts Using Substituent Electronic Effects. ACS Applied Materials & Interfaces, 12(44), 49617-49625.

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