Cyanuric bromide

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Cyanuric bromide
Cyanuric bromide.png
Names
IUPAC name
2,4,6-tribromo-1,3,5-triazine
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C3Br3N3/c4-1-7-2(5)9-3(6)8-1
    Key: VHYBUUMUUNCHCK-UHFFFAOYSA-N
  • C1(=NC(=NC(=N1)Br)Br)Br
Properties
C3Br3N3
Molar mass 317.766 g·mol−1
Melting point 264.5 °C (508.1 °F; 537.6 K) [1]
Related compounds
Other anions
Cyanuric fluoride; Cyanuric chloride
Related compounds
cyanogen bromide Tribromoisocyanuric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cyanuric bromide is a heterocyclic compound with formula C3N3Br3. It contains a six-membered ring of alternating nitrogen and carbon atoms, with a bromine atom attached to each carbon. It is formed by the spontaneous trimerisation of cyanogen bromide.

Contents

Cyanuric bromide synthesis.PNG

Reactions

Cyanuric bromide can be used to synthesize substituted triazines. [2] For example it reacts with anilines to form derivatives of melamine. [3] With ammonia, melamine is produced. Primary or secondary amines react. [1] Cyanuric trihydrazide is produced in the reaction with hydrazine. [1] When heated with urea at 140 °C, ammelide is formed. [1]

Cyanuric bromide reacts with water, particularly in alkaline conditions to cyanuric acid [4] and hydrogen bromide. [1]

Cyanuric bromide can add bromine to other compounds and when it is heated with acetic acid, acetyl bromide is produced. [1]

Formation

Cyanuric bromide can form in a reaction with potassium ferrocyanide with bromine at 200 °C. [1] The trimerization reaction of cyanogen bromide (BrCN) is catalyzed by aluminium trichloride or hydrogen bromide. [1]

Related Research Articles

<span class="mw-page-title-main">Bromine</span> Chemical element, symbol Br and atomic number 35

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.

<span class="mw-page-title-main">Halogen</span> Group of chemical elements

The halogens are a group in the periodic table consisting of six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), astatine (At), and tennessine (Ts), though some authors would exclude tennessine as its chemistry is unknown and is theoretically expected to be more like that of gallium. In the modern IUPAC nomenclature, this group is known as group 17.

<span class="mw-page-title-main">Haloalkane</span> Group of chemical compounds derived from alkanes containing one or more halogens

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 chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom that carries a partial positive charge, or have an atom that does not have an octet of electrons.

In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, drugs. This kind of conversion is in fact so common that a comprehensive overview is challenging. This article mainly deals with halogenation using elemental halogens. Halides are also commonly introduced using salts of the halides and halogen acids. Many specialized reagents exist for and introducing halogens into diverse substrates, e.g. thionyl chloride.

In organic chemistry, an aryl halide is an aromatic compound in which one or more hydrogen atoms, directly bonded to an aromatic ring are replaced by a halide. The haloarene are different from haloalkanes because they exhibit many differences in methods of preparation and properties. The most important members are the aryl chlorides, but the class of compounds is so broad that there are many derivatives and applications.

In organic chemistry, free-radical addition is an addition reaction which involves free radicals. Radical additions are known as variety of unsaturated substrates, both olefinic or aromatic and with or without heteroatoms.

<span class="mw-page-title-main">Hydrogen bromide</span> 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 (255.7 °F). Boiling less concentrated solutions releases H2O until the constant-boiling mixture composition is reached.

In chemistry, a trimer is a molecule or polyatomic anion formed by combination or association of three molecules or ions of the same substance. In technical jargon, a trimer is a kind of oligomer derived from three identical precursors often in competition with polymerization.

<span class="mw-page-title-main">Cyanuric acid</span> Chemical compound belonging to the class of triazine

Cyanuric acid or 1,3,5-triazine-2,4,6-triol is a chemical compound with the formula (CNOH)3. Like many industrially useful chemicals, this triazine has many synonyms. This white, odorless solid finds use as a precursor or a component of bleaches, disinfectants, and herbicides. In 1997, worldwide production was 160 000 tonnes.

<span class="mw-page-title-main">Triazine</span> Aromatic, heterocyclic compound

Triazines are a class of nitrogen-containing heterocycles. The parent molecules' molecular formula is C3H3N3. They exist in three isomeric forms, 1,3,5-triazines being common.

<span class="mw-page-title-main">Cyanuric chloride</span> Chemical compound

Cyanuric chloride is an organic compound with the formula (NCCl)3. This white solid is the chlorinated derivative of 1,3,5-triazine. It is the trimer of cyanogen chloride. Cyanuric chloride is the main precursor to the popular but controversial herbicide atrazine.

1,3,5-Triazine, also called s-triazine, is an organic chemical compound with the formula (HCN)3. It is a six-membered heterocyclic aromatic ring, one of several isomeric triazines. S-triazine—the "symmetric" isomer—and its derivatives are useful in a variety of applications.

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.

Iodine can form compounds using multiple oxidation states. Iodine is quite reactive, but it is much less reactive than the other halogens. For example, while chlorine gas will halogenate carbon monoxide, nitric oxide, and sulfur dioxide, iodine will not do so. Furthermore, iodination of metals tends to result in lower oxidation states than chlorination or bromination; for example, rhenium metal reacts with chlorine to form rhenium hexachloride, but with bromine it forms only rhenium pentabromide and iodine can achieve only rhenium tetraiodide. By the same token, however, since iodine has the lowest ionisation energy among the halogens and is the most easily oxidised of them, it has a more significant cationic chemistry and its higher oxidation states are rather more stable than those of bromine and chlorine, for example in iodine heptafluoride.

A cyanogen halide is a molecule consisting of cyanide and a halogen. Cyanogen halides are chemically classified as pseudohalogens.

<span class="mw-page-title-main">Carbonyl α-substitution reactions</span>

Alpha-substitution reactions occur at the position next to the carbonyl group, the α-position, and involve the substitution of an α hydrogen atom by an electrophile, E, through either an enol or enolate ion intermediate.

<span class="mw-page-title-main">1,4-Oxathiane</span> Chemical compound

1,4-Oxathiane is a heterocyclic compound containing one oxygen atom and one sulfur atom at opposite corners of a saturated six-membered ring. By systematic numbering, the oxygen atom is position number 1, sulfur is number 4, and positions 2, 3, 5, and 6 are carbon atoms.

Protactinium compounds are compounds containing the element protactinium. These compounds usually have protactinium in the +5 oxidation state, although these compounds can also exist in the +2, +3 and +4 oxidation states.

References

  1. 1 2 3 4 5 6 7 8 Smolin, Edwin M.; Rapoport, Lorence (2009). s-Triazines and Derivatives. John Wiley & Sons. pp. 62–65. ISBN   978-0-470-18812-5.
  2. Houben-Weyl Methods of Organic Chemistry Vol. E 9c, 4th Edition Supplement: Hetarenes III. Georg Thieme Verlag. 2014. p. 754. ISBN   978-3-13-181514-9.
  3. Kurzer, Frederick (1949). "639. Cyanamides. Part III. The formation of substituted triazines from o-halogenophenylureas and arylsulphonyl chlorides". Journal of the Chemical Society (Resumed): 3033. doi:10.1039/JR9490003033.
  4. Wells, Alexander Frank (2012). Structural Inorganic Chemistry. OUP Oxford. p. 931. ISBN   978-0-19-965763-6.