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235334

Sigma-Aldrich

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

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

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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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)
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

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