1,3,5-trithiane

Structural formula
General
Surname	1,3,5-trithiane
other names	sym. -Trithian Thioformaldehyde trimer Trithioformaldehyde
Molecular formula	C 3 H 6 S 3
Brief description	beige solid
External identifiers / databases
CAS number 291-21-4 EC number 206-029-7 ECHA InfoCard 100.005.482 PubChem 9264 Wikidata Q2356063
properties
Molar mass	138.27 g mol −1
Physical state	firmly
Melting point	215-220 (decomposition) ° C
solubility	sparingly soluble in many solvents
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 319 P: 305 + 351 + 338
Toxicological data	250 mg kg −1 ( LD 50 ,  mouse , intraperitoneal )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,3,5-Trithiane is a chemical compound from the group of heterocycles and the cyclic trimer of the unstable thioformaldehyde.

Extraction and presentation

1,3,5-trithiane can be obtained by reacting formaldehyde with hydrogen sulfide in hydrochloric acid .

${\displaystyle \mathrm {3\ CH_{2}=O+3\ H_{2}S\longrightarrow C_{3}H_{6}S_{3}} }$

properties

1,3,5-trithiane is a beige solid.

use

1,3,5-trithiane is used for the production of other organosulfur compounds ( e.g. for chloromethylsulfonyl chlorides).

${\displaystyle \mathrm {(CH_{2}S)_{3}+9\ Cl_{2}+6\ H_{2}O\longrightarrow 3\ ClCH_{2}SO_{2}Cl+12\ HCl} }$

Individual evidence

1. ↑ ^{a b c d e f g} data sheet 1,3,5-trithian, 97% from Sigma-Aldrich , accessed on December 17, 2015 ( PDF ).
2. ↑ Michael Hanack: Houben-Weyl Methods of Organic Chemistry Vol. E 19d, 4th Edition Supplement: Low-valent Carbon Compounds: Carbanions . Georg Thieme Verlag, 1993, ISBN 978-3-13-182044-0 ( limited preview in Google book search).
3. ↑ RW Bost, EW Constable: sym.-TRITHIANE In: Organic Syntheses . 16, 1936, p. 81, doi : 10.15227 / orgsyn.016.0081 ; Coll. Vol. 2, 1943, p. 610 ( PDF ).
4. ↑ Leo A. Paquette, Lawrence S. Wittenbrook: 2-CHLOROTHIIRANE 1,1-DIOXIDE In: Organic Syntheses . 49, 1969, p. 18, doi : 10.15227 / orgsyn.049.0018 ; Coll. Vol. 5, 1973, p. 231 ( PDF ).
5. ^ D. Seebach, AK Beck: ALDEHYDES FROM sym-TRITHIANE: n-PENTADECANAL In: Organic Syntheses . 51, 1971, p. 39, doi : 10.15227 / orgsyn.051.0039 ; Coll. Vol. 6, 1988, p. 869 ( PDF ).