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| Names | |
|---|---|
| Preferred IUPAC name 1,2-Dibromoethyne [1] | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
PubChem CID | |
CompTox Dashboard (EPA) | |
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| Properties | |
| C2Br2 | |
| Molar mass | 183.830 g·mol−1 |
| Melting point | −16.5 °C (2.3 °F; 256.6 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Dibromoacetylene is a molecular chemical compound containing acetylene, with its hydrogen substituted by bromine.
Dibromoacetylene can be made by reacting 1,1,2-tribromoethylene with potassium hydroxide. This method has a danger of causing explosions. [2]
Another way is to react acetylene with phenyl lithium (at −50 °C) to make lithium acetylide, which then reacts with bromine to yield the product. [3]
Yet another way is to react acetylene with sodium hypobromite NaOBr. [4]
Dibromoacetylene is explosive and sensitive to air. [4] Its appearance is a clear water like liquid. It has a sweetish smell, but makes a white fume in air that then smells like ozone, possibly because it forms ozone. [2] Dibromoacetylene is lachrymatory. [2]
Dibromoacetylene can be polymerised to polydibromoacetylene using catalysts like titanium tetrachloride and triethylaluminium. Polydibromoacetylene is black, electrically conducting, and stable in air to over 200 °C. [4]
The infrared spectrum has absorption at 2185 cm−1 due to symmetrical stretching on the C≡C bond, 832 cm−1 asymmetrical stretch on C-Br bond, 311 cm−1 bending on Z shape BrCC, 267 symmetrical stretch on all bonds, and 167 cm−1 for C-shaped bending. [2]
In air dibromoacetylene spontaneously inflames producing black sooty smoke and a red flame. When heated, it explodes, yielding carbon and other substances. A slower reaction with oxygen and water, yields oxalic acid and hydrobromic acid and other bromine containing substances. A reaction with hydrogen iodide yields dibromoiodoethylene. Dibromoacetylene reacts with bromine to yield tetrabromoethene. [5]
Dibromoacetylene reacts with Apiezon L, which is used as a vacuum grease in distillation, so its use is unsuitable with this chemical. [2]
In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or in the terminal position. Terminal alkenes are also known as α-olefins.
In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and no other functional groups form a homologous series with the general chemical formula CnH2n−2. Alkynes are traditionally known as acetylenes, although the name acetylene also refers specifically to C2H2, known formally as ethyne using IUPAC nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic.
Bromine is a chemical element; it has symbol Br and atomic number 35. It is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between those of chlorine and iodine. Isolated independently by two chemists, Carl Jacob Löwig and Antoine Jérôme Balard, its name was derived from the Ancient Greek βρῶμος (bromos) meaning "stench", referring to its sharp and pungent smell.
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.
The haloalkanes are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially. They are used as flame retardants, fire extinguishants, refrigerants, propellants, solvents, and pharmaceuticals. Subsequent to the widespread use in commerce, many halocarbons have also been shown to be serious pollutants and toxins. For example, the chlorofluorocarbons have been shown to lead to ozone depletion. Methyl bromide is a controversial fumigant. Only haloalkanes that contain chlorine, bromine, and iodine are a threat to the ozone layer, but fluorinated volatile haloalkanes in theory may have activity as greenhouse gases. Methyl iodide, a naturally occurring substance, however, does not have ozone-depleting properties and the United States Environmental Protection Agency has designated the compound a non-ozone layer depleter. For more information, see Halomethane. Haloalkane or alkyl halides are the compounds which have the general formula "RX" where R is an alkyl or substituted alkyl group and X is a halogen.
In organic chemistry, a thiol, or thiol derivative, is any organosulfur compound of the form R−SH, where R represents an alkyl or other organic substituent. The −SH functional group itself is referred to as either a thiol group or a sulfhydryl group, or a sulfanyl group. Thiols are the sulfur analogue of alcohols, and the word is a blend of "thio-" with "alcohol".
A glycosidic bond or glycosidic linkage is a type of ether bond that joins a carbohydrate (sugar) molecule to another group, which may or may not be another carbohydrate.
Diborane(6), commonly known as diborane, is the chemical compound with the formula B2H6. It is a toxic, colorless, and pyrophoric gas with a repulsively sweet odor. Given its simple formula, borane is a fundamental boron compound. It has attracted wide attention for its electronic structure. Several of its derivatives are useful reagents.
In chemistry, an interhalogen compound is a molecule which contains two or more different halogen atoms and no atoms of elements from any other group.
Dodecahedrane is a chemical compound, a hydrocarbon with formula C20H20, whose carbon atoms are arranged as the vertices (corners) of a regular dodecahedron. Each carbon is bound to three neighbouring carbon atoms and to a hydrogen atom. This compound is one of the three possible Platonic hydrocarbons, the other two being cubane and tetrahedrane.
n-Butyllithium C4H9Li (abbreviated n-BuLi) is an organolithium reagent. It is widely used as a polymerization initiator in the production of elastomers such as polybutadiene or styrene-butadiene-styrene (SBS). Also, it is broadly employed as a strong base (superbase) in the synthesis of organic compounds as in the pharmaceutical industry.
Isocyanic acid is a chemical compound with the structural formula HNCO, which is often written as H−N=C=O. It is a colourless, volatile and poisonous substance, with a boiling point of 23.5 °C. It is the predominant tautomer and an isomer of cyanic acid (aka. cyanol).
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.
Cyanogen bromide is the inorganic compound with the formula (CN)Br or BrCN. It is a colorless solid that is widely used to modify biopolymers, fragment proteins and peptides, and synthesize other compounds. The compound is classified as a pseudohalogen.
Bromine compounds are compounds containing the element bromine (Br). These compounds usually form the -1, +1, +3 and +5 oxidation states. Bromine is intermediate in reactivity between chlorine and iodine, and is one of the most reactive elements. Bond energies to bromine tend to be lower than those to chlorine but higher than those to iodine, and bromine is a weaker oxidising agent than chlorine but a stronger one than iodine. This can be seen from the standard electrode potentials of the X2/X− couples (F, +2.866 V; Cl, +1.395 V; Br, +1.087 V; I, +0.615 V; At, approximately +0.3 V). Bromination often leads to higher oxidation states than iodination but lower or equal oxidation states to chlorination. Bromine tends to react with compounds including M–M, M–H, or M–C bonds to form M–Br bonds.
In chemistry, a ladderane is an organic molecule containing two or more fused cyclobutane rings. The name arises from the resemblance of a series of fused cyclobutane rings to a ladder. Numerous synthetic approaches have been developed for the synthesis of ladderane compounds of various lengths. The mechanisms often involve [2 + 2] photocycloadditions, a useful reaction for creating strained 4-membered rings. Naturally occurring ladderanes have been identified as major components of the anammoxosome membrane of the anammox bacteria, phylum Planctomycetota.
Organobromine chemistry is the study of the synthesis and properties of organobromine compounds, also called organobromides, which are organic compounds that contain carbon bonded to bromine. The most pervasive is the naturally produced bromomethane.
In chemistry, molecular oxohalides (oxyhalides) are a group of chemical compounds in which both oxygen and halogen atoms are attached to another chemical element A in a single molecule. They have the general formula AOmXn, where X is a halogen. Known oxohalides have fluorine (F), chlorine (Cl), bromine (Br), and/or iodine (I) in their molecules. The element A may be a main group element, a transition element, a rare earth element or an actinide. The term oxohalide, or oxyhalide, may also refer to minerals and other crystalline substances with the same overall chemical formula, but having an ionic structure.
Cyanogen fluoride is an inorganic linear compound which consists of a fluorine in a single bond with carbon, and a nitrogen in a triple bond with carbon. It is a toxic and explosive gas at room temperature. It is used in organic synthesis and can be produced by pyrolysis of cyanuric fluoride or by fluorination of cyanogen.
Methylcyclohexene refers to any one of three organic compounds consisting of cyclohexene with a methyl group substituent. The location of the methyl group relative to the cyclohexene double bond creates the three different structural isomers. These compounds are generally used as a reagent or intermediate to derive other organic compounds.