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275123

Sigma-Aldrich

Tributyl(1-ethoxyvinyl)tin

97%

Synonym(s):

(1-Ethoxyvinyl)tri-n-butylstannane

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About This Item

Linear Formula:
[CH3(CH2)3]3SnC(OC2H5)=CH2
CAS Number:
97674-02-7
Molecular Weight:
361.15
MDL number:
MFCD00010240
UNSPSC Code:
12352103
PubChem Substance ID:
24856628
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.476 (lit.)

bp

85-86 °C/0.1 mmHg (lit.)

density

1.069 g/mL at 25 °C (lit.)

SMILES string

CCCC[Sn](CCCC)(CCCC)C(=C)OCC

InChI

1S/C4H7O.3C4H9.Sn/c1-3-5-4-2;3*1-3-4-2;/h1,4H2,2H3;3*1,3-4H2,2H3;

InChI key

HGXJOXHYPGNVNK-UHFFFAOYSA-N

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General description

This vinylstannane undergoes Stille coupling with a vinyl triflate, giving, after hydrolysis, an α,β−unsaturated ketone, thus acting as an acetyl anion equivalent.

Application

Electrophilic methyl ketone equivalent used in a recent synthesis of a 13-oxophorbine (chlorophyll) from the corresponding 13-bromochlorin.
Reagent employed in palladium-catalyzed coupling reactions with sulfoxides, α-haloethers, and chlorocyclobutenones. Also used to convert acid chlorides to α-oxygenated enones.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT RE 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

275123-VAR:
275123-250G:
275123-BULK:
275123-25G:4548173308555
275123-100G:4548173308579
275123-5G:4548173308562
275123-1G:4548173308548

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Journal of the American Chemical Society, 114, 1412-1412 (1992)
Joydev K Laha et al.
The Journal of organic chemistry, 71(18), 7049-7052 (2006-08-26)
A new route to 13(1)-oxophorbines, the parent macrocycle of chlorophylls, begins with the synthesis of a 13-bromochlorin. Pd-mediated coupling of the latter with tributyl(1-ethoxyvinyl)tin and subsequent acidic hydrolysis afforded the 13-acetylchlorin (1). Treatment of 1 with NBS afforded the 15-bromo
Younggi Choi et al.
The Journal of organic chemistry, 69(11), 3758-3764 (2004-05-22)
2-Azabicyclo[2.2.2]oct-5-enes bearing an endo alkenyl substituent were synthesized by Diels-Alder addition of methyl vinyl ketone to a 1,6-dihydropyridine derived from methyl nicotinate. Although 1,5-dienes with this skeleton were unreactive under thermal conditions, they were photochemically reactive. Irradiation of these dienes
Tetrahedron Letters, 34, 2429-2429 (1993)
Tetrahedron Letters, 33, 4885-4885 (1992)
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