67883-62-9

Basic information

• Product Name: METHALLYLTRI-N-BUTYLTIN
• Synonyms: 2-METHYLALLYLTRIBUTYLTIN;METHALLYLTRI-N-BUTYLTIN;TRIBUTY(2-METHYL-2-PROPENYL)STANNANE;Tributyl(2-methyl-2-propenyl)stannane;Methallyltri-n-butylstannane~Tri-n-butyl(2-methyl-2-propenyl)stannane;methallyltri-n-butylstannane;tri-n-butyl(2-methyl-2-propenyl)stannane;METHALLYLTRI-N-BUTYLIN
• CAS NO: 67883-62-9
• Molecular Formula: C₁₆H₃₄Sn
• Molecular Weight: 345.15
• EINECS: -0
• Mol File: 67883-62-9.mol

Chemical Properties

• Boiling Point: 328.6°C at 760 mmHg
• Flash Point: 156.7°C
• Appearance: /
• Density: 1,487 g/cm3
• Vapor Pressure: 0.000358mmHg at 25°C
• Refractive Index: 1.4875
• Water Solubility: Fully miscible with water.
• CAS DataBase Reference: METHALLYLTRI-N-BUTYLTIN(CAS DataBase Reference)
• NIST Chemistry Reference: METHALLYLTRI-N-BUTYLTIN(67883-62-9)
• EPA Substance Registry System: METHALLYLTRI-N-BUTYLTIN(67883-62-9)

Safety Data

• Statements: 21-25-36/38-48/23/25-50/53
• Safety Statements: 36/37/39-45
• RIDADR: 2788
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 67883-62-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
METHALLYLTRI-N-BUTYLTIN is used as a methallylating reagent for the introduction of methallyl groups into various organic compounds. This property makes it a valuable tool in the synthesis of complex organic molecules and the modification of existing compounds to enhance their properties.
Used as a Sole Curative:
In addition to its role as a methallylating reagent, METHALLYLTRI-N-BUTYLTIN is also used as a sole curative. This means that it can be used independently to achieve a desired outcome in a chemical reaction, without the need for additional reagents or catalysts.
Used in Pharmaceutical Industry:
METHALLYLTRI-N-BUTYLTIN is used as a primary and secondary intermediate in the pharmaceutical industry. Its versatility as a reagent and intermediate allows it to be incorporated into the synthesis of various drugs and medicinal compounds, contributing to the development of new and improved treatments for a wide range of diseases and conditions.

InChI:InChI=1/C4H7.3C4H9.Sn/c1-4(2)3;3*1-3-4-2;/h1-2H2,3H3;3*1,3-4H2,2H3;/rC16H34Sn/c1-6-9-12-17(13-10-7-2,14-11-8-3)15-16(4)5/h4,6-15H2,1-3,5H3

Upstream product

• 1461-22-9 tributyltin chloride 
• 5674-01-1 2-methylallylmagnesium chloride 
• 4226-01-1 tri-n-butyltin lithium 
• 463-49-0 1,2-propanediene 
• 7439-93-2 lithium 
• 563-47-3 3-Chloro-2-methylpropene 
• 563-52-0 2-chloro-3-butene 
• 557-91-5 1,1-Dibromoethane 
• 109-72-8 n-butyllithium 
• 1458-98-6 2-methyl-3-bromo-1-propene 
• 820-71-3 methallyl acetate 
• 1067-52-3 tributyltin methoxide 
• 598-25-4 Dimethylallene 
• 3017-69-4 2-methyl-1-propenylbromide 

Downstream Products

• 137123-81-0 2-Methyl-3-(2-methyl-allyl)-cyclohexanone 
• 137123-80-9 2-(1,3-Dimethyl-but-3-enyl)-cyclopentanone 
• 180624-70-8 (Z)-7-methyl-4,7-octadien-1-ol 
• 1308790-32-0 1-(2-methylallyl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 1350895-84-9 6,7-dimethoxy-1-(2-methylallyl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 1308790-33-1 1-(2-methylallyl)-2-(p-tolyl)-1,2,3,4-tetrahydroisoquinoline 
• 1308790-35-3 2-(4-(tert-butyl)phenyl)-1-(2-methylallyl)-1,2,3,4-tetrahydroisoquinoline 
• 1308790-36-4 2-(4-methoxyphenyl)-1-(2-methylallyl)-1,2,3,4-tetrahydroisoquinoline 
• 1644382-37-5 C₁₀H₁₂FN 
• 1644382-35-3 C₁₁H₁₅N 

Relevant articles and documents

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.

Palladium(II)-catalyzed intramolecular tandem aminoalkylation via divergent C(sp3)-H functionalization

(Chemical Equation Presented) We have developed a Pd(II)-catalyzed oxidative tandem aminoalkylation via divergent C(sp3)-H functionalization, a ffording three- and five-membered-ring fused indolines in good yields under two optimized conditions, respectively. The mechanism studies have indicated that the benzylic C - H cleavage involved in the former transformation is the rate-determining step, while the cleavage of amide α-C - H in the latter is not. This is the first example of a Pd-catalyzed tandem reaction involving C(sp3)-H activation without the employment of prefunctionalized reagents (e.g., halogenated and boron reagents) and directing groups, representing a green and economic protocol for the construction of N-containing heterocycles.

Diastereoselective addition of allyl- And crotylstannanes to dicobalt-complexed acetylenic aldehydes

In an endeavor to utilize metal carbonyl complexes of acetylenic aldehydes and ketones to control the stereoselectivity of nucleophilic acyl addition, the dicobalt hexacarbonyl and dicobalt pentacarbonyl(triphenylphosphine) complexes of 3-phenylpropynal and 2-hexynal were conveniently prepared. Crotyl transfer from either (E)- or (Z)-crotyltributylstannane to Co2(CO) 6-complexed 3-phenylpropynal and 2-hexynal produced 3,4-disubstituted-1,5-enynes with high syn diastereoselectivity. Allyl and 2-methylallyl transfer to Co2(CO)5PPh3- complexed aldehydes was also accomplished with high yields and diastereoselectivities. In all cases, decomplexation of the metal carbonyl moiety was effected, selectively, under very mild oxidative conditions. Exchange of a CO by PPh3 led to decreased overall reactivity. Two competing kinetic processes were observed: stereoselective allylation was observed at low temperature, but at higher temperatures, the first formed allylic alcohol preferentially underwent elimination leading to dienynes.

Neuraminidase inhibitors

The present invention provides compounds of formula Ia and Ib or a pharmaceutically acceptable salt, prodrug, or ester thereof, useful in the inhibition of neuraminidase enzymes from disease-causing microorganisms, especially influenza neuraminidase, phar

Quinuclidine compounds and drugs containing the same as the active ingredient

The present invention provides an excellent squalene synthesizing enzyme inhibitor. Specifically, it provides a compound (I) represented by the following formula, a salt thereof or a hydrate of them. In which R1 represents (1) hydrogen atom or (2) hydroxyl group; HAr represents an aromatic heterocycle which may be substituted with 1 to 3 groups; Ar represents an optionally substituted aromatic ring; W represents a chain represented by (1) —CH2—CH2— which may be substituted, (2) —CH=CH— which may be substituted, (3) —C≡C—, (4) —NH—CO—, (5) —CO—NH—, (6) —NH—CH2—, (7) —CH2—NH—, (8) —CH2—CO—, (9) —CO—CH2—, (10) —NH—S(O)l—, (11) —S(O)l—NH—, (12) —CH2—S(O)— or (13) —S(O)l—CH2— (l denotes 0, 1 or 2); and X represents a chain represented by (1) a single bond, (2) an optionally substituted C1-6 alkylene chain, (3) an optionally substituted C2-6 alkenylene chain, (4) an optionally substituted C2-6 alkynylene chain, (5) a formula —Q— (wherein Q represents oxygen atom, sulfur atom, CO or N(R2) (wherein R2 represents a C1-6 alkyl group or a C1-6 alkoxy group)), (6) —NH—CO—, (7) —CO—NH—, (8) —NH—CH2—, (9) —CH2—NH—, (10) —CH2—CO—, (11) —CO—CH2—, (12) —NH—S(O)m—, (13) —S(O)m—NH—, (14) —CH2—S(O)m—, (15) —S(O)m—CH2— (wherein m denotes 0, 1 or 2) or (16) —(CH2)n—O— (wherein n denotes an integer from 1 to 6).

Addition of allylstannanes to an oxy-stabilized carbenium ion on a 1,7-dioxaspiro[5.5]undecane ring system

The nucleophilic addition of allylstannanes to (2R*,5S*,6S*)-2-acetoxy-5-benzyloxy-1,7-dioxaspiro-[5.5] undecane 1 has been studied. The optimum conditions involve the use of trimethylsilyl trifluoromethanesulfonate in dichloromethane at -78°C. In the exa

Wurtz-type reductive coupling reaction of allyl bromides and haloorganotins in cosolvent/H2O(NH4Cl)/Zn media as a route to allylstannanes and hexaaryldistannanes

Twenty-one allylstannanes have been prepared via a simple Wurtz-type coupling reaction of allyl bromides and R3SnX compounds (R = Me, Et, Pr, Bu, Ph; X = Cl, I, OH), Bu2SnCl2, and (Bu2SnCl)2O in cosolvent/H2O (NH4Cl saturated) media under the mediation of zinc powder. Also R3SnSnR3 compounds (R = Ph, p- and m-Tol) have been prepared via coupling of triaryltin chlorides. The stereochemical course of the reaction between R3SnCl and (C4H7)Br (C4H7 = α-methylallyl, trans- and cis-crotyl) has been extensively studied. Two distinct reactions are involved in the overall process: (i) the coupling reaction, which gives rise stereoselectively to the sole R3SnCH(CH3)CH=CH2 (α-isomer), and (ii) the subsequent isomerization of the α-isomer furnishing mixtures of (α, trans, cis)-isomers. The occurrence of reaction ii depends upon the nature either of the R group or the employed cosolvent. In cyclohexane, the α-isomer is exclusively obtained with R = Bu, while with R = Me, Et, and Pr it is found as a major component in the ternary isomeric mixture. In tetrahydrofuran, 2-propanol, acetonitrile, and pyridine, the isomerization occurs to an extent which depends on the polarity and the coordinating ability of the cosolvent itself. The observed stereoselection has been hypothesized to occur through one-electron transfer from the zinc metal to the (C4H7)Br to form stereoselectively an adsorbed CH2=CHCH(CH3)Br?-Zn?+ radical ion which is trapped by the R3SnCl reactant to form the α-isomer. Similarly, ditin compounds are thought to be formed by interaction of R3SnCl?-Zn?+ radical ions with R3SnCl molecules.

Pyrethrinoid esters carrying an indanyl nucleus and their use as pesticides

Pyrenthrinoid esters with an indenyl nucleus having the following structural formula STR1 wherein the substituents are herein defined, have been shown to be useful as pesticides and in pesticidal compositions.

Synthesis of Allylstannanes and Vinylstannanes by the Stannyl-cupration of Allenes

Stannyl-cupration of allenes followed by electrophilic attack gives allyl- and vinyl-stannanes with a variety of substitution patterns.The regiochemistry of the reaction depends upon the temperature at which the intermediate cuprate is quenched with an electrophile.With allene itself, the allylstannane-vinylcuprate 1-(tributylstannylmethyl)vinylcuprate 5, is the product of kinetically controlled addition, but the vinylstannane-allylcuprate 2-(tributylstannyl)allylcuprate 6, is thermodynamically lower in energy.The equilibrium between these isomers begins to take place between -100 and -78 deg C.