1,3-propanedithiol
   HOME

TheInfoList



OR:

1,3-Propanedithiol is the
chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
with the formula HSCH2CH2CH2SH. This di
thiol In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl grou ...
is a useful
reagent In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...
in
organic synthesis Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...
. This liquid, which is readily available commercially, has an intense stench.


Reactions

1,3-Propanedithiol has been used for the
protection Protection is any measure taken to guard something against damage caused by outside forces. Protection can be provided to physical objects, including organisms, to systems, and to intangible things like civil and political rights. Although ...
of
aldehyde In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...
s and
ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...
s via their reversible formation of dithianes. A prototypical
reaction Reaction may refer to a process or to a response to an action, event, or exposure. Physics and chemistry *Chemical reaction *Nuclear reaction *Reaction (physics), as defined by Newton's third law * Chain reaction (disambiguation) Biology and ...
is its formation of 1,3-dithiane from
formaldehyde Formaldehyde ( , ) (systematic name methanal) is an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...
. The reactivity of this dithiane illustrates the concept of
umpolung In organic chemistry, umpolung () or polarity inversion is the chemical modification of a functional group with the aim of the reversal of Chemical polarity, polarity of that group. This modification allows secondary reactions of this functional g ...
. Alkylation gives thioethers, e.g. 1,5-dithiacyclooctane. The unpleasant odour of 1,3-propanedithiol has encouraged the development of alternative reagents that generate similar derivatives. Oxidation gives not the
1,2-dithiolane 1,2-Dithiolane is an organosulfur compound with the formula . It is also classified as a heterocycle derived from cyclopentane by replacing two methylene bridges ( units) with a disulfide group. 1,3-Dithiolane is an isomer. The parent molecule ...
, but the bis(
disulfide In chemistry, a disulfide (or disulphide in British English) is a compound containing a functional group or the anion. The linkage is also called an SS-bond or sometimes a disulfide bridge and usually derived from two thiol groups. In inorg ...
). 1,3-Propanedithiol is used in the synthesis of tiapamil. 1,3-Propanedithiol reacts with metal ions to form dithiolates. Illustrative is the synthesis of the derivative diiron propanedithiolate hexacarbonyl upon reaction with triiron dodecacarbonyl: :Fe3(CO)12 + C3H6(SH)2 → Fe2(S2C3H6)(CO)6 + H2 + Fe(CO)5 + CO


Safety

The stench of 1,3-propanedithiol can be minimized with
bleach Bleach is the generic name for any chemical product that is used industrially or domestically to remove color from (i.e. to whiten) fabric or fiber (in a process called bleaching) or to disinfect after cleaning. It often refers specifically t ...
.


See also

* 1,2-Propanedithiol


References

{{reflist Reagents for organic chemistry Thiols Foul-smelling chemicals