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16 protocols using 4 methoxybenzaldehyde

1

Purification and Characterization of Aldehydes

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All solvents used for FCC and reactions were purchased from POCH (Poland). Dichloromethane (DCM), ethyl acetate (AcOEt), hexane, toluene, diethyl ether (Et2O), and acetone were purified by fractional distillation.. All inorganic compounds were purchased from ChemPure (Poland) and used without prior purification. 2-Chloro-N,N-dimethylethylamine hydrochloride (99%), 1,3-acetonedicarboxylic acid (tech. grade), glutaraldehyde (50% wt.% in H2O), methylamine hydrochloride (≥98%), 4-fluorobenzaldehyde (98%), 4-chlorobenzaldehyde (97%), 4-bromobenzaldehyde (99%), 4-nitrobenzaldehyde (98%), 4-(trifluorometyl)benzaldehyde (97%), 4-methoxybenzaldehyde (≥98%), 3-methoxybenzaldehyde (≥97%), 3,4-dimethoxybenzaldehyde (99%), 3,4,5-trimethoxybenzaldehyde (98%), and vanillin (≥97%) were obtained from Merck and used without prepurification.
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2

Synthesis of Substituted Pyrano[2,3-c]pyrazoles

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Phenylhydrazine (97%), ethyl acetoacetate (99%), malononitrile (99%), 4-nitroBenzaldehyde (98%), furfural (99%), 5-nitro-2-furaldehyde (99%), 4-fluoroBenzaldehyde (98%), 4-chloroBenzaldehyde (97%), 4-bromoBenzaldehyde (99%), and p-toluenesulfonic acid monohydrate (TsOH) (ACS grade reagent, assay ≥ 98.5%) were purchased from Sigma-Aldrich. Benzaldehyde, 4-methylBenzaldehyde, 4-methoxyBenzaldehyde, aniline, ethanol, TLC (silica gel 60 F254), sulfuric acid (98%), hydrochloric acid (1 mol L−1), and ortho-phosphoric acid (85%) were purchased from Merck. Ethyl acetate (99.5%) and n-hexane (99.5%) were purchased from Xilong Chemical Co., Ltd (China).
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3

Flavone Synthesis from Benzaldehydes

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The substrates 2-hydroxyacetophenone, 2-methoxybenzaldehyde, 3-methoxybenzaldehyde, 4-methoxybenzaldehyde, 2,5-dimethoxybenzaldehyde and 3,4,5-trimethoxybenzaldehyde were purchased from Sigma-Aldrich (St. Louis, MO, USA). Flavones used in biotransformations were synthesized from those substrates (the reactions are described below). The resulting chalcones were used as substrates for the flavone synthesis and their NMR spectral data are identical to those previously published [34 (link),35 (link),36 (link)].
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4

Spectroscopic Analysis of Organic Compounds

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1H and 13C{1H} NMR spectra were recorded on a Bruker Avance iii-500 spectrometer (Bruker BioSpin AG, Fällanden, Switzerland) at 298 K. The 1H and 13C NMR chemical shifts were referenced with respect to residual solvent peaks (δ TMS = 0). Electrospray ionization (ESI) mass spectra were recorded using a Shimadzu LCMS-2020 instrument (Shimadzu Schweiz GmbH, Reinach, Switzerland) samples were introduced as 200–800 μM solutions in MeCN with the addition of formic acid. PerkinElmer UATR Two (Perkin Elmer, Schwerzenbach, Switzerland) and Cary-5000 (Agilent Technologies Inc., Santa Clara, CA, USA) spectrometers were used to record FT-infrared (IR) and absorption spectra, respectively.
3-Acetylpyridine was purchased from Acros Organics (Chemie Brunschwig AG, Basel, Switzerland), and 4-methoxybenzaldehyde and Co(NCS)2 were bought from Sigma Aldrich (Steinheim, Germany). All chemicals were used as received.
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5

Characterization of Organic Matter Interactions

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All chemicals were of analytical grade. Diethyl
phthalate (DEP, diethyl benzene-1,2-dicarboxylate), dibutyl phthalate
(DBP, dibutyl benzene-1,2-dicarboxylate), Rose Bengal (4,5,6,7-tetrachloro-2′,4′,5′,7′-tetraiodofluorescein,
dye content 95%), 3-methoxyacetophenone (3-MAP), 4-methoxybenzaldehyde
(4-MBA), 2-propanol-H8 (anhydrous), 2-propanol-D8 (anhydrous), hydrogen peroxide, dipotassium hydrogen phosphate (K2HPO4), potassium dihydrogen phosphate (KH2PO4), and 2,4,6-trimethyl-phenol (TMP) were purchased
from Sigma-Aldrich. The solvents n-hexane and dichloromethane
(HPLC grade) were supplied by the company Carl Roth. Pahokee Peat
humic acid (PPHA; 1R103H-2), Pahokee Peat fulvic acid (PPFA; 2S103F),
and Suwannee river natural organic matter (NOM, 2R101N) were purchased
from the International Humic Substances Society (IHSS), and Aldrich
humic acid (AHA) was derived from lignite and obtained from Sigma-Aldrich.
Pure water (18 MΩ cm) was used to prepare the solutions using
a Milli-Q system (Millipore, Billerica, MA).
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6

Cytochrome P450 Inhibitor Characterization

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Mefenamic acid (≥99%), tacrine (≥99%), carvedilol (≥98%), nifedipine (≥98%), ellipticine, α-naphthoflavone (≥97%), ticlopidine (≥99%), 1-naphtol (≥99%), 2-naphtol (≥98%), 4-methoxy-benzaldehyde (≥98%), 2-(p-tolyl)ethylamine (≥97%) were purchased from Sigma-Aldrich (Schnelldorf, Germany); phenacetin was obtained from Brocades-ACF (Maarssen, the Netherlands). 7-Methoxyresorufin was synthesized by the method of Burke and Mayer [28 (link)] and final purity was assessed to be higher than 95%.
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7

Synthesis and Cytotoxicity of Novel Heterocycles

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All chemicals were of the highest purity commercially available. Lithium borohydride (LiBH4), 3,5-dichlorophenyl isocyanate and 2,4-thiazolidinedione were obtained from Alfa Aesar (Ward Hill, MA, USA). Ethyl 2-mercaptoacetate, 4-methoxybenzaldehyde, 3,5-dichlorobenzaldehyde, piperidine, pyridine, maleimide, toluene, triethylamine, ethyl acetate, chloroform, hexane, tetrahydrofuran, triphenylphosphine, DMSO, palladium on charcoal and acetone were all obtained from Sigma-Aldrich Co. (St. Louis, MO, USA). Hydrogen Zero Grade was purchased from Airgas (Essington, PA, USA).
The CellTiter 96® AQueous Non-Radioactive Cell Proliferation Assay kit (“MTS assay”, kit no. G5421) is a product of Promega Corp. (Madison, WI, USA). Human hepatoma HepG2 cells (cat. no. HB-8065) were obtained from American Type Culture Collection (Manassas, VA, USA). Trypsin-EDTA (cat. no. 25-053-CI), penicillin-streptomycin (cat. no. 30-001-CI) and HBSS 1× (cat no. 21-023-CM, with calcium and magnesium, without phenol red) were products of Mediatech, Inc. (Manassas, VA, USA). DMEM 1× (cat. no. 11995-040) was purchased from Life Technologies, Inc. (Carlsbad, CA, USA)
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8

Spectroscopic Characterization of Substituted Benzaldehydes

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2-aminophenol, 2-methoxybenzaldehyde, and 4-methoxybenzaldehyde were purchased from Sigma-Aldrich and used without further purification. The 1H- and 13C-NMR spectra were acquired in CDCl3 at room temperature using a Bruker 400 MHz spectrometer, and their data were recorded in CDCl3, with a residual internal solvent signal of 7.26 and 77.00 ppm, respectively. On a Perkin Elmer FTIR spectrometer equipped with universal ATR, FT-IR spectra reported in wavenumbers (cm−1) were obtained. Mass spectra of the compounds were obtained from a Water synaptic GR electrospray positive spectrometer. The electronic absorption spectra were obtained using a UV-3600 Shimadzu UV–VIS-NIR spectrophotometer. Thermo Scientific FLASH 20 0 0 CHNS/O Analyzers were used for Elemental analyses.
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9

Synthesis of Novel Heterocyclic Compounds

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The starting chemicals were metal salts, ammonium acetate, hydrazine hydrate, acetyl thiophene, 4-methoxy benzaldehyde, ethyl cyanoacetate, ethyl chloroacetate, and potassium carbonate that were purchased from Sigma Aldrich and utilized without additional purification. Fisher Scientific (Loughborough, UK) supplied the solvents, which were ethanol (99%) and N,N-Dimethylformamide (99%).
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10

Electrochemical Characterization of Benzaldehyde Derivatives

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MeCN
(extra high purity,
water content <0.3%, Cryochrom) was used to prepare solutions.
Bu4NClO4 (≥99%, for electrochemical analysis)
was purchased from Sigma-Aldrich and used as a background electrolyte.
Cyclohexanone, cyclopentanone, benzaldehyde, 4-methoxybenzaldehyde,
3,4-dimethoxybenzaldehyde, 4-(methylthio)benzaldehyde, 4-dimethylaminobenzaldehyde,
and 4-diethylaminobenzaldehyde (Sigma-Aldrich) were used as received.
EtOH (chemically pure) was used without additional purification, and
(2E,6E)-2,6-bis(3,4-dimethoxybenzylidene)cyclopentanone
(2) was prepared as described previously.25 (link) DC-Alufolien Aluminiumoxid 60 F254 neutral was purchased from Merck.
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