15018-59-4

Basic information

• Product Name: 1,3,6-TRIMETHYL-5-BROMOURACIL
• Synonyms: CHEMBRDG-BB 4013655;5-BROMO-1,3,6-TRIMETHYLURACIL;1,3,6-TRIMETHYL-5-BROMOURACIL;5-Bromo-1,3,6-trimethyl-2,4(1H,3H)-pyrimidinedione;2,4(1H,3H)-Pyrimidinedione, 5-bromo-1,3,6-trimethyl-;Brn 0144941;Uracil, 5-bromo-1,3,6-trimethyl-;5-bromo-1,3,6-trimethylpyrimidine-2,4(1H,3H)-dione(SALTDATA: FREE)
• CAS NO: 15018-59-4
• Molecular Formula: C₇H₉BrN₂O₂
• Molecular Weight: 233.06
• Mol File: 15018-59-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 136-137 °C
• Boiling Point: 254.5°Cat760mmHg
• Flash Point: 107.7°C
• Appearance: /
• Density: 1.605g/cm³
• Vapor Pressure: 0.0172mmHg at 25°C
• Refractive Index: 1.565
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -3.78±0.60(Predicted)
• CAS DataBase Reference: 1,3,6-TRIMETHYL-5-BROMOURACIL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,6-TRIMETHYL-5-BROMOURACIL(15018-59-4)
• EPA Substance Registry System: 1,3,6-TRIMETHYL-5-BROMOURACIL(15018-59-4)

Safety Data

• Statements: 36
• Safety Statements: 26
• Hazardous Substances Data: 15018-59-4(Hazardous Substances Data)

Usage

General Description

1,3,6-Trimethyl-5-bromouracil is a chemical compound that is commonly used in molecular biology and genetics research. It is a modified form of uracil, a nitrogenous base found in RNA, and is used as a mutagen in experiments studying DNA replication and repair. 1,3,6-Trimethyl-5-bromouracil is unique in that it can mimic the behavior of thymine, another nitrogenous base, and form hydrogen bonds with adenine, leading to mismatches in DNA. This property makes it a valuable tool for studying the mechanisms of DNA mutation and repair. Additionally, 1,3,6-Trimethyl-5-bromouracil is also used in the development of antiviral drugs and has potential applications in cancer research.

InChI:InChI=1/C7H9BrN2O2/c1-4-5(8)6(11)10(3)7(12)9(4)2/h1-3H3

Upstream product

• 13509-52-9 1,3,6-trimethyluracil 
• 80746-00-5 5-bromo-6-bromomethyl-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione 
• 134039-54-6 1,2,3,4-Tetrahydro-5-iodo-1,3,6-trimethyl-2,4-dioxopyrimidine 
• 626-48-2 6-Methyluracil 

Downstream Products

• 13509-52-9 1,3,6-trimethyluracil 
• 54347-54-5 6-benzoyloxymethyl-1,3-dimethyluracil 
• 54347-47-6 1,3-dimethyl-6-(4-methyl-anilinomethyl)-1H-pyrimidine-2,4-dione 
• 54347-48-7 6-(4-methoxy-anilinomethyl)-1,3-dimethyl-1H-pyrimidine-2,4-dione 
• 6307-35-3 2-amino-5-bromo-6-methylpyrimidin-4(3H)-one 
• 142409-77-6 5-phenylthio-1,3,6-trimethyluracil 
• 142409-79-8 1,3-Dimethyl-6-phenylsulfanylmethyl-1H-pyrimidine-2,4-dione 
• 142409-78-7 1,3-dimethyl-5-phenylthio-6-phenylthiomethyluracil 
• 54387-33-6 6-anilinomethyl-1,3-dimethyluracil 
• 143083-09-4 5-(4-Chloro-phenylsulfanyl)-1,3,6-trimethyl-1H-pyrimidine-2,4-dione 
• 143083-06-1 5-(4-Chloro-phenylsulfanyl)-6-(4-chloro-phenylsulfanylmethyl)-1,3-dimethyl-1H-pyrimidine-2,4-dione 
• 143083-08-3 5-(2-Amino-phenylsulfanyl)-1,3,6-trimethyl-1H-pyrimidine-2,4-dione 
• 143083-02-7 6-(2-Amino-phenylsulfanylmethyl)-1,3-dimethyl-1H-pyrimidine-2,4-dione 
• 143083-05-0 5-(2-Amino-phenylsulfanyl)-6-(2-amino-phenylsulfanylmethyl)-1,3-dimethyl-1H-pyrimidine-2,4-dione 

Relevant articles and documents

Electrophilic ipso-substitution in uracil derivatives

Treatment of 5-iodo-1,3,6-trimethyluracil with 50% H2SO 4 gives 1,3,6-trimethyluracil; with 5-bromo-1,3,6-trimethyluracil, a mixture of 1,3,6-trimethyluracil and 6-bromomethyl-1,3-dimethyluracil is obtained. 5-Chloro-1,3,6-trimethyluracil remains inert under these conditions. According to the DFT modeling of the reactions of 5-halo-1,3,6-trimethyluracils, a nucleophilic agent can abstract either Hal+ or the methyl proton from the carbocation formed by protonation of the starting halouracil at position 5, which accounts for the formation of two products from the 5-bromo derivative. Under similar conditions, 6-methyluracil dibromohydrin yields N-bromo-5-bromo-6-hydroxymethyluracil. Bromination or chlorination of 5-hydroxymethyl- or 5-formyl-6-methyluracils follows the ipso-substitution scheme leading to 6-methyluracil 5-halo- and 5,5-dihalohydrins.

A facile reduction of uracil derivatives by 1,3-propanedithiol

The in situ 1,3-propanedithiol to 1,2-dithiolane oxidation causes reductive debromination and decyanation of 5-bromo-6-bromo-ethyl-1,3-dimethyluracil and 6-cyano-1,3-dimethyluracil, respectively.But, 1-propanethiol and 1,2-ethanedithiol give the expected substitution products