Ammeline

Last updated
Ammeline
Structural formula Ammeline.svg
Structural formula
Ball-and-stick model Ammeline-3D-balls.png
Ball-and-stick model
Names
Preferred IUPAC name
4,6-Diamino-1,3,5-triazin-2-ol
Other names
2,4-Diamino-6-hydroxy-1,3,5-triazine
4,6-Diamino-2-hydroxy-1,3,5-triazine
4,6-diamino-1,3,5-triazin-2(1H)-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.010.415 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C3H5N5O/c4-1-6-2(5)8-3(9)7-1/h(H5,4,5,6,7,8,9) Yes check.svgY
    Key: MASBWURJQFFLOO-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C3H5N5O/c4-1-6-2(5)8-3(9)7-1/h(H5,4,5,6,7,8,9)
    Key: MASBWURJQFFLOO-UHFFFAOYAL
  • O=C\1/N=C(/N)NC(=N/1)/N
Properties
C3H5N5O
Molar mass 127.107 g·mol−1
AppearanceWhite powder
Melting point N/A (decomposes before melting)
Trace
Solubility Soluble in aqueous alkalies and mineral acids, but not acetic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Ammeline (4,6-diamino-2-hydroxy-1,3,5-triazine) is a triazine derivative. It is the hydrolysis product of melamine. [1]

Contents

Synthesis

Ammeline can be synthesized by the pyrolysis of urea or the condensation reaction among 2 moles of dicyandiamide and 1 mole of biuret.

2 C2H4N4 + C2H5N3O2 → 2C3H5N5O + NH3

Chemical properties

Ammeline is weakly acidic with pKa ~9. It can form nitrate, sulfate, chromate, and oxalate salts. Ammeline reacts with boiling dilute hydrochloric acid to form melem and ammonia.

Ammeline is the first step in melamine hydrolysis. Further hydrolysis (e.g. boiling ammeline with dilute alkali) yields ammelide.

Related Research Articles

<span class="mw-page-title-main">Carboxylic acid</span> Organic compound containing a –C(=O)OH group

In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO2H, sometimes as R−C(O)OH with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

<span class="mw-page-title-main">Melamine</span> Fire-resistant chemical used in dinnerware, insulation, and cleaning products

Melamine is an organic compound with the formula C3H6N6. This white solid is a trimer of cyanamide, with a 1,3,5-triazine skeleton. Like cyanamide, it contains 67% nitrogen by mass, and its derivatives have fire-retardant properties due to its release of nitrogen gas when burned or charred. Melamine can be combined with formaldehyde and other agents to produce melamine resins. Such resins are characteristically durable thermosetting plastic used in high pressure decorative laminates such as Formica, melamine dinnerware including cooking utensils, plates, plastic products, laminate flooring, and dry erase boards. Melamine foam is used as insulation, soundproofing material and in polymeric cleaning products, such as Magic Eraser.

In organic chemistry, an acyl chloride is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.

The van 't Hoff factor i is a measure of the effect of a solute on colligative properties such as osmotic pressure, relative lowering in vapor pressure, boiling-point elevation and freezing-point depression. The van 't Hoff factor is the ratio between the actual concentration of particles produced when the substance is dissolved and the concentration of a substance as calculated from its mass. For most non-electrolytes dissolved in water, the van 't Hoff factor is essentially 1.

<span class="mw-page-title-main">Sulfonic acid</span> Organic compounds with the structure R−S(=O)2−OH

In organic chemistry, sulfonic acid refers to a member of the class of organosulfur compounds with the general formula R−S(=O)2−OH, where R is an organic alkyl or aryl group and the S(=O)2(OH) group a sulfonyl hydroxide. As a substituent, it is known as a sulfo group. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound is the parent sulfonic acid, HS(=O)2(OH), a tautomer of sulfurous acid, S(=O)(OH)2. Salts or esters of sulfonic acids are called sulfonates.

<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">Heptazine</span> Chemical compound

Heptazine, or tri-s-triazine or cyamelurine, is a chemical compound with formula C
6
N
7
H
3
, that consist of a planar triangular core group or three fused triazine rings, with three hydrogen atoms at the corners. It is a yellow, weakly fluorescent solid with melting point over 300 °C. It is soluble in organic solvents such as acetonitrile, but is decomposed by water in the presence of light.

<span class="mw-page-title-main">Glycolic acid</span> Chemical compound

Glycolic acid is a colorless, odorless and hygroscopic crystalline solid, highly soluble in water. It is used in various skin-care products. Glycolic acid is widespread in nature. A glycolate is a salt or ester of glycolic acid.

<span class="mw-page-title-main">Glucose syrup</span> Syrup made from the hydrolysis of starch

Glucose syrup, also known as confectioner's glucose, is a syrup made from the hydrolysis of starch. Glucose is a sugar. Maize (corn) is commonly used as the source of the starch in the US, in which case the syrup is called "corn syrup", but glucose syrup is also made from potatoes and wheat, and less often from barley, rice and cassava.p. 21

<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.

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

Fluorobenzene is the chemical compound with the formula C6H5F, often abbreviated PhF. A colorless liquid, it is a precursor to many fluorophenyl compounds.

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

Cyromazine is a triazine insect growth regulator used as an insecticide. It is a cyclopropyl derivative of melamine. Cyromazine works by affecting the nervous system of the immature larval stages of certain insects.

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

Ammelide (6-amino-2,4-dihydroxy-1,3,5-triazine) is a triazine and the hydrolysis product of ammeline.

<span class="mw-page-title-main">Melam (chemistry)</span> Chemical compound

Melam is a condensation product of melamine.

The Bergmann degradation is a series of chemical reactions designed to remove a single amino acid from the carboxylic acid (C-terminal) end of a peptide. First demonstrated by Max Bergmann in 1934, it is a rarely used method for sequencing peptides. The later developed Edman degradation is an improvement upon the Bergmann degradation, instead cleaving the N-terminal amino acid of peptides to produce a hydantoin containing the desired amino acid.

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

In chemistry, melem is a compound with formula C
6
N
10
H
6
; specifically, 2,5,8-triamino-heptazine or 2,5,8-triamino-tri-s-triazine, whose molecule can be described as that of heptazine with the three hydrogen atoms replaced by amino groups. It is a white crystalline solid.

<span class="mw-page-title-main">Melamine cyanurate</span> Chemical compound

Melamine cyanurate, also known as melamine–cyanuric acid adduct or melamine–cyanuric acid complex, is a crystalline complex formed from a 1:1 mixture of melamine and cyanuric acid. The substance is not a salt despite its non-systematic name melamine cyanurate. The complex is held together by an extensive two-dimensional network of hydrogen bonds between the two compounds, reminiscent of the guanine–cytosine base pairs found in DNA. Melamine cyanurate forms spoke-like crystals from aqueous solutions and has been implicated as a causative agent for toxicity seen in the Chinese protein export contamination and the 2007 pet food recall.

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

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.

References

  1. B. Bann and S.A. Miller (1958). "Melamines and derivatives of melamine". Chemical Reviews . 58: 131–172. doi:10.1021/cr50019a004.