24850-33-7

Basic information

• Product Name: Allyltributyltin
• Synonyms: ALLYLTRIBUTYLSTANNANE;ALLYLTRIBUTYLTIN;ALLYLTRIBUTYLTIN(IV);ALLYLTRI-N-BUTYLTIN;TRIBUTYL-2-PROPENYLSTANNANE;Stannane, tributyl-2-propenyl-;Allytri-N-Butyltin;Allyltri-n-butyltin,97%
• CAS NO: 24850-33-7
• Molecular Formula: C₁₅H₃₂Sn
• Molecular Weight: 331.12
• EINECS: 246-494-3
• Product Categories: Alkyl Metals;Sn (Tin) Compounds;Classes of Metal Compounds;Grignard Reagents & Alkyl Metals;Synthetic Organic Chemistry;Typical Metal Compounds;Organometallic Reagents;Organotin;Organotins;Stannanes;Chemical Synthesis;Organometallic Reagents
• Mol File: 24850-33-7.mol

Chemical Properties

• Melting Point: 134-135 °C
• Boiling Point: 88-92 °C0.2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless/Liquid
• Density: 1.068 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00098mmHg at 25°C
• Refractive Index: n20/D 1.486(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Immiscible with water.
• Sensitive: Air Sensitive
• BRN: 3588340
• CAS DataBase Reference: Allyltributyltin(CAS DataBase Reference)
• NIST Chemistry Reference: Allyltributyltin(24850-33-7)
• EPA Substance Registry System: Allyltributyltin(24850-33-7)

Safety Data

• Hazard Codes: T,N
• Statements: 21-25-36/38-48/23/25-50/53-23/24/25
• Safety Statements: 35-36/37/39-45-60-61-28-27-26
• RIDADR: UN 2788 6.1/PG 2
• WGK Germany: 3
• F: 13
• TSCA: No
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 24850-33-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Allyltributyltin is used as an allylation reagent for aldehydes in the chemical synthesis industry. It is particularly effective when catalyzed by chiral Lewis acids and ytterbium(III) trifluoromethanesulfonate, leading to efficient allylation and the formation of homoallylic alcohols.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, allyltributyltin is used as a key component in the synthesis of various drugs and pharmaceutical compounds. Its ability to undergo tetrakis(triphenylphosphine)palladium(0) catalyzed coupling with iodoquinones and allyl acetates makes it a valuable tool in the development of new medications.
Used in Catalyst Formulation:
Allyltributyltin is also utilized in the formulation of catalysts for various chemical reactions. Its compatibility with chiral Lewis acids and ytterbium(III) trifluoromethanesulfonate makes it a suitable candidate for creating catalysts that can enhance the efficiency and selectivity of chemical processes.
Used in Research and Development:
In the field of research and development, allyltributyltin is employed as a reagent for exploring new chemical reactions and pathways. Its unique properties and reactivity make it an interesting subject for study, potentially leading to the discovery of novel compounds and applications.

Purification Methods

A possible impurity is tributylchlorostannane — test for Cl as Cl ion after hydrolysing. Dissolve it in *C6H6 (or toluene), shake this with dilute aqueous NaOH, dry (CaCl2), filter, evaporate and distil the residue in a vacuum [Jones et al. J Chem Soc 1446 1947, Bristow Aldrichimica Acta 17 75 1984, Yamamoto Aldrichimica Acta 20 45 1987]. [Beilstein 4 IV 4317.]

InChI:InChI=1/3C4H9.C3H5.Sn/c3*1-3-4-2;1-3-2;/h3*1,3-4H2,2H3;3H,1-2H2;/rC15H32Sn/c1-5-9-13-16(12-8-4,14-10-6-2)15-11-7-3/h8H,4-7,9-15H2,1-3H3

Upstream product

• 1461-22-9 tributyltin chloride 
• 3052-45-7 allyllithium 
• 109-72-8 n-butyllithium 
• 1706-95-2 2-propenyl diphenylphosphinate 
• 100-52-7 benzaldehyde 
• 106-95-6 allyl bromide 
• 56-35-9 bis(tri-n-butyltin)oxide 
• 107-05-1 3-chloroprop-1-ene 
• 1185-08-6 2,2,3-trimethylhex-5-en-3-ol 
• 1067-52-3 tributyltin methoxide 
• 19550-90-4 methyl-isopropyl-allyl-carbinol 
• 32189-75-6 2,4-dimethyl-6-hepten-4-ol 
• 74-85-1 ethene 
• 7486-35-3 tri-n-butyl(vinyl)tin 

Downstream Products

• 960-16-7 tributylphenylstannane 
• 26118-97-8 2-allyl-3-pentanone 
• 300-57-2 allylbenzene 
• 140-67-0 Estragole 
• 1813-96-3 3-<3-(trifluoromethyl)phenyl>propene 
• 62108-07-0 4-hydroxy-4-propyl-1-heptene 
• 57082-90-3 1-allyl-4-(tert-butyl)cyclohexane 
• 3333-13-9 p-allyltoluene 
• 24165-63-7 1-p-tolyl-3-buten-1-ol 
• 1968-40-7 ethyl 4-pentenoate 
• 3240-29-7 1-Phenylpent-4-en-1-one 
• 24401-36-3 2-phenyl-4-penten-1-al 
• 67592-76-1 2-(4-chlorophenyl)pent-4-enal 
• 1737-16-2 1-allyl-4-fluorobenzene 

Relevant articles and documents

Extremely Facile and Stereoselective Preparation of Allylstannanes with Use of Ultrasound

Various allylstannanes are conveniently prepared in quantitative yields by means of ultrasound-promoted Barbier-type reaction from chlorotributylstannane and allyl halides in a stereoselective manner.

Photoredox-Catalyzed C-F Bond Allylation of Perfluoroalkylarenes at the Benzylic Position

Site-selective and direct C-F bond transformation of perfluoroalkylarenes was achieved with allylic stannanes via an iridium photoredox catalyst system. The present defluoroallylation proceeds exclusively at the benzylic position through perfluoroalkyl radicals generated by a single-electron transfer from an excited photoredox catalyst to perfluoroalkylarenes. A variety of perfluoroalkyl groups are applicable: linear perfluoroalkyl-substituted arenes such as Ar-nC4F9and Ar-nC6F13and heptafluoroisopropylarenes (Ar-CF(CF3)2) underwent site-selective defluoroallylation. DFT calculation studies revealed that thein situgenerated Bu3SnF traps F-to prevent a retroreaction from the unstable perfluoroalkyl radical intermediate, and the radical intermediate favorably reacts with allylic stannanes. The synthesis of a bis(trifluoromethyl)methylene unit containing compound, which is an analog that is useful as a pharmaceutical agent for the prophylaxis or treatment of diabetes and inflammatory diseases, demonstrated the utility of this reaction.

Novel compound 6,6-dimethyl tetrahydropyran-2-methanol and preparing method thereof

The invention discloses a novel compound that is 6,6-dimethyl tetrahydropyran-2-methanol and a preparing method thereof. The method includes preparing benzyloxy ethanol by utilizing a sodium alkoxideprocess; then oxidizing the benzyloxy ethanol into benzyloxy acetaldehyde by utilizing a swern oxidation process; reacting the benzyloxy acetaldehyde and allyltributyltin prepared by utilizing a Grignard reaction to obtain 1-(benzyloxy)-4-penten-2-ol; subjecting the 1-(benzyloxy)-4-penten-2-ol and acetone to cyclization under catalysis of trimethylchlorosilane and potassium iodide to obtain 4-iodo-6,6-dimethyl tetrahydropyran-2-methanol; and subjecting the 4-iodo-6,6-dimethyl tetrahydropyran-2-methanol to hydrogenation to remove iodine to obtain the target product that is the 6,6-dimethyl tetrahydropyran-2-methanol. According to the method, reactions are relatively mild, products can be easily treated and purified, and the method is suitable for batch preparation, and therefore the methodhas important application value.

Forging C-C Bonds with Hindered Nucleophiles and Carbonyl Electrophiles: Reactivity and Selectivity of Allylic Tin Reagents/n-BuLi

Under activation with n-BuLi, trialkylstannanes containing crotyl-, geranyl-, and phenyldienylmethyl appendages were reacted with efficiency and selectivity to various ketone and enone electrophiles with low reactivity. The straightforward process gives access to tertiary alcohols that are vicinal to quaternary carbons. With α,α′-dimethoxy-γ-pyrone, on the other hand, the grafting of a dienyl side chain was effected to prepare dienyl α′-methoxy-γ-pyrone in a stereo- and regioselective and convergent manner. Furthermore, the advantages of this route were highlighted for the preparation of organolithium species at low temperature with the formation of a minimum amount of salts. Synthetic manipulations were demonstrated to illustrate the potential of the chemistry for constructing acyclic and cyclic terpene scaffolds.

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

Practical Stannylation of Allyl Acetates Catalyzed by Nickel with Bu3SnOMe

A practical and scalable nickel-catalyzed allylic stannylation of allyl acetates with Bu3SnOMe is described. A variety of acyclic and cyclic allyl acetates, even with base-sensitive moieties, undergoes the stannylation by using NiBr2/4,4′-di-tert-butylbipyridine (dtbpy)/Mn catalyst system to afford highly functionalized allyl stannanes with excellent regioselectivity and yields. Furthermore, the scope of protocol is also extended by the reaction of propargyl acetates, giving rise to propargyl or allenyl stannanes. Additionally, a unique diastereoselectivity using the nickel catalyst different from the palladium was demonstrated for the stannylation of cyclic allyl acetates. In the reaction, inexpensive and stable nickel complexes, abundant reductant (Mn), and atom-economical stannyl source were used.

Stannyl-Lithium: A Facile and Efficient Synthesis Facilitating Further Applications

We have developed a highly efficient, practical, polycyclic aromatic hydrocarbon (PAH)-catalyzed synthesis of stannyl lithium (Sn-Li), in which the tin resource (stannyl chloride or distannyl) is rapidly and quantitatively transformed into Sn-Li reagent at room temperature without formation of any (toxic) byproducts. The resulting Sn-Li reagent can be stored at ambient temperature for months and shows high reactivity toward various substrates, with quantitative atom efficiency.

Catalytic enantioselective amide allylation of isatins and its application in the synthesis of 2-oxindole derivatives spiro-fused to the α-methylene-γ-butyrolactone functionality

This article is a full account of the work exploring the potential utility of catalytic enantioselective amide allylation of various isatins using indium-based chiral catalysts. A survey of various isatin substrates and NH-containing stannylated reagents revealed that the reaction has a remarkably wide scope to result in extremely high yields and enantioselectivities (up to >99 %, 99 % ee) of variously substituted homoallylic alcohols. Several mechanistic investigations demonstrated that the substrate-reagent hydrogen-bond interaction plays a critical role in the formation of the key transition states to result in enhanced catalytic reaction. The success of this approach allowed convenient access to chiral 2-oxindoles spiro-fused to the α-methylene- γ-butyrolactone functionality and their halogenated derivatives in almost enantiopure forms, thus highlighting the general utility of this synthetic method to deliver a large variety of antineoplastic drug candidates and pharmaceutically meaningful compounds.

Hybrid Host Materials For Electrophosphorescent Devices

Compounds (including polymers) for use in hybrid host materials which can be used in electroluminescent devices. The compounds comprise at least one electron-transporting moiety and at least one hole-transporting moiety which are joined by a flexible linker. Hybrid host materials comprising the compounds exhibit stability against phase separation, elevated glass transition temperature, morphological stability against crystallization, and isolation of the electron transporting moiety and hole transporting moiety π-systems.

Selective green coupling of alkynyltins and allylic halides to trienynes via a tandem double stille reaction

The palladium-catalyzed reaction of alkynyltin compounds with allylic chlorides leads to a 2:2 coupling to give trienynes by regio- and stereoselective formation of three new C-C bonds. The reaction can be applied to different alkynyl and allylic fragments, providing a wide range of trienynes with different substitution patterns in very good yields. They can be prepared in a green way using recyclable polymeric tin alkynyls. Copyright