N butyllithium

Manufactured by Merck Group

Sourced in Germany, United States

N-butyllithium is a clear, colorless, and volatile liquid used as a strong base and reducing agent in organic synthesis. It is a commonly used reagent in the chemical industry and academic research. The core function of N-butyllithium is to initiate and facilitate various chemical reactions, particularly in the formation of carbon-carbon bonds.

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Lab products found in correlation

48 protocols using n butyllithium

Synthesis of Arylboronic Acid Derivatives

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All reactions involving air- and moisture-sensitive
reagents were carried out under an argon atmosphere. Solvents were
stored over sodium wire before use. Key reagents including arylboronic
acids, BDEA, and n-butyllithium (10 M solution in
hexanes) were purchased from Aldrich and used as received. The NMR
chemical shifts are given relative to tetramethylsilane using known
chemical shifts of residual proton (¹H) or carbon (¹³C) solvent resonances. ¹¹B and ¹⁹F
NMR chemical shifts are given relative to BF₃·Et₂O and CFCl₃, respectively. In the ¹³C NMR spectra, the resonances of carbon atoms bound to boron were
not observed because of their broadening by quadrupolar boron nucleus.

Durka K., Urban M., Dąbrowski M., Jankowski P., Kliś T, & Luliński S. (2019). Cationic and Betaine-Type Boronated Acridinium Dyes: Synthesis, Characterization, and Photocatalytic Activity. ACS Omega, 4(2), 2482-2492.

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Synthesis and Handling of Air-Sensitive Metal Complexes

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All manipulations of metal complexes
were carried out in the absence of water and dioxygen using standard
Schlenk techniques, or in a Vigor inert atmosphere dry box under a
dinitrogen atmosphere. The bis-alkoxide ligand was synthesized as
previously reported.^{39 (link)} All glassware was
oven-dried for a minimum of 3 h and cooled in an evacuated antechamber
prior to use in the dry box. Benzene, diethyl ether, hexane, pentane,
toluene, tetrahydrofuran, 1,2-difluorobenzene, and trifluorotoluene
were dried over 4 Å molecular sieves (Research Catalysts) prior
to use. Benzene-d₆ was purchased from
Cambridge Isotope Laboratories and was degassed and stored over 4
Å molecular sieves prior to use. Pyridine, n-butyllithium, and benzophenone were purchased from Aldrich. Dibenzofuran,
3-(trifluoromethyl)Pyridine, 4-(trifluoromethyl)Pyridine, and 4-tert-butylPyridine were purchased from Oakwood Chemical.
Triphenylmethyl chloride was purchased from Acros Organics. Ferrocenium
hexafluorophosphate was synthesized following a previously reported
procedure.^{45 (link)} Fe₂Mes₄ was synthesized as previously reported.^{46 (link)} Celite 545 (J. T. Baker) was dried in a Schlenk flask for 24 h under
dynamic vacuum while heating to at least 150 °C prior to use
in a dry box. Silica gel 32–63 μ (AIC, Framingham, MA)
was used as received.

Gwinn R.K., Williams M., Latendresse T.P., Slebodnick C., Troya D., Tarannum T, & Thornton D.A. (2024). Synthesis, Characterization, and the Effect of Lewis Bases on the Nuclearity of Iron Alkoxide Complexes. Inorganic Chemistry, 63(17), 7692-7704.

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Synthesis of Dibenzyldithioether (DBDT)

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Example 2

3.19 g (25 mmol) of metal tellurium (trade name: Tellurium (−40 mesh), manufactured by Aldrich Corporation) was suspended in 25 ml of THF. 17.2 mL (27.5 mmol) of n-butyllithium (manufactured by Aldrich Corporation, 1.6 M hexane solution) were gradually added dropwise to the obtained suspension at 0° C. (for 10 minutes). The obtained reaction solution was stirred until the metal tellurium was completely dissolved (for 10 minutes). Next, 20 mL of ammonium chloride solution were added at room temperature and stirred for 1 hour. After completion of the reaction, the organic layer was separated and the water layer was extracted 3 times with diethyl ether. The collected organic layer was dried with anhydrous sodium sulfate and then concentrated under reduced pressure, thereby obtaining 4.41 g (11.93 mmol; yield: 95%) of a grape oily substance of DBDT.

US10167405B2. Aqueous coloring agent dispersion for inkjet, ink composition, inkjet recording method, and colored body (2019-01-01). Nippon Kayaku Kabushiki Kaisha [JP]. Inventors: Akira Kawaguchi [JP], Akio Kuwahara [JP].

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Synthesis of BTEE from Tellurium

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Example 1

6.38 g (50 mmol) of metal tellurium (trade name: Tellurium (−40 mesh), manufactured by Aldrich Corporation) was suspended in 50 ml of THF. 34.4 mL (55 mmol) of n-butyllithium (manufactured by Aldrich Corporation, 1.6 M hexane solution) were gradually added dropwise to the obtained suspension at room temperature (for 10 minutes). The obtained reaction solution was stirred until the metal tellurium was completely dissolved (for 20 minutes). Next, 10.7 g (55 mmol) of ethyl-2-bromo-isobutyrate were added at room temperature and stirred for 2 hours. After completion of the reaction, the solvent was concentrated under reduced pressure, and subsequently, was distilled under reduced pressure, thereby obtaining 8.98 g (yield: 59.5%) of a yellow oily substance of BTEE.

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Synthesis of Conjugated Thiophene Derivatives

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n-Butyllithium (2.5 M in hexane), 3,4-ethylenedioxythiophene (97%), bis(triphenylphosphine)palladium (II) dichloride (98%) were purchased from Aldrich. Selenophene (98.0%) and 5-(4,4,5,5-tetramrthyl-1,3,2-dioxaborolan-2-yl-2,2′-bithiophene (98%), were purchased from TCI Europe. Anhydrous potassium carbonate (99%) was received from Chempur. Anhydrous tetrahydrofuran was purchased from POCH. Tetrahydrofuran was dried over Na/benzophenone ketal before use. Other commercially available substances and reagents were used without the prior purification. Preparative column chromatography was performed on the glass column with Acros Organics silica gel for chromatography, 0.035–0.075 mm; 60 Å. The 600 MHz ¹H NMR and ¹³C NMR spectra were recorded in deuterated chloroform (CDCl₃) on Bruker Avance II 600 Instruments, respectively. Chemical shifts were locked to chloroform δ_H 7.26 (s) and δ_C 77.16 (t) signals.

Zając D., Honisz D., Łapkowski M, & Sołoducho J. (2019). Synthesis and Properties of New Dithienosilole Derivatives as Luminescent Materials. Molecules, 24(12), 2259.

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Synthesis and Characterization of Novel Compounds

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4-Bromobenzyl bromide, 4-bromoaniline, 4-pyridylboronic acid, 1,3-dichlorobenzene, p-tolylmagnesium bromide, n-butyllithium and N-bromosuccinimide were purchased from Aldrich and used as received. Benzoyl peroxide was purchased from Acros and used as received. Compounds 3 [18 (link)], [5][OTf]₂ [19 (link)–20 (link)] and 6 [21 (link)] were prepared using literature methods. Solvents were dried using an Innovative Technologies solvent purification system. Thin-layer chromatography (TLC) was performed using Teledyne Silica gel 60 F254 plates and viewed under UV light. Column chromatography was performed using Silicycle ultra-pure silica gel (230–400 mesh). The solvents were dried and distilled prior to use. NMR spectra were recorded on a Bruker Avance III console equipped with an 11.7 T magnet (e.g., 500 MHz for ¹H). Samples were locked to the deuterated solvent and all chemical shifts reported in ppm referenced to tetramethylsilane. Mass spectra were recorded on a Waters Xevo G2-XS instrument. Solutions with concentrations of 0.001 molar were prepared in methanol and injected for analysis at a rate of 5 µL/min using a syringe pump.

Vella S.J, & Loeb S.J. (2018). A pyridinium/anilinium [2]catenane that operates as an acid–base driven optical switch. Beilstein Journal of Organic Chemistry, 14, 1908-1916.

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Enzymatic Assay Development for Pancreatitis

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All the chemicals and reagents were commercially available and used as received without further purification. Superdry tetrahydrofuran (THF) was purchased from J&K Scientific. Titanium tetrachloride (TiCl₄), 4-dimethylaminopyridine (DMAP), 4-hydroxybenzophenone, and n-butyllithium were purchased from Aldrich. Dicyclohexylcarbodiimide (DCC), p-toluene sulfonic acid (PTSA) monohydrate, and Boc-l-glutamic acid 1-tert-butyl ester (Boc-Glu-OtBu) were purchased from Acros Organics. Lipases from Pseudomonas cepacia (PCL), Candida rugosa (CRL), Candida Antarctica B (CALB), Pseudomonas fluorescens (PFL), Porcine pancreas (PPL), and Aspergillus niger (ANL) were all ordered from Amano Enzymes. Glucose oxidase, alkaline phosphatase, acylase, laccase, and α-amylase were all purchased from Sigma-Aldrich. The Lipase Assay Kit was purchased from the Nanjing Jiancheng Bioengineering Institute. The human serum samples were supplied by Union Hospital, Tongji Medical College, Huazhong University of Science and Technology, and the serum samples were from both healthy people and acute pancreatitis patients. The water used in the tests was triple distilled, treated with an ion exchange column, and then treated with a Milli-Q water purification system.

Shi J., Deng Q., Wan C., Zheng M., Huang F, & Tang B. (2017). Fluorometric probing of the lipase level as acute pancreatitis biomarkers based on interfacially controlled aggregation-induced emission (AIE) †Electronic supplementary information (ESI) available: Synthesis, characterisation, test conditions and other supplementary data. See DOI: 10.1039/c7sc02189e Click here for additional data file.. Chemical Science, 8(9), 6188-6195.

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Synthesis of 2-Bromonaphthalene Derivatives

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All other chemicals were used without further purification unless otherwise noted. 2-Bromo-6-methoxynaphthalene (1) (TCI), n-butyllithium (TCI), 1,2-dibromoethane (TCI), boron tribromide (TCI), trifluoromethanesulfonic anhydride (TCI), ethynyltrimethylsilane (Aldrich), copper(I) iodide (Nacalai Tesque), sodium sulfide nonahydrate (Nacalai Tesque), 1,4-benzenedimethanol (TCI), acetic anhydride (Wako), iodine (Nacalai Tesque), orthoperiodic acid (Wako), sodium hydroxide (Nacalai Tesque), pyridinium chlorochromate (TCI), zinc chloride (TCI), trimethylsulfonium iodide (Aldrich), potassium hydroxide (Nacalai Tesque), and indium trichloride (TCI) were purchased and used as received. Moreover, 2,5-Diiodo-1,4-benzendicarboxaldehyde (2) [46 (link)] was prepared according to the synthetic procedure and exhibited the identical spectra reported in the literature.

Ishida T., Sawanaka Y., Toyama R., Ji Z., Mori H, & Nishihara Y. (2020). Synthesis of Dinaphtho[2,3-d:2’,3’-d’]anthra[1,2-b:5,6-b’]dithiophene (DNADT) Derivatives: Effect of Alkyl Chains on Transistor Properties. International Journal of Molecular Sciences, 21(7), 2447.

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Synthesis of Brominated Organic Compounds

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2-Bromobiphenyl and 1,4-dibromobutane were reagent grade and purchased from Fluorochem (Hadfield, UK). n-Butyllithium (BuLi, 2.5 M in hexane), tetrahydrofuran (THF, anhydrous), dichloromethane (DCM), 1,1,1-trifluoroacetone, trifluoromethanesulfonic acid (TFSA), trimethylamine (TMA, 4.2 M in ethanol), poly(vinyl alcohol) (PVA, Mw = 89–98,000, 99% hydrolyzed), polyvinylidene difluoride (PVDF, Mw = 534,000), glutaraldehyde (GA) (50 wt% in water), N-methyl-2-pyrrolidone (NMP), and methanol (anhydrous) were reagent grade and purchased from Sigma-Aldrich (Milano, Italy). All the reagents were used as received.

Narducci R., Becerra-Arciniegas R.A., Pasquini L., Ercolani G., Knauth P, & Di Vona M.L. (2022). Anion-Conducting Polymer Electrolyte without Ether Linkages and with Ionic Groups Grafted on Long Side Chains: Poly(Alkylene Biphenyl Butyltrimethyl Ammonium) (ABBA). Membranes, 12(3), 337.

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Synthesis of Organic Semiconductors

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Anhydrous solvents, tri(o-tolyl)phosphine, tris(dibenzylideneacetone)dipalladium(0), trimethyltin chloride, and n-Butyllithium were purchased from Sigma-Aldrich, (Seoul, Republic of Korea). N-bromosuccinimide (NBS) was purchased from Alfa Aesar (Gongduk-Dong, Mapo-Gu, Republic of Korea) a, and thienothiophene, thiophene, and tetrakis(triphenylphosphine)-palladium(0) were purchased from TCI Chemical (Tokyo Chemical Industry Co., LTD., Tokyo, Japan). All chemicals were used without further purification. 4-(2-Ethylhexyl)-2,6-bis(trimethylstannyl)-4H-dithieno[3,2-b:2′,3′-d]pyrrole) were purchased from J’s science (Daejeon, Republic of Korea).

Kim J., Suh E.H., Lee K., Kim G., Kim H., Jang J, & Jung I.H. (2023). Development of Alkylthiazole-Based Novel Thermoelectric Conjugated Polymers for Facile Organic Doping. Nanomaterials, 13(7), 1286.

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