Names | |||
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Preferred IUPAC name 1,3,5-Trithiane | |||
Other names Thioformaldehyde trimer, Trimethylentrisulfide, Trimethylene trisulfide, Trithioformaldehyde, 1,3,5-Trithiacyclohexane, sym-Trithiane, Thioform, s-Trithiane | |||
Identifiers | |||
3D model (JSmol) | |||
ChEBI | |||
ChemSpider | |||
ECHA InfoCard | 100.005.482 | ||
EC Number |
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PubChem CID | |||
UNII | |||
CompTox Dashboard (EPA) | |||
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Properties | |||
C3H6S3 | |||
Molar mass | 138.27 | ||
Appearance | Colourless solid | ||
Density | 1.6374 g/cm3 [1] | ||
Melting point | 215 to 220 °C (419 to 428 °F; 488 to 493 K) | ||
Slightly soluble | |||
Solubility | Benzene | ||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards | Toxic (T) | ||
GHS labelling: | |||
Warning | |||
H319 | |||
P264, P280, P305+P351+P338, P313 | |||
NFPA 704 (fire diamond) | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
1,3,5-Trithiane is the chemical compound with the formula (CH2S)3. This heterocycle is the cyclic trimer of the otherwise unstable species thioformaldehyde. It consists of a six-membered ring with alternating methylene bridges and thioether groups. It is prepared by treatment of formaldehyde with hydrogen sulfide. [2]
Trithiane is a building block molecule in organic synthesis, being a masked source of formaldehyde. In one application, it is deprotonated with organolithium reagents to give the lithium derivative, which can be alkylated. [3]
Trithiane is the dithioacetal of formaldehyde. Other dithioacetals undergo similar reactions to the above.
It is also a precursor to other organosulfur reagents. For example, chlorination in the presence of water affords the chloromethyl sulfonyl chloride: [4]
Trithiane is the parent of a class of heterocycles called trithianes, that formally result from substitution of various monovalent groups for one or more of the hydrogen atoms. The species often arise from thiation of ketones and aldehydes. The incipient thioketones and thioaldehydes undergo trimerization. One example is 2,2,4,4,6,6-hexamethyl-1,3,5-trithiane, or trithioacetone, the trimer of thioacetone (propane-2-thione). Alternatively 1,3,5-trithiane can be deprotonated and alkylated to afford (SCH2)n(SCHR)3-n. [5]
The conformation of trithianes has been well investigated. [6]
Hydrazones are a class of organic compounds with the structure R1R2C=N−NH2. They are related to ketones and aldehydes by the replacement of the oxygen =O with the =N−NH2 functional group. They are formed usually by the action of hydrazine on ketones or aldehydes.
Chloroacetic acid, industrially known as monochloroacetic acid (MCA), is the organochlorine compound with the formula ClCH2CO2H. This carboxylic acid is a useful building block in organic synthesis. It is a colorless solid. Related compounds are dichloroacetic acid and trichloroacetic acid.
The Friedel–Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877 to attach substituents to an aromatic ring. Friedel–Crafts reactions are of two main types: alkylation reactions and acylation reactions. Both proceed by electrophilic aromatic substitution.
A diol is a chemical compound containing two hydroxyl groups. An aliphatic diol is also called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified.
Acetylacetone is an organic compound with the chemical formula CH3COCH2COCH3. It is a colorless liquid, classified as a 1,3-diketone. It exists in equilibrium with a tautomer CH3C(O)CH=(OH)CH3. These tautomers interconvert so rapidly under most conditions that they are treated as a single compound in most applications. It is a colorless liquid that is a precursor to acetylacetonate anion, a bidentate ligand. It is also a building block for the synthesis of heterocyclic compounds.
Sulfuryl chloride is an inorganic compound with the formula SO2Cl2. At room temperature, it is a colorless liquid with a pungent odor. Sulfuryl chloride is not found in nature, as can be inferred from its rapid hydrolysis.
Thioacetals are the sulfur analogues of acetals. There are two classes: monothioacetals and dithioacetals. Monothioacetals are less common, have the functional group RC(OR')(SR")H. Dithioacetals have the formula RC(SR')2H (symmetric dithioacetals) and RC(SR')(SR")H (asymmetric dithioacetals).
Tebbe's reagent is the organometallic compound with the formula (C5H5)2TiCH2ClAl(CH3)2. It is used in the methylenation of carbonyl compounds, that is it converts organic compounds containing the R2C=O group into the related R2C=CH2 derivative. It is a red solid that is pyrophoric in the air, and thus is typically handled with air-free techniques. It was originally synthesized by Fred Tebbe at DuPont Central Research.
Stephen aldehyde synthesis, a named reaction in chemistry, was invented by Henry Stephen (OBE/MBE). This reaction involves the preparation of aldehydes (R-CHO) from nitriles (R-CN) using tin(II) chloride (SnCl2), hydrochloric acid (HCl) and quenching the resulting iminium salt ([R-CH=NH2]+Cl−) with water (H2O). During the synthesis, ammonium chloride is also produced.
Acetone cyanohydrin (ACH) is an organic compound used in the production of methyl methacrylate, the monomer of the transparent plastic polymethyl methacrylate (PMMA), also known as acrylic. It liberates hydrogen cyanide easily, so it is used as a source of such. For this reason, this cyanohydrin is also highly toxic.
1-Methylimidazole or N-methylimidazole is an aromatic heterocyclic organic compound with the formula CH3C3H3N2. It is a colourless liquid that is used as a specialty solvent, a base, and as a precursor to some ionic liquids. It is a fundamental nitrogen heterocycle and as such mimics for various nucleoside bases as well as histidine and histamine.
In nitrile reduction a nitrile is reduced to either an amine or an aldehyde with a suitable chemical reagent.
The Jones oxidation is an organic reaction for the oxidation of primary and secondary alcohols to carboxylic acids and ketones, respectively. It is named after its discoverer, Sir Ewart Jones. The reaction was an early method for the oxidation of alcohols. Its use has subsided because milder, more selective reagents have been developed, e.g. Collins reagent.
Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO. It is the 3-carbon aldehyde. It is a colourless, flammable liquid with a slightly fruity odour. It is produced on a large scale industrially.
Thiocarboxylic acids are organosulfur compounds related to carboxylic acids by replacement of one of the oxygen atoms with a sulfur atom. Two tautomers are possible: a thione form (RC OH) and a thiol form (RC SH). These are sometimes also referred to as "carbothioic O-acid" and "carbothioic S-acid" respectively. Of these the thiol form is most common.
Propargyl bromide, also known as 3-bromo-prop-1-yne, is an organic compound with the chemical formula HC≡CCH2Br. A colorless liquid, it is a halogenated organic compound consisting of propyne with a bromine substituent on the methyl group. It has a lachrymatory effect, like related compounds. The compound is used as a reagent in organic synthesis.
Thioanisole is an organic compound with the formula CH3SC6H5. It is a colorless liquid that is soluble in organic solvents. It is the simplest alkyl–aryl thioether. The name indicates that this compound is the sulfur analogue—the thioether rather than the oxygen-centered ether—of anisole.
Chloroacetonitrile is the organic compound with the formula ClCH2CN. A colorless liquid, it is derived from acetonitrile (CH3CN) by replacement of one H with Cl. In practice, it is produced by dehydration of chloroacetamide. The compound is an alkylating agent, and as such is handled cautiously.
Hydroxymethylation is a chemical reaction that installs the CH2OH group. The transformation can be implemented in many ways and applies to both industrial and biochemical processes.
Methylenation is a chemical reaction that installs the methylene (CH2) group. Typically, the reaction is used to prepare terminal alkenes from aldehydes and, less frequently, ketones.