1,3-Diethyl-2-thiobarbituric acid

Base Information

• Chemical Name: 1,3-Diethyl-2-thiobarbituric acid
• CAS No.: 5217-47-0
• Deprecated CAS: 61732-60-3,1190104-61-0,2606824-87-5
• Molecular Formula: C8H12N2O2S
• Molecular Weight: 200.261
• Hs Code.: 29335400
• European Community (EC) Number: 226-010-7
• NSC Number: 158284
• UNII: BXB40M6A7W
• DSSTox Substance ID: DTXSID0022222
• Nikkaji Number: J68.143A
• Wikidata: Q27274941
• ChEMBL ID: CHEMBL2136061
• Mol file: 5217-47-0.mol

Synonyms:1,3-DETB;1,3-diethyl-2-thiobarbituric acid

Chemical Property of 1,3-Diethyl-2-thiobarbituric acid

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 3.36E-12mmHg at 25°C
• Melting Point: 109-112 °C(lit.)
• Refractive Index: 1.67
• Boiling Point: 273.4 °C at 760 mmHg
• PKA: 5.48±0.20(Predicted)
• Flash Point: 119.2 °C
• PSA: 72.71000
• Density: 1.29g/cm³
• LogP: 0.24780
• Storage Temp.: Hormones
• Solubility.: 1 M NaOH: soluble50mg/mL, clear, colorless to light yellow
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 200.06194880
• Heavy Atom Count: 13
• Complexity: 241

Purity/Quality:

97% ^*data from raw suppliers

1,3-Diethyl-2-thiobarbituric acid 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-43
• Safety Statements: 24/25-22-45-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1C(=O)CC(=O)N(C1=S)CC
• General Description: 1,3-Diethyl-2-thiobarbituric acid is a thiobarbituric acid derivative used as a key reactant in the synthesis of polyfunctional heterocyclic compounds, such as 4H-pyrano[2,3-d]thiopyrimidines and 1,4-di-ionic organophosphorus derivatives. It participates in one-pot reactions with activated acetylenes in the presence of isocyanides or triphenylphosphine, demonstrating its utility in forming structurally complex and synthetically valuable products. 1,3-Diethyl-2-thiobarbituric acid's reactivity highlights its role as a versatile building block in organic synthesis.

Technology Process of 1,3-Diethyl-2-thiobarbituric acid

There total 4 articles about 1,3-Diethyl-2-thiobarbituric 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: 96.0%

N,N'-diethylthiourea (105-55-5) + diethyl malonate (105-53-3) → N,N'-diethyl-2-thiobarbituric acid (5217-47-0)

Guidance literature:

With acetic anhydride; acetic acid; for 14h; Inert atmosphere; Reflux;

Reference yield:

C8H12N2O2S*H3N → N,N'-diethyl-2-thiobarbituric acid (5217-47-0)

Guidance literature:

at 100 - 175 ℃;

DOI:10.1016/j.poly.2015.05.048

Reference yield:

→ N,N'-diethyl-2-thiobarbituric acid (5217-47-0)

Guidance literature:

/BRN= 127305/;

DOI:10.1021/ja01155a095

upstream raw materials:

N,N'-diethylthiourea

diethyl malonate

Downstream raw materials:

1,3-diethyl-5-(3,5,5-trimethyl-2-cyclohexen-1-ylidene)-2-thiobarbituric acid

1,3-Diethyl-6-{[(E)-methylimino]-phenyl-methyl}-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one

(1,3-Diethyl-6-oxo-2-thioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl)-methylamino-phenyl-acetonitrile

Refernces

Study of reaction between activated acetylenes and N,N'-diethyl-2- thiobarbituric acid in the presence of isocyanides or triphenylphosphine

10.1002/hc.20601

The research study on the reaction between activated acetylenes and N,N′-diethyl-2-thiobarbituric acid in the presence of isocyanides or triphenylphosphine. The purpose of the study was to synthesize highly functionalized 4H-pyrano[2,3-d]thiopyrimidine or 1,4-di-ionic organophosphorus derivatives. The researchers concluded that the reaction provides a simple one-pot method for the synthesis of these polyfunctional compounds, which are of potential synthetic interest. Key chemicals used in the process include N,N′-diethyl-2-thiobarbituric acid, acetylenic diesters, isocyanides, and triphenylphosphine. The study also observed a dynamic NMR effect attributed to restricted rotation around the aryl-nitrogen single bond in the product, and the activation free energy for this process was calculated to be about 54.85 ± 2 kJ mol?1.