1,3-Propanedithiol
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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 gro ...
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 special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...
. This liquid, which is readily available commercially, has an intense stench.


Use in organic synthesis

1,3-Propanedithiol is mainly used for the
protection Protection is any measure taken to guard a thing 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 th ...
of
aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...
s and
ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...
s via their reversible formation of
dithiane A dithiane is a heterocyclic compound composed of a cyclohexane core structure wherein two methylene bridges (-- units) are replaced by sulfur centres. The three isomeric parent heterocycles are 1,2-dithiane, 1,3-dithiane and 1,4-dithiane. 1,3- ...
s. 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 me ...
is its formation of 1,3-dithiane from
formaldehyde Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section F ...
. 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 polarity of that group. This modification allows secondary reactions of this functional group that would oth ...
. Alkylation gives thioethers, e.g.
1,5-dithiacyclooctane 1,5-Dithiacyclooctane (DTCO) is an organosulfur compound with the formula (CHCH)CHS). This cyclic dithioether is a colorless oil that is soluble in polar solvents. It forms a variety of transition metal thioether complexes. DTO can be oxidized ...
. The unpleasant odour of 1,3-propanedithiol has encouraged the development of alternative reagents that generate similar derivatives. 1,3-Propanedithiol is used in the synthesis of
tiapamil Tiapamil (INN; also known as dimeditiapramine) is a calcium antagonist or calcium channel blocker. It is an experimental drug that has never been marketed. Tiapamil has been described as an antianginal agent. It exhibits properties of anti-arrh ...
.


Use in inorganic synthesis

1,3-Propanedithiol reacts with metal ions to form chelate rings. Illustrative is the synthesis of the derivative
diiron propanedithiolate hexacarbonyl Diiron propanedithiolate hexacarbonyl is the organoiron complex with the formula Fe2(S2C3H6)(CO)6. It is a red diamagnetic solid. It adopts a symmetrical structure with six terminal CO ligands. The complex is a precursor to hydrogenase mimics. ...
upon reaction with
triiron dodecacarbonyl Triiron dodecarbonyl is the organoiron compound with the formula Fe3(CO)12. It is a dark green solid that sublimes under vacuum. It is soluble in nonpolar organic solvents to give intensely green solutions. Most low-nuclearity clusters are pale ...
: :Fe3(CO)12 + C3H6(SH)2 → Fe2(S2C3H6)(CO)6 + H2 + Fe(CO)5 + CO


Safety

The stench of 1,3-propanedithiol can be neutralized with
bleach Bleach is the generic name for any chemical product that is used industrially or domestically to remove color (whitening) from a fabric or fiber or to clean or to remove stains in a process called bleaching. It often refers specifically, to ...
.


See also

* 1,2-Propanedithiol


References

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