1,3-propanedithiol

Structural formula
General
Surname	1,3-propanedithiol
other names	Trimethylene mercaptan; 1,3-dimercaptopropane;
Molecular formula	C 3 H 8 S 2
Brief description	light yellow smelly liquid
External identifiers / databases
EC number	203-706-9
ECHA InfoCard	100.003.371
PubChem	8013
ChemSpider	13848090
Wikidata	Q4545685
properties
Molar mass	108.23 g mol −1
Physical state	liquid
density	1.077 g cm −3
Melting point	−79 ° C
boiling point	168-170 ° C
Vapor pressure	5 Torr (38 ° C)
solubility	slightly soluble in water; miscible with ethanol , ether , chloroform ;
Refractive index	1.540 (20 ° C)
safety instructions
H and P phrases	H: 226-301-315-319-335
	P: 210-303 + 361 + 353-264-301 + 310-337 + 313-304 + 340-280-332 + 313
Toxicological data	50–300 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

1,3-Propanedithiol is a chemical compound from the group of thiols .

Extraction and presentation

The preparation of 1,3-propanedithiol by reacting 1,3-dibromopropane with potassium hydrogen sulfide was first described in 1890. Alternatively, the compound can be obtained by reacting 1,3-dibromopropane with potassium thiocyanate to form 1,3-propanediyl bis (thiocyanate) and subsequent reduction with zinc and hydrochloric acid .

properties

1,3-Propanedithiol is a light yellow, smelly liquid that is sparingly soluble in water, but miscible with ethanol , chloroform and diethyl ether .

use

1,3-Propanedithiol is used as a reagent in the manufacture of thioketals and thioacetals . It acts as a flavoring agent and is used as a precursor in the synthesis of cyclic dithioacetal (1,3-dithiane) derivatives of carbonyl compounds . It is also used to protect aldehydes and ketones through their reversible formation of dithianes . In addition, it reacts with metal ions to form chelate rings.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ data sheet 1,3-propanedithiol, 97% from AlfaAesar, accessed on March 13, 2020 ( PDF )(JavaScript required) .
↑ L. Hagelberg: About some sulfur cyan and selenium compounds . In: Reports of the German Chemical Society . tape 23 , no. 1 , January 1890, p. 1083-1091 , doi : 10.1002 / cber.189002301179 .
↑ Adalbert Wollrab: Organic Chemistry An introduction for teacher training and minor students . Springer-Verlag, 2009, ISBN 978-3-642-00781-1 , p. 499 ( limited preview in Google Book search).

[Alfa-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ data sheet 1,3-propanedithiol, 97% from AlfaAesar, accessed on March 13, 2020 ( PDF )(JavaScript required) .

[2] L. Hagelberg: About some sulfur cyan and selenium compounds . In: Reports of the German Chemical Society . tape 23 , no. 1 , January 1890, p. 1083-1091 , doi : 10.1002 / cber.189002301179 .

[Adalbert_Wollrab-3] Adalbert Wollrab: Organic Chemistry An introduction for teacher training and minor students . Springer-Verlag, 2009, ISBN 978-3-642-00781-1 , p. 499 ( limited preview in Google Book search).