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N buli

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N-BuLi is a highly reactive organolithium compound. It is commonly used as a strong base and nucleophile in organic synthesis reactions.

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Lab products found in correlation

Titanium 4 isopropoxide, by Merck Group (2 mentions) Acetonitrile, by Merck Group (2 mentions) Silica gel 60, by Merck Group (2 mentions) Mose2, by Thermo Fisher Scientific (1 mentions) Avance 250, by Bruker (1 mentions) Ipr2nh, by Merck Group (1 mentions) Me3sicl, by Merck Group (1 mentions) Libh4, by Merck Group (1 mentions) Avance 400, by Bruker (1 mentions) Avance 500, by Bruker (1 mentions) Chlorobenzene, by Thermo Fisher Scientific (1 mentions) Hydrazine hydrate, by Merck Group (1 mentions) Nitromethane, by Merck Group (1 mentions) Potassium phthalimide, by Merck Group (1 mentions) Litfsi, by Merck Group (1 mentions) 1 4 dibromobutane, by Fluorochem (1 mentions) N n dimethylformamide (dmf), by Thermo Fisher Scientific (1 mentions) Tio2 paste 18nr t, by Greatcell Solar (1 mentions) Lialh4, by Merck Group (1 mentions) Dimethyl sulfoxide (dmso), by Merck Group (1 mentions)

15 protocols using n buli

1

Synthesis of Li-Intercalated MX2 Flakes

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Bulk MX2 (MoS2, WSe2, and MoSe2) flakes of 99.8% purity were purchased from Alfa Aesar. MoTe2 crystals were purchased from Sigma Aldrich and ground to powder. All samples were first degassed by keeping under vacuum at 60 °C for 48 h. Degassed MX2 (100 mg) was treated with different concentrations of n-butyl lithium (n-BuLi) (stock concentration of 1.6 M, Sigma Aldrich) in hexane at a fixed dose of 10 mg/ml under different temperature from 20 to 120 °C. The treatment time was varied from ~6 to 100 h to synthesize LixMX2. After a predetermined intercalation time, the suspension was filtered over Millipore membrane and washed several times with high purity hexane to separate the intercalated MX2 from residual n-BuLi. The entire procedure was carried out in a glove box under extra pure N2 atmosphere. Since lithium compounds react violently in the presence of humid air, dealing with a large amount of Lithium compounds requires cautious treatment. We have made several small batches (2 ml) inside the N2-filled glove box to acquire a sufficient amount of materials for this study.
Padmajan Sasikala S., Singh Y., Bing L., Yun T., Koo S.H., Jung Y, & Kim S.O. (2020). Longitudinal unzipping of 2D transition metal dichalcogenides. Nature Communications, 11, 5032.
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2

Phosphine Synthesis and Characterization

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All manipulations were carried out under an atmosphere of dry nitrogen, using standard Schlenk and drybox techniques. Solvents were purified, dried and degassed according to standard procedures and stored under 3 Å molecular sieves or a sublimed sodium mirror. 1H and 13C{1H} NMR spectra were recorded on a Bruker Avance 250, Bruker Avance 400 or Bruker Avance 500 and internally referenced to the residual solvent resonances (CDCl3: 1H δ=7.26, 13C{1H} δ=77.2; THF‐D8: 1H δ=3.58, 1.72, 13C{1H} δ=67.2, 5.3 ppm or TMS; 31P{1H}, 31P, 11B{1H}, 11B, 7Li and 29Si NMR spectra were recorded on a Bruker Avance 250 or Bruker Avance 400 and externally referenced (85 % H3PO4, BF3⋅OEt2 and LiCl, respectively). Chemical shifts are reported in ppm. High resolution mass spectra were recorded on a Bruker MicroTOF with ESI nebulizer (ESI). Melting points were measured in sealed capillaries and are uncorrected. PhPCl2, tBuPCl2, PCl3, iPr2NH, Cy2NH, TMP, (Me3Si)2NNa (1.0 m in THF), Li[BH4] (2 m in THF) and nBuLi (1.6 m in hexanes) were purchased from Sigma and used as received. Me3SiCl was bought from Sigma and freshly distilled before use. The various dichlorophosphines RPCl2 (R=Mes,[24]iPr2N,[25] Cy2N,[26] TMP,[27] and (Me3Si)2 
n)[28] were prepared according to known literature procedures.
de Jong G.B., Ortega N., Lutz M., Lammertsma K, & Slootweg J.C. (2020). Easy Access to Phosphine‐Borane Building Blocks. Chemistry (Weinheim an Der Bergstrasse, Germany), 26(68), 15944-15952.
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3

Perovskite Solar Cell Fabrication

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PbI2 (99.999 %, Sigma–Aldrich), methylammonium iodide (Greatcell solar), phenylethylammonium iodide (Sigma–Aldrich), N,N‐dimethylformamide (extra dry, 99.8 %, Acros Organics), dimethyl sulfoxide (>99.5 %, Sigma–Aldrich), ethyl acetate (anhydrous, 99.8 %, Sigma Aldrich), chlorobenzene (extra dry, 99.8 %, Acros Organics), Spiro‐MeOTAD (Luminescence Technology Corp), LiTFSI (99.95 %, Sigma–Aldrich), 4‐tert‐butylpyridine (>96 %, TCI), acetonitrile (anhydrous, 99.8 %, Sigma–Aldrich), TiO2 paste (18 NR‐T, Greatcell Solar), titanium(IV) isopropoxide (>97 %, Sigma–Aldrich), PEDOT:PSS (M124 HTL Solar, Ossila), benzo[1,2‐b:4,5‐b′]dithiophene (BDT, TCI, 98 %), n‐butyllithium solution (n‐BuLi, 1.6 M in hexane, Sigma–Aldrich), 1,4‐dibromobutane (Fluorochem, 99 %), 1,6‐dibromohexane (Fluorochem, 95 %), ammonium acetate (ABCR, 97 %), nitromethane (Sigma‐Aldrich, 95 %), lithium aluminum hydride (LiAlH4, Sigma–Aldrich, 95 %), potassium phthalimide (Sigma–Aldrich, 98 %), and hydrazine hydrate (Alfa Aesar, 98 %) were used as received. Conductive patterned FTO was purchased from Lyoyang Guluo Glass Co. with a resistance of 7 Ω/sq.
Primera Darwich B., Guijarro N., Cho H., Yao L., Monnier L., Schouwink P., Mensi M., Yum J, & Sivula K. (2021). Benzodithiophene‐Based Spacers for Layered and Quasi‐Layered Lead Halide Perovskite Solar Cells. Chemsuschem, 14(14), 3001-3009.
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4

Synthesis of Bis(2-bromoaryl)amines

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Unless specified otherwise, all manipulations were performed under an inert atmosphere using standard Schlenk or glovebox techniques. Glassware was pre-dried in an oven before use. Pentane, toluene, and diethyl ether (Et2O) were dried using a GlassContours drying column. Chloro­from-d1 (Cambridge Isotopes) was dried over anhydrous CaCl2; vacuum transferred, passed over a plug of basic alumina, and stored over 4 Å mol­ecular sieves. Di-p-tolyl­amine, nBuLi (2.5 M in hexa­nes), titanium(IV)isopropoxide, and HCl (1 M in Et2O) were purchased from Sigma Aldrich and used as received. Tri­methyl­aceto­nitrile was vacuum distilled and freeze pump thawed prior to use. Bis(2-bromo-4-methyl­phen­yl)amine was prepared by literature methods (Corey et al., 2010 ▸ ).
Pedziwiatr J., Ghiviriga I., Abboud K.A, & Veige A.S. (2017). Crystal structures of a novel NNN pincer ligand and its dinuclear titanium(IV) alkoxide pincer complex. Acta Crystallographica Section E: Crystallographic Communications, 73(Pt 2), 122-126.
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5

Synthesis of 2-Isopropenyl-2-Oxazoline

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2-Isopropenyl-2-oxazoline (Sigma-Aldrich, 98%, iPOx) was distilled over CaH2 under reduced pressure before use. Tetrahydrofuran (Sigma-Aldrich, THF) was freshly distilled over Na/benzophenone under Ar flow before use. n-Butyllithium solution 2.5 M in hexane (Sigma-Aldrich, n-BuLi) was used as received. 5-Fluorouracil (5-FU), tris(2-carboxyethyl)phosphine) (TCEP), and 3,3′-dithiodipropionic acid (DTDPA) were obtained from TCI Europe and used as such. All solvents (HPLC grade) were obtained from Sigma-Aldrich.
Cegłowski M., Jerca V.V., Jerca F.A, & Hoogenboom R. (2020). Reduction-Responsive Molecularly Imprinted Poly(2-isopropenyl-2-oxazoline) for Controlled Release of Anticancer Agents. Pharmaceutics, 12(6), 506.
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6

Air-Sensitive Synthesis and Handling

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All manipulations and syntheses were performed under an N2 atmosphere using either a Vigor glovebox or Schlenk techniques. Glassware was either oven-dried at 150 °C for at least four hours and/or flame-dried before bringing into the glovebox. Toluene, tetrahydrofuran (THF), diethyl ether (Et2O), and hexanes were dried using a commercial solvent purification system from LC Technology Solutions and were stored over 3 or 4 Å molecular sieves prior to use. 3 or 4 Å molecular sieves were stored in a 150 °C oven and were activated at 250 °C under reduced pressure for at least 12 h prior to use. n-BuLi (1.6 M in hexanes) was purchased from Sigma-Millipore and used as is. C6D6 was distilled from CaH2 and stored over molecular sieves inside of an N2-glovebox. C6D6, THF, Et2O, and hexanes were subjected to a test with a standard purple solution of sodium benzophenone ketyl in THF to confirm low O2 and H2O content prior to use. 2,3,5,6-Tetramethyl-p-phenylenediamine was purchased from Sigma-Aldrich (electronic grade, 99% trace metal basis) or TCI Chemicals and used as received. [Fe{N(SiMe3)2}2]2 and p-{HN(SiMe3)}2(C6Me4) (L) were prepared following literature procedures (See Fig. S1 for an NMR spectrum of L) [25 (link),26 (link)].
Moseley I.P., Lin C.Y., Zee D.Z, & Zadrozny J.M. (2019). Synthesis and magnetic characterization of a dinuclear complex of low-coordinate iron(II). Polyhedron, 175, 114171.
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7

Phosphate 2a Synthesis under Argon

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All reactions were performed under argon atmosphere. NMR spectra were measured on Varian MercuryPlus 300 (1H, 300.13 MHz; 13C, 75.46 MHz), Agilent 400 MR DD2 (1H, 400.13 MHz; 13C, 100.61 MHz) or Bruker Avance III 500 (31P, 202.45 MHz) spectrometer at 298 K. Chemical shifts of 31P NMR spectra are referenced to the signal of 85% H3PO4 that was assigned the chemical shift of 0. Mass spectra were measured on ZAB-SEQ (VG Analytical). The dry and degassed THF was prepared by PureSolv MD7. Silica gel (Merck, Silica Gel 60, 40–63 μm or Merck Silica Gel 60, 63–200 μm) was used for column chromatography. A phosphate 2a was prepared according to a published procedure.30 (link)n-BuLi (2.5 M solution in hexane), and other compounds were purchased from Sigma-Aldrich, FLuorochem and Acros Organics. Concentration of BuLi was determined by titration using menthol and 1,10-phenanthroline before use.
Oeser P., Koudelka J., Dvořáková H, & Tobrman T. (2020). Formation of trisubstituted buta-1,3-dienes and α,β-unsaturated ketones via the reaction of functionalized vinyl phosphates and vinyl phosphordiamidates with organometallic reagents. RSC Advances, 10(58), 35109-35120.
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8

Synthesis of Bi2O3 Catalyst

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Bi2O3 (300 mg, Sigma Aldrich) was mixed with 10 mL nBuLi (2.5 M in hexanes, Sigma Aldrich) in an argon-filled glove box. The above solution was heated to 80 °C for 24 h under continuous stirring. After cooling to room temperature, the obtained products were washed using excess dry hexane to remove any possible residual nBuLi. The treated powder was then soaked in water to violently leach out all Li2O and remaining Li compounds. The powder was further washed using DI water and isopropanol, and then collected by centrifugation. Finally, the as-obtained catalyst was dried at 60 °C.
Fan L., Xia C., Zhu P., Lu Y, & Wang H. (2020). Electrochemical CO2 reduction to high-concentration pure formic acid solutions in an all-solid-state reactor. Nature Communications, 11, 3633.
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9

Synthesis and Characterization of Iron-Sulfur Complexes

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Unless indicated otherwise, all manipulations were performed using oven-dried glassware in an M-Braun nitrogen-atmosphere glove box or on a Schlenk line using standard Schlenk techniques. Molecular sieves were activated by heating at 200 °C for 48 h under high vacuum. THF, toluene, diethyl ether, hexanes and pentane were purchased anhydrous from Sigma, further dried over sodium/benzophenone ketyl, vacuum-transferred before use and stored over 4 Å molecular sieves. KC8, C10H8 and n-BuLi (2.5 M in hexanes) were purchased from Sigma and used as received. 57Fe metal was purchased from EurIsotop (Cambridge Isotope Laboratories) and used as received. SePMe3, TePCy3 (Cy = cyclohexyl), LH, 57FeCl2, LFe(PhMe), L2Fe2S2 (1ox) and [K(THF)6][L2Fe2S2]·2THF (1) were prepared as previously reported27 ,46 (link)–50 .
Henthorn J.T., Cutsail GE I.I.I., Weyhermüller T, & DeBeer S. (2022). Stabilization of intermediate spin states in mixed-valent diiron dichalcogenide complexes. Nature Chemistry, 14(3), 328-333.
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10

Synthesis of Air-Sensitive Organometallics

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All reactions and manipulations of air-and moisture-sensitive reagents were carried out under an argon atmosphere. Tellurium (Aldrich), n-BuLi (Aldrich), HgCl 2 (Merck), and CuCl 2 (Aldrich) were used as purchased. 1,4-Dibromobutane (Aldrich) and 1-bromonaphthalene (Merck) were dried with molecular sieves and bubbled with argon prior to use. CuBr was prepared according to a literature method. 10 All solvents were dried and distilled under an argon atmosphere prior to use. Tetrahydrofuran (Lab-Scan) and diethyl ether (Lab-Scan) were dried over Na/benzophenone and dichloromethane (Lab-Scan) over P 4 O 10 .
Poropudas M.J., Rautiainen J.M., Oilunkaniemi R, & Laitinen R.S. (2016). Synthesis, characterization, and ligand behaviour of a new ditelluroether (C10H7)Te(CH2)4Te(C10H7) and the concurrently formed ionic [(C10H7)Te(CH2)4]Br. Dalton transactions (Cambridge, England : 2003), 45(43).
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