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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:
5244-34-8
Molecular Weight:
182.30
Beilstein:
1739193
EC Number:
226-045-8
MDL number:
MFCD00002911
UNSPSC Code:
12352100
PubChem Substance ID:
24854098
NACRES:
NA.22

Assay

97%

bp

170 °C/0.5 mmHg (lit.)

mp

63-64 °C (lit.)

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

Related Categories

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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