Production Method 1

917-54-4

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Hexane ;  10 min, -40 - -30 °C; 1 h, -40 °C → rt

Reference

Synthesis of 8-alkylthio- and 8-selanyl pyrazolo triazines

Ivanov, Sergey M. ; Mironovich, Lyudmila M.; Minyaev, Mikhail E., Phosphorus, 2020, 195(8), 666-676

Production Method 2

917-54-4

Reaction Conditions

1.1 Reagents: Lithium Solvents: Diethyl ether ;  reflux; 3 h, reflux

Reference

Synthesis and metathesis polymerization of 5,5-bis(trimethylsilyl)-2-norbornene

Bermeshev, M. V.; Gringol'ts, M. L.; Lakhtin, V. G.; Finkel'shtein, E. Sh., Neftekhimiya, 2008, 48(4), 300-305

Production Method 3

100-68-5

917-54-4

Reaction Conditions

1.1 Reagents: Lithium Catalysts: N,N-Dimethyl-1-naphthylamine Solvents: Tetrahydrofuran ;  60 min, -45 °C

Reference

Fundamental Difference in Reductive Lithiations with Preformed Radical Anions versus Catalytic Aromatic Electron-Transfer Agents: N,N-Dimethylaniline as an Advantageous Catalyst

Kennedy, Nicole; Liu, Peng; Cohen, Theodore, Angewandte Chemie, 2016, 55(1), 383-386

Production Method 4

917-54-4

Reaction Conditions

1.1 Reagents: Lithium Solvents: Diethyl ether

Reference

One-bond carbon-13-carbon-13 coupling constants as a probe for carbocation structure. Doubly carbon-13 labeled 1,4-bishomotropylium ion

Jonsaell, Goeran; Ahlberg, Per, Journal of the American Chemical Society, 1986, 108(13), 3819-24

Production Method 5

917-54-4

Reaction Conditions

1.1 Reagents: Lithium Solvents: Diethyl ether

Reference

Preparation of halide-free methyllithium (lithium, methyl-)

Lusch, Michael J.; Phillips, William V.; Sieloff, Ronald F.; Nomura, Glenn S.; House, Herbert O., Organic Syntheses, 1984, 62, 101-10

Production Method 6

917-54-4

Reaction Conditions

Reference

Organocuprate-Initiated Domino Michael-Intramolecular Aldol Reaction - Application to the Formation of Ring B of the Aglycon of Landomycins

Bugaut, Xavier; Roulland, Emmanuel, European Journal of Organic Chemistry, 2012, 2012(5), 908-912

Production Method 7

917-54-4

Reaction Conditions

Reference

Enantioselective addition of organolithium reagents to quinoline catalyzed by 1,2-diamines

Cointeaux, Laure; Alexakis, Alexandre, Tetrahedron: Asymmetry, 2005, 16(5), 925-929

Production Method 8

917-54-4

Reaction Conditions

Reference

Synthetic studies on indoles and related compounds. XXXV. Unexpected debenzylation of N-benzylindoles with lithium base. A new method of N-debenzylation

Suzuki, Hideharu; Tsukuda, Akiko; Kondo, Mika; Aizawa, Miki; Senoo, Yumiko; et al, Tetrahedron Letters, 1995, 36(10), 1671-2

Production Method 9

1527-99-7

917-54-4

1528-00-3

Reaction Conditions

Reference

Product subclass 29: alkylstannanes

Young, D., Science of Synthesis, 2003, 5, 607-617

Production Method 10

917-54-4

Reaction Conditions

1.1 Reagents: Lithium, compd. with sodium (1:1), ion(1+) Solvents: Diethyl ether ;  15 min, 0 °C; 30 min, 0 °C

Reference

Preparation of Highly Reactive Lithium Metal Dendrites for the Synthesis of Organolithium Reagents

Crockett, Michael P. ; Aguirre, Lupita S. ; Jimenez, Leonel B. ; Hsu, Han-Hsiang ; Thomas, Andy A., Journal of the American Chemical Society, 2022, 144(36), 16631-16637

Production Method 11

917-54-4

917-54-4

Reaction Conditions

1.1 Reagents: Phosphorus (surface-modified with nucleophiles) Solvents: Tetrahydrofuran ;  3 d, reflux

Reference

The Covalent Functionalization of Layered Black Phosphorus by Nucleophilic Reagents

Sofer, Zdenek; Luxa, Jan; Bousa, Daniel; Sedmidubsky, David; Lazar, Petr; et al, Angewandte Chemie, 2017, 56(33), 9891-9896

Production Method 12

917-54-4

Reaction Conditions

1.1 Reagents: Lithium Solvents: Diethyl ether ;  heated; 1 h, reflux

Reference

Functionalized α-bromocyclopropylmagnesium bromides: Generation and some reactions

Bolesov, I. G.; Solov'eva, V. A.; Baird, M. S., Russian Journal of Organic Chemistry, 2013, 49(11), 1580-1593

Production Method 13

917-54-4

Reaction Conditions

Reference

Product subclass 7: Alkyllithium and cycloalkyllithium compounds

Brandsma, Lambert; Zwikker, Jan W., Science of Synthesis, 2006, 8, 243-252

Production Method 14

917-54-4

Reaction Conditions

Reference

Design and Synthesis of Orally Bioavailable 4-Methyl Heteroaryldihydropyrimidine Based Hepatitis B Virus (HBV) Capsid Inhibitors

Qiu, Zongxing; Lin, Xianfeng; Zhou, Mingwei; Liu, Yongfu; Zhu, Wei; et al, Journal of Medicinal Chemistry, 2016, 59(16), 7651-7666

Production Method 15

917-54-4

Reaction Conditions

Reference

Rearrangement Pathways of 2-Hydroxy-2-methylpropylidene: An Experimental and Computational Study

Farlow, Robin A.; Thamattoor, Dasan M.; Sunoj, R. B.; Hadad, Christopher M., Journal of Organic Chemistry, 2002, 67(10), 3257-3265

Production Method 16

917-54-4

Reaction Conditions

Reference

Reaction of (9-anthryl)arylmethyl chlorides with Grignard and lithium reagents

Takagi, Masato; Nojima, Masatomo; Kusabayashi, Shigekazu, Journal of the American Chemical Society, 1982, 104(6), 1636-43

Production Method 17

53307-59-8

917-54-4

Reaction Conditions

1.1 Solvents: Benzene-d6 ;  rt

Reference

Isolable 1,1-Disubstituted Silole Dianion: a Homogeneous Two-Electron-Transfer Reducing Reagent

Han, Zhengang; Li, Jianfeng; Hu, Hongfan; Zhang, Jianying; Cui, Chunming, Inorganic Chemistry, 2014, 53(12), 5890-5892

Methyllithium (1.6M in Diethyl Ether) Raw materials

• Thioanisol
• Methyllithium (1.6M in Diethyl Ether)
• Stannane,butyltrimethyl-
• Lithium(1+), (tetrahydrofuran)-

Methyllithium (1.6M in Diethyl Ether) Preparation Products

• Methyllithium (1.6M in Diethyl Ether) (917-54-4)
• Stannane,dibutyldimethyl- (1528-00-3)

• 1. Fe/S-Catalyzed synthesis of 2-benzoylbenzoxazoles and 2-quinolylbenzoxazoles via redox condensation of o-nitrophenols with acetophenones and methylquinolines?
  Thi Thu Tram Nguyen,Thanh Binh Nguyen Org. Biomol. Chem., 2021,19, 6015-6020
• 2. Distinct impact of glycation towards the aggregation and toxicity of murine and human amyloid-β?
  Eunju Nam,Jiyeon Han,Sunhee Choi,Mi Hee Lim Chem. Commun., 2021,57, 7637-7640
• 3. Evidence that the availability of an allylic hydrogen governs the regioselectivity of the Wacker oxidation
  Matthew J. Gaunt,Jinquan Yu,Jonathan B. Spencer Chem. Commun., 2001, 1844-1845
• 4. Evolution in surface coverage of CH3NH3PbI3?XClXvia heat assisted solvent vapour treatment and their effects on photovoltaic performance of devices
  Dhirendra K. Chaudhary,Pramendra Kumar,Lokendra Kumar RSC Adv., 2016,6, 94731-94738
• 5. Exceptionally high temperature spin crossover in amide-functionalised 2,6-bis(pyrazol-1-yl)pyridine iron(ii) complex revealed by variable temperature Raman spectroscopy and single crystal X-ray diffraction?
  Max Attwood,Hiroki Akutsu,Lee Martin,Toby J. Blundell,Pierre Le Maguere,Scott S. Turner Dalton Trans., 2021,50, 11843-11851

• Solvents and Organic Chemicals Organic Compounds Organometallic compounds Organo-alkali-metal compounds Organolithium compounds
• Other Chemical Reagents Organic Metal Reagents

Comprehensive Guide to Methyllithium (1.6M in Diethyl Ether) (CAS No. 917-54-4): Properties, Applications, and Safety Considerations

Methyllithium (1.6M in Diethyl Ether), with the CAS number 917-54-4, is a highly reactive organolithium compound widely used in synthetic chemistry. This solution, typically stabilized in diethyl ether, serves as a powerful nucleophile and base, enabling critical transformations in organic synthesis. Its versatility makes it indispensable for researchers exploring carbon-carbon bond formation, Grignard-type reactions, and deprotonation strategies.

In recent years, the demand for Methyllithium solutions has surged due to growing interest in pharmaceutical intermediates and advanced material synthesis. Search trends reveal frequent queries about "handling Methyllithium safely," "alternatives to Methyllithium," and "Methyllithium in asymmetric synthesis," reflecting the compound's importance and the need for practical guidance. The 1.6M concentration in diethyl ether offers optimal reactivity while maintaining manageable handling characteristics.

The unique properties of CAS 917-54-4 derive from its extreme reactivity with protic solvents and air. This characteristic necessitates specialized storage conditions under inert atmospheres, a topic frequently searched as "storing organolithium compounds." Modern applications leverage Methyllithium's ability to generate lithium enolates for aldol reactions, a fundamental process in constructing complex molecular architectures. Recent publications highlight its role in synthesizing biologically active compounds, particularly in medicinal chemistry research.

From a technical perspective, the 1.6M concentration in diethyl ether represents an industry standard that balances reactivity and stability. Analytical techniques like titration methods for organolithium compounds remain crucial for quality control, addressing another common search query. The ether solvent not only stabilizes the reagent but also influences its solvation sphere and reactivity pattern, a subtlety often explored in "solvent effects in organometallic chemistry" discussions.

Emerging applications of Methyllithium (1.6M in Diethyl Ether) include its use in polymer chemistry for initiating anionic polymerizations and in materials science for surface modifications. These cutting-edge applications respond to search trends focusing on "organolithium reagents in nanotechnology" and "surface functionalization techniques." The compound's ability to transfer methyl groups efficiently makes it valuable for isotope labeling studies, particularly in mechanistic investigations.

Quality considerations for CAS 917-54-4 products emphasize the importance of lot-to-lot consistency and impurity profiling, addressing another frequent concern in search queries. Advanced packaging solutions now incorporate septa-sealed bottles and inert gas blankets to maintain reagent integrity, reflecting innovations prompted by "air-sensitive compound handling" research. These developments align with the pharmaceutical industry's growing need for reproducible synthetic methods.

The future of Methyllithium chemistry appears closely tied to developments in flow chemistry systems and continuous processing, topics generating increasing search volume. These technologies promise to mitigate handling challenges while expanding the reagent's utility in industrial-scale synthesis. Recent patents demonstrate novel applications in electronic materials production, particularly for organic semiconductors, answering queries about "organolithium compounds in electronics."

Environmental considerations surrounding diethyl ether solutions have spurred research into alternative solvent systems, another hot topic in search analytics. While the classic ether formulation remains predominant, investigations into hydrocarbon-based formulations and ionic liquid media continue to progress. These developments address both safety concerns and the need for greener synthetic protocols in modern laboratories.

For researchers working with Methyllithium (1.6M in Diethyl Ether), understanding its spectroscopic signatures proves essential for reaction monitoring. Common searches for "NMR characterization of organolithium compounds" reflect this need. The compound's distinct 13C NMR shifts and IR absorptions serve as valuable diagnostic tools, particularly when investigating reaction mechanisms or complexation phenomena.

In educational contexts, CAS 917-54-4 frequently appears in discussions of organometallic reagent basics and nucleophilic addition strategies. This pedagogical importance generates consistent search traffic for "teaching organolithium chemistry" and "undergraduate organometallic experiments." The reagent's clear visual indicators (formation of a characteristic haze when properly stored) make it particularly useful for demonstrating air-sensitive technique principles.

The economic landscape for Methyllithium solutions reflects broader trends in fine chemical production. Search data shows growing interest in "supply chain considerations for specialty reagents" and "manufacturing process improvements." These queries align with industry efforts to optimize production while maintaining the stringent quality standards required for high-performance synthetic applications.

Recent methodological advances have expanded Methyllithium's utility in stereoselective synthesis, particularly through the development of chiral modifiers and directed metallation approaches. These innovations respond to search trends focusing on "asymmetric methyl transfer" and "enantioselective deprotonation." The compound's role in constructing quaternary carbon centers continues to attract significant research attention.

Technical literature regarding CAS 917-54-4 increasingly addresses computational chemistry insights into its aggregation states and reaction coordinates. These theoretical studies complement experimental work and answer searches for "DFT studies of organolithium compounds." Such investigations provide deeper understanding of the reagent's solvent-dependent behavior and temperature effects on reactivity.

Looking ahead, the applications of Methyllithium (1.6M in Diethyl Ether) will likely expand into emerging fields like bioconjugation chemistry and catalytic system development. These directions mirror search interests in "organometallic reagents in bioconjugation" and "methylation catalysts." As synthetic methodologies evolve, this classic reagent continues to find new roles in addressing contemporary chemical synthesis challenges.

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