827-43-0

Basic information

• Product Name: 4-Methyl-2-phenyl-1H-imidazole
• Synonyms: 2-PHENYL-4-METHYLIMIDAZOLE;4-METHYL-2-PHENYL-1H-IMIDAZOLE;4-METHYL-2-PHENYLIMIDAZOLE;4-methyl-2-phenyl-1h-imidazol;1H-Imidazole, 4-methyl-2-phenyl-;4-METHYL-2-PHENYLIMIDAZOLE 93+%;4-Methyl-4-methylimidazole;2-Phenyl-4-methyl-1H-imidazole
• CAS NO: 827-43-0
• Molecular Formula: C₁₀H₁₀N₂
• Molecular Weight: 158.2
• EINECS: 212-571-5
• Product Categories: Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Imidazoles
• Mol File: 827-43-0.mol

Chemical Properties

• Melting Point: 180-183 °C(lit.)
• Boiling Point: 352.7 °C at 760 mmHg
• Flash Point: 184.5 °C
• Appearance: /
• Density: 1.109 g/cm³
• Vapor Pressure: 7.66E-05mmHg at 25°C
• Refractive Index: 1.591
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 13.22±0.10(Predicted)
• Water Solubility: Insoluble in water
• BRN: 4112
• CAS DataBase Reference: 4-Methyl-2-phenyl-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methyl-2-phenyl-1H-imidazole(827-43-0)
• EPA Substance Registry System: 4-Methyl-2-phenyl-1H-imidazole(827-43-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 827-43-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
4-Methyl-2-phenyl-1H-imidazole is used as a research compound for investigating the cytotoxic activity of 4-trifluoromethylimidazoles against human tumor and normal cells. Its unique structure and properties make it a valuable tool in the development of new therapeutic agents and understanding the mechanisms of action in cancer treatment.
Used in Epoxy Resin Curing:
In the materials industry, 4-Methyl-2-phenyl-1H-imidazole is used as a curing agent for epoxy systems, specifically for a diglycidyl ether of bisphenol-F epoxy resin and 1,4-butanediol. Its ability to cure these resins contributes to the formation of thermoset materials with enhanced mechanical properties and chemical resistance, making them suitable for various applications, such as coatings, adhesives, and composites.
Used in Synthesis of Aza-Heterocyclic Compounds:
4-Methyl-2-phenyl-1H-imidazole serves as a key intermediate in the synthesis of various aza-heterocyclic compounds. These compounds are important in the development of pharmaceuticals, agrochemicals, and other specialty chemicals due to their diverse biological activities and potential applications.
Used in Chemical Research:
4-Methyl-2-phenyl-1H-imidazole is also used in the preparation of 1-[(2-chlorophenyl)(diphenyl)methyl]-4-methyl-2-phenyl-1H-imidazole, which is a complex organic molecule with potential applications in chemical research and development. This specific derivative may have unique properties that can be explored for various purposes, such as in the synthesis of new materials or as a precursor to other valuable compounds.

InChI:InChI=1/C10H10N2/c1-8-7-11-10(12-8)9-5-3-2-4-6-9/h2-7H,1H3,(H,11,12)

Upstream product

• 28824-94-4 5-methyl-2-phenyl-1⁽³⁾H-imidazole-4-carboxylic acid 
• 18735-74-5 5-methyl-2-phenyloxazole-4-carboxylic acid 
• 298-08-8 glycine methyl ketone 
• 64-19-7 acetic acid 
• 7471-86-5 methyl benzimidate 
• 7737-17-9 1-aminopropan-2-one hydrochloride 
• 67-66-3 chloroform 
• 78-95-5 chloroacetone 
• 618-39-3 benzamidin 
• 80919-37-5 4-iodomethyl-2-phenylimidazoline 
• 88346-57-0 1-cyano-4-methyl-2-phenylimidazole 
• 671-59-0 anti-chloroacetone oxime 
• 57767-07-4 N-methyl-N-phenylbenzimidamide 
• 877-39-4 4-methyl-2-phenyloxazole 

Downstream Products

• 109892-69-5 4-bromo-5-methyl-2-phenyl-1⁽³⁾H-imidazole 
• 850338-83-9 4-methyl-1-(4-nitrophenyl)-2-phenyl-1H-imidazole 
• 749152-44-1 1,4-dimethyl-2-phenyl-1H-imidazole 
• 954213-71-9 1,5-dimethyl-2-phenyl-1H-imidazole 
• 954213-72-0 4-iodo-1,5-dimethyl-2-phenyl-1H-imidazole 
• 954213-73-1 1,5-dimethyl-2-phenyl-4-((trimethylsilyl)ethynyl)-1H-imidazole 
• 954213-67-3 9,10-bis((1,5-dimethyl-2-phenyl-1H-imidazol-4-yl)ethynyl)anthracene 
• 954213-69-5 5-iodo-1,4-dimethyl-2-phenyl-1H-imidazole 
• 954213-70-8 1,4-dimethyl-2-phenyl-5-((trimethylsilyl)ethynyl)-1H-imidazole 
• 856659-47-7 2-(4-methyl-2-phenyl-imidazol-1-ylmethyl)-phenylamine 
• 167017-55-2 8-(4-Methyl-2-phenyl-1H-imidazol-1-yl)-7-trifluoromethyl[1,2,4]triazolo-[4,3-a]quinoxaline-1,4(2H,5H)-dione, hydrochloride 
• 439571-70-7 1-butyl-4-methyl-2-phenyl-1H-imidazole 
• 55981-80-1 1-butyl-5-methyl-2-phenyl-1H-imidazole 
• 1299490-85-9 (S)-1-(tert-butoxycarbonyl)-4-methyl-2-phenylimidazoline 

Relevant articles and documents

Base-promoted annulation of amidoximes with alkynes: Simple access to 2,4-disubstituted imidazoles

An efficient construction of imidazole ring by a Cs2CO3-promoied annulation of amidoximes with terminal alkynes in DMSO has been developed. This protocol provides a simple synehetic ropte with high atom-utilieation for the synthesis of 2,4-disubstituted imidazoles in good yields under transition-metal-free and ligand-free conditions. Intornal alkynes can also undetgo the annulation to give 2,4,5-trisubstituted imidazoles.

Base-Promoted Cycloisomerization for the Synthesis of Oxazoles and Imidazoles

Treatment of propargylamides or propargylamidines with cesium carbonate in DMSO results in the formation of the corresponding oxazoles or imidazoles in good yields. A large variety of substrates with various functional groups are tolerated. DFT study on a model substrate reveals that the reactions proceed via a sequence involving allene formation, intramolecular cyclization, and double-bond isomerization.

Synthesis of Imidazoles and Pyrimidines Using Palladium-Catalyzed Decarboxylative Intramolecular Condensation of 1,2,4-Oxadiazol-5(4 H)-ones

We found that 1,2,4-oxadiazol-5(4H)-ones acted as iminonitrene equivalents in the presence of a palladium catalyst and a stoichiometric amount of phosphine and that aza-Wittig-type condensation with the internal carbonyl moiety occurred to afford the corresponding imidazoles and pyrimidines. Georg Thieme Verlag Stuttgart. New York.

A novel Zn-catalyzed hydroamination of propargylamides: A general synthesis of di- and tri-substituted imidazoles

Starting from commercially available amines and propargylamides a variety of substituted imidazoles were synthesized via a novel hydroamination- cyclization sequence. The target compounds are obtained in good to excellent yields in the presence of catalytic amounts of zinc triflate.

Atom-economical synthesis of N-heterocycles via cascade inter-/intramolecular C-N Bond-forming reactions catalyzed by Ti amides

Direct and efficient catalytic reactions with excellent regioselectivity for the preparation of a series of substituted isoindoles, isoquinolines, and imidazoles are reported. Reaction of C6H4(2-CN)C≡C-R with an array of amines, catalyzed by 10 mol % of [σ:η1: η5-(OCH2)(Me2NCH2)C 2B9H9]Ti(NMe2) (1), gives a series of substituted isoindoles in very high yields. In a similar manner, interaction of C6H4(2-CH2CN)C≡C-Ph with various kinds of amines affords a wide range of substituted isoquinolines. On the other hand, treatment of propargylamines (R′C≡CCH2NHR′′) with nitriles in the presence of 10 mol % of 1 produces a class of substituted imidazoles in high yields. A possible reaction mechanism is proposed, involving sequential inter- and intramolecular C-N bond formation via hydroamination/ cyclization reaction of cyanoalkynes with amines or nitriles with propargylamines catalyzed by titanium amides.

Highly active and recyclable silica gel-supported palladium catalyst for mild cross-coupling reactions of unactivated heteroaryl chlorides

Silica gel-supported β-ketoiminatophosphane-Pd complex (Pd@SiO 2) was shown to be a highly active and long-lived catalyst for aqueous Suzuki, Stille and Sonogashira coupling reactions of heteroaryl chlorides. A wide range of heteroaryl chlorides could be efficiently coupled with different nucleophilic partners in the presence of only 0.5 mol% catalyst and under mild conditions. This is one of the most powerful heterogeneous catalysts for the couplings of diverse heteroaryl chlorides. Furthermore, the catalyst could be reused with almost consistent activity. The Royal Society of Chemistry 2010.

Expanded heterogeneous Suzuki-Miyaura coupling reactions of aryl and heteroaryl chlorides under mild conditions

A mesoporous LTA zeolite (MP-LTA)-supported palladium catalyst was developed for the highly efficient Suzuki-Miyaura reaction of aryl and heteroaryl chlorides. The couplings of various aryl chlorides with arylboronic acids in aqueous ethanol were efficiently achieved in the presence of 1.0 mol% of the catalyst. Furthermore, the scope of this catalyst was extended to the coupling of heteroaryl chlorides. Regardless of the substituents, all of the coupling reactions were very clean and highly efficient under mild heating. It shows that our catalyst is one of the most powerful heterogeneous catalysts for the coupling of a wide range of aryl and heteroaryl chlorides. The catalyst could be repetitively used at least 10 times without a significant loss of its catalytic activity. Compared to mesoporous SBA-15 and MCM-41 materials, the MP-LTA support proved to be very stable and robust to prevent degradation upon reuse.

Palladium catalyzed synthesis of 4-substituted-2-phenylimidazoles from N-propargyl-benzamidine

Preliminary results of an original approach to 4-substituted-2-phenylimidazoles starting from readily available N-propargyl-benzamidine and aryl halides are reported. Best yields were obtained using aryl halides bearing an electron-withdrawing group. Plausible mechanisms are also discussed.

Direct α-oxytosylation of carbonyl compounds: One-pot synthesis of heterocycles

N-Methyl-O-tosylhydroxylamine is an effective reagent for the direct α-oxytosylation of carbonyl compounds. The reactions proceed smoothly at room temperature in the presence of both moisture and air and functional group tolerance in the substrate is good. With nonsymmetrical substrates regioselectivity for primary over secondary centers is observed and complete regiospecificity for primary over tertiary centers is obtained. Addition of a bis-heteronucleophile directly to the crude reaction mixture in a one-pot process leads to the corresponding heterocyclic product.