Names | |||
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Preferred IUPAC name Thietane | |||
Systematic IUPAC name Thiacyclobutane | |||
Other names Trimethylene sulfide | |||
Identifiers | |||
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3D model (JSmol) | |||
102383 | |||
ChEBI | |||
ChemSpider | |||
ECHA InfoCard | 100.005.469 | ||
EC Number |
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PubChem CID | |||
UNII | |||
UN number | 1993 | ||
CompTox Dashboard (EPA) | |||
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Properties | |||
C3H6S | |||
Molar mass | 74.14 g·mol−1 | ||
Appearance | Colourless liquid | ||
Odor | Sulfurous | ||
Density | 1.028 g cm−3 | ||
Boiling point | 94 to 95 °C (201 to 203 °F; 367 to 368 K) | ||
Hazards | |||
GHS labelling: | |||
Danger | |||
H225, H302 | |||
P210 | |||
NFPA 704 (fire diamond) | |||
Flash point | -11(9) °C | ||
Related compounds | |||
Other anions | Oxetane, Azetidine, Phosphetane | ||
Related compounds | Thiirane, Dithietane, Tetrahydrothiophene, Thiane, Thiepane, Thiocane, Thionane | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Thietane is a heterocyclic compound containing a saturated four-membered ring with three carbon atoms and one sulfur atom. [1] [2]
Thietane, and its derivative 2-propylthietane, are strong-smelling mouse alarm pheromones and predator scent analogues. [3] [4] Both the mouse and human olfactory receptors MOR244-3 and OR2T11, respectively, were found to respond to thietane in the presence of copper. [5]
Thietane can be produced from the reaction of trimethylene carbonate and potassium thiocyanate, but the yield is low. [6]
An improved synthesis method is the reaction of 1,3-dibromopropane and sodium sulfide. [7]
Nucleophiles like butyllithium can open the ring in thietane. [8] Thietane also reacts with bromine. [9]
Thiazole, or 1,3-thiazole, is a 5-membered heterocyclic compound that contains both sulfur and nitrogen. The term 'thiazole' also refers to a large family of derivatives. Thiazole itself is a pale yellow liquid with a pyridine-like odor and the molecular formula C3H3NS. The thiazole ring is notable as a component of the vitamin thiamine (B1).
In organic chemistry, hydroboration refers to the addition of a hydrogen-boron bond to certain double and triple bonds involving carbon. This chemical reaction is useful in the organic synthesis of organic compounds.
In organic chemistry, episulfides are a class of organic compounds that contain a saturated, heterocyclic ring consisting of two carbon atoms and one sulfur atom. It is the sulfur analogue of an epoxide or aziridine. They are also known as thiiranes, olefin sulfides, thioalkylene oxides, and thiacyclopropanes. Episulfides are less common and generally less stable than epoxides. The most common derivative is ethylene sulfide.
The Negishi coupling is a widely employed transition metal catalyzed cross-coupling reaction. The reaction couples organic halides or triflates with organozinc compounds, forming carbon-carbon bonds (C-C) in the process. A palladium (0) species is generally utilized as the metal catalyst, though nickel is sometimes used. A variety of nickel catalysts in either Ni0 or NiII oxidation state can be employed in Negishi cross couplings such as Ni(PPh3)4, Ni(acac)2, Ni(COD)2 etc.
Boroxine is a 6-membered heterocyclic compound composed of alternating oxygen and singly-hydrogenated boron atoms. Boroxine derivatives such as trimethylboroxine and triphenylboroxine also make up a broader class of compounds called boroxines. These compounds are solids that are usually in equilibrium with their respective boronic acids at room temperature. Beside being used in theoretical studies, boroxine is primarily used in the production of optics.
Bromous acid is the inorganic compound with the formula of HBrO2. It is an unstable compound, although salts of its conjugate base – bromites – have been isolated. In acidic solution, bromites decompose to bromine.
The tetrafluoroammonium cation is a positively charged polyatomic ion with chemical formula NF+
4. It is equivalent to the ammonium ion where the hydrogen atoms surrounding the central nitrogen atom have been replaced by fluorine. Tetrafluoroammonium ion is isoelectronic with tetrafluoromethane CF
4, trifluoramine oxide ONF
3 and the tetrafluoroborate BF−
4 anion.
Thiete is a heterocyclic compound containing an unsaturated four-membered ring with three carbon atoms and one sulfur atom. It is more commonly encountered not on its own, but in anellated derivatives, several of which have been synthesized. Thietes are generally not very stable.
Germylenes are a class of germanium(II) compounds with the general formula :GeR2. They are heavier carbene analogs. However, unlike carbenes, whose ground state can be either singlet or triplet depending on the substituents, germylenes have exclusively a singlet ground state. Unprotected carbene analogs, including germylenes, has a dimerization nature. Free germylenes can be isolated under the stabilization of steric hindrance or electron donation. The synthesis of first stable free dialkyl germylene was reported by Jutzi, et al in 1991.
Metal carbon dioxide complexes are coordination complexes that contain carbon dioxide ligands. Aside from the fundamental interest in the coordination chemistry of simple molecules, studies in this field are motivated by the possibility that transition metals might catalyze useful transformations of CO2. This research is relevant both to organic synthesis and to the production of "solar fuels" that would avoid the use of petroleum-based fuels.
Marjorie Constance Caserio was an English chemist. In 1975, she was awarded the Garvan Medal by the American Chemical Society.
In chemistry, a boranylium ion is an inorganic cation with the chemical formula BR+
2, where R represents a non-specific substituent. Being electron-deficient, boranylium ions form adducts with Lewis bases. Boranylium ions have historical names that depend on the number of coordinated ligands:
Montréalone is a mesoionic heterocyclic chemical compound. It is named for the city of Montréal, Canada, which is the location of McGill University, where it was first discovered.
David Markham Lemal is the Albert W. Smith Professor of Chemistry Emeritus and Research Professor of Chemistry at Dartmouth College. He received an A.B. degree (summa) from Amherst College in 1955 and a Ph.D. in chemistry from Harvard University in 1959. At Harvard he worked with R. B. Woodward on deoxy sugars and a synthesis of the alkaloid yohimbine.
In organometallic chemistry, the activation of cyclopropanes by transition metals is a research theme with implications for organic synthesis and homogeneous catalysis. Being highly strained, cyclopropanes are prone to oxidative addition to transition metal complexes. The resulting metallacycles are susceptible to a variety of reactions. These reactions are rare examples of C-C bond activation. The rarity of C-C activation processes has been attributed to Steric effects that protect C-C bonds. Furthermore, the directionality of C-C bonds as compared to C-H bonds makes orbital interaction with transition metals less favorable. Thermodynamically, C-C bond activation is more favored than C-H bond activation as the strength of a typical C-C bond is around 90 kcal per mole while the strength of a typical unactivated C-H bond is around 104 kcal per mole.
Phosphenium ions, not to be confused with phosphonium or phosphirenium, are divalent cations of phosphorus of the form [PR2]+. Phosphenium ions have long been proposed as reaction intermediates.
Vinylcyclopropane [5+2] cycloaddition is a type of cycloaddition between a vinylcyclopropane (VCP) and an olefin or alkyne to form a seven-membered ring.
F. Dean Toste is the Gerald E. K. Branch Distinguished Professor of Chemistry at the University of California, Berkeley and faculty scientist at the chemical sciences division of Lawrence Berkeley National Lab. He is a prominent figure in the field of organic chemistry and is best known for his contributions to gold chemistry and asymmetric ion-pairing catalysis. Toste was elected a member of the National Academy of Sciences in 2020, and a member of the American Academy of Arts and Sciences in 2018.
T.V. (Babu) RajanBabu is an organic chemist who holds the position of Distinguished Professor of Chemistry in the College of Arts and Sciences at the Ohio State University. His laboratory traditionally focuses on developing transition metal-catalyzed reactions. RajanBabu is known for helping develop the Nugent-RajanBabu reagent, a chemical reagent used in synthetic organic chemistry as a single electron reductant.
Bromocyclopropane is a organobromine compound with the chemical formula C3H5Br. It is a member of haloalkane family.