31197-41-8

Basic information

• Product Name: (2-Butenyl)tributylstannane
• Synonyms: (2-Butenyl)tributylstannane;1-(Tributylstannyl)-2-butene;2-Butenyltributylstannane;Tributyl 2-butenylstannane;Crotyltributyltin;Tributylcrotylstannane;Tributylcrotyltin
• CAS NO: 31197-41-8
• Molecular Formula: C₁₆H₃₄Sn
• Molecular Weight: 345.15116
• Mol File: 31197-41-8.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2-Butenyl)tributylstannane(CAS DataBase Reference)
• NIST Chemistry Reference: (2-Butenyl)tributylstannane(31197-41-8)
• EPA Substance Registry System: (2-Butenyl)tributylstannane(31197-41-8)

Safety Data

• Hazardous Substances Data: 31197-41-8(Hazardous Substances Data)

Usage

General Description

(2-Butenyl)tributylstannane is an organotin compound with the chemical formula C16H34Sn. It is commonly used as a reagent in organic synthesis, particularly in the Stille coupling reaction, which involves the coupling of an organic halide with an organotin compound to form a carbon-carbon bond. (2-Butenyl)tributylstannane is known for its ability to act as a source of an organic group in a variety of chemical reactions. It is a colorless liquid with a pungent odor and is typically handled and stored under inert gas to prevent degradation. Additionally, (2-Butenyl)tributylstannane is considered to be toxic and should be handled with caution.

Upstream product

• 4784-77-4 (E/Z)-crotyl bromide 
• 22037-73-6 3-bromo-1-butene 
• 1461-22-9 tributyltin chloride 
• 28638-29-1 2,3,4-trimethyl-5-hexen-3-ol 
• 1067-52-3 tributyltin methoxide 
• 4894-61-5 trans-but-2-enyl chloride 
• 21969-32-4 crotylmagnesium chloride 
• 56-35-9 bis(tri-n-butyltin)oxide 
• 31197-41-8 crotyltributylstannane 
• 591-97-9 1-chloro-2-butene 
• 1067-24-9 dimethylamino tributyltin 
• 40894-18-6 (C₄H₉)3SnOCH₂CH₂CH₂Cl 
• 41968-75-6 (C₄H₉)3SnO(CH₂)4Cl 
• 76505-19-6 tributyl(1-methyl-2-propenyl)stannane 

Downstream Products

• 75238-62-9 benzyl but-3-en-2-yl sulfide 
• 115093-13-5 3,4-dimethyl-1-phenyl-5-hexen-1-one 
• 115093-13-5 3,4-dimethyl-1-phenyl-5-hexen-1-one 
• 91819-54-4 2-(1-methyl-2-propenyl)cyclohexanone 
• 4187-81-9 2-(2¹-butenyl)-1-cyclohexanone 
• 128913-54-2 4,6-Dimethyl-1-phenyl-oct-7-ene-2,5-dione 
• 140135-90-6 2-methyl-1-phenyl-3-butenyl benzoate 
• 140135-89-3 (Z)-1-phenyl-3-pentenyl benzoate 
• 140135-92-8 (Z)-1-ethyl-3-pentenyl benzoate 
• 140135-93-9 (Z)-1-t-butyl-3-pentenyl benzoate 
• 140135-94-0 (E)-1-<(Z)-1-propenyl>-3-pentenyl benzoate 
• 504-61-0 (E)-but-2-enol 
• 4088-60-2 cis-2-buten-1-ol 
• 1502-88-1 (3S*,4S*)-2,2,4-trimethylhex-5-en-3-ol 

Relevant articles and documents

ALLYLIC REARRANGEMENT IN REDISTRIBUTION REACTIONS. THE SYSTEM cis/trans-n-Bu3SnCH2CH=CHCH3/n-Bu2SnCl2

Allylic rearrangement occurs in the solvent-free redistribution reaction between trans/cis-Bu3SnCH2CH=CHCH3 and Bu2SnCl2: .Subsequent isomerization of I is catalyzed by Bu2SnCl2 (see eq. 2) to an equilibrium mixture of cis-II (72-74percent) trans

Photochemical 1,3-stannyl rearrangement of allylic stannanes

The photochemical 1,3-stannyl rearrangement of allylic stannanes has been investigated. The photorearrangement of (E)-cinnamyl(triphenyl)stannane is not observed in benzene under anaerobic conditions, while the photoinduced 1,3-stannyl migration takes place in the same solvent under aerobic conditions, or in the presence of organic halides or a radical-trapping agent to give a photoequllibrium mixture of the cinnamylstannane and its branched regioisomer, 1-phenylprop-2-enyl(triphenyl)stannane, with the latter predominating. Cinnamyl(trialkyl)stannanes and their homologues also afford the corresponding branched allylstannanes under similar photochemical conditions. These 1,3-stannyl migrations proceed intramolecularly via cinnamyl π-π* excitation in competition with homolytic (cinnamyl)C-Sn bond fission. In contrast, the 1,3-stannyl migration of crotyl- and prenyl-(tributyl)-stannanes is not efficient, but their triphenyl or dibutylphenyl derivatives undergo the 1,3-rearrangement via excitation of the phenyl group(s) on the tin atom to give a regioisomeric mixture of the starting linear tin compounds and the branched ones with the former predominating.

Tributyl(3-methyl-2-butenyl)tin

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