Home > Compound List > Compound details
505-23-7 molecular structure
click picture or here to close

1,3-dithiane

ChemBase ID: 137582
Molecular Formular: C4H8S2
Molecular Mass: 120.23632
Monoisotopic Mass: 120.00674226
SMILES and InChIs

SMILES:
C1CSCSC1
Canonical SMILES:
C1CCSCS1
InChI:
InChI=1S/C4H8S2/c1-2-5-4-6-3-1/h1-4H2
InChIKey:
WQADWIOXOXRPLN-UHFFFAOYSA-N

Cite this record

CBID:137582 http://www.chembase.cn/molecule-137582.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1,3-dithiane
IUPAC Traditional name
1,3-dithiane
Synonyms
1,3-Dithiane
1,3-Dithiane
1,3-二噻烷
CAS Number
505-23-7
EC Number
208-006-7
MDL Number
MFCD00006654
Beilstein Number
102534
PubChem SID
24849705
162231844
24867374
PubChem CID
10451

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 1.498092  LogD (pH = 7.4) 1.498092 
Log P 1.498092  Molar Refractivity 34.0023 cm3
Polarizability 13.498343 Å3 Polar Surface Area 0.0 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
52-54 °C expand Show data source
52-54 °C(lit.) expand Show data source
52-55°C expand Show data source
Boiling Point
207-208°C expand Show data source
Flash Point
194 °F expand Show data source
90 °C expand Show data source
90°C(194°F) expand Show data source
RTECS
JO5070000 expand Show data source
UN Number
UN3335 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
9 expand Show data source
Packing Group
III expand Show data source
TSCA Listed
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
≥97.0% (GC) expand Show data source
97% expand Show data source
98% expand Show data source
Grade
purum expand Show data source
Empirical Formula (Hill Notation)
C4H8S2 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 157872 external link
Packaging
1, 5, 25, 100 g in glass bottle
Sigma Aldrich - 43745 external link
Other Notes
Review1,2

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Chloramine-T: Synth. Commun., 2, 7 (1972); NCS, AgNO3, acetonitrile-water: J. Org. Chem., 36, 3553 (1971); 48, 1552 (1983); SO2Cl2, silica, DCM-water: Synthesis, 678 (1976); Bromodimethylsulfonium bromide (from DMSO and bromine): Synthesis, 720 (1979); DMSO-HCl-dioxane: Synthesis, 679 (1982); CuCl2, CuO, acetone: Org. Synth. Coll., 6, 109 (1988); CAN, acetonitrile-water: Synth. Commun., 11, 423 (1981); DDQ, acetonitrile-water: J. Chem. Soc., Perkin 1, 453 (1996); Phenyl phosphorodichloridate, NaI, acetonitrile-DMF: Tetrahedron Lett., 29, 5471 (1988); Glyoxylic acid in AcOH: Synthesis, 694 (1976); HIO4, THF-ether: Tetrahedron Lett., 37, 4331 (1996); PhI(OAc)2, acetone-water: Syn. Commun., 30, 4081 (2000). For facilitation of cleavage of 1,3-dithianes by S-alkylation, see Trimethyloxonium tetrafluoroborate, A15175.
  • • The 2-lithio derivative, normally generated with n-BuLi, behaves as a formyl anion equivalent. It has been shown that the rigorous exclusion of atmospheric oxygen minimizes side reactions and is critical in obtaining optimum results in these lithiation procedures: J. Org. Chem., 60, 4258 (1995).
  • • Monoalkylation of the 2-lithio-derivative and cleavage of the dithiane leads to an aldehyde. Successive dialkylation provides a route to ketones. For reviews of the reversal of the normal reactivity of groups, "umpolung", see: Angew. Chem. Int. Ed., 18, 239 (1979), and of the umpolung of carbonyl activity through sulfur-containing reagents: Synthesis, 357 (1977). See also 1,3-Propanedithiol, A15261, 1,3-Dithiolane, L11914, and 1,2-Ethanedithiol, L12865.
  • • Reaction with 2-cyclohexenone proceeds via 1,2-addition. For details of this and subsequent cleavage and rearrangement, see: Org. Synth. Coll., 8, 309 (1993):
  • • For conversion to the dithienium salt by hydride abstraction, see Triphenylcarbenium tetrafluoroborate, A12949.
  • • Reviews: Synthetic uses of 1,3-dithianes: Tetrahedron, 45, 7643 (1989); Chemistry of 1,3-dithioacetals: Organosulfur Chemistry, P. Page, Ed., Academic Press N.Y. (1995).
  • • For an example of successive acylation and alkylation of 1,3-dithiane, which can be carried out as a one-pot sequence, see: Synthesis, 625 (1980).
  • • Cleavage of 1,3-dithianes has been effected by a variety of methods, including:
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle