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220817

Sigma-Aldrich

2-(Trimethylsilyl)-1,3-dithiane

≥99%

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About This Item

Empirical Formula (Hill Notation):
C7H16S2Si
CAS Number:
13411-42-2
Molecular Weight:
192.42
Beilstein:
1616463
EC Number:
236-504-4
MDL number:
MFCD00006655
UNSPSC Code:
12352100
PubChem Substance ID:
24853194
NACRES:
NA.22

Assay

≥99%

refractive index

n20/D 1.533 (lit.)

bp

54-55 °C/0.17 mmHg (lit.)

density

1.014 g/mL at 25 °C (lit.)

functional group

thioether

SMILES string

C[Si](C)(C)C1SCCCS1

InChI

1S/C7H16S2Si/c1-10(2,3)7-8-5-4-6-9-7/h7H,4-6H2,1-3H3

InChI key

BTTUMVHWIAXYPJ-UHFFFAOYSA-N

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General description

2-(Trimethylsilyl)-1,3-dithiane participates in Lewis base-catalyzed 1,3-dithiane addition to electrophiles such as carbonyl compounds and N-substituted aldimines. It undergoes novel diazo transfer reaction with tosyl azide in hexamethylphosphoramide-THF to yield 2-diazo-1,3-dithiane, which on decomposition yields formal carbene adducts. It is a versatile acyl anion equivalent.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

204.8 °F - closed cup

Flash Point(C)

96 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
09412HW
09403KZ
10413LG
00118KF
00118AO

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Diazo transfer reaction of 2-(trimethylsilyl)-1, 3-dithiane with tosyl azide. Carbenic reactivity of transient 2-diazo-1, 3-dithiane.
Benati L, et al.
Tetrahedron, 53(27), 9269-9278 (1997)
Smith, A. B., III; Boldi, A. M.
Journal of the American Chemical Society, 119, 6925-6925 (1997)
Makoto Michida et al.
Chemistry, an Asian journal, 3(8-9), 1592-1600 (2008-06-21)
Lewis base-catalyzed 1,3-dithiane addition to electrophiles such as carbonyl compounds and N-substituted aldimines with 2-trimethylsilyl-1,3-dithiane (TMS-dithiane) is described. By the activation of the carbon-silicon bond in the presence of a Lewis base catalyst such as tetrabutylammonium phenoxide (PhONnBu(4)), a 1,3-dithiane
Amos B Smith et al.
Journal of the American Chemical Society, 125(47), 14435-14445 (2003-11-20)
The development, application, and advantages of a one-flask multicomponent dithiane linchpin coupling protocol, over the more conventional stepwise addition of dithiane anions to electrophiles leading to the rapid, efficient, and stereocontrolled assembly of highly functionalized intermediates for complex molecule synthesis

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