1,2-Propanedithiol

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1,2-Propanedithiol
1,2-propanedithiol.png
Names
Preferred IUPAC name
Propane-1,2-dithiol [1]
Other names
1,2-Dimercaptopropane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.271 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C3H8S2/c1-3(5)2-4/h3-5H,2H2,1H3 Yes check.svgY
    Key: YGKHJWTVMIMEPQ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C3H8S2/c1-3(5)2-4/h3-5H,2H2,1H3
    Key: YGKHJWTVMIMEPQ-UHFFFAOYAG
  • SCC(S)C
Properties
C3H8S2
Molar mass 108.22 g·mol−1
Boiling point 152 °C (306 °F; 425 K)
Insoluble
Solubility in organic solventssoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

1,2-Propanedithiol, sometimes called 1,2-dimercaptopropane, is a thiol with the formula HSCH2CH(SH)CH3. This colorless, intensely odorous liquid is the simplest chiral dithiol. Related dithiols include 1,2-ethanedithiol, 2,3-dimercapto-1-propanesulfonic acid, and 1,3-propanedithiol. It is generated by the addition of H2S to the related episulfide, CH3CHCH2S.

Refractive index = 1.531-1.541

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Allicin is an organosulfur compound obtained from garlic, a species in the family Alliaceae. It was first isolated and studied in the laboratory by Chester J. Cavallito and John Hays Bailey in 1944. When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic. The allicin generated is unstable and quickly changes into a series of other sulfur-containing compounds such as diallyl disulfide. Allicin is part of a defense mechanism against attacks by pests on the garlic plant.

Propene, also known as propylene, is an unsaturated organic compound with the chemical formula . It has one double bond, and is the second simplest member of the alkene class of hydrocarbons. It is a colorless gas with a faint petroleum-like odor.

Dehydrogenation is the a chemical reaction that involves the removal of hydrogen, usually from an organic molecule. It is the reverse of hydrogenation. Dehydrogenation is important, both as a useful reaction and a serious problem. At its simplest, it is useful way of converting alkanes, which are relatively inert and thus low-valued, to olefins, which are reactive and thus more valuable. Alkenes are precursors to aldehydes, alcohols, polymers, and aromatics. As a problematic reaction, the fouling and inactivation of many catalysts arises via coking, which is the dehydrogenative polymerization of organic substrates.

Hydrogen bromide Chemical compound

Hydrogen bromide is the inorganic compound with the formula HBr. It is a hydrogen halide consisting of hydrogen and bromine. A colorless gas, it dissolves in water, forming hydrobromic acid, which is saturated at 68.85% HBr by weight at room temperature. Aqueous solutions that are 47.6% HBr by mass form a constant-boiling azeotrope mixture that boils at 124.3 °C. Boiling less concentrated solutions releases H2O until the constant-boiling mixture composition is reached.

1-Propanol Primary alcohol compound

1-Propanol is a primary alcohol with the formula CH3CH2CH2OH and sometimes represented as PrOH or n-PrOH. It is a colorless liquid and an isomer of 2-propanol. It is formed naturally in small amounts during many fermentation processes and used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent.

Ethane-1,2-dithiol Chemical compound

Ethane-1,2-dithiol, also known as EDT, is a colorless liquid with the formula C2H4(SH)2. It has a very characteristic odor which is compared by many people to rotten cabbage. It is a common building block in organic synthesis and an excellent ligand for metal ions.

1,4-Dihydropyridine Chemical compound

1,4-Dihydropyridine (DHP) is an organic compound with the formula CH2(CH=CH)2NH. The parent compound is uncommon, but derivatives of 1,4-dihydropyridine are important commercially and biologically. The pervasive cofactors NADH and NADPH are derivatives of 1,4-dihydropyridine. 1,4-Dihydropyridine-based drugs are L-type calcium channel blockers, used in the treatment of hypertension. 1,2-Dihydropyridines are also known.

Dithiane Chemical compound

A dithiane is a heterocyclic compound composed of a cyclohexane core structure wherein two methylene bridges are replaced by sulfur centres. The three isomeric parent heterocycles are 1,2-dithiane, 1,3-dithiane and 1,4-dithiane.

Propane-1,3-dithiol Chemical compound

1,3-Propanedithiol is the chemical compound with the formula HSCH2CH2CH2SH. This dithiol is a useful reagent in organic synthesis. This liquid, which is readily available commercially, has an intense stench.

Dithiete Chemical compound

Dithiete is an unsaturated heterocyclic compound that contains two adjacent sulfur atoms and two sp2-hybridized carbon centers. Derivatives are known collectively as dithietes or 1,2-dithietes. With 6 π electrons, 1,2-dithietes are examples of aromatic organosulfur compounds. A few 1,2-dithietes have been isolated.

Thiocarbonate describes a family of anions with the general chemical formula CS
3−x
O2−
x
. Like the carbonate dianion, the thiocarbonates are planar, with carbon at the center. The average bond order from C to S or O is 1+13. The state of protonation is usually not specified. These anions are good nucleophiles and good ligands.

3-Hydroxybutanal (acetaldol) is an organic compound with the formula CH3CH(OH)CH2CHO. It is classified as an aldol, formally the product of the dimerization of acetaldehyde. A colorless liquid, it is a versatile and valuable intermediate with diverse impacts. The compound is chiral although this aspect is not often exploited.

Benzene-1,2-dithiol Chemical compound

Benzene-1,2-dithiol is the organosulfur compound with the formula C6H4(SH)2. This colourless viscous liquid consists of a benzene ring with a pair of adjacent thiol groups. The conjugate base of this diprotic compound serves as chelating agent in coordination chemistry and a building block for the synthesis of other organosulfur compounds.

1,2-Dithietane Chemical compound

1,2-Dithietane is a dithietane. It is a heterocyclic compound with a four-membered ring. Two sulfur atoms are adjacent, and the molecule is saturated. 1,2-Dithietane has not been produced as of 2000. The combination of ring strain, and lone pairs of electrons, which repel each other, on the sulfur atoms makes the sulfur-sulfur bond too weak to produce the molecule. However a few derivatives are known. 3,4-Diethyl-1,2-dithietane 1,1-dioxide has one sulfur fully oxidised. Dithiatopazine is a tricyclic compound with the -S-S- as a bridge. 1,2-Dithietan-3-one, the ketone of 1,2-dithietane, was produced in 2008 by reacting α-dithiolactone with ethoxycarbonylformonitrile oxide. 4,4-di-tert-butyl-1,2-dithietan-3-one and the spiro compound 4,4-(2',2',6',6'-tetramethylcyclohexyl)1,2-dithietan-3-one have also been made.

Dithiol

A dithiol is a type of organosulfur compound with two thiol functional groups. Their properties are generally similar to those of monothiols in terms of solubility, odor, and volatility. They can be classified according to the relative location of the two thiol group on the organic backbone.

Ethane-1,1-dithiol Chemical compound

Ethane-1,1-dithiol is an organosulfur compound with formula CH3CH(SH)2. It is a colourless smelly liquid that is added to or found in some foods. The compound is an example of a geminal dithiol.

Thioacetone Chemical compound

Thioacetone is an organosulfur compound with the chemical formula (CH3)2CS. It is an unstable orange or brown substance that can be isolated only at low temperatures. Above −20 °C (−4 °F), thioacetone readily converts to a polymer and a trimer, trithioacetone. It has an extremely potent, unpleasant odour, hence thioacetone has been considered as the worst-smelling chemical.

1,5-Dithiacyclooctane Chemical compound

1,5-Dithiacyclooctane (DTCO) is an organosulfur compound with the formula (CH2CH2)CH2S)2. This cyclic dithioether is a colorless oil that is soluble in polar solvents. It forms a variety of transition metal thioether complexes.

Trithioacetone Chemical compound

Trithioacetone (2,2,4,4,6,6-hexamethyl-1,3,5-trithiane) is an organic chemical with formula C
9
H
18
S
3
. Its covalent structure is [–C(CH
3
)
2
–S–]
3
, that is, a six-membered ring of alternating carbon and sulfur atoms, with two methyl groups attached to each carbon. It can be viewed as a derivative of 1,3,5-trithiane, with methyl-group substituents for all of the hydrogen atoms in that parent structure.

Nereistoxin Chemical compound

Nereistoxin is a natural product identified in 1962 as the toxic organic compound N,N-dimethyl-1,2-dithiolan-4-amine. It had first been isolated in 1934 from the marine annelid Lumbriconereis heteropoda and acts by blocking the nicotinic acetylcholine receptor. Researchers at Takeda in Japan investigated it as a possible insecticide. They subsequently developed a number of derivatives that were commercialised, including those with the ISO common names bensultap, cartap, thiocyclam and thiosultap.

References

  1. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 697. doi:10.1039/9781849733069-FP001. ISBN   978-0-85404-182-4.