70744-47-7

Usage

Uses

Used in Organic Synthesis:
TRIBUTYL(4-METHOXYPHENYL)STANNANE is used as a reagent for facilitating Stille coupling reactions, which are crucial for the synthesis of complex organic molecules. This application is significant in creating a variety of chemical compounds that are vital for pharmaceutical and agrochemical development.
Used in Pharmaceutical Production:
In the pharmaceutical industry, TRIBUTYL(4-METHOXYPHENYL)STANNANE serves as a precursor in the preparation of tin-containing materials and complexes. These materials are essential for the development of new drugs and medicinal compounds, contributing to advancements in medicinal chemistry.
Used in Agrochemical Production:
Similarly, in agrochemicals, TRIBUTYL(4-METHOXYPHENYL)STANNANE is utilized as a precursor for the synthesis of compounds that are integral to the development of pesticides and other agricultural chemicals, enhancing crop protection and yield.
Used in Catalysis:
TRIBUTYL(4-METHOXYPHENYL)STANNANE is also used as a component in catalytic processes, where it aids in the acceleration of chemical reactions, playing a significant role in industrial chemical production and the synthesis of various compounds.
Used in Materials Science:
In the field of materials science, TRIBUTYL(4-METHOXYPHENYL)STANNANE contributes to the development of new materials with unique properties, such as those used in electronic devices, sensors, and other advanced technologies.
Safety Note:
Due to the potential toxicity of organotin compounds and their environmental impacts, TRIBUTYL(4-METHOXYPHENYL)STANNANE should be handled with care and proper safety precautions to mitigate any risks associated with its use.

InChI:InChI=1/C7H7O.3C4H9.Sn/c1-8-7-5-3-2-4-6-7;3*1-3-4-2;/h3-6H,1H3;3*1,3-4H2,2H3;/rC19H34OSn/c1-5-8-15-21(16-9-6-2,17-10-7-3)19-13-11-18(20-4)12-14-19/h11-14H,5-10,15-17H2,1-4H3

Upstream product

• 623-12-1 4-chloromethoxybenzene 
• 688-73-3 tri-n-butyl-tin hydride 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 1461-22-9 tributyltin chloride 
• 7440-66-6 zinc 
• 696-62-8 para-iodoanisole 
• 7646-78-8 tin(IV) chloride 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 813-19-4 bis(tri-n-butyltin) 
• 17955-46-3 trimethylsilyltributyltin 
• 24850-33-7 allyltributylstanane 
• 5720-07-0 4-methoxyphenylboronic acid 
• 1067-52-3 tributyltin methoxide 
• 701-53-1 p-methoxybenzoyl fluoride 

Downstream Products

• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 84132-74-1 2-(4-methoxyphenyl)-2,5-dihydrofuran 
• 17494-29-0 4-(4-methoxy-benzyl)-morpholine 
• 122439-15-0 N-(4-methoxybenzyl)pyrrolidine 
• 103348-78-3 2-(4-methoxyphenyl)hexahydrooxepine 
• 132723-33-2 2-(4-methoxyphenyl)-tetrahydro-2H-pyran 
• 79623-15-7 2-p-methoxyphenyltetrahydrofuran 
• 103348-77-2 3-chloro-4-(4-methoxyphenyl)-butan-1-ol 
• 103348-70-5 6-(4-Methoxy-phenyl)-2,2-dimethyl-tetrahydro-pyran 
• 103348-68-1 (2R,4R)-2-(4-Methoxy-phenyl)-4-methyl-tetrahydro-pyran 
• 103348-68-1 (2R,4S)-2-(4-Methoxy-phenyl)-4-methyl-tetrahydro-pyran 
• 15175-54-9 N,N-dimethyl-4-methoxylbenzylamine 
• 103348-73-8 (2R,3R)-2-(4-Methoxy-phenyl)-3-methyl-tetrahydro-pyran 
• 103348-74-9 (5S,6S)-6-(4-Methoxy-phenyl)-2,2,5-trimethyl-tetrahydro-pyran 

Relevant academic research and scientific papers

Mild and Robust Stille Reactions in Water using Parts Per Million Levels of a Triphenylphosphine-Based Palladacycle

An inexpensive and new triphenylphosphine-based palladacycle has been developed as a pre-catalyst, leading to highly effective Stille cross-coupling reactions in water under mild reaction conditions. Only 500–1000 ppm of Pd suffices for couplings involving a variety of aryl/heteroaryl halides with aryl/hetaryl stannanes. Several drug intermediates can be prepared using this catalyst in aqueous nanoreactors formed by 2 wt % Brij-30 in water.

Development of oxathiino[6,5-b]pyridine 2,2-dioxide derivatives as selective inhibitors of tumor-related carbonic anhydrases IX and XII

Oxathiino[6,5-b]pyridine 2,2-dioxides are identified as a new class of isoform-selective nanomolar inhibitors of tumor associated human carbonic anhydrases (hCA) IX and XII. At the same time they do not inhibit or poorly inhibit cytosolic isoforms hCA I and II. Oxathiino[6,5-b]pyridine 2,2-dioxides exhibited good antiproliferative properties on tumor cell lines MCF-7 (Human breast adenocarcinoma), A549 (human lung (alveolar) adenocarcinoma) and HeLa (epithelioid cervix carcinoma).

Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions

Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions was disclosed. A variety of aromatic acyl fluorides are capable of reacting with silylstannanes in the presence of cesium fluoride. A one-pot decarbonylative stannylation/Migita-Kosugi-Stille reaction of benzoyl fluoride, giving rise to the direct formation of the corresponding cross-coupled products, further demonstrated the synthetic utility of the present method. This newly developed methodology with a good functional-group compatibility via C-F bond cleavage and C-Sn bond formation under nickel catalysis opens a new area for the functionalization of acyl fluorides in terms of carbon-heteroatom bond formation.

Stannylation of Aryl Halides, Stille Cross-Coupling, and One-Pot, Two-Step Stannylation/Stille Cross-Coupling Reactions under Solvent-Free Conditions

Solvent-free protocols for palladium-catalyzed stannylation of aryl halides, Stille cross-coupling, and one-pot, two-step stannylation/Stille cross-coupling (SSC) are reported for the first time. (Het)aryl halides bearing acceptor, donor, as well as sterically demanding substituents are stannylated and/or coupled in high yields. The reactions are catalyzed by conventional palladium(II) acetate/PCy3 [Pd(OAc)2/PCy3] under air, using available base CsF, and without the use of high purity reagents. The developed synthetic procedures are versatile, robust, and easily scalable. The absence of solvent, and the elimination of isolation procedures of aryl stannanes makes the SSC protocol simple, step economical, and highly efficient for the synthesis of biaryls in a one-pot two-step procedure.

Gold(i)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes

Gold(i)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes are described. This redox neutral strategy offers an efficient approach to diverse biaryls, vinyl arenes and arylacetylenes. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the in situ formation of Ph3PAuIR (R = aryl, vinyl and alkynyl) species which is crucial for the activation of aryldiazonium salts.

Controllable Stereoselective Synthesis of (Z)- and (E)-Homoallylic Alcohols Using a Palladium-Catalyzed Three-Component Reaction

Diastereoselective synthesis of (Z)- and (E)-homoallylic alcohols using a Pd-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl benzoates, aldehydes, and aryl stannanes was developed, which provides an alternative method for the allylboration of aldehydes using α, γ-diaryl-substituted allylboronates. Both sets of reaction conditions enable access to either (Z)- or (E)-homoallylic alcohols with good to high alkene stereocontrol. The present method showed good functional group compatibility and generality. Efficient chirality transfer reactions to afford enantioenriched (Z)- and (E)-homoallylic alcohols were also achieved.

Pd-mediated cross-coupling of C-17 lithiated androst-16-en-3-ol-access to functionalized arylated steroid derivatives

Herein, we report on Pd-mediated cross-coupling of vinyllithium steroids and aryl bromides to introduce various substituted aryls at C-17 of steroidal frameworks based on the structure of epi-androsterone. Compared to other C-C cross-couplings, this method turned out to be an easy and competitive access to biologically interesting C-17 modified steroids.

Stille and Suzuki Cross-Coupling Reactions as Versatile Tools for Modifications at C-17 of Steroidal Skeletons – A Comprehensive Study

Herein, we report on a comparative Stille and Suzuki cross-coupling study of steroidal vinyl (pseudo)halides with different boronic acids and tributyltin organyls. Furthermore, we have investigated the “inverse” case of those cross-coupling reactions, i.e., the reaction of a steroidal vinylpinacolatoborane or a tributyltin steroid with various bromides. The development of both methods allows the introduction of different residues at C-17 of steroid skeletons providing access to a broad variety of steroid analogues which are of high interest for biological screenings or natural product synthesis. (Figure presented.).

METHOD FOR PRODUCING 14 GROUP METAL LITHIUM COMPOUND

PROBLEM TO BE SOLVED: To provide a method for quantitatively producing a group 14 metal lithium compound under a mild condition. SOLUTION: The method for producing a group 14 metal lithium compound represented by formula (4): R4-nMLin comprises reacting a compound represented by formula (1): R4-nMXn and lithium in the presence of a polycyclic aromatic compound represented by formula (2) or formula (3). [In formula (1) and formula (2), R is a hydrocarbon group; M is a metal atom selected from Si, Ge and Sn; X is a halogen atom or R3M- (R and M are the same as mentioned above); and n is 1 or 2] and [R1 is H or a hydrocarbon group; and m is an integer of 0 to 5.] SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

A Sn atom-economical approach toward arylstannanes: Ni-catalysed stannylation of aryl halides using Bu3SnOMe

Stannylation of carbon-halogen bonds is one of the most promising and straightforward approaches for the preparation of organostannane compounds. Although a wide variety of methods are now available, all protocols require the use of highly nucleophilic organometals or wasteful stannyl sources like distannanes. Here, we report a new nickel-catalysed stannylation of aryl and alkenyl-halides using Bu3SnOMe as a stannyl source to afford aryl and vinyl-stannanes, respectively. This method enables the stannylation of not only bromides, but also chlorides and triflates to furnish functionalized aryl- and alkenyl-stannanes without the release of wasteful and toxic stannyl byproducts.