1,3-propanedithiol

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Structural formula
Structural formula of 1,3-propanedithiol
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
CAS number 109-80-8
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
Refractive index

1.540 (20 ° C)

safety instructions
GHS labeling of hazardous substances
02 - Highly / extremely flammable 06 - Toxic or very toxic

danger

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 50ratoral )

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

  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 .
  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).