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183954

Sigma-Aldrich

1,4-Dithiane-2,5-diol

97%

Synonym(s):

2,5-Dihydroxy-1,4-dithiane, Mercaptoacetaldehyde dimer

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About This Item

Empirical Formula (Hill Notation):
C4H8O2S2
CAS Number:
40018-26-6
Molecular Weight:
152.24
Beilstein:
104402
EC Number:
254-751-6
MDL number:
MFCD00006659
UNSPSC Code:
12352100
PubChem Substance ID:
24851084
NACRES:
NA.22

Assay

97%

form

powder

mp

130 °C (dec.) (lit.)

storage temp.

2-8°C

SMILES string

OC1CSC(O)CS1

InChI

1S/C4H8O2S2/c5-3-1-7-4(6)2-8-3/h3-6H,1-2H2

InChI key

YUIOPHXTILULQC-UHFFFAOYSA-N

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General description

1,4-Dithiane-2,5-diol undergoes bifunctional squaramide catalyzed sulfa-Michael/aldol cascade reaction with chalcones to afford trisubstituted tetrahydrothiophenes. It participates in diastereoselective [3+3] cycloaddition with azomethine imines catalyzed by 1,4-diazabicyclo[2.2.2]octane. It is a mercaptoacetaldehyde dimer and an efficient synthon for incorporating a thiol group to in situ generated nitroalkenes.

Application

1,4-Dithiane-2,5-diol was used in the synthesis of:
  • substituted tetrahydrothiophene derivatives
  • 2-amino-3-(arylsulfonyl)thiophenes, potential antiviral and antitumor agents

Signal Word

Danger

Hazard Statements

H301,H317,H330,H373,H410

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Skin Sens. 1A - STOT RE 2

WGK

WGK 2

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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C E Stephens et al.
Bioorganic & medicinal chemistry, 9(5), 1123-1132 (2001-05-30)
Based on general SARs previously described for anti-HIV-1 diarylsulfone derivatives, a series of 2-amino- and 2-carboxamido-3-arylsulfonylthiophenes has been prepared and evaluated as potential antiviral and antitumor agents. In cell culture, some of the 2-aminothiophenes exhibited moderate and selective activity against
1, 4-Dithiane-2, 5-diol as an efficient synthon for a straightforward synthesis of functionalized tetrahydrothiophenes via sulfa-Michael/aldol-type reactions with electrophilic alkenes.
Baricordi N, et al.
Tetrahedron, 68(1), 208-213 (2012)
Xin Fang et al.
Organic letters, 15(21), 5554-5557 (2013-11-05)
An effective diastereoselective [3 + 3] cycloaddition of 1,4-dithiane-2,5-diol with azomethine imines catalyzed by DABCO is described. A variety of highly functionalized six-membered dinitrogen-fused heterocycles can be obtained in good yield with excellent diastereoselectivity, which was controlled by anomeric effect.
Jun-Bing Ling et al.
Organic letters, 14(4), 1090-1093 (2012-02-09)
A bifunctional squaramide catalyzed sulfa-Michael/aldol cascade reaction between 1,4-dithiane-2,5-diol and chalcones with a low catalyst loading has been developed. Trisubstituted tetrahydrothiophenes with three contiguous stereogenic centers are obtained in a highly stereocontrolled manner. Additionally, a remarkable temperature effect on reaction
Y Inamori et al.
Chemical & pharmaceutical bulletin, 38(1), 243-245 (1990-01-01)
2,5-Dihydroxy-1,4-dithiane (I) and its derivatives (II-IV) showed rather marked inhibitory activities on the growth of the roots of two plant species. All compounds tested had phytogrowth-inhibitory activities. These compounds markedly inhibited the growth of the two plant species at the

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