| Identification | More | [Name]
1,3-Dimethylbarbituric acid | [CAS]
769-42-6 | [Synonyms]
1,3-DIMETHYL-2,4,6(1H,3H,5H)-PYRIMIDINETRIONE
1,3-DIMETHYLBARBITURIC ACID
1,3-DIMETHYLPYRIMIDINE-2,4,6(1H,3H,5H)-TRIONE
AKOS B029702
2,4,6(1H,3H,5H)-Pyrimidinetrione, 1,3-dimethyl-
6(1h,3h,5h)-pyrimidinetrione,1,3-dimethyl-4
Barbituric acid, 1,3-dimethyl-
N,N'-Dimethylbarbituric acid
1,3-Dimethyl-2,4,6-Trihydroxy-Pyrimidine
1,3-dimethyl-4,6(1h,3h,5h)-pyrimidinetrione
1,3-Dimethylbarbituric acid, 99% (dry wt.) water < 6%
1,3-Dimethylbarbituric acid, 99%, ca. 6% water
1,3-Dimethylhexahydropyrimidine-2,4,6-trione
1,3-Dimethylpyrimidine-2,4,6(1H,2H,5H)-trione
Hexahydro-1,3-dimethylpyrimidine-2,4,6-trione | [EINECS(EC#)]
212-211-7 | [Molecular Formula]
C6H8N2O3 | [MDL Number]
MFCD00006675 | [Molecular Weight]
156.14 | [MOL File]
769-42-6.mol |
| Chemical Properties | Back Directory | [Appearance]
Yellow or brownish powder | [Melting point ]
121-123 °C (lit.)
121-123 °C | [Boiling point ]
228.1±23.0 °C(Predicted) | [bulk density]
500kg/m3 | [density ]
1.322±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer | [solubility ]
hot water: soluble0.5g/10 mL, clear, colorless to faintly yellow | [form ]
Crystalline Powder | [pka]
pK1:4.68(+1) (25°C) | [color ]
White/cream/pale yellow | [PH]
2.5 (20°C, 100g/L in H2O, slurry) | [Water Solubility ]
Soluble in water. | [Detection Methods]
GC | [BRN ]
139810 | [InChI]
1S/C6H8N2O3/c1-7-4(9)3-5(10)8(2)6(7)11/h3H2,1-2H3 | [InChIKey]
VVSASNKOFCZVES-UHFFFAOYSA-N | [SMILES]
CN1C(=O)CC(=O)N(C)C1=O | [CAS DataBase Reference]
769-42-6(CAS DataBase Reference) | [NIST Chemistry Reference]
1,3-Dimethylbarbituric acid(769-42-6) | [EPA Substance Registry System]
769-42-6(EPA Substance) |
| Questions And Answer | Back Directory | [Preparation]
1.1 mol of dimethyl malonate and 1.0 mol of 1,3-dimethylurea were added to a reactor, along with 900 g of n-butanol solvent, 900 g of toluene, and 58 g of sodium ethoxide catalyst. The mixture was stirred and heated to 90–110 °C, then refluxed for 10 hours. After the reaction was complete, the reactants were cooled, and a solid precipitated. The solid was dissolved in water, and the pH was adjusted to 1–2 with hydrochloric acid. After cooling, crystals precipitated, and the crude product was filtered to obtain 132 g. Recrystallization yielded 119 g of 1,3-dimethylbarbituric acid with a melting point of 121.4–123.2 °C, a yield of 76%, and a purity of 99.7%. |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS05,GHS07 | [Signal word ]
Danger | [Hazard statements ]
H302-H318 | [Precautionary statements ]
P264-P270-P280-P301+P312-P305+P351+P338-P501 | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R41:Risk of serious damage to eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/39:Wear suitable protective clothing and eye/face protection . | [WGK Germany ]
3
| [TSCA ]
Yes | [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Dam. 1 |
| Raw materials And Preparation Products | Back Directory | [Preparation Products]
6-[N-(2-Hydroxyethyl)amino]-1,3-dimethyl-2,4(1H,3H)-dione-->ISOCAFFEINE-->1,3-dimethyl-5-(thiophen-2-ylmethylene)pyrimidine-2,4,6(1H,3H,5H)-trione-->7-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-5H-pyrano[2,3-d]pyrimidine-5,5,6-tricarbonitrile-->5-((1H-indol-3-yl)methylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione-->2-[(1,3-dimethyl-2,4,6-trioxo-1,3-diazinan-5-ylidene)methyl]phenyl acetate-->1,3-dimethyl-5-[(4-oxo-4H-chromen-3-yl)methylidene]-1,3-diazinane-2,4,6-trione-->1,3-Dimethyl-5-([4-(methylsulfanyl)phenyl]methylene)-2,4,6(1H,3H,5H)-pyrimidinetrione-->6-chloro-1,3-dimethyl-5-nitro-pyrimidine-2,4-quinone-->1,3-Dimethyl-5-[(dimethylamino)methylene]2,4,6-(1H,3H,5H)-trioxopryimidine |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow or brownish powder | [Uses]
1,3-Dimethylbarbituric acid is used as a catalyst in the Knoevenagel condensation of a series of aromatic aldehydes. It is also used in the synthesis of 5-aryl-6-(alkyl- or aryl-amino)-1,3-dimethylfuro [2,3-d]pyrimidine derivatives and enantioselective synthesis of isochromene pyrimidinedione derivatives. | [General Description]
1,3-Dimethylbarbituric acid (1,3-Dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione) is an active methylene compound. It undergoes hollow Pd6 water-soluble cage, [{(tmen)Pd}6(timb)4](NO3)12 (tmen= N,N,N′,N′-tetramethylethylenediamine, timb=1,3,5-tris(1-imidazolyl)benzene)-catalyzed Knoevenagel condensation reaction with pyrene-1-carboxaldehyde. It undergoes self-sorted Pd7 molecular boat having an internal nanocavity (catalyst)-assisted Knoevenagel condensation reaction with various aromatic aldehydes. It has been synthesized by reacting 1,3-dimethylurea, malonic acid and acetic anhydride in acetic acid. It is widely used for the synthesis of various synthetic intermediates and heterocyclic compounds. | [Purification Methods]
Crystallise the acid from water and sublime it in a vacuum. Also purify it by dissolving 10g in 100mL of boiling CCl4/CHCl3 (8:2) (1g charcoal), filtering and cooling to 25o. Dry it in vacuo [Kohn et al. Anal Chem 58 3184 1986]. [Beilstein 24 III/IV 1875.] |
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J & K SCIENTIFIC LTD.
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18210857532 18210857532 |
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https://www.jkchemical.com |
| Company Name: |
Alfa Aesar
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400-6106006 |
| Website: |
http://chemicals.thermofisher.cn |
| Company Name: |
Energy Chemical
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400-0056266 |
| Website: |
www.energy-chemical.com |
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