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Methyl iodide

Methyl iodide (CH3I) is a highly reactive organic compound used in a variety of chemical syntheses and industrial processes.
It serves as a versatile alkylating agent, finding applications in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Methyl iodide is also used as a soil fumigant and as a laboratory reagent.
Researchers must carefully optimize protocols to ensure accurate and reproducible results when working with this potent substance.
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Most cited protocols related to «Methyl iodide»

The overall reaction scheme is shown in Figure 1, and is described in detail below both in a standard protocol for chemists, as well as a less technical protocol intended for biochemists without formal training in organic chemistry. Additional notes on the synthesis are provided as supplemental information. All of the procedures involving organic solvents should be performed in a fume hood, and some of the reagents are especially toxic (methyl iodide and dicyclohexylcarbodiimide). Proper safety equipment should be used to handle these compounds and care should be taken to minimize exposure. The procedures described below are identical for all four isotopic tags; although the molecular weights and densities of the methyl iodide vary, the differences are so small as to be negligible. The use of CH3I results in the production of D0-TMAB-NHS (Figure 2), which was previously referred to as H9-TMAB-NHS22 (link). The use of methyl iodide with 3 deuterium atoms in place of the hydrogen atoms (Cd3I) produces D9-TMAB-NHS, as previously described 22 (link);23 (link). The two new labels are produced from CH2dI and CHd2I and result in the formation of D3-TMAB-NHS and D6-TMAB-NHS, respectively (Figure 2).
Publication 2008
Deuterium Dicyclohexylcarbodiimide Isotopes methyl iodide Solvents Tritium
The following commercial chemicals were used: ortho phosphoric acid (p.a., or TraceSELECT Ultra) from Fluka (Buchs, Switzerland); pyridine from Merck (Merck, Darmstadt, Germany); and hydrogen peroxide 30 % (p.a.), aqueous ammonia 25 % (suprapure), 65 % nitric acid (p.a.), and formic acid (p.a.) from Roth (Carl Roth, Karlsruhe, Germany). Chemicals were used without further purification except for the nitric acid which was distilled in a quartz sub-boiling distillation unit. Water used throughout was from a Milli-Q Academic water purification system (Millipore GmbH, Vienna, Austria) with a specific resistivity of 18.2 MΩ*cm.
Individual standard solutions (1000 ± 3 μg L−1 in 2 % nitric acid) for total element determinations of As, Cd, Mo, Pb, Sb, Se, U, W, and Zn (in the urine samples) and Ge, In, and Lu (internal standards) were obtained from CPI International (Santa Rosa, CA, US). For arsenic speciation, stock solutions containing 1000 mg As L−1 of each of the following species were prepared in water: arsenite (As(III) and arsenate (As(V)) prepared from NaAsO2 and Na2HAsO4.7 H2O, respectively, purchased from Merck (Darmstadt, Germany); dimethylarsinate (DMA) prepared from sodium dimethylarsinate purchased from Fluka (Buchs, Switzerland); methylarsonate (MA) prepared in-house from sodium arsenite and methyl iodide (Meyer reaction); and arsenobetaine (AB), as the bromide salt, prepared in-house following the method of Cannon et al.11 The purity of the synthesized standards (MA and AB) was established by NMR and HPLC/mass spectrometry. Other arsenic standards (trimethylarsine oxide, arsenocholine, tetramethylarsonium ion, oxo and thio-dimethylarsinylethanol and oxo- and thio-dimethylarsinylacetic acid) were prepared as previously reported;12 ,13 (link) these standards were used to check the identity of minor peaks which occasionally appeared in the chromatograms.
The certified reference materials for total element measurements were NIST 1643e, trace elements in water (National Institute of Standards & Technology, Gaithersburg, Maryland, US) certified for As, Cd, Mo, Pb, Sb, Se, & Zn; and NIES No. 18, human urine (National Institute for Environmental Studies, Tsukuba, Japan) certified for As, Se & Zn. In addition, Seronorm control urine (Sero AS, Billingstad, Norway) and an in-house urine sample served as non-certified reference materials. The certified reference material for determining arsenic species was NIES No 18, human urine, certified for AB and DMA. Our in-house reference urine was used as a control for iAs, MA, DMA, and AB.
Publication 2012
Acids Ammonia arsenate Arsenic arsenite arsenobetaine arsenocholine Bromides Cacodylate Distillation formic acid High-Performance Liquid Chromatographies Homo sapiens Mass Spectrometry methylarsonate methyl iodide Nitric acid Peroxide, Hydrogen Phosphoric Acids pyridine Quartz Rosa Sodium sodium arsenite Sodium Chloride tetramethylarsonium Trace Elements trimethylarsine oxide Urine
Chemical synthesis of potential inhibitors. Reagents and solvents were from Aldrich, Alfa Aesar or Acros. Reactions were monitored by TLC, which was performed on precoated aluminum-backed plates (Merck, silica 60 F254). Melting points were determined using a Leica Galen III hot-stage melting point apparatus and microscope. Infrared spectra were recorded from Nujol mulls between sodium chloride discs, on a Bruker Tensor 27 FT-IR spectrometer. NMR spectra were acquired using a Bruker DPX500 NMR spectrometer. Chemical shifts (δ) are given in ppm, and the multiplicities are given as singlet (s), doublet (d), triplet (t), quartet (q), multiplet (m), broad (br). Coupling constants J are given in Hz (± 0.5 Hz). High resolution mass spectra (HRMS) were recorded using a Bruker MicroTOF spectrometer. The purity of all compounds synthesized were ≥95% as determined by analytical reverse-phase HPLC (Ultimate 3000). Daminozide (Alar) and compound 28 are commercially available. The synthesis and characterisation of compounds 2225 , 2526 (link), 2727 , 3628 , 3729 and 3826 (link) has been reported. The synthesis of compounds 31-35, 39-41 and 13C NMR spectra for 22, 23, 24, 26, 31-35 are given in the Supporting Information.
4-(2,2,2-Trimethylhydrazinyl)-4-oxobutanoate 22. The synthesis of compound 22 was as reported25 , thus reaction of daminozide (500mg, 3.1 mmol) with methyl iodide (700mg, 0.31 mL, 5.0 mmol) gave 22 as a white solid (75% yield), mp: 137-138 °C (lit.1 137-138.5 °C); 1H NMR (500 MHz, MeOD): δ 2.40 (t, J = 6.5 Hz, 2H), 2.51 (t, J = 6.5 Hz, 2H), 3.56 (s, 9H); 13C NMR (125 MHz, MeOD): δ 28.5, 29.1, 56.1, 170.4, 173.4; IR (neat) υ/cm−1: 3405, 3312, 1729, 1693; HRMS (m/z): [M]+ calcd. for C7H15N2O3, 175.1077; found, 175.1081.
General procedure for the coupling of hydrazine to succinic anhydride. To a stirred solution of the appropriate hydrazine (1 equiv.) in acetonitrile (5 mL) was added dropwise a solution of succinic anhydride (200 mg, 2.0 mmol, 1 equiv.) in acetonitrile (5 mL). The mixture was stirred at room temperature for 24 h, after which the solvent was evaporated in vacuo and the resulting crude purified using semipreparative reverse-phase HPLC, performed on a phenomenex C18 column (150 mm × 4.6 mm). Separation was achieved using a linear gradient of solvent A (water + 0.1% CF3CO2H) and solvent B (acetonitrile + 0.1% CF3CO2H), eluting at a flow rate of 1 mL/min and monitoring at 220 nm: 0% B to 40% B over 30 min.
4-(2-Methylhydrazinyl)-4-oxobutanoic acid 23. Compound 23 is a colourless oil (63% yield), 1H NMR (500 MHz, DMSO-d6): δ 2.35 (t, J = 7.0 Hz, 2H), 2.68 (t, J = 7.0 Hz, 2H), 2.98 (s, 3H), 4.76 (s, 1H), 7.74 (s, 1H); 13C NMR (125 MHz, DMSO-d6): δ 28.3, 29.1, 170.1, 173.6; IR (neat) υ/cm−1: 33 3219, 3057, 1708, 1632; HRMS (m/z): [M+Na]+ calcd. for C5H10N2NaO3, 169.0584; found, 169.0577.
4-Hydrazinyl-4-oxobutanoic acid 24. Compound 24 is a colourless oil (87% yield), 1H NMR (500 MHz, DMSO-d6): δ 2.34 (t, J = 7.0 Hz, 2H), 2.60 (t, J = 7.0 Hz, 2H), 5.86 (s, 1H), 8.99 (s, 1H); 13C NMR (125 MHz, DMSO-d6): δ 28.2, 29.1, 170.8, 173.9; IR (neat) υ/cm−1: 3303, 3290, 3199, 1712, 1624; HRMS (m/z): [M-H]- calcd. for C4H7N2O3, 131.0462; found, 131.0468.
4-Oxo-4-(1,2,2-trimethylhydrazinyl)butanoic acid 26. Compound 26 is a white solid (56% yield), mp: 97-98 °C, 1H NMR (500 MHz, DMSO-d6): δ 2.37 (t, J = 7.0 Hz, 2H), 2.66 (t, J = 7.0 Hz, 2H), 2.74 (s, 3H), 11.98 (s, 1H); 13C NMR (125 MHz, DMSO-d6): δ 28.2, 29.8, 43.4, 48.7, 173.5, 175.0; IR (neat) υ/cm−1: 2958, 1723, 1615; HRMS (m/z): [M+Na]+ calcd. for C7H14N2NaO3, 197.0897; found, 197.0895.
4-((Dimethylamino)oxy)-4-oxobutanoic acid 29. N,N-Dimethylhydroxylamine (39 mg, 0.63 mmol, 1.1 equiv. ) was added to a solution of 4-(tert-butoxy)-4-oxobutanoic acid (100 mg, 0.57 mmol, 1 equiv.), hydroxybenzotriazole (100 mg, 0.74 mmol, 1.3 equiv.), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide ( 140 mg, 0.74 mmol, 1.3 equiv.) and diisopropylethylamine ( 0.2 mL, 1.14 mmol, 2.0 equiv.) in CH2Cl2 (10 mL). The reaction was stirred at room temperature overnight, washed with water, HCl 1N, brine, dried on MgSO4. The organic phase was evaporated in vacuo and purified by chromatography (MeOH/CH2Cl2 0.5/9.5) to obtain 110 mg of tert-butyl 4((dimethylamino)oxy)-4-oxobutanoate (90% yield). CF3CO2H (0.04 ml, 0.37 mmol, 4 equiv.) was added to a solution of tert-butyl 4((dimethylamino)oxy)-4-oxobutanoate (20 mg, 0.09 mmol, 1 equiv.) in CH2Cl2 (1.5 ml). The reaction was stirred at room temperature for 4h and evaporated in vacuo to give 14 mg of 29 (yield 95%). 1H NMR (500 MHz, CD3OD) δ 2.59 (s, 6H), 2.57 (s, 4H); 13C NMR (500 MHz, CD3OD) δ 176.2, 172.0, 48.5, 29.9; IR (neat) 3341, 2485,1717, 1120, 1026, 975 cm−1; HRMS (m/z):[M+]calcd. for C6H11NO4 161.0688; found 161.0923.
N‘1, N‘1, N‘4, N‘4-Tetramethylsuccinohydrazide 30. A solution of succinic acid (100 mg, 0.85 mmol, 1 equiv.), hydroxybenzotriazole (350 mg, 2.11 mmol, 2.3 equiv.), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (421 mg, 2.11 mmol, 2.3 equiv.), diisopropylethylamine (0.6 mL, 3.4 mmol, 4 equiv.) and 1,1-dimethylhydrazine (0.16 mL, 2.04 mmol, 2.2 equiv.) in CH2Cl2 (20 mL) was stirred at room temperature overnight. CH2Cl2 (10 mL) was added and the reaction mixture was washed with water, a saturated solution of NaHCO3, brine and dried on MgSO4. The organic phase was evaporated in vacuo and purified by chromatography (MeOH/ CH2Cl2 1/9) to give 77 mg of 30 (45% yield). 1H NMR (500 MHz, CD3OD) δ 2.87 (s, 6H), 2.65 (s, 2H); 13C NMR (500 MHz, CD3OD) δ 178.2, 43.8, 27.6; IR (neat) 3356, 2485, 2071, 1695, 1120, 1027, 974 cm−1; HRMS (m/z):[(M-2CH3)]calcd. for C6H14N4O2, 174.1117; found, 174.1022.
Publication 2012
Chemicals, reagents, standards preparation, and fatty acids extraction from red blood cells (RBC) information is provided in supplemental notes in the Supporting Information. Both the FA standards and RBC samples underwent the same extraction, hydrolysis, and derivatization steps before LC–MS analysis. The derivatization procedure was modified from Johnson’s method.9 In brief, 150 μL of standard (0.1–100 μg/mL) and 20 μL of internal standard mixture were mixed and dried under nitrogen. To the dried residue was added 200 μL of oxalyl chloride (2 M in dichloromethane), and the mixture was incubated at 65 °C on a heating block for 5 min and then dried under nitrogen. To the residue was added 150 μL of dimethylaminoethanol, 3-picolylamine, or 3-pyridylcarbinol, respectively (1% in acetonitrile, v/v) to form the dimethylaminoethyl ester (FA-DMAE), 3-picolylamide (FA-PA), and 3-picolinyl ester (FA-PE) derivatives (Figure 1), respectively. The mixture was incubated at room temperature for 5 min, followed by drying under nitrogen to give the derivatized FAs. The FA-DMAE product was further converted to trimethylaminoethyl ester (FA-TMAE) by incubating with 150 μL of methyl iodide (50% in methanol, v/v) at room temperature for 5 min, followed by drying under nitrogen. The dried FAs derivatives were dissolved in 1000 μL of ethanol and further diluted up to 10-fold with ethanol prior to LC–MS analysis.
Publication 2011
acetonitrile Deanol derivatives Erythrocytes Esters Ethanol Fatty Acids Hydrolysis Methanol Methylene Chloride methyl iodide Nicotinyl Alcohol Nitrogen oxalyl chloride Standard Preparations
Matching CID spectra of an unknown plasma metabolite with identical retention time and mass-to-charge ratio (m/z) as authentic L-carnitine (m/z = 162) were obtained as described in Supplementary Methods. Concentrations of carnitine, TMA and TMAO isotopologues in mouse and human plasma samples were determined by stable isotope dilution LC/MS/MS in positive MRM mode using deuterated internal standards on an AB Sciex API 5000 triple quadrupole mass spectrometer (Applied Biosystems) as described in Supplementary Methods. In studies quantifying endogenous carnitine and ingested d3-carnitine, d9-carnitine was used as internal standard. D9-carnitine was prepared by dissolving 3-hydroxy-4-aminobutyric acid (Chem-Impex Intl.) in methanol and exhaustive reaction with d3-methyl iodide (Cambridge Isotope Labs) in the presence of potassium hydrogen carbonate. Further details regarding synthesis, purification and characterization of d9-carnitine can be found in Supplementary Methods.
Publication 2013
Aminobutyric Acid Anabolism Carnitine Homo sapiens Isotopes Methanol methyl iodide Mice, House Plasma potassium bicarbonate Retention (Psychology) Tandem Mass Spectrometry Technique, Dilution trimethyloxamine

Most recents protocols related to «Methyl iodide»

Dynamic adsorption experiments were executed utilizing a laboratory-scale fixed-bed reactor operating at a temperature of 150 °C. Specifically, 30 mg of adsorbent was loaded into a quartz column (4.6 mm I.D. × 200 mm) with silane-treated glass wool employed to occupy the interstitial void space. The column was subsequently activated at 150 °C for 6 h under a dry helium flow (10 mL/min). To evaluate performance under a partial pressure of 0.2 bar, a nitrogen carrier flow at a rate of 3 mL/min was directed through a CH3I vapor generator, subsequently passing through the adsorbent-packed column at a linear velocity of 18 cm/min, corresponding to a residence time of approximately 5 s. The concentration of CH3I in the effluent was continuously monitored using an online mass spectrometry (MS) system. The flow rate of CH3I under these conditions was determined to be approximately 4.408 mg/min by trial and error.
To assess performance under a partial pressure of 0.01 bar, a nitrogen carrier flow at a rate of 0.3 mL/min was directed through the CH3I vapor generator, subsequently combined with another dry nitrogen flow at a rate of 5.7 mL/min before passing through the adsorbent column. Under these conditions, the linear velocity was 36 cm/min, with a residence time of ~2.5 s. The flow rate of CH3I under this configuration was approximately 0.426 mg/min. Experiments conducted under humid conditions (RH = 50%) at 0.01 bar involved mixing a nitrogen flow passing through the CH3I vapor generator at a rate of 0.3 mL/min with a nitrogen flow passing through the water vapor generator at a rate of 3 mL/min, along with a dry nitrogen flow at a rate of 2.7 mL/min. The combined gas stream was then directed through the adsorbent column. Monitoring of CH3I in the effluent was performed using an online MS system.
The adsorption capacities at breakthrough (Qbreakthrough) were determined using the following equation: Qbreakthrough=v×t1%m1 Where v represents the flow rate of CH3I (mg/min); t1% (corresponding to C/C0 = 1%, min) denotes the breakthrough point when the concentration of CH3I in the effluent stream (C) reaches 1% of the initial concentration (C0); m signifies the weight of the adsorbent (mg).
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Publication 2024
[11C]CH4 was produced from a methane target via the 14N(p, α)11C nuclear reaction in a cyclotron. The target was filled with nitrogen gas mixed with 10% hydrogen and bombarded for 2–5 min at 35 µA. [11C]CH3I was synthesized using the TracerMaker module with in-target-produced [11C]CH4 as previously reported [30 (link)]. After the production of [11C]CH3I (~3–5.5 GBq), it was transferred through a separate line directly connected to the iMiDEV™ radiosynthesizer. The flow rate of [11C]CH3I was set at 8 mL/min [24 (link)].
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Publication 2024
A mixture of 1 (3.95 g, 10 mmol), methyl iodide (0.7 mL, 10 mmol), ethyl chloroacetate (1 mL, 10 mmol), 2-chloroacetamide (0.93 g, 10 mmol), chloroacetonitrile (0.8 mL, 10 mmol)or N-aryl-2-chloroacetamide 2a–e (10 mmol), and sodium acetate trihydrate (1.50 g, 11 mmol) in ethanol (100 mL) was refluxed for one hour. The reaction mixture was then allowed to stand at room temperature overnight. After that the precipitate was collected and recrystallized from ethanol as colorless crystals of title compounds 3, 4, 5, 6, and 7a–e respectively.
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Publication 2024
P4VP was quaternized according
to an adapted procedure from Sadman and co-workers.39 (link) To obtain QP4VP, 4.00 g (38 mmol) of P4VP was dissolved
in 40 mL of DMSO before 10.8 g (76 mmol, 2 equiv) of MeI was added
dropwise, and the reaction was stirred for 4 h at room temperature.
Excess MeI was first removed by bubbling the solution with nitrogen
before precipitation was performed in acetone, and the polymer was
redissolved in water. QP4VP was retrieved after freeze-drying and
with high yield, i.e., quaternization ≥99%, 9.06 g (yield 96%)
(Figure S6).
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Publication 2024
F-doped tin oxide (FTO) glass substrate (8 Ω per square) was purchased from Suzhou Shangyang Solar Energy Technology Co. Ltd. Formamidine hydroiodate (FAI), methyl ammonium iodide (MAI), cesium iodide (CsI), methyl ammonium chloride (MACl), and 2,2′,7,7′-tetrakis(N,N-di-p-methoxyphenylamine)-9,9′-spirobifluorene (spiro-MeOTAD) were purchased from Liaoning Optimum New Energy Technology Co. Ltd. Lead iodide (PbI2), lead bromide (PbBr2), and isopropanol (IPA) were purchased from TCI. Phenethylmethoxy iodide (PEAI), bistrifluoromethanesulfonimide lithium salt (Li-TFSI), 4-tert-butylpyridine (t-BP), and tris(2-(1H-pyrazol-1-yl)-4-tert-butylpyridine)-cobalt(III)-tris(bis-(trifluoromethylsulfonyl)imide) (FK-209) were purchased from Xi’an Yuri Solar Co. Ltd. Titanium tetrachloride (TiCl4), dimethylformamide (DMF), dimethyl sulfoxide (DMSO), acetonitrile (ACN), and chlorobenzene (CB) were purchased from Sigma-Aldrich.
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Publication 2024

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DMSO is a versatile organic solvent commonly used in laboratory settings. It has a high boiling point, low viscosity, and the ability to dissolve a wide range of polar and non-polar compounds. DMSO's core function is as a solvent, allowing for the effective dissolution and handling of various chemical substances during research and experimentation.
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Propidium iodide is a fluorescent dye commonly used in molecular biology and flow cytometry applications. It binds to DNA and is used to stain cell nuclei, allowing for the identification and quantification of cells in various stages of the cell cycle.
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Methyl iodide is a colorless, volatile, and highly reactive chemical compound. It is primarily used as a laboratory reagent and as a precursor in organic synthesis. Methyl iodide has a distinct odor and is considered a hazardous material due to its toxicity and flammability. Detailed information about its specific applications or intended uses is not provided in order to maintain an unbiased and factual approach.
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Sodium hydroxide is a chemical compound with the formula NaOH. It is a white, odorless, crystalline solid that is highly soluble in water and is a strong base. It is commonly used in various laboratory applications as a reagent.
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Chlorobenzene is a colorless, volatile liquid used as an intermediate in the production of various chemicals. It serves as a precursor for the synthesis of other organic compounds.
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Propidium iodide is a fluorescent dye used in flow cytometry to stain and quantify DNA content in cells. It binds to DNA by intercalating between the bases. Propidium iodide is commonly used to distinguish viable from non-viable cells.
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Potassium iodide is a chemical compound that is commonly used in laboratory settings. It is a white, crystalline solid that is soluble in water and has a wide range of applications in various industries, including pharmaceuticals, photography, and water treatment. The core function of potassium iodide is to serve as a source of iodide ions, which are essential for various chemical reactions and processes.
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Methanol is a clear, colorless, and flammable liquid that is widely used in various industrial and laboratory applications. It serves as a solvent, fuel, and chemical intermediate. Methanol has a simple chemical formula of CH3OH and a boiling point of 64.7°C. It is a versatile compound that is widely used in the production of other chemicals, as well as in the fuel industry.

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DMSO, Propidium iodide, Methyl iodide, Sodium hydroxide, FBS, Chlorobenzene, Potassium iodide, Acetonitrile, Methanol