66222-29-5

Basic information

• Product Name: tributyl(iodoMethyl)stannane
• Synonyms: tributyl(iodoMethyl)stannane;iodoMethyl)tri-n-butylstannane;tributyltiniodoMethane;Tributylstannyliodomethane
• CAS NO: 66222-29-5
• Molecular Formula: C₁₃H₂₉ISn
• Molecular Weight: 430.98383
• Product Categories: organic tin
• Mol File: 66222-29-5.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 106 °C(Press: 0.05 Torr)
• Appearance: /
• CAS DataBase Reference: tributyl(iodoMethyl)stannane(CAS DataBase Reference)
• NIST Chemistry Reference: tributyl(iodoMethyl)stannane(66222-29-5)
• EPA Substance Registry System: tributyl(iodoMethyl)stannane(66222-29-5)

Safety Data

• Hazardous Substances Data: 66222-29-5(Hazardous Substances Data)

Usage

General Description

Tributyl(iodomethyl)stannane is a synthetic chemical compound with the formula Bu3SnCH2I. This organic tin compound is primarily used in chemistry as an organometallic reagent. Not much information is available about its physical characteristics such as color, odor, or state at room temperature; however, like most organotin compounds, it is presumed to be toxic and should be handled with care. The compound has properties common to several different fields of chemistry including organometallics, halogens, and alkyls - which suggests its usage in various chemical reactions and processes. Tributyl(iodomethyl)stannane is not naturally occurring and must be synthesized in a laboratory setting.

Upstream product

• 27490-33-1 tri-n-butylstannylmethanol 
• 516-12-1 N-iodo-succinimide 
• 23895-61-6 tributyl(chloromethyl)stannane 
• 7681-82-5 sodium iodide 
• 75-11-6 diiodomethane 
• 1461-22-9 tributyltin chloride 
• 142-71-2 copper diacetate 
• 1066-45-1 trimethyltin(IV)chloride 
• 688-73-3 tri-n-butyl-tin hydride 

Downstream Products

• 123933-98-2 Benzyl-(2-hydroxy-4-phenyl-butyl)-carbamic acid benzyl ester 
• 2520-97-0 N-allyl-N-α-methylbenzylamine 
• 17150-62-8 N-benzyl-3-butenylamine 
• 98204-75-2 3,3,5-Trimethyl-bicyclo[4.1.0]heptane-1,5-diol 
• 98204-77-4 1,5,5-Trimethyl-3-methylene-cyclohexane-1,2-diol 
• 87711-46-4 C₁₂H₁₇⁽²⁾H₂NOSi 
• 87711-45-3 C₁₂H₁₇⁽²⁾H₂NOSi 
• 13668-59-2 3-hydroxymethyl-cyclopentene 
• 152582-70-2 1,1,1,3,3,3-Hexafluoro-2-[2-(2-hydroxy-2,2-diphenyl-ethylselanyl)-phenyl]-propan-2-ol 
• 123934-02-1 Benzyl-(1-hydroxy-cyclohex-2-enylmethyl)-carbamic acid benzyl ester 
• 72246-03-8 Tributyl-((2R,4aR,8S,8aS)-2-phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxymethyl)-stannane 
• 107856-18-8 2-(tri-n-butylstannylmethyl)-3-phenylpropionate 
• 135569-03-8 <<<<1-(1-methyl-2-propenyl)cyclohexyl>oxy>methyl>seleno>benzene 
• 135569-05-0 <<(2-cyclohexen-1-ylmethoxy)methyl>seleno>benzene 

Relevant articles and documents

Homologation of halostannanes with carbenoids: a convenient and straightforward one-step access to α-functionalized organotin reagents

A direct, single synthetic homologative transformation of halostannanes into mono- or di-substituted methyl analogues is documented. Critical for the success of the operation is the excellent nucleophilicity of carbenoid-like methyllithium reagents (LiCHXY, X, Y = halogen, OR, and CN): by simply individuating the reagents' substitution pattern, the desired functionalized fragment is delivered to the electrophile. The wide scope of the protocol is evidenced also in the case of analogous halogermanium compounds. The tandem homologation-quenching with nucleophiles and the use of α-chloroallyllithium is also discussed.

Preparation of tributyl(Iodomethyl)stannane

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On the configurational stability of chiral, nonracemic fluoro- and iodo-[D1]methyllithiums

Enantiomerically pure fluoro-[D1]methyllithium and iodo-[D 1]methyllithiums of up to 92% ee were generated by transmetalation of the corresponding stannanes with MeLi in THF at various temperatures. The intermediate halo-[D1]methyllithiums were trapped with benzaldehyde or acetophenone already present in excess in the reaction mixture to either give halohydrins or to disintegrate to carbene. The fluoro-[D1] methyllithiums were found to be microscopically configurationally stable within the tested range of -95 to 0°C, but chemically only stable at temperatures below -95°C due to a rapidly increasing portion disintegrating to carbene. The iodo-[D1]methyllithiums were configurationally labile relative to the rate of addition to PhCHO at all temperatures tested (-95 to -30°C). Disintegration to carbene interfered as well. The microscopic configurational stability of enantiomerically pure fluoro-[D1]methyllithiums prepared by tin-lithium exchange in the presence of excess benzaldehyde or acetophenone has been investigated. Depending on the reaction temperature, a portion of the generated fluoro-[D1]methyllithiums was added to the electrophiles to give fluorohydrins; the remaining portions disintegrated to carbene and LiF (see scheme).