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Sigma-Aldrich

Tetrahydro-4H-thiopyran-4-one

99%

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About This Item

Empirical Formula (Hill Notation):
C5H8OS
CAS Number:
1072-72-6
Molecular Weight:
116.18
Beilstein:
106464
EC Number:
214-015-7
MDL number:
MFCD00006660
UNSPSC Code:
12352100
PubChem Substance ID:
24849491
NACRES:
NA.22
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Quality Level

200

Assay

99%

form

crystals

mp

60-64 °C (lit.)

functional group

ketone
thioether

SMILES string

O=C1CCSCC1

InChI

1S/C5H8OS/c6-5-1-3-7-4-2-5/h1-4H2

InChI key

OVRJVKCZJCNSOW-UHFFFAOYSA-N

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General description

The diastereoselectivity of the aldol reaction of tetrahydro-4H-thiopyran-4-one has been studied[1].

Application

Tetrahydro-4H-thiopyran-4-one was used in the preparation of meso 1,9-diketones[2].
The product has been utilized in various condensation reactions for the preparation of dipeptides,[3] spiroimidazolones,[4] and tetrahydrocarbazoles[5] and α-hydroxy esters.[6]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH2705
BCBB3715V
BCBB3715
1370210
01601LE

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Dale E Ward et al.
Organic letters, 8(12), 2631-2634 (2006-06-02)
Meso 1,9-diketones (six to seven stereocenters) are readily obtained by stepwise or simultaneous two-directional aldol reactions of tetrahydro-4H-thiopyran-4-one with a thiopyran-derived aldehyde or dialdehyde. Enantioselective enolizations of these diketones with the lithium amide from (R,R)-bis(1-phenylethyl)amine occur with simultaneous kinetic resolution
Synlett, 1605-1605 (2007)
Dale E Ward et al.
The Journal of organic chemistry, 67(5), 1618-1629 (2002-03-02)
The diastereoselectivity of the aldol reaction of tetrahydro-4H-thiopyran-4-one (3) with 1,4-dioxa-8-thiaspiro[4.5]decane-6-carboxaldehyde (9a) under a variety of conditions is examined. Under optimized conditions, three of the four possible diastereomers from this aldol reaction can be obtained selectively (3-16:1). Reactions of 9a
Journal of Heterocyclic Chemistry, 30, 81-81 (1993)
Journal of Heterocyclic Chemistry, 31, 397-397 (1994)
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