1,3,5-Trithiane

Chemical compound

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

CAS Number

291-21-4^N

3D model (JSmol)

Interactive image

ChEBI

CHEBI:39196^Y

ChemSpider

8907^Y

ECHA InfoCard

100.005.482

EC Number

206-029-7

PubChem CID

9264

UNII

4AM764YC6X^Y

CompTox Dashboard (EPA)

DTXSID2059778

InChI

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

Chemical formula

C₃H₆S₃

Molar mass

138.27

Appearance

Colourless solid

Density

1.6374 g/cm³^[1]

Melting point

215 to 220 °C (419 to 428 °F; 488 to 493 K)

Solubility in water

Slightly soluble

Solubility

Benzene

Hazards

Occupational safety and health (OHS/OSH):

Main hazards

Toxic (T)

GHS labelling:

Pictograms

Signal word

Warning

Hazard statements

H319

Precautionary statements

P264, P280, P305+P351+P338, P313

NFPA 704 (fire diamond)

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

Chemical compound

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.^[2]

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.^[3]

(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:^[4]

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

Trithianes

Trithiane is the parent of a class of heterocycles called trithianes, that formally result from substitution of various monovalent groups for one or more of the hydrogen atoms. The species often arise from thiation of ketones and aldehydes. The incipient thioketones and thioaldehydes undergo trimerization. One example is 2,2,4,4,6,6-hexamethyl-1,3,5-trithiane, or trithioacetone, the trimer of thioacetone (propane-2-thione). Alternatively 1,3,5-trithiane can be deprotonated and alkylated to afford (SCH₂)_n(SCHR)_3-n.^[5]

The conformation of trithianes has been well investigated.^[6]

References

^ David R. Lide, ed. Handbook of Chemistry and Physics, 85th Edition, Internet Version 2005. CRC Press, 2005.
^ Bost, R. W.; Constable, E. W. "sym-Trithiane" Organic Syntheses, Collected Volume 2, p.610 (1943). http://orgsyn.org/Content/pdfs/procedures/CV2P0610.pdf
^ Seebach, D.; Beck, A. K. "Aldehydes From sym-Ttrithiane: n-Pentadecanal" Organic Syntheses, Collected Volume 6, p.869 (1988). http://orgsyn.org/Content/pdfs/procedures/CV6P0869.pdf
^ Paquette, L. A.; Wittenbrook, L. S. "2-Chlorothiirane 1,1-Dioxide" Organic Syntheses, Collected Volume 5, p.231 (1973). http://orgsyn.org/Content/pdfs/procedures/CV5P0231.pdf
^ Edema, Jilles J. H.; Hoogenraad, Marcel; Schoonbeek, Franck S.; Kellogg, Richard M.; Kooijman, Huub; Spek, Anthony L. (2010). "Alkylation of the SCS linkage. Towards lipophilic mono- and ditopic heavy-metal receptors containing trithiane building blocks. Molecular structure of cis-2,4,6-tribenzyl-1,3,5-trithiane". Recueil des Travaux Chimiques des Pays-Bas. 112 (6): 370–375. doi:10.1002/recl.19931120611.
^ Breslow, David S.; Skolnik, Herman (2009). "C3S3 Ring Systems". Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles, Part 2. Vol. 21. John Wiley & Sons. p. 689. ISBN 978-0-470-18833-0.

Molecules detected in outer space

Molecules

Diatomic	Aluminium monochloride Aluminium monofluoride Aluminium(II) oxide Argonium Carbon cation Carbon monophosphide Carbon monosulfide Carbon monoxide Cyano radical Diatomic carbon Fluoromethylidynium Helium hydride ion Hydrogen chloride Hydrogen fluoride Hydrogen (molecular) Hydroxyl radical Iron(II) oxide Magnesium monohydride Methylidyne radical Nitric oxide Nitrogen (molecular) Imidogen Sulfur mononitride Oxygen (molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfur monohydride Sulfur monoxide Titanium(II) oxide
Triatomic	Aluminium(I) hydroxide Aluminium isocyanide Amino radical Carbon dioxide Carbonyl sulfide CCP radical Chloronium Diazenylium Dicarbon monoxide Disilicon carbide Ethynyl radical Formyl radical Hydrogen cyanide (HCN) Hydrogen isocyanide (HNC) Hydrogen sulfide Hydroperoxyl Iron cyanide Isoformyl Magnesium cyanide Magnesium isocyanide Methylene radical N₂H⁺ Nitrous oxide Nitroxyl Ozone Phosphaethyne Potassium cyanide Protonated molecular hydrogen Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide SiNC Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Water
Four atoms	Acetylene Ammonia Cyanic acid Cyanoethynyl Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methylene amidogen Methyl cation Methyl radical Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thioformaldehyde Tricarbon monoxide Tricarbon monosulfide Thiocyanic acid
Five atoms	Ammonium ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy radical Methylenimine Propadienylidene Protonated formaldehyde Silane Silicon-carbide cluster
Six atoms	Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC₄N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene
Seven atoms	Acetaldehyde Acrylonitrile Vinyl cyanide Cyanodiacetylene Ethylene oxide Glycolonitrile Hexatriynyl radical Methylacetylene Methylamine Methyl isocyanate Vinyl alcohol
Eight atoms	Acetic acid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Hexapentaenylidene Methylcyanoacetylene Methyl formate Propenal
Nine atoms	Acetamide Cyanohexatriyne Cyanotriacetylene Dimethyl ether Ethanol Methyldiacetylene Octatetraynyl radical Propene Propionitrile
Ten atoms or more	Acetone Benzene Benzonitrile Buckminsterfullerene (C₆₀, C₆₀⁺, fullerene, buckyball) C₇₀ fullerene Cyanodecapentayne Cyanopentaacetylene Cyanotetra-acetylene Ethylene glycol Ethyl formate Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propanal n-Propyl cyanide Pyrimidine Heptatrienyl radical