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
Beilstein:
1739193
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Quality Level
Assay
97%
bp
170 °C/0.5 mmHg (lit.)
mp
63-64 °C (lit.)
functional group
hydroxyl
thioether
SMILES string
OCCSCCSCCO
InChI
1S/C6H14O2S2/c7-1-3-9-5-6-10-4-2-8/h7-8H,1-6H2
InChI key
PDHFSBXFZGYBIP-UHFFFAOYSA-N
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General description
3,6-Dithia-1,8-octanediol is a secondary sulfur-based catalyst poison.
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
Storage Class Code
11 - Combustible Solids
WGK
WGK 1
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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
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
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)
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