70744-47-7

Basic information

• Product Name: TRIBUTYL(4-METHOXYPHENYL)STANNANE
• Synonyms: TRIBUTYL(4-METHOXYPHENYL)STANNANE;(4-Methoxyphenyl)tributyltin;Stannane, tributyl(4-methoxyphenyl)-;(4-Methoxyphenyl)tributylstannane, 1-Methoxy-4-(tributylstannyl)benzene;(p-Methoxyphenyl)tributylstannane;p-(Tributylstannyl)anisole;Tributyl(4-methoxyphenyl)tin;Tributyl(p-methoxyphenyl)stannane
• CAS NO: 70744-47-7
• Molecular Formula: C₁₉H₃₄OSn
• Molecular Weight: 397.18
• Mol File: 70744-47-7.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 398℃
• Flash Point: 195℃
• Appearance: /
• Vapor Pressure: 3.51E-06mmHg at 25°C
• CAS DataBase Reference: TRIBUTYL(4-METHOXYPHENYL)STANNANE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIBUTYL(4-METHOXYPHENYL)STANNANE(70744-47-7)
• EPA Substance Registry System: TRIBUTYL(4-METHOXYPHENYL)STANNANE(70744-47-7)

Safety Data

• Hazardous Substances Data: 70744-47-7(Hazardous Substances Data)

Usage

General Description

Tributyl(4-methoxyphenyl)stannane is a chemical compound primarily used in organic synthesis and as a reagent in the production of pharmaceuticals and agrochemicals. It is a tin-based organometallic compound that contains a butyl group and a 4-methoxyphenyl group attached to a central tin atom. Tributyl(4-methoxyphenyl)stannane is commonly used as a reagent in Stille coupling reactions, which are widely employed in the synthesis of complex organic molecules. It is also used as a precursor in the preparation of various tin-containing materials and complexes, which have applications in catalysis, materials science, and medicinal chemistry. TRIBUTYL(4-METHOXYPHENYL)STANNANE should be handled with care and proper safety precautions, as organotin compounds can be toxic and have potential environmental impacts.

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 articles and documents

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.

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.