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Topic: N-butyllithium

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Synthesis of a Spiroacetal Intermediate for the Synthesis of the Anti-Helicobacter Pylori Butyllithium (0.20 mL, 1.6 M in hexane, 0.32 mmol) was added to a mixture of alkyne 13 (90 mg, 0.27 mmol) and tetramethylethylenediame (94 mg, 0.8 mmol) in THF (2.5 mL) at —78 °C under nitrogen. Butyllithium (2.5 mL, 1.6 M in hexanes, 4.0 mmol) was added to a stirred solution of 1-allyloxy-3-trimethylsilylprop-2-yne 16 (1.0 g, 4.0 mmol) in THF (40 mL) at —78 °C under nitrogen. Butyllithium (2 mL, 1.6 M in hexane, 3.24 mmol) was added to a mixture of acetylene 14 (570 mg, 2.7 mmol), tetramethylethylenediamine (1.21 mL, 8.1 mmol) in THF (10 mL) at —78 www.arkat-usa.org /ark/journal/2001/I01_General/310/310.asp

General procedure for preparation of phosphanes butyl­lithium reagent was added dropwise to a solution of brominated organic reagent in diethyl ether, after which a solution of the appropriate chlorophosphane in diethyl ether was added. herkules.oulu.fi /isbn9514270452/html/x340.html

Nat' Academies Press, Prudent Practices in the Laboratory: Handling and Disposal of Chemicals (1995) Butyllithium solutions should be handled in the laboratory using the "basic prudent practices" described in Chapter 5.C, supplemented by the additional precautions for work with flammable (Chapter 5.F) and reactive (Chapter 5.G) substances. The risk of fire or explosion on exposure of butyllithium solutions to the atmosphere depends on the identity of the organolithium compound, the nature of the solvent, the concentration of the solution, and the humidity. In particular, butyllithium should be stored and handled in areas free of ignition sources, and containers of butyllithium should be stored under an inert atmosphere. www.nap.edu /openbook.php?record_id=4911&page=272

Lycaeum > Leda > PIHKAL #148 There was then added 30 mL of 1.6 N butyllithium in hexane which resulted in the generation of a clear yellow solution. There was then added 25 mL of 1.6 N butyllithium in hexane and the mixture stirred for 15 min. The reaction mixture was brought up to room temperature, and 7.0 g 3,4-diethoxy-5-(methylthio)benzaldehyde in 50 mL THF was added dropwise, dispelling the color, and the mixture was held at reflux on the steam bath for 1 h. leda.lycaeum.org /?ID=10051

Publications - 1993 Butyllithium cubane-tetramers linked by Li-TMEDA-Li bridges in an infinite, zig-zag chain arrangement: first crystallographic study of a simple butyl compound of an early main group element. homepages.strath.ac.uk /~cbas70/1993.htm

Chemetall - the international specialty chemicals group By far the most important application of butyllithium is as an anionic initiator for the manufacture of synthetic rubber. Besides butyllithium also methyl-, hexyl- as well as phenyllithium find increasing use.In addition, butyllithium as well as other lithium organics became valuable tools for the synthesis of pharmaceutical and agrochemical intermediates. Due to the commercial availability and high reactivity butyllithium is the most commonly used organolithium reagent. www.chemetall.com /basic.jsp?xml=BDFC2C6609E2023CC1256ED00031F20D

PiHKAL #179 4-T-TRIS There was added 66 mL of 1.6 M butyllithium in hexane. An additional 2.5 mL dry CH3CN was added, followed immediately by a solution of lithium diisopropylamide prepared separately from 14 mL isopropylamine in 50 mL hexane treated with 60 mL butyllithium solution. (C12H17BrO2S) C,H. To a solution of 20.2 g diisopropylamine in 200 mL anhydrous THF that had been cooled to -10 °C under a He atmosphere with an external ice/MeOH bath, there was added 125 mL of a 1.6 M solution of butyllithium in hexane. thrashinc.dynu.com /drugs/pihkal179.html

C251.02 Lab -- Ibuprofen Project -- Superbase Approach A mixture of p -xylene (20 mmol), butyllithium (22 mmol), and potassium tert butoxide (22 mmol) in hexane (15 mL) was vigorously stirred 2 h at 25 ° C. Methyl iodide (22 mmol) was introduced dropwise, in the course of 5 min, at -75 ° C. Then let warm to room temperature. This strategy uses the "superbasic" mixture of butyllithium and potassium tert -butoxide to deprotonate benzylic positions. This is the total amount of material available for each group to use on the project. www.ups.edu /faculty/hanson/c251lab.02/ibu_supbase.html

KCRE/About us/Publications Landon, T.R. and R.G. Anthony, "A Mathematical Model for Polymerization of Styrene with Butyllithium in Cyclohexane," AIChE J., 18 (1972) 843. Porter, R.E., A. Ahmad and R.G. Anthony, "Mathematical Model for the Polymerization of Isoprene with Butyllithium in Hexane," J. Appl. Maggott, R.J., A. Ahmad and R.G. Anthony, "Mathematical Model for the Polymerization of Isoprene with Butyllithium in Benzene," J. Appl. cheweb.tamu.edu /orgs/groups/anthony/Website/Pages/Publications.htm

n-Butyllithium - CAS 109-72-8 - Catalog of Chemical Suppliers Butyllithium solution; ButyllithiuminhexaneM; n-Butyllithium, 2.2M in n-hexane; n-Butyllithium, 1.6M solution in hexane; sec-Butyllithium, 1.3M in cyclohexane, packaged under Argon in resealable ChemSeal­ bottles; n-Butyl lithium; n-BuLi You may also add your own catalog of chemicals for free. www.chemexper.com /chemicals/supplier/cas/109-72-8.html

Chelate Ring Size Controls the Formation of Mixed Complexes Involving Butyllithium and Sodium Amides It is shown that addition of butyllithium ( n- BuLi) to sodium amide dimers Na- 3 and Na- 4 in THF solution results in the formation of mixed 1:1 dimer complexes between n- BuLi and sodium amide. H HOESY experiments it is found that lithium prefers the five-membered chelate while sodium prefers the six-membered chelate in these mixed complexes. No such mixed complexes containing one lithium and one sodium are found from the amines 1 and 2. pubs.acs.org /cgi-bin/abstract.cgi/orgnd7/2002/21/i11/abs/om0109410.html

Chemie.DE News-Center: FMC Lithium Announces Butyllithium Price Increase The increase applies to all butyllithium pricing worldwide and takes effect on January 1, 2004, or as contracts allow. 10/17/2003 - Gastonia, N.C. -- FMC Lithium is implementing a price increase of three percent (3%) for all grades of butyllithium. Chemie.DE News-Center: FMC Lithium Announces Butyllithium Price Increase www.chemie.de /news/e/29727

Software-Entwicklung in der Chemie*10 - van Eikema Hommes, N. Dimeric n-butyllithium was found to be only 10 ± 3 times more reactive than tetrameric butyllithium. studied the reaction of n-butyllithium with benzaldehyde in THF at low temperature by means of rapid-injection NMR.[16] Under these conditions, an equilibrium exists between dimeric and tetrameric butyllithium. The difference in the degree of aggregation is obviously due to the steric demand of the carbanion, but this is likely to affect the reaction rate as well. www2.ccc.uni-erlangen.de /external/cic/tagungen/workshop95/hommes

Craig Ogle, Professor A Rapid-Injection NMR Study of the Effect of Lithium Alkoxides on the Butyllithium Initiated Polymerization and Propagation of Styrene "Lithium Alkoxide Modifiers: Their Effect on the Rate of Polymerization and Propagation of Styrene by Butyllithium, in THF at -80°C." C. Ogle, Harry C. Johnson IV, X. Wang, C. Carlin, F. Strickler and B. Gordon III, J. Poly. www.chem.uncc.edu /faculty/ogle

Forschungsschwerpunkte Classification of polar additives with respect to their influence on the microstructure in anionic polymerization of Isoprene with Butyllithium by transition energy measurements Classification of polar additives with respect to their influence on the microstructure in anionic polymerization of Butadiene with Butyllithium by transition energy measurements www.uni-essen.de /tech1chem/publiken.htm

Laboratory Notebook and Prelab Example Data for butyllithium found in: Ibid., p 314. 7. Add butyllithium slowly via syringe over 10 min Data for 2-methylaziridine found in: Aldrich Handbook of Fine Chemicals and Laboratory Equipment, 1996-1997, p 1089. www.wooster.edu /chemistry/organic/Writing/LaboratoryNotebook&Prelab/labNotebook&PrelabExample.html

Energy Citations Database (ECD) - Energy and Energy-Related Bibliographic Citations Energy Citations Database (ECD) Document #6035687 - Reaction of 2-nitropentachloro-1,3-butadiene with methyl- and butyllithium Availability information may be found in the Availability, Publisher, Research Organization, Resource Relation and/or Author (affiliation information) fields and/or via the "Full-text Availability" link. www.osti.gov /energycitations/product.biblio.jsp?osti_id=6035687

General procedure for preparation of phosphanes butyl­lithium reagent was added dropwise to a solution of brominated organic reagent in diethyl ether, after which a solution of the appropriate chlorophosphane in diethyl ether was added. herkules.oulu.fi /isbn9514270452/html/x340.html

Butyllithium.html - - - - - - - - - CHEMICAL IDENTIFICATION- - - - - - - - - - CATALOG #: 230707 NAME: BUTYLLITHIUM, 2.5M SOLUTION IN HEXANES SECTION 2. www.uiowa.edu /~chemsafe/MSDS/Butyllithium.html

expersec.htm n -Butyllithium (0.8 mmol, 0.5 ml of 1.6 M hexane solution) was added to a solution of 1-(di- tert -butylhydroxymethyl)-3,3-dimethylcyclopropene (0.084 g, 0.4 mmol) and PMDTA (0.07 ml, 0.4 mmol) in a mixture of THF (0.3 ml) and hexane (1.0 ml) at -50°C. The solution was then stirred for 30 min. n -Butyllithium (1.8 mmol, 1.15 ml of 1.6 M hexane solution) was added to a solution of 1-(di- tert -butylhydroxymethyl)-3,3-dimethylcyclopropene (0.388 g, 1.8 mmol) in hexane (0.5 ml) at 0°C. The solution was stirred for 2 h at this temperature and 1 h at room temperature. C, n -butyllithium (0.027 mol, 16.9 ml of a 1.6 M hexane solution) was added dropwise to a solution of diisopropylamine (2.7 g, 0.027 mol) in 20 ml Et The mixture was stirred and allowed to warm to room temperature (within 30 min). www2.ccc.uni-erlangen.de /services/dissonline/data/dissertation/Klas_Sorger/html/expersec.htm

HHMI Lab Safety: LCSS: BUTYLLITHIUMS Butyllithium solutions should be handled in the laboratory using the "basic prudent practices" described in Chapter 5.C, supplemented by the additional precautions for work with flammable (Chapter 5.F) and reactive (Chapter 5.G) substances. In particular, butyllithium should be stored and handled in areas free of ignition sources, and containers of butyllithium should be stored under an inert atmosphere. The risk of fire or explosion on exposure of butyllithium solutions to the atmosphere depends on the identity of the organolithium compound, the nature of the solvent, the concentration of the solution, and the humidity. www.hhmi.org /about/labsafe/lcss/lcss18.html

Patent 4048427: Preparation of solution polymers For the butyllithium initiated copolymerization of butadiene with styrene carried out in the presence of lithium t-butoxide a block polymer is obtained with a negligible change in the styrene incorporated with conversion [Wofford, C.F., and Hsieh, H.L., "J. Polymer Sci.," 7, Part A-1, 461 (1969)]. It was found the number-average molecular weight of the polymers prepared with the complex of n-butyllithium and the barium salts was equal to the ratio of the weight of polymer formed to the moles of butyllithium. The rate of polymerization is less with the butyllithium-barium salt catalyst than with a control polymerization with butyllithium at the same butyllithium concentration. www.freepatentsonline.com /4048427.html

Thieme-connect - Abstract tert -butyllithium is employed and at the position next to the halogen atom if the stoichiometric mixture of butyllithium and potassium 2- and 4-Fluoroanisole undergo hydrogen/metal exchange at the position next to the alkoxy moiety if butyllithium or Institut de Chimie organique de l'Université, Rue de la Barre 2, CH-1005 Lausanne, Switzerland www.thieme-connect.com /ejournals/abstract/synlett/doi/10.1055/s-1991-34754

Software-Entwicklung in der Chemie*10 - van Eikema Hommes, N. studied the reaction of n-butyllithium with benzaldehyde in THF at low temperature by means of rapid-injection NMR.[16] Under these conditions, an equilibrium exists between dimeric and tetrameric butyllithium. Only a few years ago, results from computational chemistry studies were frequently treated sceptically or overly critically.[1] No doubt, one of the reasons for this attitude was the inability of computational methods, at that time, to provide chemical information at a sufficiently high level of accuracy. The difference in the degree of aggregation is obviously due to the steric demand of the carbanion, but this is likely to affect the reaction rate as well. www2.ccc.uni-erlangen.de /external/cic/tagungen/workshop95/hommes

Patent 4348529: Synthesis of cyclic disulfone compounds (a) reacting a 1,3-dithio compound, ##STR25## wherein n is an integer 2, 3 or 4 with n-butyllithium in tetrahydrofuran to generate the anion of said 1,3-dithio compound; A method as defined in claim 1 wherein said n is 3. The subject invention also is concerned with the novel intermediates of step (c). www.freepatentsonline.com /4348529.html

Functionalized Organolithium Compounds Through an Arene-Catalyzed Lithiation To a solution of amine 7 (0.21g, 2mmol) in THF (2ml) was added a solution of n -butyllithium in hexane (1.25ml, 2mmol) at -78deg.C for 10 min. The successive reaction of chlorinated benzylic derivatives 4 with n -butyllithium and lithium in the presence of a catalytic amount of 4,4'-di- tert -butylbiphenyl (DTBB, 4 mol %) in THF at -78deg.C led to a solution of the corresponding dianion 5, which by treatment with different electrophiles [Bu t Deprotonation of amine 7 with n -butyllithium in THF at -78[integral]C followed by lithiation in the presence of a catalytic amount (2.5 mmol%) of DTBB led to the dianionic intermediate 8, which reacted with carbonyl compounds [Bu t pages.unibas.ch /mdpi/ecsoc/a0006/a0006.htm

United States Patent: 4,525,309 A solution of 3 mmol of lithium dicyclohexylamide was prepared from 3 mmol of 1.6M butyllithium in hexane and 3 mmol of dicyclohexylamine in 5 mL of tetrahydrofuran. This solution was cooled with an ice bath and added dropwise under argon to a stirred solution of 0.71 g (3 mmol) of (+)-pinanediol butane-1-boronate in 8 mL of tetrahydrofuran; cooled with an ice bath. wsurf5.respark.wsu.edu /US%20Issued%20Patents%20as%20of%207-22-2002/United%20States%20Patent%204,525,309.htm

Intro to Transition Metal Carbides Ceramic materials of mixed C, N, and O composition are also common, with oxycarbides of definite stoichiometry having been reported for a number of the early transition metals. Sample homogeneity and local compositions may be measured by microprobe analysis, in which the X-ray emission of elements on irradiation with an electron beam, as in an electron microscope, is measured and correlated with the concentration of the element. The Group IV-V carbides are able to form continuous solid solutions with each other over a wide range of compositions, but are only partially miscible with the carbides of the Group VI - VIII metals. www.ropine.com /chapter8.html

Substituted pyridopyrimidinones and related heterocycles as angiotensin II antagonists US Patent 5330987 Scheme 10 describes a method for preparing 2,3-disubstituted pyrido[3,4-d]pyrimidin-4(3H)-ones where E=O, N, S, or C 34 from an ortho aminopyridine carboxylic acid 35 combined with an imidate ester where E=O, N, S, or C. The resulting heterocycle may subsequently be alkylated in the usual fashion to give the desired 2,3-disubstituted pyrido[3,4-d]-pyrimidin-4(3H)-one 34. J and L are connected together to form a 6 membered aromatic ring containing one N atom that is not at J and five C atoms which may be substituted at the carbon atoms with R.sup.8a and R.sup.8b. J and L are connected together to form a 6 membered aromatic ring containing one N atom that is not at J and five C atoms which may be substituted at the carbon atoms with R.sup.7, R.sup.8a and R.sup.8b. patents.nimblewisdom.com /patent/5330987-Substituted-pyridopyrimidinones-and-related-heterocycles-as-angiotensin-

Erowid Online Texts : PiHKAL #178 3-T-TRIS There was then added 27.6 mL of 1.6 N butyllithium in hexane which resulted in the generation of a yellow color which was at first transient, and then stable. There was then added 25 mL of 1.6 N butyllithium in hexane and the mixture stirred for 15 min. The reaction mixture was brought up to room temperature, and 6.8 g 3,4-diethoxy-5-(ethylthio)benzaldehyde in 50 mL THF was added dropwise dispelling the color, and the mixture was held at reflux on the steam bath for 1 h. www.erowid.org /library/books_online/pihkal/pihkal178.shtml

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