13566-71-7

Basic information

• Product Name: 4,6-Dihydroxy-2-phenylpyrimidine
• Synonyms: 2-Phenyl-4,6-pyrimidinediol;4-hydroxy-2-phenyl-1H-pyrimidin-6-one;6-Hydroxy-2-phenyl-4(1H)-pyrimidinone
• CAS NO: 13566-71-7
• Molecular Formula: C₁₀H₈N₂O₂
• Molecular Weight: 188.18272
• Mol File: 13566-71-7.mol

Chemical Properties

• Melting Point: 325-330 °C
• Boiling Point: 292.6 °C at 760 mmHg
• Flash Point: 130.8 °C
• Appearance: /
• Density: 1.33 g/cm³
• Vapor Pressure: 0.00104mmHg at 25°C
• Refractive Index: 1.651
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 5.04±0.10(Predicted)
• CAS DataBase Reference: 4,6-Dihydroxy-2-phenylpyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-Dihydroxy-2-phenylpyrimidine(13566-71-7)
• EPA Substance Registry System: 4,6-Dihydroxy-2-phenylpyrimidine(13566-71-7)

Safety Data

• Hazardous Substances Data: 13566-71-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4,6-Dihydroxy-2-phenylpyrimidine is used as an intermediate in the synthesis of pharmaceuticals for its ability to form heterocyclic compounds, which are essential in the development of new drugs with potential therapeutic applications.
Used in Dye Industry:
4,6-Dihydroxy-2-phenylpyrimidine is used as a precursor in the production of dyes due to its ability to form colored compounds, contributing to the development of new dyes with specific properties.
Used in Organic Chemistry:
4,6-Dihydroxy-2-phenylpyrimidine is used as a building block in the synthesis of various organic compounds, including heterocyclic compounds, which have a wide range of applications in different fields.
Used in Medicinal Chemistry and Drug Discovery:
4,6-Dihydroxy-2-phenylpyrimidine is used in the field of medicinal chemistry and drug discovery for its potential to form bioactive molecules with therapeutic properties, contributing to the development of new drugs and treatments.

InChI:InChI=1/C10H8N2O2/c13-8-6-9(14)12-10(11-8)7-4-2-1-3-5-7/h1-6H,(H2,11,12,13,14)

Upstream product

• 152335-99-4 2-fluoro-5-(methyloxy)benzenecarboximidamide 
• 108-59-8 malonic acid dimethyl ester 
• 5333-86-8 ethyl benzimidate hydrochloride 
• 100-47-0 benzonitrile 
• 32260-07-4 ethyldimethyl malonate 
• 206752-36-5 benzamidine hydrochloride hydrate 
• 1670-14-0 benzamidine monohydrochloride 
• 105-53-3 diethyl malonate 
• 618428-22-1 4,6-bis(1-methylhydrazinyl)-2-phenyl-1-pyrimidine 
• 618-39-3 benzamidin 

Downstream Products

• 91520-64-8 5-iodo-4-phenoxy-2-phenylpyrimidin-6(1H)-one 
• 1415583-56-0 2-phenyl-4,6-dichloro-5-phenylazopyrimidine 
• 1415583-54-8 C₂₂H₃₃N₇O₂ 
• 1415583-65-1 C₃₀H₄₂N₁₀ 
• 1415583-66-2 C₂₄H₃₉N₉ 
• 1415583-53-7 C₂₂H₃₁N₇O₄ 
• 1415583-40-2 C₂₃H₃₁N₇O₃ 
• 1415583-57-1 C₂₃H₂₆ClN₇ 
• 1415583-58-2 C₂₉H₃₉N₉O 
• 1415583-59-3 C₂₃H₃₆N₈O 
• 1415583-41-3 C₂₄H₃₄N₈O₂ 
• 1415583-60-6 C₂₄H₃₄N₈O₂ 
• 1415583-43-5 C₂₃H₃₁N₇O₂ 
• 1415583-44-6 C₂₅H₃₇N₉ 

Relevant articles and documents

Tandem Schiff-Base Formation/Heterocyclization: An Approach to the Synthesis of Fused Pyrazolo-Pyrimidine/Isoxazolo-Pyrimidine Hybrids

A new synthesis of pyrazolo[4,3-d]pyrimidines and isoxazolo[4,5-d]pyrimidines is described. Key steps in the synthesis involve Stille coupling of 4,6-dichloro-2-phenyl-pyrimidine with tributyl(1-ethoxyvinyl)stannane and tandem Schiff-base formation/heterocyclization of 2,6-di-aryl-5-fluoro-4-acetylpyrimidine with hydrazines or hydroxylamine to give pyrazolo[4,3-d]pyrimidines and isoxazolo[4,5-d]pyrimidines, respectively. The position of the fluoro group in the A-pyrimidine ring is important for the success of heterocylization reaction.

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Several ditopic ligands containing two tridentate bishydrazone coordination subunits and their Zn(II) and Cd(II) [2 × 2] grid-type complexes were prepared and their photoluminescent properties studied. A special attention was devoted to the influence of the orientation of the hydrazone group N–N[dbnd]in the core of the ligands and their complexes. Its reversal from [pyridine[dbnd]N–N–pyrimidine] (L1) to [pyridine–N–N[dbnd]pyrimidine] (L2) has a strong impact on the observed absorption and emission behaviour of particular ligands (L1 and L2) as well as of their [2 × 2] grid assemblies. The further lateral functionalization of the ligands led to different emission quantum yields of the resulting grids, while their emission and absorption spectra varied very little. The simplest derivative L1 turned out to have the best performance with, for its Zn(II) complex, relatively high quantum yield 60%.

Preparation and application of neutral C-H bond anion recognition receptor

The invention discloses a novel compound capable of detecting and recognizing chloride ions, particularly relates to preparation and application of a neutral C-H bond anion recognition receptor, and belongs to the technical field of supramolecular chemistry molecular recognition. The structural formula of the receptor compound is as follows (as shown in the description). Through the pyrimidine receptor compound based on a neutral C-H bond, the anion recognition property can be greatly improved, and the pyrimidine receptor compound and the chloride ion can form a stable complex compound in the proportion of the pyrimidine receptor compound to the chloride ions being 1 to 1. The compound is good in selectivity, high in combining capacity and high in sensitivity, can be used for detecting and recognizing the chloride ions in biological samples or environmental samples, and has good application prospects.

'Green' synthesis of 2-substituted 6-hydroxy-[3H]-pyrimidin-4-ones and 4,6-dichloropyrimidines: Improved strategies and mechanistic study

An improved route to 2-substituted 6-hydroxy-[3H]-pyrimidin-4-ones 4 and to 2-substituted 4,6-dichloropyrimidines 5 is reported. Without using highly toxic reactants, compounds 4 can be prepared conveniently in a one pot synthesis on a one mol scale with average yields up to 80%. 4,6-Dichloropyrimidines 5, which are usually prepared in small quantities, are synthesized with average yields of 80%, using up to 80g of starting material. The mechanism of the chlorination of 4 is investigated computationally for the first time. The results suggest that the chlorination with phosphoryl chloride occurs in an alternating phosphorylation-chlorination manner (pathway 1) which is preferred over a sequence which starts with two phosphorylations. The investigated 4,6-dichloropyrimidines described herein form strong complexes with dichlorophosphoric acid but weak complexes with hydrochloric acid (generated during workup). These latter complexes explain the necessity of using aqueous sodium carbonate during the working up. In order to prevent possible formation of pyrimidinium salts between intermediates or the final dichloropyrimidines and unreacted hydroxypyrimidone, the latter could be deactivated with a strong acid such as dichlorophosphoric acid, thus allowing chlorination but prohibiting salt formation. Because of its general applicability to all nitrogen heterocycle chlorinations with phosphoryl chloride, the proposed route to dichloropyrimidines without solvent or side products, using less toxic reactants, is of general synthetic interest.

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