3051-09-0

Basic information

• Product Name: Murexide
• Synonyms: CALCIUM HARDNESS INDICATOR;CALCIUM HARDNESS INDICATOR TABLETS;CI 56085;CI NO 56085;5,5'-NITRILODIBARBITURIC ACID MONOAMMONIUM SALT;ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate;AMMONIUM PERPURATE;AMMONIUM PURPURATE
• CAS NO: 3051-09-0
• Molecular Formula: C₈H₅N₅O₆*H₃N
• Molecular Weight: 284.19
• EINECS: 221-266-6
• Product Categories: Colours, Dyes, Indicators & Pigments;Chemical Synthesis
• Mol File: 3051-09-0.mol

Chemical Properties

• Melting Point: 300 °C
• Boiling Point: 443.25°C (rough estimate)
• Flash Point: 244.6 °C
• Appearance: Reddish-violet/Solid
• Density: 1.5756 (rough estimate)
• Vapor Pressure: 4.81E-11mmHg at 25°C
• Refractive Index: 1.8000 (estimate)
• Storage Temp.: Storage temperature: no restrictions.
• Solubility: 1g/l
• PKA: pK1:0.0;pK2:9.20;pK3:10.50 (25°C)
• Water Solubility: Slightly soluble
• Merck: 14,6306
• BRN: 3582175
• CAS DataBase Reference: Murexide(CAS DataBase Reference)
• NIST Chemistry Reference: Murexide(3051-09-0)
• EPA Substance Registry System: Murexide(3051-09-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-40
• Safety Statements: 24/25-22-36/37
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 3051-09-0(Hazardous Substances Data)

Usage

Uses

Used in Analytical Chemistry:
Murexide is used as a complexometric indicator for complexometric titrations of calcium, copper, nickel, and cobalt. It helps in accurately determining the concentration of these metal ions in various samples.
Used in Pharmaceutical Industry:
Murexide is used as an inhibitor of dihydrofolate reductase, an enzyme involved in the synthesis of DNA and RNA. This property makes it a potential candidate for the development of drugs targeting this enzyme.
Used in Environmental Applications:
Murexide acts as an enhancer of sonochemical destruction of chlorinated hydrocarbon pollutants. This application helps in the degradation of harmful environmental pollutants, contributing to a cleaner and safer environment.

Purification Methods

The sample may be grossly contaminated with uramil, alloxanthine, etc., and may be difficult to purify. It is better to synthesise it from pure alloxanthine [Davidson J Am Chem Soc 58 1821 1936]. Recrystallise it from water. [Kuhn & Lyman Chem Ber 69 1547 1936, Beilstein 25 I 709, 25 III/IV 4236.]

InChI:InChI=1/C8H5N5O6.H3N/c14-3-1(4(15)11-7(18)10-3)9-2-5(16)12-8(19)13-6(2)17;/h1H,(H2,10,11,14,15,18)(H2,12,13,16,17,19);1H3

Synthetic route

5-hydroxy-2,4,6-trioxo-hexahydro-pyrimidine-5-sulfonic acid ; compound with dimethylamine → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0) + dimethyl amine (124-40-3)

Conditions	Yield
at 120℃;

hydrogenchloride (7647-01-0) + pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + N-(4-methylphenyl)-5-methyl-1,2-phenylenediamine (13556-70-2) → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + 5-methylamino-pyrimidine-2,4,6-trione (29458-44-4) + ammonium hydroxide → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

ethanol (64-17-5) + ammonia (7664-41-7) + Alloxantin (76-24-4) → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + ammonia (7664-41-7) + water (7732-18-5) + Alloxantin (76-24-4) → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + ammonia (7664-41-7) + uramil (118-78-5) → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

Alloxantin (76-24-4) + absolute alcoholic. ammonia → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

Conditions	Yield
at 100℃;

ammonium hydroxide + uramil (118-78-5) + air → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

uramil (118-78-5) + alkaline hypochlorite solution → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

ammonium acetate (631-61-8) + water (7732-18-5) + 5-acetoxy-5'-hydroxy-[5,5']bipyrimidinyl-2,4,6,2',4',6'-hexaone + ammonium carbonate → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

Conditions	Yield
at 80℃;

pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + Alloxantin (76-24-4) + ammonium carbonate → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + water (7732-18-5) + Alloxantin (76-24-4) + ammonium carbonate → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

ammonium acetate (631-61-8) + water (7732-18-5) + Alloxantin (76-24-4) + ammonium carbonate → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + 5-ethylamino-barbituric acid (633299-48-6) + aqueous ammonium carbonate → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

Conditions	Yield
at 80℃;

8-methylxanthine (17338-96-4) + chloro water → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + ammonium acetate (631-61-8) + water (7732-18-5) + dialurate ammonium → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

Conditions	Yield
at 80℃;

pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + water (7732-18-5) + dialurate ammonium + ammonium carbonate → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

Conditions	Yield
at 80℃;

Alloxantin (76-24-4) + dry ammonia → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

Conditions	Yield
at 100℃;

pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + water (7732-18-5) + ethyluramil + ammonium carbonate → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

water (7732-18-5) + uramil (118-78-5) + mercury oxide → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

uramil (118-78-5) + mercury oxide + ammoniacal → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

water (7732-18-5) + uramil (118-78-5) + silver oxide → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

uramil (118-78-5) + silver oxide + ammoniacal → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

uric Acid (69-93-2) + ammonia (7664-41-7) + nitric acid (7697-37-2) → pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0)

Conditions	Yield
aufeinanderfolgender Einw.;

pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + water (7732-18-5) + glycine (56-40-6) → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0) + 4.5.4'-trioxy-2.6.2'.6'-tetraoxo-5-methylenamino-dodecahydro-dipyrimidyl-(4.4')

pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + water (7732-18-5) + rac-Ala-OH (302-72-7) → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0) + acetaldehyde (75-07-0) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5)

ammonium acetate (631-61-8) + water (7732-18-5) + Alloxantin (76-24-4) + ammonium carbonate → ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0) + uramil (118-78-5)

Conditions	Yield
at 80℃;

ammonium 5-(2,4,6-trioxoperhydropyrimidin-5-ylideneamino)barbiturate (3051-09-0) → uramil (118-78-5)

Conditions	Yield
With water
With potassium hydroxide
With sulfuric acid
With hydrogen sulfide; water
With hydrogenchloride

Upstream product

• 61066-33-9 pyrimidine-2,4,5,6(1H,3H)-tetraone 
• 7732-18-5 water 
• 56-40-6 glycine 
• 631-61-8 ammonium acetate 
• 76-24-4 Alloxantin 
• 302-72-7 rac-Ala-OH 
• 69-93-2 uric Acid 
• 7664-41-7 ammonia 
• 7697-37-2 nitric acid 
• 118-78-5 uramil 
• 17338-96-4 8-methylxanthine 
• 633299-48-6 5-ethylamino-barbituric acid 
• 64-17-5 ethanol 
• 29458-44-4 5-methylamino-pyrimidine-2,4,6-trione 

Downstream Products

• 118-78-5 uramil 
• 61066-33-9 pyrimidine-2,4,5,6(1H,3H)-tetraone 

Relevant articles and documents

Compound instability in dimethyl sulphoxide, case studies with 5-aminopyrimidines and the implications for compound storage and screening

The oxidation reactions of 5-aminopyrimidine derivatives in dimethyl sulphoxide (DMSO) were studied. The DMSO solutions of the studied compounds became deeply coloured within a few hours or days. The oxidation products can undergo further condensation reactions with the starting pyrimidines to yield bipyrimidines and/or pyrimidopteridines. The reaction mechanism of the oxidation-condensation reaction was also supported by reactions of the 5-aminopyrimidines with alloxan (2,4,5,6-tetraoxopyrimidine). DMSO is often used as the solvent in in vitro tests of biological activities, but it is also an oxidising agent and may react with solute molecules and significantly affect the quality of the generated biochemical data.

Electrophilic Amination of C-H-Acidic Compounds with 1-Oxa-2-azaspirooctane

The reactions of 1-oxa-2-azaspirooctane (1, 3,3-pentamethyleneoxaziridine) with malonic (e. g. 4, 35) and cyanoacetic acid derivatives (e. g. 11, 13, 20) and other C-H acids have been studied.After the introduction of a 1-hydroxycyclohexylamino group at the acidic position, five different stabilisation reactions of the intermediate 2 could be classified.The most important one is an intramolecular nucleophilic attack to a nitrile group giving disubstituted 1,4-diazaspiro decanones 2a.Their ring transformations (e. g. 2a -> 3) or the introduction of a second amino group at the same carbon atom (2a -> 3a) are further new reactions.Geminal diamino acid derivatives 3a thus obtained can be stable or rearrange to 3 (R1 = NH2) or eliminate cyclohexanone (formation of 42) and/or ammonia (formation of 41 or 43).Amination of N-cyanoacetyl-protected amino acid esters (20, NHR = amino acid unit) with 1 yields cyclic dipeptide derivatives 41. Key Words: 1-Oxa-2-azaspirooctane / C-H acids / Electrophilic amination / Diamination / Amino acid derivatives / Dehydro peptides