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%
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
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 220817-5G | 04061838118615 |
| 220817-25G | 04061838118608 |