626-08-4

Basic information

• Product Name: 6-AZA-2-THIOURACIL
• Synonyms: 6-AZA-2-THIOURACIL;LABOTEST-BB LTBB000006;3,4-dihydro-3-thioxo-1,2,4-triazin-5(2H)-one;6-AZA-2-THIOURACIL CRYSTALLINE;3-Thioxo-2,3,4,5-tetrahydro-1,2,4-triazine-5-one;3-sulfanylidene-2,3,4,5-tetrahydro-1,2,4-triazin-5-one;3-Thioxo-3,4-dyhydro-1,2,4-triazin-5(2H)-one;3-Thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one
• CAS NO: 626-08-4
• Molecular Formula: C₃H₃N₃OS
• Molecular Weight: 129.14
• EINECS: 210-929-5
• Mol File: 626-08-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 251 °C (decomp)(Solv: water (7732-18-5))
• Boiling Point: 373.1 °C at 760 mmHg
• Flash Point: 179.5 °C
• Appearance: /
• Density: 1.79 g/cm³
• Vapor Pressure: 4.26E-06mmHg at 25°C
• Refractive Index: 1.812
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 5.80±0.20(Predicted)
• CAS DataBase Reference: 6-AZA-2-THIOURACIL(CAS DataBase Reference)
• NIST Chemistry Reference: 6-AZA-2-THIOURACIL(626-08-4)
• EPA Substance Registry System: 6-AZA-2-THIOURACIL(626-08-4)

Safety Data

• Hazardous Substances Data: 626-08-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 29, p. 233, 1992 DOI: 10.1002/jhet.5570290142

InChI:InChI=1/C3H3N3OS/c7-2-1-4-6-3(8)5-2/h1H,(H2,5,6,7,8)

Upstream product

• 928-74-5 2-[2-(aminothioxomethyl)hydrazinyl]acetic acid 
• 1117-63-1 ethyl glyoxylate thiosemicarbazone 
• 79-19-6 thiosemicarbazide 
• 298-12-4 Glyoxilic acid 
• 60432-10-2 C₄H₇N₃O₂S 
• 90997-75-4 3-propargylmercapto-1,2,4-triazin-5(2H)-one 
• 7338-75-2 5-oxo-3-thioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carboxylic acid 

Downstream Products

• 37132-61-9 N,N'-Bis<2-(3,4-dimethoxyphenyl)ethyl>-1,2,4-triazine-3,5-diamine 
• 118788-44-6 3-(3-tert-butyl-5-methyl-4-hydroxyphenyl)-7H-thiazolo[3,2-b][1,2,4]triazin-7-one 
• 18060-72-5 3-SMe-1,2,4-triazin-5(4H)-one 
• 461-89-2 6-azauracil 
• 118788-42-4 3-[(3,5-di-tert.butyl-4-hydroxyphenacyl)-thio]-2H-1,2,4-triazin-5-one 
• 461-90-5 3,5-dithioxo-2,3,4,5-tetrahydrotriazine 
• 90997-82-3 3-But-3-ynylsulfanyl-2H-[1,2,4]triazin-5-one 

Relevant articles and documents

Regioselective synthesis of 1,2,4-triazin-5-one via gas-phase pyrolysis of 4-arylidenimino-3(2H)-thioxo-1,2,4-triazin-5(4H)-one. Kinetic and mechanistic study

4-Arylidenimino-3(2H)-thioxo-1,2,4-triazin-5(4H)-ones (1a-e) and 4-arylidenimino-3-methylthio-1,2,4-triazin-5(4H)-ones (2a-e) were synthesized. Pyrolytic deprotection of these substrates were carried out. The kinetic results, product analysis and theoretical studies lend support to a reaction pathway involving a six-membered transition state in which the carbonyl and not thione bond attacks the hydrogen atom of the arylidenimino group. This reaction represents an efficient, clean and general synthetic procedure for the protection and selective synthesis of potential biologically active triazines and their derivatives. Copyright

Infrared spectra of 6-azathiouracils: An experimental matrix isolation and theoretical ab initio SCF/6-311G study

The infrared (IR) absorption spectra of 2-thio-6-azauracil, 4-thio-6-azauracil and 2,4-dithio-6-azauracil isolated in low-temperature Ar and N2 matrices are reported. These compounds have been found to exist in low-temperature matrices exclusively in the oxothione and dithione tautomeric forms. An assignment of the observed infrared bands is proposed on the basis of comparison of the experimental matrix spectra with the spectra calculated at the ab initio SCF/6-311G** level. The IR spectra of the title compounds are compared with the previously published IR spectra of matrix isolated 2-thiouracil, 4-thiouracil and 2,4-dithiouracil.

Photochemical Cyclization of Some Aldehyde Thiosemicarbazones

The photochemical behaviour of some substituted aldehyde thiosemicarbazones 1a-k has been investigated in methanol at 254 nm.Thiosemicarbazones of glyoxil methyl ester 1a-f cyclized to furnish the 3-thioxo-1,2,4-triazin-5-one 2-ring system.The remaining thiosemicarbazones 1g-j gave 1,2,4-triazoline 4-derivatives.