1,3,5-Trithiane

1,3,5-Trithiane is the chemical compound with the formula (CH2S)3. This heterocycle is the cyclic trimer of the otherwise unstable species thioformaldehyde. It consists of a six-membered ring with alternating methylene bridges and thioether groups. It is prepared by treatment of formaldehyde with hydrogen sulfide.

1,3,5-Trithiane
Names
Preferred IUPAC name
1,3,5-Trithiane
Other names
Thioformaldehyde trimer, Trimethylentrisulfide, Trimethylene trisulfide, Trithioformaldehyde, 1,3,5-Trithiacyclohexane, sym-Trithiane, Thioform, s-Trithiane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.005.482
EC Number
  • 206-029-7
PubChem CID
UNII
  • InChI=1S/C3H6S3/c1-4-2-6-3-5-1/h1-3H2 Y
    Key: LORRLQMLLQLPSJ-UHFFFAOYSA-N Y
  • InChI=1/C3H6S3/c1-4-2-6-3-5-1/h1-3H2
    Key: LORRLQMLLQLPSJ-UHFFFAOYAA
SMILES
  • S1CSCSC1
Properties
C3H6S3
Molar mass 138.27
Appearance Colourless solid
Density 1.6374 g/cm3
Melting point 215 to 220 °C (419 to 428 °F; 488 to 493 K)
Slightly soluble
Solubility Benzene
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic (T)
GHS labelling:
Warning
H319
P264, P280, P305+P351+P338, P313
NFPA 704 (fire diamond)
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Trithiane is a building block molecule in organic synthesis, being a masked source of formaldehyde. In one application, it is deprotonated with organolithium reagents to give the lithium derivative, which can be alkylated.

(CH2S)3 + RLi → (CH2S)2(CHLiS) + RH
(CH2S)2(CHLiS) + R′Br → (CH2S)2(CHR′S) + LiBr
(CH2S)2(CHR′S) + H2O → R′CHO + ....

Trithiane is the dithioacetal of formaldehyde. Other dithioacetals undergo similar reactions to the above.

It is also a precursor to other organosulfur reagents. For example, chlorination in the presence of water affords the chloromethyl sulfonyl chloride:

(CH2S)3 + 9 Cl2 + 6 H2O → 3 ClCH2SO2Cl + 12 HCl
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