220817
2-(Trimethylsilyl)-1,3-dithiane
≥99%
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About This Item
Empirical Formula (Hill Notation):
C7H16S2Si
CAS Number:
Molecular Weight:
192.42
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
236-504-4
Beilstein/REAXYS Number:
1616463
MDL number:
Assay:
≥99%
Product Name
2-(Trimethylsilyl)-1,3-dithiane, ≥99%
InChI key
BTTUMVHWIAXYPJ-UHFFFAOYSA-N
InChI
1S/C7H16S2Si/c1-10(2,3)7-8-5-4-6-9-7/h7H,4-6H2,1-3H3
SMILES string
C[Si](C)(C)C1SCCCS1
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
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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
10 - Combustible liquids
wgk
WGK 3
flash_point_f
204.8 °F - closed cup
flash_point_c
96 °C - closed cup
ppe
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
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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)
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
Smith, A. B., III; Boldi, A. M.
Journal of the American Chemical Society, 119, 6925-6925 (1997)
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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