Barbital

Base Information

• Chemical Name: Barbital
• CAS No.: 57-44-3
• Deprecated CAS: 145630-92-8,53527-29-0,6599-82-2
• Molecular Formula: C8H12N2O3
• Molecular Weight: 184.195
• European Community (EC) Number: 200-331-2
• NSC Number: 759567,31352
• UNII: 5WZ53ENE2P
• DSSTox Substance ID: DTXSID5022643
• Nikkaji Number: J2.326D
• Wikipedia: Barbital
• Wikidata: Q412409
• NCI Thesaurus Code: C76526
• Metabolomics Workbench ID: 52047
• ChEMBL ID: CHEMBL444
• Mol file: 57-44-3.mol

Synonyms:Barbital;Barbitone;Diemal;Diethylmalonylurea;Dormileno;Ethylbarbital;Medinal;Veronal

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Chemical Property of Barbital

Chemical Property:

• Appearance/Colour: odorless, slightly bitter, white crystalline powder
• Melting Point: 188-192°C
• Refractive Index: 1.458
• Boiling Point: 318.14°C (rough estimate)
• PKA: 7.43(at 25℃)
• Flash Point: 11 °C
• PSA: 75.27000
• Density: 1.14 g/cm³
• LogP: 0.81640
• Storage Temp.: 2-8°C
• Water Solubility.: 7.149g/L(25 oC)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 184.08479225
• Heavy Atom Count: 13
• Complexity: 247

Purity/Quality:

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 22-39/23/24/25-23/24/25-11-63-40-20
• Safety Statements: 36-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC1(C(=O)NC(=O)NC1=O)CC
• Description: Barbital is an analytical reference material that is categorized as a barbiturate. It acts as an agonist at GABAA receptors to induce central nervous system depression. Formulations containing barbital have been used as a sedative to treat insomnia and seizures in human and veterinary medicine. Barbital is regulated as a Schedule IV compound in the United States. This product is intended for research and forensic applications. Barbital (CRM) (Item No. 22854) is a certified reference material categorized as a barbiturate. Barbital is regulated as a Schedule IV compound in the United States. Barbital (CRM) (Item No. 22854) is provided as a DEA exempt preparation. This product is intended for research and forensic applications.
• Uses: Prototype of the barbiturate hypnotics.

Technology Process of Barbital

There total 104 articles about Barbital 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: 71.0%

trans-[PtCl2(2-hmpy)2] (13869-77-7,1427026-67-2) + sodium barbital (144-02-5) → diethylbarbituric acid (57-44-3) + C12H12N2O2Pt*4H2O

Guidance literature:

In water; at 20 - 70 ℃; for 72h;

DOI:10.1016/j.bmcl.2013.01.119

Reference yield: 71.0%

phenyl carbamate (64-10-8) + urea (57-13-6) → diethylbarbituric acid (57-44-3)

Guidance literature:

With tetraethylammonium perchlorate; In N,N-dimethyl-formamide; Ambient temperature; electrolysis;

DOI:10.1248/cpb.37.3117

Reference yield:

N,N'-bis-ethoxycarbonyl-2,2-diethyl-malonic acid diamide (63884-60-6) → diethylbarbituric acid (57-44-3)

Guidance literature:

With sodium ethanolate;

upstream raw materials:

bis(phenyl) carbonate

2,2-Diethyl-malonamide

phosgene

oxalyl dichloride

Downstream raw materials:

5,5-diethyl-1-pentyl-barbituric acid

4-dimethylamino-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one; compound with 3,3-diethyl-1H-pyridine-2,4-dione

5,5-diethyl-1,3-bis-(4-nitro-benzyl)-pyrimidine-2,4,6-trione

1-benzyl-5,5-diethyl-2,4,6(1H,3H,5H)pyrimidinetrione

Refernces

Some Naphthyl Derivatives of Barbituric Acid

10.1021/ja01334a060

The study explores the synthesis and properties of various naphthyl derivatives of barbituric acid. The research focuses on creating compounds where the naphthyl group is either directly attached to the 5-carbon atom or connected via methylene groups. The chemicals involved include a-naphthylmethyl bromide and a-naphthylethyl bromide, which were used for alkylation to introduce naphthylmethyl and naphthylethyl groups into barbituric acids. The study also utilized alkyl barbituric acids, sodium acetate, and urea in the synthesis processes. The goal was to investigate the potential therapeutic properties of these derivatives as sedatives and hypnotics, similar to known compounds like barbital and amytal. The study reports the successful synthesis of several derivatives, including 5,5-ethyl-a-naphthylmethylbarbituric acid, 5,5-n-butyl-a-naphthylmethylbarbituric acid, and 5,5-allyl-a-naphthylmethylbarbituric acid, among others. However, none of the synthesized compounds exhibited desirable physiological effects comparable to barbital or amytal. The study also details the preparation methods and the physical and analytical data of the synthesized compounds.

Determination of binding constants of hydrogen-bonded complexes by ITC, NMR CIS, and NMR diffusion experiments

10.1002/ejoc.201001684

The research study on the host-guest complex formation between barbital and various acylaminopyridyl isophthalamides, also known as Hamilton receptors, with the aim of quantitatively determining the binding constants of these hydrogen-bonded complexes. The study involves the synthesis of nine different isophthalamides, which differ in their substitution patterns on the central isophthalic unit and the nature of the acyl residues. The researchers utilized techniques such as 1H NMR titrations monitoring chemically induced shifts (CIS), 1H NMR diffusion experiments, and isothermal titration calorimetry (ITC) to determine the association constants (Kass) of the complexes in chloroform at 298 K, which ranged between 33×10^3 and 100×10^3 M–1.