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10 protocols using n n dimethylformamide (dmf)

1

Flavonoids and Organic Acid Synthesis

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Rutin and naringinase were purchased from Sigma-Aldrich Co. LLC., St. Louis, MO, USA. DMF, tert-butyldiphenylsilyl chloride (TBDPSCl), EDC·HCl, 4-DMAP, TBAF, and tetrahydrofuran (THF) were purchased from Tokyo Chemical Industry Co., Ltd., Tokyo, Japan. Flavonols (17, 18, and 2021), organic acids (2231), and other chemicals, unless otherwise indicated, were purchased from Nakalai Tesque Inc., Kyoto, Japan.
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2

Synthesis of Silicone-based Nanocomposite

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Silicone polyol (DMS-C15) was purchased from Gelest, USA. IPDI, DMF, glycerol 1,2-carbonate, and furfurylamine were purchased from Tokyo Chemical Industry, Japan. DMF-d7, dibutyltin dilaurate, and BMI were purchased from Sigma-Aldrich, USA. All chemicals were used as received without purification. An AgNW solution dispersed in IPA was purchased from Dittotechnology Ltd., Korea. The average diameter and length of the nanowires were 35 nm and 20 μm, respectively.
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3

Antisolvent Vapor-Assisted MAPbCl3 Crystals

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The MAPbCl3 single crystals were grown using the antisolvent vapor–assisted crystallization method (14 (link)). The equimolar starting materials, MACl (Tokyo Chemical Industry Co. Ltd.) and PbCl2 (Sigma-Aldrich), were first dissolved in dimethyl sulfoxide (FUJIFILM Wako Pure Chemical Corporation) to yield a perovskite solution with a concentration of 1 M. Then, the solution was diluted to a 0.5 M perovskite solution by adding N,N-dimethylformamide (Tokyo Chemical Industry Co. Ltd.). A small vial without lid and partially filled with the perovskite solution was loaded into a bigger vial containing toluene (antisolvent) so that the smaller vial is bathing in toluene. The lid of the bigger vial was closed tightly, and the vapor diffusion resulted in growth of large MAPbCl3 single crystals. The x-ray diffraction pattern obtained from a cleaved MAPbCl3 single crystal is provided in fig. S1. The sharp peaks verify a good crystal quality.
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4

Purification and Characterization of MWNTs

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Example 1

MWNTs with a diameter of 10 nm to 15 nm and a length of 10 μm to 20 μm were supplied by Iljin Nano Tech, Korea. They were purified via thermal oxidation at 350° C. for 2 h in air, followed by refluxing in 6 M HCl solution overnight. 3,3′-Dihydroxy-4,4′-diaminobiphenyl (HAB, 97%) was purchased from Tokyo Chemical Industry and purified by recrystallization from N,N′-dimethylformamide (DMF)/ethanol mixture. 3,3′,4,4′-biphenyltetracarboxylic dianhydride (BPDA), poly(vinyl pyrrolidone) (PVP, Mw=29 000), N,N′-dimethylacetamide (DMAc), and all other chemicals were obtained from Sigma-Aldrich. BPDA was purified via sublimation under reduced pressure. DMAc was distilled over calcium hydride. All other chemicals were used without purification.

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5

Synthesis and Purification of Diamines

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Hydrogenated pyromellitic anhydride (HPMDA) and hydrogenated 3,3’,4,4’-biphenyltetracarboxylic dianhydride (HBPDA) were purchased from Weihai Newera Kesense New Materials Co. Ltd. (Shandong, China) and dried at 150 °C in vacuo for 24 h prior to use. 2-Chloro-4,4’-diaminobenzanilide (ClDABA) was purchased from Changzhou Sunlight Pharmaceutical Co. Ltd. (Jiangsu, China) and recrystallized from absolute ethanol and discolored with active charcoal powder before use. N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), N,N-dimethylformamide (DMF), γ-butyrolactone (GBL), and other solvents were obtained from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan) and purified by distillation prior to use.
2-Methyl-4,4’-diaminobenzanilide (MeDABA) was synthesized in our laboratory according to the literature [32 ] and purified by recrystallization from absolute ethanol. MeDABA was obtained as colorless needles with the purity of 99.5% according to the gas chromatography analysis.
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6

Synthesis of Poly(Amino Acid) Derivatives

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n-Butylamine and β-benzyl-L-aspartate-N-carboxyanhydride (BLA-NCA) were obtained from NOF Corporation (Tokyo, Japan). Ethylene oxide was obtained from 3M Japan Co., Ltd. (Tokyo, Japan). Tetrahydrofuran (THF) (super dehydrated, purity >99.5%) and Toluene (super dehydrated, purity >99.5+%) were purchased from Kanto Chemical, Co., Inc. (Tokyo, Japan). Ethanol, diethyl ether, N,N-dimethylformamide (DMF) and piperidine (purity >98.0%) were purchased from Fujifilm Wako Pure Chemical, Co., Inc. (Tokyo, Japan). 1,1,3,3-Tetramethylguanidine (purity >99.0%), 2-methoxyEthanol (purity >99.0%) epichlorohydrin (purity >99.0%), triisobutylaluminum, N,N-dimethylformamide (purity >99.5%), 4-dimethylaminopyridine (purity >99.0%), 1-(3-dimethylaminopropyl)-3-ethylcordiimide hydrochloride (purity >98.0%), N-[(9H-fluoren-9-ylmethoxy)carbonyl]glycine (purity >98.0%), N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-leucine (purity >98.0%) and N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-tyrosine (purity >95.0%) were purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). Sodium hydroxide, hydrochloric acid and HEPES buffer were purchased from Sigma-Aldrich (St. Louis, MO, U.S.A). Fetal bovine serum (FBS), Dulbecco’s Modified Eagle’s Medium and Penicillin-Streptomycin were obtained from Thermo Fisher Scientific (Waltham, MA, U.S.A).
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7

Synthesis of Mannose-Derived Compounds

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3,5-Dihydroxybenzaldehyde, potassium carbonate, propargyl bromide, and RPMI-1640 medium were purchased from Wako Pure Chemical Industries, Ltd., (Osaka, Japan). 1-Bromododecane, sodium borohydride, sodium hydride, 2,3,4,6-tetra-O-benzoly-D-mannopyranose, trifluoromethanesulfonic anhydride, diphenyl sulfoxide, N,N-dimethylformamide, trimethylsilyl azide, and 2-chloro-1,3-dimethylimidazolium chloride were purchased from Tokyo Chemical Industry Co., (Tokyo Japan). Sodium methoxide was purchased from Kanto Chemical Co., (Tokyo Japan). Copper(II)sulfate pentahydrate was purchased from Sigma-Aldrich (St. Louis, MO).
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8

Synthesis of Cyclic Aliphatic Amines

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All chemicals were used
as received. Isophorone diamine [IPDA, 3-(aminomethyl)-3,5,5-trimethylcyclohexylamine; cis/trans mixture, >99.0%], 2-aminoethanol
(MEA, monoethanolamine; >99.0%), cyclohexylamine (>99.0%), cycloheptylamine
(>97.0%), cyclopentylamine (>98.0%), hexylamine (>99.0%),
dihexylamine
(>98.0%), trihexylamine (>98.0%), 4,4′-methylenebis(2-methylcyclohexanamine)
(cis/trans mixture, >99.0%), cyclohexane-1,2-diamine
(cis/trans mixture, >98.0%),
cyclohexane-1,3-diamine
(cis/trans mixture, >95.0%),
cyclohexane-1,4-diamine
(cis/trans mixture, >97.0%),
1,3-phenylenedimethanamine
(>99.0%), phenylmethanamine (>99.0%), N,N-dimethylformamide (DMF; >99.0), and dimethyl sulfoxide
(DMSO; >99.0%)
were purchased from Tokyo Chemical Industry Co., Ltd. Aniline (>99.0%)
and KOH (>85.0%) were purchased from FUJIFILM Wako Pure Chemical
Corp.
Toluene (>99.5%), methanol (99.8%), and diethyl ether (>99.5%)
were
purchased from Kanto Chemical Co., Inc.
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9

Synthesis of Polyurethane Materials

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Isophorone diisocyanate (IPDI) was purchased from Evonik Japan Co., Ltd. (Tokyo, Japan); hexamethylene diisocyanate (HDI), from Tosoh Co., Ltd. (Tokyo, Japan); and polycaprolactone diol (PCL diol MW: 2000), from Daicel Corporation (Osaka, Japan). 2,2-bis (Hydroxymethyl)propionic acid (DMPA), 2-propanol (IPA), 3-methyl-1,5-pentandiol (MPD), polyethylene glycol monomethyl ether (MW: 400), 1,4-butanediamine (BDA), butylamine (BA), N,N-dimethylformamide (DMF), methylethylketone (MEK), and triethylamine (TEA) were purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). Zirconium octylate was obtained from Daiichi Kigenso Kagaku-Kogyo Co., Ltd. (Fukui, Japan).
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10

Synthesis of Styrene-grafted Silica Nanoparticles

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Vinylphosphonic acid (VPA, >95.0%) and N,N-dimethylformamide (DMF, >99.5%) were purchased from Tokyo Chemical Industry Co., Ltd. 2,2′-Azobis(isobutylnitrile) (AIBN, >98.0%), styrene (>99.0%), and acetonitrile (>99.9%) were purchased from FUJIFILM Wako Pure Chemical Corporation. Bare silica nanoparticles (average particle size 235 nm determined from SEM images) were purchased from UBE EXSYMO CO., Ltd. Polycarbonate (PC) was purchased from TEIJIN Ltd.
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