28456-54-4

Basic information

• Product Name: 5,6-DIMETHYL-2-THIOURACIL
• Synonyms: 5,6-dimethyl-2-sulfanylidene-1H-pyrimidin-4-one;5,6-dimethyl-2-thioxo-1H-pyrimidin-4-one;5,6-Dimethyl-2-thioxo-2,3-dihydropyrimidin-4(1H);2-Mercapto-5,6-dimethylpyrimidin-4(3H)-one;5,6-DIMETHYL-2-THIOURACIL;5,6-dimethyl-2-thio-uraci;2-Mercapto-5,6-dimethylpyrimidine-4-ol;5,6-Dimethyl-2(1H)-thioxopyrimidine-4(3H)-one
• CAS NO: 28456-54-4
• Molecular Formula: C₆H₈N₂OS
• Molecular Weight: 156.21
• Product Categories: Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Pyrimidines
• Mol File: 28456-54-4.mol
• Article Data: 12

Chemical Properties

• Melting Point: 284-288 °C(lit.)
• Boiling Point: 347.3°Cat760mmHg
• Flash Point: 163.9°C
• Appearance: /
• Density: 1.2069 (rough estimate)
• Vapor Pressure: 2.7E-05mmHg at 25°C
• Refractive Index: 1.6490 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 7.88±0.25(Predicted)
• Water Solubility: 1.373g/L(25 oC)
• CAS DataBase Reference: 5,6-DIMETHYL-2-THIOURACIL(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DIMETHYL-2-THIOURACIL(28456-54-4)
• EPA Substance Registry System: 5,6-DIMETHYL-2-THIOURACIL(28456-54-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: YQ9887000
• HazardClass: IRRITANT
• Hazardous Substances Data: 28456-54-4(Hazardous Substances Data)

Usage

Description

5,6-dimethyl-2-Thiouracil is a heterocyclic building block that has been used in the synthesis of anti-HIV-1 pyrimidinones. It has also been used as an internal standard for the quantification of thyreostats, including 2-thiouracil, in bovine plasma.

Uses

5,6-Dimethylthiouracil is a heterocyclic building block.

InChI:InChI=1/C6H8N2OS/c1-3-4(2)7-6(10)8-5(3)9/h1-2H3,(H2,7,8,9,10)

Upstream product

• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 17356-08-0 thiourea 
• 17094-21-2 2-methyl-acetoacetic acid methyl ester 

Downstream Products

• 54855-79-7 5,6-dimethyl-2-methylthio-4-pyrimidone 
• 677024-69-0 C₁₃H₁₃BrN₂OS 
• 877798-45-3 2,3-dimethylpyrimido[1,2-a]benzimidazol-4(10H)-one 
• 1342843-79-1 diethyl 2-(cyclohexylamino)-6,7-dimethyl-8-oxo-4,8-dihydropyrimido[2,1-b][1,3]thiazine-3,4-dicarboxylate 
• 31408-09-0 5,6-dimethyl-3-methyluracil 
• 67434-65-5 4-chloro-5,6-dimethylpyrimidine 
• 922581-39-3 2-(4-fluoro-benzylsulfanyl)-5,6-dimethyl-1H-pyrimidin-4-one 
• 26305-13-5 5,6-dimethyluracil 
• 34916-78-4 5,6-dimethyl-3H-pyrimidin-4-one 
• 54855-79-7 5,6-dimethyl-2-(methylsulfanyl)-3,4-dihydropyrimidin-4-one 
• 1450808-81-7 2-chloro-N-cyclohexyl-5,6-dimethylpyrimidin-4-amine 
• 1450809-22-9 N₄-(4,4-difluorocyclohexyl)-5,6-dimethyl-N₂-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine 
• 1780-32-1 2,4-dichloro-5,6-dimethylpyrimidine 

Relevant articles and documents

Synthesis and Functionalization of 5-Alkyl-6-methyl-2-thiouracils

Abstract: A number of 5-alkyl-6-methyl-2-thiouracils were obtained, the further introduction of which into the reaction with dialkyl chloroethynylphosphonates afforded a series of new dialkyl (6-alkyl-5-oxo-7-methyl-5H-thiazolo[3,2-a]pyrimidin- 3-yl)phosphonates.

Laccase-catalyzed green synthesis and cytotoxic activity of novel pyrimidobenzothiazoles and catechol thioethers

The laccase-catalyzed reaction between unsubstituted catechol and 2-thioxopyrimidin-4(1H)-ones using aerial O2 as the oxidant delivers novel pyrimidobenzothiazoles with high yields in an aqueous solvent system under mild reaction conditions. With 4-substituted catechols, catechol thioethers are formed exclusively. The synthetic protocols developed provide a sustainable approach for these compound classes. In addition, the cytotoxicity of the products against HepG2 cell line is reported. Most compounds exhibit antiproliferative activities with IC50 values at the micromolar level. A structure-activity relationship study will facilitate the further development of these compounds as cytotoxic agents.

POTENT DUAL BRD4-KINASE INHIBITORS AS CANCER THERAPEUTICS

Disclosed herein are compounds that are inhibitors of BRD4 and their use in the treatment of cancer. Methods of screening for selective inhibitors of BRD4 are also disclosed. In certain aspects, disclosed are compounds of Formula I-IV.