High purity grade lithium hydroxide monohydrate, esterase, acetone, ethyl chloroacetate, ethyl acetate, dimethylformamide, sodium cholate, anhydrous potassium carbonate, hydrochloric acid, formic acid, acetic acid, amylase, thionyl chloride, ammonia solution, hexane, sodium bicarbonate, phosphate-buffered saline (PBS) buffer, sodium chloride, sodium sulfate, potassium iodide, dichloromethane, dialysis tubing, porcine pancreatin, silica gel, dimethyl sulfoxide, acetonitrile, porcine pepsin, 2-chloroacetamide, and 1,2-dibromoethane were purchased from Millipore Sigma (Burlington, MA, USA). The high purity grade apigenin, quercetin and luteolin were obtained from Indofine chemical company (Hillsborough, NJ, USA).
Thionyl chloride
Manufactured by Merck Group
Sourced in United States, Germany
Thionyl chloride is a colorless, fuming liquid chemical compound. It is commonly used as a reagent in organic synthesis reactions. The primary function of thionyl chloride is to convert alcohols, carboxylic acids, and other compounds into more reactive derivatives such as acyl chlorides and sulfinyl chlorides.
Automatically generated - may contain errors
Lab products found in correlation
Triethylamine, by Merck Group (10 mentions)
Hydrochloric acid (hcl), by Merck Group (8 mentions)
Dimethylformamide, by Merck Group (7 mentions)
Chloroform, by Merck Group (7 mentions)
4 dimethylaminopyridine, by Merck Group (7 mentions)
Dichloromethane, by Merck Group (5 mentions)
Ethyl acetate, by Merck Group (5 mentions)
Tetrahydrofuran, by Merck Group (5 mentions)
Methanol, by Merck Group (5 mentions)
Acetone, by Merck Group (4 mentions)
Ethanol, by Merck Group (4 mentions)
Sodium hydroxide (naoh), by Merck Group (4 mentions)
Pyridine, by Merck Group (4 mentions)
Hexane, by Merck Group (3 mentions)
Dimethyl sulfoxide (dmso), by Merck Group (3 mentions)
Sodium bicarbonate, by Merck Group (3 mentions)
Acetic acid, by Merck Group (3 mentions)
Acetonitrile, by Merck Group (3 mentions)
N n dicyclohexylcarbodiimide, by Merck Group (3 mentions)
Hydrogen peroxide, by Merck Group (3 mentions)
59 protocols using thionyl chloride
1
Extraction and Derivatization of Flavonoids
2
Flavonoids Synthesis and Characterization
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High purity flavonoids, quercetin, apigenin, luteolin, fisetin, kaempferol (Indofine Chemical Company, Hillsborough, NJ, USA), and ethyl chloroacetate, dimethylformamide, anhydrous potassium carbonate, lithium hydroxide, hydrochloric acid, ethyl acetate, thionyl chloride, acetone, ammonia solution, hexane, silica gel, sodium bicarbonate, sodium chloride, sodium sulfate, sodium cholate, porcine pepsin, dialysis tubing, amylase, esterase, porcine pancreatin, dimethyl sulfoxide, and phosphate-buffered saline were purchased from Millipore Sigma (Burlington, MA, USA).
3
Carboxylation of Multi-Walled Carbon Nanotubes
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Functionalized multi walled carbon nanotubes (MWCNTs-COOH) and BRC were prepared from the US Research Nanomaterials, USA and Iran Hormone Company, respectively. For acylation of carboxylated MWCNTs, 1 g of carboxylated MWCNTs with 20 ml of thionyl chloride (Merk, Germany) was mixed at 60 °C for 14 h in the reflux system. The final product was washed and separated with tetrahydrofuran (Merk, Germany) and acetone, and then, it was dried in an oven at 70 °C.
4
Carboxylation and Acylation of MWCNTs
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Functionalized CNTs were prepared by the use of acylation reactions.22 (link),23 (link) For carboxylation of MWCNTs, 1.5 g of MWCNTs was combined with 20 mL of sulfuric acid and nitric acid at a ratio of 3:1 for 30 min in the ultrasonic device and was replaced in reflux system for 24 h at 45 ° C. Subsequently, 100 mL of and were added to the previous phase at a ratio of 4:1, and again, placed to the ultrasonic device for 30 min.24 (link) The reaction mixture was centrifuged, the precipitate was separated, and the supernatant was centrifuged again by adding deionized water. After several steps of washing with the solvents at the pH up to 6, the sample was washed with methanol. The solution was filtered through a 0.2 μm polytetrafluoroethylene filter, and the black solid was dried under vacuum at room temperature. For acylation of carboxylated MWCNTs, 1 g of MWCNTs with 20 mL of thionyl chloride (Merk, Germany) was mixed at 60 °C for 14 h in the reflux system. The final product was washed and separated with tetrahydrofuran (Merk, Germany) and acetone; then, it was dried in an oven at 70 °C.
5
Quantification of Phenolic Compounds
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p‐Coumaric acid, ellagic acid, piceid, coumarin, emodin and cinnamic acid standards, sodium chloride, sodium bromide, glucose, glycerol, streptozotocin (STZ), sodium azide, thionyl chloride, dichloromethane, and trifluoroacetic acid anhydride were purchased from Sigma‐Aldrich. HPLC grade methanol, ethanol, acetic acid, acetonitrile, chloroform, acetone, as well as hydrochloric acid were ordered from Thermo Fisher Scientific Co. Whey protein isolate (WPI) was purchased from Davisco Foods International, Inc. (Eden Prairie, MN). Nε‐(Carboxymethyl)‐L‐lysine (CML) standard was supplied by Toronto Research Chemicals Inc.
6
Synthesis of Boc-Phe-Phe Dipeptide
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l -Phenylalanine (Phe), 1-hydroxybenzotriazole (HOBt), N,N-dicyclohexylcarbodiimide (DCC), thionyl chloride and di-tert-butylpyrocarbonate (Boc2O) were purchased from Sigma-Aldrich or Alfa Aesar and used as received. Polymethylmethacrylate (PMMA, Mw 120 000 purchased from Alpha Cimit), poly(l -lactic acid) (PLLA, Mw 217–225 000 purchased from Polysciences) and poly-ε-caprolactone (PCL, Mw 80 000, purchased from Aldrich). All solvents were purchased from Sigma-Aldrich and used as received.
Boc-Phe-Phe (Fig. 1 ) was synthesized by a conventional solution-phase coupling reaction between Boc-Phe-OH and H-Phe-OMe mediated by DCC/HOBt. The Boc group was used for amino acid N-terminal protection and the C-terminal was protected as a methyl ester, by standard protecting group chemistry. Removal of the methyl ester group was performed using aqueous NaOH (2 mol L−1) and the saponification progress was monitored by thin layer chromatography.50 (link) All the intermediates were characterized by NMR spectroscopy on a Bruker Avance III 400 at an operating frequency of 400 MHz for 1H.
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Boc-Phe-Phe (
7
Porphyrin-PEG Conjugate Synthesis
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Poly(ethyleneglycol)methyl ether, thionyl chloride, silver nitrate, sodium borohydride, 3-chloro-1-propanethiol, PBS solution, 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin, p-nitroso-N,N’-dimethylaniline, hydrochloric acid (≥37%), tetrahydrofuran, chloroform, ethanol, triethylamine, water (LC-MS grade), acetone, acetone-d6 and trans-2-[3-(4-tert-Butylphenyl)-2-methyl-2-propenylidene] malononitrile were purchased from Sigma-Aldrich (Merck Group, Milan, Italy).
The 5,10,15,20-[p-(ω-methoxy-polyethyleneoxy)phenyl]-porphyrin (P(PEG750)4) was obtained as reported elsewhere [39 (link)].
The 5,10,15,20-[p-(ω-methoxy-polyethyleneoxy)phenyl]-porphyrin (P(PEG750)4) was obtained as reported elsewhere [39 (link)].
8
Graphite-Based Nanomaterial Synthesis
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Graphite flakes, sulfuric acid (H2SO4 98%), sodium nitrate (NaNO3), potassium permanganate (KMnO4), hydrochloric acid (HCl 37%), hydrogen peroxide (H2O2 30%), thionyl chloride (SOCl2), fumaric acid, pyridine, chitosan (MW 50–190 kDa with deacetylation degree > 90%), chlorosulfonic acid (CSA), sodium borohydride (NaBH4), ammonium hydroxide (NH4OH) and silver nitrate (AgNO3) were procured from Sigma-Aldrich, Johannesburg, South Africa. These reagents were used as obtained. All aqueous solutions were prepared using ultrapure water. Acronyms and parameters used in this article are listed in Table 1 .
9
Synthesis of HDI-functionalized Graphene Oxide
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Pyrrole-3-carboxylic acid (C5H5NO2 > 97%, Mw = 111.1 g/mol, d25°C = 0.862 g/cm3), ammonium persulfate ((NH4)2S2O8, 98%, Mw = 228.20 g/mol, d25°C = 1.98 g/cm3), dimethylformamide (DMF, 99% C3H7NO, Mw = 73.09 g/mol, d25°C = 0.944 g/cm3), N,N-dicyclohexylcarbodiimide (DCC, 99%, C13H22N2, Mw = 206.33 g/mol; d25°C = 1.32 g/cm3), 4-dimethylaminopyrydine (DMAP, 99%, C7H10N2, Mw = 122.17 g/mol, d25°C = 0.96 g/cm3), and thionyl chloride (SOCl2, 97%, Mw = 118.96 g/mol, d25°C = 1.64 g/cm3) were obtained from Sigma-Aldrich (Madrid, Spain). Hexamethylene diisocyanate-modified graphene oxide (HDI-GO), with a functionalization degree of 18.1%, was synthesized according to our previous works [22 (link),23 (link)]. The organic solvents (HPLC grade) were obtained from Scharlau S.L. (Barcelona, Spain). High purity deionized water was obtained from a Millipore water purification system (≥18 MΩ). The monomer and DMF were distilled under vacuum prior to use; the rest of the reagents were used as received.
10
Chlorine-Based Chemical Exposure Assessment of Hair
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Pure Cl2, sulfuryl chloride, thionyl
chloride, oxalyl chloride, and NaOCl solution (10–15%) were
purchased from Sigma-Aldrich. Certified diluted Cl2 in
N2 was purchased from Messer Schweiz AG. HCl gas was synthesized
from CaCl2 and HCl 32% (Merck KGaA, Darmstadt, Germany),
according to a protocol by Arnáiz.34 (link) Household bleach was purchased as Cillit Bang Kraftreiniger Schimmel
& Hygiene Duo. Diluted NaOCl was obtained by dilution with high-performance
LC (HPLC)-grade H2O from J.T. Baker. Phosgene and chloropicrin
were provided by Spiez Laboratory. The amino acid reference standards
were purchased as follows: 3-chlorotyrosine, cysteic acid, methionine
sulfoxide, and methionine sulfone were purchased from Sigma-Aldrich,
and 3,5-dichlorotyrosine was purchased from abcr GmbH.
The exposure
experiments were conducted under the adequate safety standards. The
detailed exposure conditions are given in theSupporting Information (Table S1). All exposure experiments
were carried out at room temperature with an exposure time of 10 min
(except for one low Cl2 exposure carried out for 8 h at
room temperature). Human hair samples (in biological triplicate) were
exposed to the different chemicals under the conditions given inTable S1 . The concentration given for bleach
samples (NaOCl and household bleach) is the amount of “available
chlorine”, which stands for hypochlorous acid and/or hypochlorite.35
chloride, oxalyl chloride, and NaOCl solution (10–15%) were
purchased from Sigma-Aldrich. Certified diluted Cl2 in
N2 was purchased from Messer Schweiz AG. HCl gas was synthesized
from CaCl2 and HCl 32% (Merck KGaA, Darmstadt, Germany),
according to a protocol by Arnáiz.34 (link) Household bleach was purchased as Cillit Bang Kraftreiniger Schimmel
& Hygiene Duo. Diluted NaOCl was obtained by dilution with high-performance
LC (HPLC)-grade H2O from J.T. Baker. Phosgene and chloropicrin
were provided by Spiez Laboratory. The amino acid reference standards
were purchased as follows: 3-chlorotyrosine, cysteic acid, methionine
sulfoxide, and methionine sulfone were purchased from Sigma-Aldrich,
and 3,5-dichlorotyrosine was purchased from abcr GmbH.
The exposure
experiments were conducted under the adequate safety standards. The
detailed exposure conditions are given in the
were carried out at room temperature with an exposure time of 10 min
(except for one low Cl2 exposure carried out for 8 h at
room temperature). Human hair samples (in biological triplicate) were
exposed to the different chemicals under the conditions given in
samples (NaOCl and household bleach) is the amount of “available
chlorine”, which stands for hypochlorous acid and/or hypochlorite.35
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