13C-15N-labeled Trp was purchased from Sigma-Aldrich (574597). The photo-CIDNP sensitizers fluorescein (FL, 46955), eosin Y (230251) and erythrosin B (200964) were purchased from Sigma-Aldrich. The heavy-atom-containing additives potassium iodide (60399), 3-iodo-1-propanol (451061), 3-bromo-1-propanol (167188), 3-chloro-1-propanol (292087) and ethyl iodide (17780) were purchased from Sigma-Aldrich.
Ethyl iodide
Manufactured by Merck Group
Sourced in United States
Ethyl iodide is a clear, colorless liquid compound used in various laboratory applications. It has the chemical formula C2H5I. Ethyl iodide is commonly used as a reagent and precursor in organic synthesis reactions.
Automatically generated - may contain errors
Lab products found in correlation
Hexyl iodide, by Merck Group (2 mentions)
Benzyl bromide, by Merck Group (2 mentions)
Silver oxide, by Merck Group (2 mentions)
4 5 diphenylimizadole, by Thermo Fisher Scientific (2 mentions)
Lithium bis trimethyl silyl amide, by Thermo Fisher Scientific (2 mentions)
Deuterated solvent, by Cambridge Isotopes (2 mentions)
Haucl4, by Strem Chemicals (2 mentions)
Erythrosin b, by Merck Group (1 mentions)
13c 15n labeled trp, by Merck Group (1 mentions)
3 chloro 1 propanol, by Merck Group (1 mentions)
Tetraethylene glycol, by Tokyo Chemical Industry (1 mentions)
1 vinylimidazole, by Merck Group (1 mentions)
Hydroquinone, by Merck Group (1 mentions)
Dioxane, by Merck Group (1 mentions)
P toluenesulfonic acid, by Merck Group (1 mentions)
Abietic acid, by Tokyo Chemical Industry (1 mentions)
Toluene, by Merck Group (1 mentions)
Xylene, by Merck Group (1 mentions)
Dichloromethane, by Vetec (1 mentions)
Benzoyl peroxide, by Merck Group (1 mentions)
9 protocols using ethyl iodide
1
Photochemical Labeling with Isotopically-Enriched Tryptophan
2
Abietic Acid-Based Polymer Synthesis
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Abietic acid (AA ˃ 80%) was supplied by Tokyo Chemical Industry Co. Tetraethylene glycol (TEG ˃ 99%), 1-vinylimidazole (VIM ≥ 99), p-toluene sulfonic acid (PTSA ≥ 99), hydroquinone (≥99), ethyl iodide (EI 99%), hexyl iodide (HI ≥ 98%), toluene (≥99.7), dioxane (≥99), and xylene (≥98.5) were supplied by Sigma-Aldrich Co (Louis, MO, USA). Heavy crude oil was supplied by Aramco Co, Riyadh, Saudi Arabia. Its full specification is reported in our earlier work [18 (link)]. Brine (35,000 ppm) was prepared in our laboratory using distilled water and sodium chloride.
3
Ketoconazole-Loaded Polymeric Films
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The reagents used for the films and incorporation with ketoconazole were sodium hydroxide (NaOH), acetic anhydride (CH3COOCOCH3), acetic acid (CH3COOH), hydrochloric acid (HCl), sodium bicarbonate (NaHCO3), sulfuric acid (H2SO4), commercial ketoconazole, and dichloromethane (CH2Cl2), purchased from Vetec. Poly (vinyl alcohol) (average mol wt 30,000–70,000), ethyl iodide (CH2CH3I), chloride sodium (NaCl), benzoyl peroxide, methyl methacrylate (MMA), and distilled water were purchased from Sigma Aldrich. The copolymers PMMA-g-PEG 4000 and derivatives were synthesized by our research group and published in scientific journals [19 (link),20 (link),21 (link),22 (link),23 (link)].
4
Synthesis of Organic Compounds via Anhydrous Solvents
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N,N-dimethylacetamide anhydrous 99.8% (DMAc Anh), N,N-dimethylacetamide 99.5% (DMAc), N,N-dimethylformamide 99.5% (DMF), dimethylsulfoxide 99.0% (DMSO), dimethylsulfoxide-d6 99.8% (DMSO-d6), N-methyl-2-pyrrolidinone 99.5% (NMP), 3,5-dinitrobenzoyl chloride 98.0%, 4,4′-oxydianiline 98.0% (ODA), Pd/C (10% w/w), pyridin-4-ylmethanoamine 98.0%, isophthaloyl chloride 98.0%, methyl iodide 98.0%, ethyl iodide 99%, buthyl iodide 99.0%, and hexyl iodide 99% were obtained from Sigma-Aldrich. Ethanol absolute 99.5%, n-hexane 99.5%, diethyl ether 99.5%, tetrahydrofuran 99.5% (THF), lithium bis(trifluoromethanesulfonyl)imide 98.0% (LiTFSI), and hydrazine (80% solution in water) were obtained from Merck. All solvents were purified by distillation under reduced pressure, except for DMAc Anh and DMSO-d6, which were used directly, as were the liquid reagents. The chlorides used were recrystallized twice from n-hexane, and ODA was sublimated at 300 °C under vacuum (4 × 10−4 mbar).
5
Synthesis of Gold Compound Au-1
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The preparation of gold compound Au-1 was was performed following a reported synthetic method. 53 (link) H[AuCl 4 ] was purchased from Strem Chemicals (Newburyport, MA). Benzyl bromide, ethyl iodide, and silver oxide were purchased from Sigma Aldrich (St. Louis, MO). 4,5-diphenylimizadole and lithium bis(trimethyl silyl)amide were purchased from Alfa Aesar (Haverhill, MA). Reaction solvents were purchased anhydrous from Fisher Scientific (BDH, ACS Grade) and Sigma-Aldrich. Solvents were dried in a SPS machine, and kept over molecular sieves (3 Å, beads, 4-8 mesh); otherwise over sodium, if necessary. Deuterated solvents were purchased from Cambridge Isotope Laboratories, Inc., and were kept over molecular sieves (3 Å, beads, 4-8mesh). Celite (Celite 545, Diatomaceous Earth) was purchased from VWR International and used as received.
6
Synthesis of Gold Compounds
7
Synthesis and Characterization of Compound QS4B and Derivative 4m
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Example 4
A. Preparation of Compound QS4B
2,3,3-Trimethylbenzindole-5,7-disulfonate (compound 4, 3.1 g, 7 mmol) was dissolved in 25 mL of dry DMF resulting in a clear orange solution. Ethyl iodide, 3 mL (5.85 g, 37.5 mmol, Aldrich) was added and the solution was heated to 130° C. in a sealed tube for 16 hours. The reaction mixture, which turned dark purple was cooled and poured into 150 mL of ethyl ether. The mixture was centrifuged and the solvent decanted off. The solid product was further washed in the tube with three 25 mL portions of 2-propanol followed by 25 mL of ether and dried in vacuum. 2.6 g of dark purple solid (85%) was obtained and confirmed by MALDI-TOF-MS. m/e 397.1 [M]+ calculated for C17H19NO6S2+, found 397.6.
Compound 4m was synthesized using compounds QS4B and 9 through 4h-4l by following the same procedure that was described for the synthesis of compound 1f. The overall yield was around 15%. Abs. max: 775 nm (water), 780 nm (MeOH); Em. Max: 795 nm (water), 8053 nm (MeOH).
8
Synthesis of Fluorescent Benzindole Compound QS4B
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Example 4
A. Preparation of Compound QS4B
2,3,3-Trimethylbenzindole-5,7-disulfonate (compound 4, 3.1 g, 7 mmol) was dissolved in 25 mL of dry DMF resulting in a clear orange solution. Ethyl iodide, 3 mL (5.85 g, 37.5 mmol, Aldrich) was added and the solution was heated to 130° C. in a sealed tube for 16 hours. The reaction mixture, which turned dark purple was cooled and poured into 150 mL of ethyl ether. The mixture was centrifuged and the solvent decanted off. The solid product was further washed in the tube with three 25 mL portions of 2-propanol followed by 25 mL of ether and dried in vacuum. 2.6 g of dark purple solid (85%) was obtained and confirmed by MALDI-TOF-MS. m/e 397.1 [M]+ calculated for C17H19NO6S2+. found 397.6.
Compound 4m was synthesized using compounds QS4B and 9 through 4h-4l by following the same procedure that was described for the synthesis of compound 1f. The overall yield was around 15%. Abs. max: 775 nm (water), 780 nm (MeOH); Em. Max: 795 nm (water), 8053 nm (MeOH).
9
Synthesis of Photoactive Compound QS4B and Derivative 4m
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Example 4
A. Preparation of Compound QS4B
2,3,3-Trimethylbenzindole-5,7-disulfonate (compound 4, 3.1 g, 7 mmol) was dissolved in 25 mL of dry DMF resulting in a clear orange solution. Ethyl iodide, 3 mL (5.85 g, 37.5 mmol, Aldrich) was added and the solution was heated to 130° C. in a sealed tube for 16 hours. The reaction mixture, which turned dark purple was cooled and poured into 150 mL of ethyl ether. The mixture was centrifuged and the solvent decanted off. The solid product was further washed in the tube with three 25 mL portions of 2-propanol followed by 25 mL of ether and dried in vacuum. 2.6 g of dark purple solid (85%) was obtained and confirmed by MALDI-TOF-MS. m/e 397.1 [M]+ calculated for C17H19NO6S2+, found 397.6.
Compound 4m was synthesized using compounds QS4B and 9 through 4h-4l by following the same procedure that was described for the synthesis of compound 1f. The overall yield was around 15%. Abs. max: 775 nm (water), 780 nm (MeOH); Em. Max: 795 nm (water), 8053 nm (MeOH).
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