235334
3,6-Dithia-1,8-octanediol
97%
Synonym(s):
2,2′-(Ethylenedithio)diethanol, Lindlar Catalyst Poison
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About This Item
Linear Formula:
HO(CH2)2S(CH2)2S(CH2)2OH
CAS Number:
Molecular Weight:
182.30
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
226-045-8
Beilstein/REAXYS Number:
1739193
MDL number:
Assay:
97%
Product Name
3,6-Dithia-1,8-octanediol, 97%
assay
97%
InChI key
PDHFSBXFZGYBIP-UHFFFAOYSA-N
InChI
1S/C6H14O2S2/c7-1-3-9-5-6-10-4-2-8/h7-8H,1-6H2
SMILES string
OCCSCCSCCO
bp
170 °C/0.5 mmHg (lit.)
mp
63-64 °C (lit.)
functional group
hydroxyl
thioether
Quality Level
Related Categories
Application
3,6-Dithia-1,8-octanediol has been used:
- as exogeneous chelator to evaluate a membrane-permeable copper-selective fluorescent sensor for imaging of kinetically labile copper pools
- in asymmetric total synthesis of (+)-6-epi-castanospermine and polyhydroxylated alkaloid
General description
3,6-Dithia-1,8-octanediol is a secondary sulfur-based catalyst poison.
Storage Class
11 - Combustible Solids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Liuchun Yang et al.
Proceedings of the National Academy of Sciences of the United States of America, 102(32), 11179-11184 (2005-08-03)
Copper is an essential micronutrient that plays a central role for a broad range of biological processes. Although there is compelling evidence that the intracellular milieu does not contain any free copper ions, the rapid kinetics of copper uptake and
Asymmetric Total Synthesis of (+)-6-epi-Castanospermine by the Stereoselective Formation of a syn, anti Acetylenic 2-Amino-1, 3-diol Stereotriad.
Louvel J, et al.
European Journal of Organic Chemistry, 2010(15), 2921-2926 (2010)
Eric J Stoner et al.
The Journal of organic chemistry, 68(23), 8847-8852 (2003-11-08)
Functionalized erythromycin 9-oxime derivatives are 6-O-allylated under mild conditions using substituted allyl tert-butyl carbonates under palladium(0) catalysis. This allylation works well where traditional ether-forming protocols function poorly. Allyl tert-butyl carbonates provide higher yields in this reaction than lesser substituted carbonates
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