Names | |
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Preferred IUPAC name (Ethylselanyl)ethane | |
Other names Ethyl selenide | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
PubChem CID | |
UN number | 2630 |
CompTox Dashboard (EPA) | |
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Properties | |
C4H10Se | |
Molar mass | 137.09 g/mol |
Appearance | colorless liquid |
Density | 1.232 g/ml |
Melting point | −87 °C (−125 °F; 186 K) |
Boiling point | 108 °C (226 °F; 381 K) |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | Flammability, toxicity |
GHS labelling: | |
Danger | |
H225, H301, H331, H373, H410 | |
P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P301+P310, P303+P361+P353, P304+P340, P311, P314, P321, P330, P370+P378, P391, P403+P233, P403+P235, P405, P501 | |
NFPA 704 (fire diamond) | |
Flash point | 22 °C (72 °F; 295 K) |
Not available | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Diethyl selenide is an organoselenium compound with the formula C
4 H
10 Se . First reported in 1836, it was the first organoselenium compound to be discovered. [1] [2] It is the selenium analogue of diethyl ether. It has a strong and unpleasant smell.
Diethyl selenide has been detected in biofuel produced from plantain peel. [3] It is also a minor air pollutant in some areas.
It may be prepared by a substitution reaction similar to the Williamson ether synthesis: reaction of a metal selenide, such as sodium selenide, with two equivalents of ethyl iodide or similar reagent to supply the ethyl groups:
In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula R−O−R′, where R and R′ represent the alkyl or aryl groups. Ethers can again be classified into two varieties: if the alkyl or aryl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether". Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.
Selenium is a chemical element with the symbol Se and atomic number 34. It is a nonmetal with properties that are intermediate between the elements above and below in the periodic table, sulfur and tellurium, and also has similarities to arsenic. It seldom occurs in its elemental state or as pure ore compounds in the Earth's crust. Selenium – from Greek selḗnē – was discovered in 1817 by Jöns Jacob Berzelius, who noted the similarity of the new element to the previously discovered tellurium.
An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties react to form a β-hydroxyaldehyde or β-hydroxyketone, and this is then followed by dehydration to give a conjugated enone.
Diethyl ether, or simply ether, is an organic compound in the ether class with the formula (CH3CH2)2O or (C2H5)2O, sometimes abbreviated as Et2O, where Et stands for monovalent ethyl group CH3CH2 which is often written as C2H5. It is a colourless, highly volatile, sweet-smelling, extremely flammable liquid. It is commonly used as a solvent in laboratories and as a starting fluid for some engines. It was formerly used as a general anesthetic, until non-flammable drugs were developed, such as halothane. It has been used as a recreational drug to cause intoxication.
A selenide is a chemical compound containing a selenium with oxidation number of −2. Similar to sulfide, selenides occur both as inorganic compounds and as organic derivatives, which are called organoselenium compound.
In organic chemistry, the Michael reaction or Michael 1,4 addition is a reaction between a Michael donor and a Michael acceptor to produce a Michael adduct by creating a carbon-carbon bond at the acceptor's β-carbon. It belongs to the larger class of conjugate additions and is widely used for the mild formation of carbon-carbon bonds.
Diethyl azodicarboxylate, conventionally abbreviated as DEAD and sometimes as DEADCAT, is an organic compound with the structural formula CH3CH2−O−C(=O)−N=N−C(=O)−O−CH2CH3. Its molecular structure consists of a central azo functional group, RN=NR, flanked by two ethyl ester groups. This orange-red liquid is a valuable reagent but also quite dangerous and explodes upon heating. Therefore, commercial shipment of pure diethyl azodicarboxylate is prohibited in the United States and is carried out either in solution or on polystyrene particles.
Hydrogen selenide is an inorganic compound with the formula H2Se. This hydrogen chalcogenide is the simplest and most commonly encountered hydride of selenium. H2Se is a colorless, flammable gas under standard conditions. It is the most toxic selenium compound with an exposure limit of 0.05 ppm over an 8-hour period. Even at extremely low concentrations, this compound has a very irritating smell resembling that of decayed horseradish or 'leaking gas', but smells of rotten eggs at higher concentrations.
Ethyl sulfate, also known as sulfovinic acid, is an organic chemical compound used as an intermediate in the production of ethanol from ethylene. It is the ethyl ester of sulfuric acid.
Organoselenium chemistry is the science exploring the properties and reactivity of organoselenium compounds, chemical compounds containing carbon-to-selenium chemical bonds. Selenium belongs with oxygen and sulfur to the group 16 elements or chalcogens, and similarities in chemistry are to be expected. Organoselenium compounds are found at trace levels in ambient waters, soils and sediments.
Selenols are organic compounds that contain the functional group with the connectivity C–Se–H. Selenols are sometimes also called selenomercaptans and selenothiols. Selenols are one of the principal classes of organoselenium compounds. A well known selenol is the amino acid selenocysteine.
Diethylzinc (C2H5)2Zn, or DEZ, is a highly pyrophoric and reactive organozinc compound consisting of a zinc center bound to two ethyl groups. This colourless liquid is an important reagent in organic chemistry. It is available commercially as a solution in hexanes, heptane, or toluene, or as a pure liquid.
In organic chemistry, the Ei mechanism, also known as a thermal syn elimination or a pericyclic syn elimination, is a special type of elimination reaction in which two vicinal (adjacent) substituents on an alkane framework leave simultaneously via a cyclic transition state to form an alkene in a syn elimination. This type of elimination is unique because it is thermally activated and does not require additional reagents, unlike regular eliminations, which require an acid or base, or would in many cases involve charged intermediates. This reaction mechanism is often found in pyrolysis.
Sodium aluminium hydride or sodium alanate is an inorganic compound with the chemical formula NaAlH4. It is a white pyrophoric solid that dissolves in tetrahydrofuran (THF), but not in diethyl ether or hydrocarbons. It has been evaluated as an agent for the reversible storage of hydrogen and it is used as a reagent for the chemical synthesis of organic compounds. Similar to lithium aluminium hydride, it is a salt consisting of separated sodium cations and tetrahedral AlH−
4 anions.
Selenoxide elimination is a method for the chemical synthesis of alkenes from selenoxides. It is most commonly used to synthesize α,β-unsaturated carbonyl compounds from the corresponding saturated analogues. It is mechanistically related to the Cope reaction.
Sodium selenide is an inorganic compound of sodium and selenium with the chemical formula Na2Se.
A seleninic acid is an organoselenium compound and an oxoacid with the general formula RSeO2H, where R ≠ H. It is a member of the family of organoselenium oxoacids, which also includes selenenic acids and selenonic acids, which are RSeOH and RSeO3H, respectively. The parent member of this family of compounds is methaneseleninic acid (CH3SeO2H), also known as methylseleninic acid or "MSA".
Diethyl oxomalonate is the diethyl ester of mesoxalic acid (ketomalonic acid), the simplest oxodicarboxylic acid and thus the first member (n = 0) of a homologous series HOOC–CO–(CH2)n–COOH with the higher homologues oxalacetic acid (n = 1), α-ketoglutaric acid (n = 2) and α-ketoadipic acid (n = 3) (the latter a metabolite of the amino acid lysine). Diethyl oxomalonate reacts because of its highly polarized keto group as electrophile in addition reactions and is a highly active reactant in pericyclic reactions such as the Diels-Alder reactions, cycloadditions or ene reactions. At humid air, mesoxalic acid diethyl ester reacts with water to give diethyl mesoxalate hydrate and the green-yellow oil are spontaneously converted to white crystals.
Bis(2-chloroethyl)selenide is the organoselenium compound with the formula Se(CH2CH2Cl)2. As a haloalkyl derivative of selenium, it is an analogue of bis(2-chloroethyl)sulfide, the prototypical sulfur mustard used in chemical warfare. Bis(2-chloroethyl)selenide has not been used as a chemical warfare agent, however it is still a potent alkylating agent and has potential in chemotherapy.
In chemistry, a selenosulfide refers to distinct classes of inorganic and organic compounds containing sulfur and selenium. The organic derivatives contain Se-S bonds, whereas the inorganic derivatives are more variable.