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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.)

functional group

hydroxyl
thioether

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

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF4085
BCCC5562
BCBZ1868
BCBV3076
BCBS0328V

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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)
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
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.
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
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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