269410-01-7

Basic information

• Product Name: 1,3-DIMETHYLURACIL-5-BORONIC ACID PINACOL ESTER
• Synonyms: 1,3-DIMETHYLURACIL-5-BORONIC ACID PINACOL ESTER;1,3-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,4(1H,3H)-pyrimidinedione
• CAS NO: 269410-01-7
• Molecular Formula: C12H19BN2O4
• Molecular Weight: 266.1
• Mol File: 269410-01-7.mol

Chemical Properties

• Boiling Point: 291.7±50.0 °C(Predicted)
• Appearance: /
• Density: 1.18±0.1 g/cm3(Predicted)
• Storage Temp.: Room temperature.
• PKA: -1.80±0.40(Predicted)
• CAS DataBase Reference: 1,3-DIMETHYLURACIL-5-BORONIC ACID PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DIMETHYLURACIL-5-BORONIC ACID PINACOL ESTER(269410-01-7)
• EPA Substance Registry System: 1,3-DIMETHYLURACIL-5-BORONIC ACID PINACOL ESTER(269410-01-7)

Safety Data

• Hazardous Substances Data: 269410-01-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
1,3-Dimethyluracil-5-boronic acid pinacol ester is used as a key intermediate in the synthesis of pharmaceutical compounds for various therapeutic applications. Its unique structure allows it to be a versatile building block in the development of new drugs.
Used in Organic Synthesis:
In the field of organic synthesis, 1,3-dimethyluracil-5-boronic acid pinacol ester is used as a reagent for the formation of carbon-carbon and carbon-heteroatom bonds. Its boronic acid functionality enables selective reactions with a wide range of organic substrates.
Used in Medicinal Chemistry:
1,3-Dimethyluracil-5-boronic acid pinacol ester is used as a molecular probe in medicinal chemistry to study the interactions between biological targets and potential drug candidates. Its ability to bind selectively to specific molecules aids in the discovery of new bioactive compounds.
Used in the Development of New Materials:
1,3-DIMETHYLURACIL-5-BORONIC ACID PINACOL ESTER is also used in the development of new materials with unique properties, such as sensors, catalysts, and advanced materials for various industrial applications. Its versatility and reactivity make it a valuable component in material science research.

Upstream product

• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 40738-83-8 5-iodo-1,3-dimethyluracil 
• 874-14-6 1,3-dimethyluracil 
• 73183-34-3 bis(pinacol)diborane 

Relevant articles and documents

Iridium-Catalyzed Site-Selective C-H Borylation of 2-Pyridones

An iridium-catalyzed site-selective C-H borylation of 2-pyridones has been developed. The site selectivity is predominantly controlled by steric factors, and we can access C4, C5, and C6 C-H on the 2-pyridone ring by the judicious choice of ligand and sol

C-H trifluoromethylations of 1,3-dimethyluracil and reactivity of the products in C-H arylations

Diverse electrophilic, nucleophilic and radical C-H trifluoromethylations of 1,3-dimethyluracil were systematically studied in order to prepare either 5- or 6-(trifluoromethyl)uracil derivatives. Electrophilic reagents led only to dimeric bis-uracil products, whereas the radical trifluoromethylation by CF 3SO2Na in presence of t-BuOOH gave 1,3-dimethyl-5- (trifluoromethyl)uracil (2) in good yield. The 6-(trifluoromethyl)uracil derivative 3 was only prepared in low yield and in a mixture with 2 by Ir-catalyzed borylation followed by treatment with the Togni's reagent. Attempted Pd-catalyzed C-H arylations of 2 in the presence of Cs 2CO3 gave mixtures of de-trifluoromethylated products, whereas the reaction with 4-iodotoluene in the presence of CsF gave the desired 6-aryl-5-trifluoromethyluracil derivative 8 in moderate yield and the reaction was not general for other aryl halides.

Hydroboronation process

The invention relates to processes for the synthesis of aryl or alkene borates which comprises reacting: (i) an olefinic compound having a halogen or halogen-like substituent in a vinylic substitution position, or (ii) an aromatic ring having a halogen or halogen-like substituent in a ring substitution position, with a disubstituted monohydroborane in the presence of a Group 8-11 metal catalyst. The invention also relates to the use of these borates in coupling reactions. The invention further relates to certain disubstituted monohydroboranes and aryl or alkene borates.