Iodoethane

Manufactured by Merck Group

Sourced in Germany

Iodoethane is a chemical compound with the molecular formula C2H5I. It is a colorless, dense liquid with a pungent odor. Iodoethane serves as a precursor for the synthesis of other organic compounds and is used in various laboratory applications.

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Lab products found in correlation

12 protocols using iodoethane

Synthesis of 1-Ethylimidazolium Iodide

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Example 7

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1-ethylimidazole (4.81 g, 50 mmol, Sigma-Aldrich, 99%) in 50 mL ethyl acetate was cooled to 0° C. in an ice bath. Once cool, iodoethane (8.69 g, 55.7 mmol, Sigma-Aldrich, 99%) was added dropwise via an addition funnel. The solution was allowed to warm slowly to room temperature then stirred overnight. The precipitate was filtered off and washed with diethyl ether. The filtrate was collected and an additional 8.96 g (57.4 mmol) iodoethane was added and stirring continued at room temperature for 6 days. The solution was filtered again and the residue was washed with diethyl ether. The combined solids were dried overnight under high vacuum yielding 9.76 g white solids (38.7 mmol, 77% yield) that were used without further purification.

¹H NMR (300 MHz, DMSO-d₆): 9.25, 7.83, 4.20, 1.42. ¹³C NMR (75 MHz, DMSO-d₆): 135.4, 122.1, 44.2, 15.1. Analysis calculated for C₇H₁₃IN₂: C, 33.35; H, 5.20; N, 11.11 (C/N=3.00). Found: C, 33.26; H, 5.29; N, 10.95 (C/N=3.04).

US09957166B2. Molecular sieves and related methods and structure directing agents (2018-05-01). CALIFORNIA INSTITUTE OF TECHNOLOGY [US]. Inventors: Raymond Archer [US], Mark E. Davis [US].

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STXBP1 Mutant Constructs and Lipid Extraction

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HPLC/analytical grade reagents were used throughout. 1,1-carbonydiimidiazole, triethylamine, iodomethane, iodomethane-d3, iodoethane, iodoethane-d5, iodopropane, formic acid, citric acid, methanol, disodium hydrogen phosphate, chloroform, ammonium formate, acetonitrile, 1-butanol, and analytical standards for saturated and unsaturated fatty acids were purchased from Sigma-Aldrich. All lipid extractions were performed in 2 mL polypropylene LoBind safe-lock tubes (Eppendorf).
Cell culture reagents were purchased from Life Technologies. Mouse anti-STXBP1 antibody was purchased from BD Biosciences. pCMV-STXBP1-emGFP, pCMV-STXBP1, NPY-hPLAP, and NPY-mCherry were prepared as previously described (Arunachalam et al, 2008 (link); Martin et al, 2013 (link); Tomatis et al, 2013 (link)). STXBP1^Δ317-333 and STXBP1^F115E mutants were made using the quick-change lightning site-directed mutagenesis kit (Strategene, USA) and the mutational primer
5′-GACTTTTCCTCTAGCAAGAGGATGATGCCCCAGTACCAGAAGGAGC-3′, as previously described (Martin et al, 2013 (link)). All constructs were sequenced at The Australian Genome Research Facility, located at The University of Queensland.

Akefe I.O., Saber S.H., Matthews B., Venkatesh B.G., Gormal R.S., Blackmore D.G., Alexander S., Sieriecki E., Gambin Y., Bertran-Gonzalez J., Vitale N., Humeau Y., Gaudin A., Ellis S.A., Michaels A.A., Xue M., Cravatt B., Joensuu M., Wallis T.P, & Meunier F.A. (2024). The DDHD2-STXBP1 interaction mediates long-term memory via generation of saturated free fatty acids. The EMBO Journal, 43(4), 533-567.

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Halogenated Alkane Synthesis and Extraction

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GT, iodomethane, iodoethane, N,N-diisopropylethylamine, sodium borohydride, tert-butanol were obtained from Sigma-Aldrich, and chloroform was obtained from Macron. HPLC grade solvents were obtained from Burdick & Jackson. WAX and t-C18 microelution solid phase extraction plates were obtained from Waters.

Sugui J.A., Rose S.R., Nardone G., Swamydas M., Lee C.C., Kwon-Chung K.J, & Lionakis M.S. (2017). Host immune status-specific production of gliotoxin and bis-methyl-gliotoxin during invasive aspergillosis in mice. Scientific Reports, 7, 10977.

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Lipid Extraction and Derivatization Protocol

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Saturated and unsaturated FFAs were obtained from Sigma-Aldrich. Phospholipid standards (PC 17:0/17:0, PE 17:0/17:0, PS 17:0/17:0, PA 17:0/17:0, PG 17:0/17:0, PC 12:0/13:0, PE 17:0/14:1, PS 17:0/14:1, PA 12:0/13:0 and PG 12:0/13:0) were purchased from Avanti Polar Lipids. 1,1-carbonydiimidiazole, 1,4 dioxane, triethylamine, iodomethane, iodomethane-d₃, iodoethane, formic acid, citric acid, disodium hydrogen phosphate ammonium formate, acetonitrile, 1-butanol, methanol and chloroform were purchased from Sigma Aldrich. All reagents were analytical grade or equivalent. All lipid extractions were performed in 2 mL polypropylene LoBind safe-lock tubes (Eppendorf).

Wallis T.P., Venkatesh B.G., Narayana V.K., Kvaskoff D., Ho A., Sullivan R.K., Windels F., Sah P, & Meunier F.A. (2021). Saturated free fatty acids and association with memory formation. Nature Communications, 12, 3443.

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Synthesis of Alkylated Amines

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D-glucose, tetramethylenediamine, hexamethylenediamine, iodoethane, 1-iodopropane, 1-iodododecane were purchased from Sigma-Aldrich. Hexanal was obtained from Fluka. Octanal, decanal, dodecanal, sodium borohydride and sodium cyanoborohydride were purchased from Merck. Sodium hydroxide, potassium hydroxide, hydrochloric acid, acetic acid, methanol, 2-propanol, N,N-dimethylformamide and diethyl ether were obtained from Chempur. Nitromethane was purchased from POCH. All reagents and solvents were used as obtained without further purification.

Brycki B, & Szulc A. (2014). Gemini Alkyldeoxy-D-Glucitolammonium Salts as Modern Surfactants and Microbiocides: Synthesis, Antimicrobial and Surface Activity, Biodegradation. PLoS ONE, 9(1), e84936.

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Synthesis of Alkyl Halide Derivatives

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Naringenin, iodomethane, iodoethane, 1-iodopentane and 1-iodododecane were purchased from Sigma-Aldrich Chemical Co. (Steinheim, Germany), hydroxylamine hydrochloride from LOBA Feinchemie GmbH (Fischamed, Austria), anhydrous sodium acetate and potassium carbonate from Chempur (Piekary Śląskie, Poland). Anhydrous solvents were prepared according to standard procedures. All organic solvents were of analytical grade.

Kozłowska J., Potaniec B., Żarowska B, & Anioł M. (2017). Synthesis and Biological Activity of Novel O-Alkyl Derivatives of Naringenin and Their Oximes. Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry, 22(9), 1485.

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Peptide and Protein Modification Reagents

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Methanol and glacial acetic acid were purchased from Mallinckrodt (Phillipsburg, NJ, USA). Sodium periodate, iodoethane, dimethylformamide (DMF), trifluoroacetic acid (TFA), n-propanol, zinc acetate (Zn(OAc)₂), and trans,trans-farnesyl chloride were purchased from Sigma-Aldrich (St. Louis, MO, USA). RAKGCKGR was synthesized by CHI Scientific (Maynard, MA, USA). KGAILCGIALK was synthesized by CPC Scientific (Sunnyvale, CA, USA). A-factor was a generous gift from the Hrycyna Lab at Purdue University. The carbamidomethyl (cam)-modified BSA tryptic digest was purchased from ThermoFisher Scientific (Waltham, MA, USA). All peptide stock solutions for positive nanoelectrospray were prepared in a 49.5:49.5:1 (v/v/v) solution of Methanol/water/acetic acid at an initial concentration of ~1 mg/mL and diluted 100-fold prior to use. The solution of Sodium periodate (50:50 v/v Methanol/water) anions was prepared at a concentration of ~1 mg/mL and diluted 10-fold prior to use.

Pilo A.L., Zhao F, & McLuckey S.A. (2016). Selective Gas-Phase Oxidation and Localization of Alkylated Cysteine Residues in Polypeptide Ions via Ion/Ion Chemistry. Journal of proteome research, 15(9), 3139-3146.

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Synthesis of Pyridine-based Compounds

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Pyridine-2-carboxaldehyde, 6-methylPyridine-2-carboxaldehyde, 2-(aminomethyl)pyridine, nickel(ii) perchlorate hexahydrate, nitrilotriacetic acid, iodoethane (Sigma-Aldrich), sodium triacetoxyborohydride, 1,2-diaminobenzene, 3-hydroxyflavone (Alfa Aesar), ethyl acetate, triethylamine, sodium sulphate (Merck, India), were used as received. Dichloromethane, diethylether, tetrahydrofuran, acetonitrile (Merck, India) and methanol, acetone (Sisco Research Laboratory, Mumbai) were distilled before use. The supporting electrolyte tetra-N-butylammonium perchlorate (Aldrich) was recrystallized and used.

Ajaykamal T, & Palaniandavar M. (2023). Mononuclear nickel(ii)–flavonolate complexes of tetradentate tripodal 4N ligands as structural and functional models for quercetin 2,4-dioxygenase: structures, spectra, redox and dioxygenase activity. RSC Advances, 13(35), 24674-24690.

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Synthesis and Purification of Ethylated Peptide Derivative

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Example 18

Synthesis was initiated from 0.3 mmol of the peptide intermediate, Cbz-D-Phe-D-Phe-D-Leu-D-Orn(Cbz)-[homopiperazine amide], which was prepared during the synthesis of compound (19). For ethylation of the homopiperazine at C-terminus, the peptide was treated with a solution of iodoethane (0.4 mmol; Aldrich) and DIEA (0.5 ml, 6 mmol) in DMF (3 ml) for 1 day at room temperature. The subsequent deprotection/hydrolysis and HPLC purification were carried out according to the procedure described in the synthesis of compound (19). Final purified peptide: amorphous powder, 75 mg in yield. HPLC analysis: t_R=10.43 min, purity 98.4%, gradient 10% B to 30% B over 20 min; MS (M+H⁺): expected molecular ion mass 650.4, observed 650.3.

US10913769B2. Synthetic peptide amides and dimers thereof (2021-02-09). CARA THERAPEUTICS, INC. [US]. Inventors: Claudio D. Schteingart [US], Frédérique Menzaghi [US], Guangcheng Jiang [US], Roberta Vezza Alexander [US], Javier Sueiras-Diaz [US], Robert H. Spencer [US], Derek T. Chalmers [US], Zhiyong Luo [US].

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Ethylation of Homopiperazine Peptide

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Example 18

US10017536B2. Synthetic peptide amides and dimers thereof (2018-07-10). CARA THERAPEUTICS, INC. [US]. Inventors: Claudio D. Schteingart [US], Frédérique Menzaghi [US], Guangcheng Jiang [US], Roberta Vezza Alexander [US], Javier Sueiras-Diaz [US], Robert H. Spencer [US], Derek T. Chalmers [US], Zhiyong Luo [US].

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