3438-48-0

Basic information

• Product Name: 4-Phenylpyrimidine
• Synonyms: 5-CHLORO-2-ANISIC ACID;4-PHENYLPYRIMIDINE;2-METHOXY-5-CHLOROBENZOIC ACID;RARECHEM AL BO 0576;4-Phenylpyrimidine,96%;NSC 84249;4-phenyl-pyrimidin;6-phenylpyrimidine
• CAS NO: 3438-48-0
• Molecular Formula: C₁₀H₈N₂
• Molecular Weight: 156.19
• EINECS: 222-345-8
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Pyrimidines
• Mol File: 3438-48-0.mol

Chemical Properties

• Melting Point: 98-100 °C(lit.)
• Boiling Point: 270.42°C (rough estimate)
• Flash Point: >230 °F
• Appearance: light yellow crystalline powder
• Density: 1.1566 (rough estimate)
• Vapor Pressure: 0.00256mmHg at 25°C
• Refractive Index: 1.6057 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 1.57±0.10(Predicted)
• CAS DataBase Reference: 4-Phenylpyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Phenylpyrimidine(3438-48-0)
• EPA Substance Registry System: 4-Phenylpyrimidine(3438-48-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-36-22
• Safety Statements: 26-37/39-24/25
• WGK Germany: 3
• RTECS: UV9640000
• Hazardous Substances Data: 3438-48-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Phenylpyrimidine is used as an intermediate compound for the synthesis of various pharmaceuticals. Its unique chemical structure allows it to be a key component in the development of new drugs targeting specific medical conditions.
Used in Chemical Research:
In the field of chemical research, 4-Phenylpyrimidine serves as a valuable compound for studying the properties and reactions of biaryl systems. Its light yellow crystalline powder form makes it suitable for various experimental setups and analyses.
Used in Material Science:
4-Phenylpyrimidine can be utilized as a building block in the development of novel materials with specific optical, electronic, or structural properties. Its incorporation into these materials can lead to advancements in various applications, such as optoelectronics, sensors, and advanced coatings.
Used in Dye and Pigment Industry:
Due to its light yellow crystalline nature, 4-Phenylpyrimidine can be employed as a dye or pigment in the colorants industry. It can be used to create specific shades and hues in various products, such as inks, paints, and plastics.

Synthesis Reference(s)

The Journal of Organic Chemistry, 47, p. 2673, 1982 DOI: 10.1021/jo00134a034

InChI:InChI=1/C10H8N2/c1-2-4-9(5-3-1)10-6-7-11-8-12-10/h1-8H

Upstream product

• 289-95-2 PYRIMIDINE 
• 60-29-7 diethyl ether 
• 591-51-5 phenyllithium 
• 13036-50-5 2-chloro-4-phenylpyrimidine 
• 3435-26-5 4-chloro-6-phenylpyrimidine 
• 26032-72-4 2,4-dichloro-6-phenyl-pyrimidine 
• 1201-93-0 1-phenyl-3-dimethylaminoprop-2-enone 
• 540-69-2 ammonium formate 
• 77287-34-4 formamide 
• 33603-87-1 β-chlorocinnamaldehyde 
• 55735-49-4 3-acetoxy-1-phenyl-propenone 
• 3506-54-5 3-(diethylamino)-1-phenylprop-2-en-1-one 
• 41125-10-4 benzoylacetaldehyde sodium salt 
• 4774-33-8 tris(formylamino)methane 

Downstream Products

• 16495-81-1 4-(3-nitrophenyl)pyrimidine 
• 10198-90-0 6-phenyl-4-(2-pyridyl)pyrimidine 
• 74647-32-8 ethyl 6-phenylpyrimidine-4-carboxylate 
• 74502-98-0 (6-phenylpyrimidin-4-yl)methanol 
• 16495-79-7 2,4-diacetoxy-1,3,5-trinitro-6-phenyl-1,2,3,4-tetrahydropyrimidine 
• 67074-00-4 4-benzoyl-6-phenylpyrimidine 
• 64571-51-3 4-acetyl-6-phenylpyrimidine 
• 28840-36-0 6-phenylpyrimidine-4-carboxamide 
• 67073-98-7 6-phenyl-4-propionylpyrimidine 
• 67073-99-8 4-isobutyroyl-6-phenylpyrimidine 
• 74647-41-9 N,N-dimethyl-6-phenylpyrimidine-2-carboxamide 
• 74503-00-7 N,N-dimethyl-6-phenylpyrimidine-4-carboxamide 
• 2305-87-5 4-phenylpyrimidin-2-amine 
• 3435-29-8 4-Amino-6-phenylpyrimidine 

Relevant articles and documents

INVESTIGATION OF SOME ELECTROPHILIC REACTIONS OF 4-PHENYL-5-HYDROXYPYRIMIDINE AND ITS 1-OXIDE

A difference in the reactivities of the 2 and 6 positions of the 5-hydroxypyrimidine ring and an effect of the N-oxide group on the direction of electrophilic substitution reactions were demonstrated in the case of synthesized 4-phenyl-5-hydroxypyrimidine and its 1-oxide.

Transition-Metal-Free Decarboxylative Arylation of 2-Picolinic Acids with Arenes under Air Conditions

A facile, transition-metal-free, and direct decarboxylative arylation of 2-picolinic acids with simple arenes is described. The oxidative decarboxylative arylation of 2-picolinic acids with arenes proceeds readily via N-chloro carbene intermediates to afford 2-arylpyridines in satisfactory to good yields under transition-metal-free conditions. This new type of decarboxylative arylation is operationally simple and scalable and exhibits high functional-group tolerance. Various synthetically useful functional groups, such as halogen atoms, methoxycarbonyl, and nitro, remain intact during the decarboxylative arylation of 2-picolinic acids.

Catalyst free synthesis of mono- and disubstituted pyrimidines from O-acyl oximes

Transition-metal or iodine catalyzed transformations of O-acyl oximes to various N-heterocycles are well established. Herein, we report a catalyst free, oxime carboxylate based, three-component condensation method to access mono- and disubstituted pyrimidines. A broad range of substituted pyrimidines were prepared in moderate to excellent yields. Control experiments reveal that in situ generated formamidine is the key intermediate.

Oxidative Annulations Involving DMSO and Formamide: K2S2O8 Mediated Syntheses of Quinolines and Pyrimidines

An efficient strategy toward 4-arylquinolines and 4-arylpyrimidines from readily available precursors is described. Oxidative annulation promoted by K2S2O8 involving anilines, aryl ketones, and DMSO as a methine (=CH-) equivalent leads to 4-arylquinolines via a cascade that entails generation of a sulfenium ion, subsequent C-N and C-C bond formations, and cyclization. The application of this strategy to the activation of acetophenone-formamide conjugates toward the synthesis of 4-arylpyrimidines is also described.

Pd-catalyzed decarboxylative cross-coupling of sodium pyrimidinecarboxylates with (hetero)aryl bromides

A straightforward method for the synthesis of functionalized 4- or 5-(hetero)arylpyrimidines via decarboxylative cross-coupling reaction from readily available pyrimidine-4- and pyrimidine-5-carboxylates was described. In the presence of dual-catalyst system of Pd(PPh3)4/Cu2O, the reaction proceeds smoothly, tolerates a variety of functional groups, and provides easy access to the synthesis of different (hetero)arylpyrimidines compounds.

Selective aryl radical transfers into N-heteroaromatics from diaryliodonoium salts with trimethoxybenzene auxiliary

We have found that a series of trimethoxybenzene-based diaryliodonium(III) salts I (ArI+Ar’X-, where Ar = various aryl groups, Ar’ = 2,4,6-trimethoxyphenyl, X- = counterion) can exclusively cause Ar-transfers during the base-induced radical couplings with N-heteroaromatic compounds 1 by working the trimethoxybenzene ring (Ar’) as an inert coupling auxiliary. By the treatment with N-heteroaromatics 1 as the solvent, the metal-free arylations utilizing the specific salts I initiated by solid NaOH upon heating selectively produced the corresponding biaryls 2 in good yields without the formation of the trimethoxybenzene (Ar’) coupling product.

Preparation method of polysubstituted pyrimidine

The invention belongs to the field of chemical synthesis, and particularly relates to a preparation method of polysubstituted pyrimidine. The method comprises the following step that amidine hydrochloride and a propiophenone compound react in the presence of an iron source compound, 1,10-phenanthroline and tetramethyl piperidine nitric oxide to obtain polysubstituted pyrimidine, wherein propiophenone or a propiophenone derivative is adopted as the propiophenone compound. According to the method, polysubstituted pyrimidine can be generated through a reaction by taking the propiophenone compound and amidine hydrochloride as reacting raw materials under combined promotion of the iron source compound, 1,10-phenanthroline and the tetramethyl piperidine nitric oxide; a strong alkaline or strong acidic environment is not needed, the reaction conditions are simple and mild, and the yield of polysubstituted pyrimidine is high. Experiment results show that the maximum yield of polysubstituted pyrimidine prepared through the method can reach 93% or above.

Iron Catalysis for Modular Pyrimidine Synthesis through β-Ammoniation/Cyclization of Saturated Carbonyl Compounds with Amidines

An efficient method for the modular synthesis of various pyrimidine derivatives by means of the reactions of ketones, aldehydes, or esters with amidines in the presence of an in situ prepared recyclable iron(II)-complex was developed. This operationally simple reaction proceeded with broad functional group tolerance in a regioselective manner via a remarkable unactivated β-C-H bond functionalization. Control experiments were performed to gain deep understanding of the mechanism, and the reactions are likely to proceed through a designed TEMPO complexation/enamine addition/transient α-occupation/β-TEMPO elimination/cyclization sequence.

Metal free C-H functionalization of diazines and related heteroarenes with organoboron species and its application in the synthesis of a CDK inhibitor, meriolin 1

Here, we report a metal-free cross-coupling reaction of diazines and related heteroarenes with organoboron species via C-H functionalization. The optimized conditions represent a metal-free method for the activation of aryl/heteroarylboronic acids, which undergo coupling with diazines and related heteroarenes. Optimized conditions also find application in the synthesis of a pyrimidine-based potent CDK inhibitor, meriolin1.

Quinoline compound and its preparation method and application (by machine translation)

The invention relates to the general formula I shown quinoline derivatives and their pharmaceutically acceptable salt, hydrate, solvate and prodrug, wherein substituent R1 , R2 , X, Y, Z, n has the meaning given in the specification. The invention also relates to the compounds of the general formula I has strong inhibition of c - Met kinase function, and also relates to the compounds and its pharmaceutically acceptable salt, hydrate, solvate or prodrug thereof in the preparation of the treatment because the c - Met kinase abnormal high expression of diseases caused by the use of the medicaments, in particular in preparing and treating and/or preventing cancer of the use of the medicament. (by machine translation)