Murexide

Title: Murexide
CAS Registry Number: 3051-09-0
CAS Name: 5-[(Hexahydro-2,4,6-trioxo-5-pyrimidinyl)imino]-2,4,6(1H,3H,5H)-pyrimidinetrione monoammonium salt
Additional Names: 5,5¢-nitrilodibarbituric acid monoammonium salt; acid ammonium purpurate; ammonium purpurate
Molecular Formula: C8H8N6O6
Molecular Weight: 284.19
Percent Composition: C 33.81%, H 2.84%, N 29.57%, O 33.78%
Literature References: Prepn from alloxan + NH3: Hartley, J. Chem. Soc. 87, 1791 (1905); Schwartz, Handritschk, DD 17589 (1959), C.A. 55, 3630a (1961); from alloxantin + ammonium acetate: Davidson, J. Am. Chem. Soc. 58, 1821 (1936). Structure: Hartley, J. Chem. Soc. 87, 1796 (1905); Winslow, J. Am. Chem. Soc. 61, 2089 (1939); Schreiber, Mitt. Dtsch. Pharm. Ges. 28, 20 (1958).
Properties: Purple-red crystals with green metallic luster. Absorption max in water: 520 nm. Sparingly sol in cold water, more in hot water; practically insol in alcohol, ether. The H2O soln is deep purple and the aq NaOH soln is deep blue.
Absorption maximum: Absorption max in water: 520 nm
Use: Indicator for complexometric titrations.
Murexine Muromonab CD3 Muscalure Muscarine Muscazone

Murexide
Murexide.png
Identifiers
CAS number 3051-09-0 YesY
[6032-80-0] (hydrate)
PubChem 18275
ChemSpider 17264 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H8N6O6
Molar mass 284.19 g mol−1
Hazards
R-phrases R20 R21 R22
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Murexide (NH4C8H4N5O6, or C8H5N5O6·NH3), also called ammonium purpurate or MX, is the ammonium salt of purpuric acid. It may be prepared by heating alloxantin in ammonia gas to 100 °C, or by boiling uramil (5-aminobarbituric acid) with mercury oxide. W.N. Hartley[1] found considerable difficulty in obtaining specimens of murexide sufficiently pure to give concordant results when examined by means of their absorption spectra, and consequently devised a new method of preparation for murexide. In this process alloxantin is dissolved in a large excess of boiling absolute alcohol, and dry ammonia gas is passed into the solution for about three hours. The solution is then filtered from the precipitated murexide, which is washed with absolute alcohol and dried. The salt obtained in this way is in the anhydrous state. It may also be prepared by digesting alloxan with alcoholic ammonia at about 78 °C; the purple solid so formed is easily soluble in water, and the solution produced is indistinguishable from one of murexide.

Murexide in its dry state has the appearance of a reddish purple powder, slightly soluble in water. In solution, its color ranges from yellow in strong acidic pH through reddish-purple in weakly acidic solutions to blue-purple in alkaline solutions. The pH for titration of calcium is 11.3.

Justus von Liebig and Friedrich Wöhler in Giessen, Germany, had investigated the purple product, murexide, obtained from snake excrement in the 1830s but this was not an abundant raw material and a method of using it as a dyestuff was not established at that time.[2] In the 1850s, French colorists and dye-producers, such as Depoully in Paris, succeeded in making murexide from abundant South American guano, and of applying it to natural fibers. It was then widely adopted in Britain, France and Germany.

Murexide is presently used[citation needed] in analytical chemistry as a complexometric indicator for complexometric titrations, most often of calcium ions, but also for Cu, Ni, Co, Th and rare earth metals. Cf. Eriochrome Black T. Due to the minute amounts needed for this purpose, it is often used in a 1:250 mixture with potassium sulfate.[citation needed]

Murexide is also used as a colorimetric reagent for measurement of calcium and rare earth metals; for calcium, the pH required is 11.3, detection range lies between 0.2 and 1.2 ppm, and the maximum absorbance wavelength is 506 nm.[citation needed]

Murexide and methyl red are investigated as promising enhancers of sonochemical destruction of chlorinated hydrocarbon pollutants.[citation needed]