Barbituric acid

Base Information

• Chemical Name: Barbituric acid
• CAS No.: 67-52-7
• Deprecated CAS: 117491-80-2,118738-52-6,154254-45-2,158217-19-7,160336-60-7,16564-27-5,20964-57-2,223674-02-0,32267-40-6,42910-84-9,51159-18-3,53853-41-1,63896-95-7,1194-23-6,253678-06-7,253678-07-8,253678-08-9,408335-37-5,465532-08-5,477705-05-8,678184-94-6,774592-06-2,860760-03-8,888733-51-5,914348-20-2,944357-77-1,1030660-92-4,1175001-15-6,1227251-16-2,1333204-15-1,1351684-07-5,1392108-86-9,1696408-95-3,1802859-89-7,1811546-22-1,1825368-05-5,1888309-80-5,1906914-02-0,2171459-71-3,2258646-20-5,1030660-92-4,1175001-15-6,118738-52-6,1194-23-6,1227251-16-2,1333204-15-1,1351684-07-5,1392108-86-9,154254-45-2,158217-19-7,160336-60-7,16564-27-5,1696408-95-3,1802859-89-7,1811546-22-1,1825368-05-5,20964-57-2,223674-02-0,253678-06-7,253678-07-8,253678-08-9,32267-40-6,408335-37-5,42910-84-9,465532-08-5,477705-05-8,51159-18-3,53853-41-1,63896-95-7,678184-94-6,774592-06-2,860760-03-8,888733-51-5,914348-20-2,944357-77-1
• Molecular Formula: C4H4N2O3
• Molecular Weight: 128.087
• Hs Code.: 2933.52
• European Community (EC) Number: 200-658-0,224-507-3
• NSC Number: 7889
• UNII: WQ92Y2793G
• DSSTox Substance ID: DTXSID8020129
• Nikkaji Number: J348D
• Wikipedia: Barbituric_acid
• Wikidata: Q410278
• NCI Thesaurus Code: C67084
• Metabolomics Workbench ID: 49568
• ChEMBL ID: CHEMBL574699
• Mol file: 67-52-7.mol

Synonyms:barbiturate;barbituric acid;barbituric acid, monosodium salt;sodium barbiturate

Chemical Property of Barbituric acid

Chemical Property:

• Appearance/Colour: cream coloured fine crystalline powder
• Vapor Pressure: 3.64E-15mmHg at 25°C
• Melting Point: 248-252 °C (dec.)(lit.)
• Refractive Index: 1.581
• Boiling Point: 260 °C
• PKA: 4.01(at 25℃)
• Flash Point: 150 °C
• PSA: 75.27000
• Density: 1.455 g/cm³
• LogP: -0.59990
• Storage Temp.: Store below +30°C.
• Solubility.: 11.45g/l
• Water Solubility.: 142 g/L (20 ºC)
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 128.02219199
• Heavy Atom Count: 9
• Complexity: 168

Purity/Quality:

99%min ^*data from raw suppliers

Barbituric acid for analysis EMSURE ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyrimidines
• Canonical SMILES: C1C(=O)NC(=O)NC1=O
• Description: Barbiturates are derivatives of barbituric acid, barbituric acid is formed by the condensation of malonic acid and urea, itself has no anesthetic effect, but if its C2 and C5 atoms are substituted by different genes, it can generate many species of barbiturate agents ,for example, oxygen of C2 is replaced by sulfur, which generates sulfur barbiturates, such as thiopental. Barbiturates'mechanism is basically the same, they act on different levels of the central nervous system, and have a non-specific inhibition. Its sedative and hypnotic effects may be related to selective inhibition of thalamic reticular upstream activating system , thereby blocking the excite transduction to cerebral cortex. Its Anticonvulsant effect is performed through inhibiting synaptic transmission in the central nervous system ,to improve the electrical stimulation threshold in motor cortex.barbiturates having a therapeutic effect play a inhibiting role in the central nervous system , such as phenobarbital (phenobarbitone), amobarbital (amylobarbitone), thiopental , methohexital (methohexi-tone ). Inhibitory barbiturates have sedative, hypnotic, anticonvulsant and anesthetic effects, but its sedative-hypnotic agent has been eliminated, because in the process it is easy to produce severe tolerance, drug dependence and drug liver enzyme induction.Because of some differences in their chemical structure, the body eliminate and fat-soluble manner of every drug are different , thus the speed of appearing effect and time of continuing also vary . Long-acting barbiturates such as phenobarbital (phenobarbi-tone) are still used in the treatment of epilepsy anticonvulsant. Ultrashort acting barbiturates (thiopental and methohexital) are often applied as an intravenous anesthetic.Barbiturate intravenous anesthetics used clinically are now about ten kinds, but three to five species are commonly used . According to the view of Anesthesiology, barbiturates can be divided into two categories, namely hypnotic barbiturates and barbiturate anesthesia. The former are markedly slower drugs such as phenobarbital,having a sedative effect, before anesthesia,its administration can make the patient quiet. After intravenous injection of the latter, consciousness soon disappear,it is mainly used for general anesthesia, in which the most commonly used drug is thiopental, so this drug is representative.Phenobarbital is a barbituric acid derivative, having weak acid,it is the central inhibitor, mainly inhibiting brain ascending reticular activating system. The shallow to deep degree of inhibition of the drug are due to the amount of small to large ,it has different levels of sedative, hypnotic and anticonvulsant, anesthetic effect. In addition, the drug also has antiepileptic effect.The above information is edited by the lookchem of Tian Ye.
• Uses: Barbituric acid is widely used in the manufacturing of plastics, textiles, polymers and pharmaceuticals. It is an active ingredient in the production of Vitamin B2. It is a strong acid in an aqueous medium with an active methylene group involved Knoevenegal condensation. It is used as precursor for the preparation of 5-arylidene barbituric acid by reacting with aromatic aldehyde. It is also used in electrochemical oxidation of iodine using cyclic voltammetry and controlled potential coulometry.

Technology Process of Barbituric acid

There total 78 articles about Barbituric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6,157796-99-1,924832-30-4) → BARBITURIC ACID (67-52-7,944357-77-1)

Guidance literature:

With quinolinium monofluorochromate(VI); In acetonitrile; for 1.5h; Heating;

Reference yield: 72.0%

urea (57-13-6) + diethyl malonate (105-53-3) → BARBITURIC ACID (67-52-7,944357-77-1)

Guidance literature:

With sodium; In ethanol; for 7h; Reflux;

DOI:10.1021/acs.joc.6b00640

Reference yield: 50.0%

malonic acid (141-82-2) + urea (57-13-6) → BARBITURIC ACID (67-52-7,944357-77-1)

Guidance literature:

With acetic anhydride; acetic acid; at 90 ℃; for 3h;

DOI:10.1080/07328300601039328

upstream raw materials:

oxalyl dichloride

malonodiamide

5,5-Dichloro-barbituric acid

5,5-dibromobarbituric acid

Downstream raw materials:

5-anilinomethylenebarbituric acid

riboflavin

5-phenylaminomethylenepyrimidine-2,4,6(1H,3H,5H)-trione

1-(2,4,6-trioxo-hexahydro-pyrimidin-5-yl)-5-(2,4,6-trioxo-tetrahydro-pyrimidin-5-ylidene)-penta-1,3-diene

Refernces

• 1、 Marshall, Madalynn G.,Lopez-Diaz, Valerie,Hudson, Bruce S.. "Single-Crystal X-ray Diffraction Structure of the Stable Enol Tautomer Polymorph of Barbituric Acid at 224 and 95K". . p. 1309 - 1312. Retrieved 2016.
• 2、 Eldin A. Osman, Essam,Hanafy, Noura S.,George, Riham F.,El-Moghazy, Samir M.. "Design and synthesis of some barbituric and 1,3-dimethylbarbituric acid derivatives: A non-classical scaffold for potential PARP1 inhibitors". . . Retrieved 2020/09/16.
• 3、 Arrous, S.,Boudebouz, I.,Parunov, I. V.. "Oxidation of Thioamides to Amides with Tetrachloro- and Tetrabromoglycolurils". . p. 1874 - 1877. Retrieved 2020/02/03.