2-PHENYLPYRIMIDINE

Base Information

• Chemical Name: 2-PHENYLPYRIMIDINE
• CAS No.: 7431-45-0
• Molecular Formula: C10H8N2
• Molecular Weight: 156.187
• Hs Code.: 2933599590
• Mol file: 7431-45-0.mol

Synonyms:2-Phenylpyrimidine;phenylpyrimidine;

Chemical Property of 2-PHENYLPYRIMIDINE

Chemical Property:

• Vapor Pressure: 0.84mmHg at 25°C
• Melting Point: 37.0 to 41.0 °C
• Refractive Index: 1.58
• Boiling Point: 188.1 °C at 760 mmHg
• PKA: 1.00±0.13(Predicted)
• Flash Point: 51.4 °C
• PSA: 25.78000
• Density: 1.106 g/cm³
• LogP: 2.14360
• Storage Temp.: Inert atmosphere,Room Temperature

Purity/Quality:

97% ^*data from raw suppliers

2-phenylpyrimidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 2-Phenylpyrimidine is a heterocyclic compound that serves as a key substrate in cyclopalladation studies, particularly when modified with pendant pyrazole donors. The research demonstrates that the cyclopalladation behavior of 2-phenylpyrimidine derivatives depends significantly on the nature and positioning of substituents, such as pyrazole groups, on the pyrimidine ring. While some derivatives undergo monocyclopalladation, others form regioisomers or mixtures of singly and doubly cyclopalladated products, highlighting the structural sensitivity of these reactions. This work underscores the role of ligand design in controlling cyclometallation outcomes.

Technology Process of 2-PHENYLPYRIMIDINE

There total 71 articles about 2-PHENYLPYRIMIDINE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

2-chloropyrimidine (1722-12-9,1195939-87-7) + phenylboronic acid (98-80-6) → 2-phenylpyrimidine (7431-45-0)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; at 90 ℃;

DOI:10.1002/ejoc.201000631

Reference yield: 97.0%

2-bromopyrimidine (4595-60-2) + phenylboronic acid (98-80-6) → 2-phenylpyrimidine (7431-45-0)

Guidance literature:

With sodium carbonate; In ethanol; water; at 90 ℃; for 7h; Inert atmosphere;

DOI:10.1016/j.tetlet.2009.05.064

Reference yield: 91.0%

2-chloropyrimidine (1722-12-9,1195939-87-7) + triphenylindium (3958-47-2) → 2-phenylpyrimidine (7431-45-0)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; at 80 ℃; for 4h; Inert atmosphere;

DOI:10.3390/molecules23071582

upstream raw materials:

2-phenyl-1,4,5,6-tetrahydropyrimidine

5-chloro-2-phenylpyrimidine

4-chloro-2-phenylpyrimidine

(E)-3-(diethylamino)acrylaldehyde

Downstream raw materials:

2-Phenylimidazole

2-phenylpyrimidine N-oxide

benzoic acid

2-(2,6-distyrylphenyl)pyrimidine

Refernces

Cyclometallated compounds VI. Cyclopalladation of 2-phenylpyrimidines with pendant pyrazole donors

10.1016/0022-328X(90)85300-N

The research investigates the potential of pendant pyrazole groups to induce double cyclopalladation of 2-phenylpyrimidines. The study aimed to explore whether the addition of extra nitrogen donors at the 4- and 6-positions of the pyrimidine ring could facilitate double cyclopalladation of a 2-phenyl-pyrimidine, a process that was previously resistant in simpler substrates. The researchers synthesized and tested various 2-phenylpyrimidines with different substituents to observe their cyclopalladation behavior. The key chemicals used in this process included 4,6-bis(pyrazol-1-yl)-2-phenylpyrimidine, 4-methyl-2-phenyl-6-(pyrazol-1-ylmethyl)pyrimidine, and 4,6-bis(pyrazol-1-ylmethyl)-2-phenylpyrimidine, along with lithium tetrachloropalladate as the palladium source. The conclusions drawn from the study were that while 4,6-bis(pyrazol-1-yl)-2-phenylpyrimidine underwent only monocyclopalladation, 4-methyl-2-phenyl-6-(pyrazol-1-ylmethyl)pyrimidine reacted preferentially to give a cyclopalladated regioisomer with tridentate coordination, and 4,6-bis(pyrazol-1-ylmethyl)-2-phenylpyrimidine resulted in a mixture of both singly and doubly cyclopalladated products. This research provides insights into the influence of ligand structure on the cyclopalladation process and contributes to the understanding of cyclometallation reactions.