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**1H-Imidazole, 2,4,5-triphenyl-1-(phenylmethyl)-** is a tetrasubstituted imidazole derivative synthesized via multicomponent reactions involving benzil, aromatic aldehydes, primary amines, and ammonium acetate or related precursors. It is typically prepared under solvent-free conditions using catalysts such as Br?nsted acidic ionic liquids, molecular iodine, silica gel, or carbon-based solid acids, often with microwave irradiation to enhance efficiency. 1H-Imidazole, 2,4,5-triphenyl-1-(phenylmethyl)- is characterized by high yields, mild reaction conditions, and operational simplicity, making it accessible for synthetic applications. Its structure features a phenylmethyl (benzyl) group at the 1-position and phenyl substituents at the 2, 4, and 5-positions of the imidazole ring. **Other names for 1H-Imidazole, 2,4,5-triphenyl-1-(phenylmethyl)- may include:** - 1-Benzyl-2,4,5-triphenyl-1H-imidazole - 2,4,5-Triphenyl-1-benzylimidazole - N-Benzyl-2,4,5-triphenylimidazole

13269-91-5

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13269-91-5 Usage

Structure

1H-Imidazole, 2,4,5-triphenyl-1-(phenylmethyl)-

Explanation

1H-Imidazole, 2,4,5-triphenyl-1-(phenylmethyl)- is a derivative of imidazole, which is a five-membered aromatic ring containing two nitrogen atoms. It has three phenyl groups and a phenylmethyl group attached to the imidazole ring, making it a substituted imidazole.

Explanation

The imidazole ring in 1H-Imidazole, 2,4,5-triphenyl-1-(phenylmethyl)- is aromatic, meaning it has a planar structure and exhibits resonance stabilization due to the delocalization of electrons.

Explanation

The imidazole ring is substituted with three phenyl groups (C6H5) and one phenylmethyl group (C6H5-CH2-), which are aromatic hydrocarbons.

Explanation

1H-Imidazole, 2,4,5-triphenyl-1-(phenylmethyl)- is used as a building block for the synthesis of various heterocyclic compounds, which have applications in the pharmaceutical industry.

Explanation

1H-Imidazole, 2,4,5-triphenyl-1-(phenylmethyl)has been studied for its potential biological and pharmacological activities, including its possible use as an anti-cancer agent.

Explanation

The solubility of 1H-Imidazole, 2,4,5-triphenyl-1-(phenylmethyl)- in different solvents is not mentioned in the provided material. Solubility can be an important property for determining the compound's reactivity and its use in various applications.

Explanation

The stability of 1H-Imidazole, 2,4,5-triphenyl-1-(phenylmethyl)- under different conditions (e.g., temperature, pH, etc.) is not mentioned in the provided material. Stability can be an important factor in determining the compound's suitability for specific applications.

Explanation

The reactivity of 1H-Imidazole, 2,4,5-triphenyl-1-(phenylmethyl)- with other chemicals or under different conditions is not mentioned in the provided material. Reactivity can be an important property for determining the compound's potential applications and its use in chemical reactions.

Aromaticity

Five-membered aromatic ring

Substituents

Three phenyl groups and a phenylmethyl group

Applications

Pharmaceutical industry and synthesis of heterocyclic compounds

Biological and Pharmacological Activities

Potential anti-cancer agent

Solubility

Not specified in the provided material

Stability

Not specified in the provided material

Reactivity

Not specified in the provided material

Check Digit Verification of cas no

The CAS Registry Mumber 13269-91-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,2,6 and 9 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 13269-91:
(7*1)+(6*3)+(5*2)+(4*6)+(3*9)+(2*9)+(1*1)=105
105 % 10 = 5
So 13269-91-5 is a valid CAS Registry Number.

13269-91-5Downstream Products

13269-91-5Relevant academic research and scientific papers

Experimental and computational study of metal-free Br?nsted acidic ionic liquid catalyzed benzylic C(sp3)–H bond activation and C–N, C–C cross couplings

Valiyev, Isa,Abdullayev, Yusif,Yagubova, Sevinj,Baybekov, Shamkhal,Salmanov, Cavanshir,Autschbach, Jochen

, p. 410 - 419 (2019)

Metal and solvent free synthesis of tetrasubstituted imidazoles and tetrasubstituted pyrazines from 1,2-diketones and aliphatic amines is studied experimentally and computationally. Various ionic liquids (ILs) are taken as a catalyst in 10 mol% for the re

A solvent-free synthesis of 1,2,4,5-tetrasubstituted imidazoles using molecular iodine as catalyst

Ren, Yi-Ming,Cai, Chun

, p. 133 - 134 (2010)

An efficient method for the synthesis of 1,2,4,5-tetrasubstituted imidazoles by three-component condensation of benzil, benzonitrile derivatives and primary amines under solvent-free conditions using molecular iodine as catalyst is described with high product yields. The significant features of the iodine-catalysed condensation are operational simplicity, inexpensive reagents, high yield of products and use of non-toxic reagents.

One-pot synthesis of tetra-substituted imidazoles on silica gel under microwave irradiation

Xu, Yu,Liu, Yan-Zhi,Rui, Lei,Liu, Lei,Guo, Qing-Xiang

, p. 87 - 93 (2004)

A new procedure for synthesis of tetra-substituted imidazoles was developed. A series of imidazole derivatives including six new compounds were synthesized by this procedure via condensation of benzoin, aromatic aldehyde, amine and ammonium acetate in the presence of silica gel under solvent-free microwave irradiation.

Carbon-based solid acid as an efficient and reusable catalyst for one-pot synthesis of tetrasubstituted imidazoles under solvent-free conditions

Tavakoli-Hoseini, Niloofar,Davoodnia, Abolghasem

, p. 203 - 206 (2011)

Carbon-based solid acid catalyst was found to be highly efficient, eco-friendly and recyclable heterogeneous catalyst for the multicomponent reaction of benzil, aromatic aldehyde, primary amine and ammonium acetate, giving rise to 1,2,4,5-tetrasubstituted imidazoles in good to excellent yields. The present methodology offers several advantages, such as high yields, short reaction time, mild reaction condition and a recyclable catalyst with a very easy work up. Carbon-based solid acid catalyst was found to be highly efficient, eco-friendly and recyclable heterogeneous catalyst for the multicomponent reaction of benzil, aromatic aldehyde, primary amine and ammonium acetate for the synthesis of 1,2,4,5- tetrasubstituted imidazoles in good to excellent yields. The present methodology offers several advantages, such as high yields, short reaction time, mild reaction condition and a recyclable catalyst with a very easy work up. Copyright

A novel one-pot synthesis of tetrasubstituted imidazoles under solvent-free conditions and microwave irradiation

Balalaie, Saeed,Hashemi, Mohammed M.,Akhbari, Maryam

, p. 1709 - 1711 (2003)

The one-pot, three-component condensation of benzil, benzonitrile derivatives and primary amines on the surface of silica gel under solvent-free conditions and microwave irradiation provided tetrasubstituted imidazoles in high yields.

Increased SBA-15-SO3H catalytic activity through hydrophilic/hydrophobic fluoroalkyl-chained alcohols (RFOH/SBA-15-Pr-SO3H)

Rostamnia, Sadegh,Doustkhah, Esmail

, p. 1345 - 1347 (2015)

A superior catalytic activity for the SBA-15-functionalized sulfonic acid containing fluoroalkyl chain alcohols (RFOH/SBA-15-Pr-SO3H adduct) is presented for the synthesis of highly substituted imidazoles. The advantages of this method include low catalyst loading, simple procedure, excellent yields, recyclability of catalyst, and short reaction times.

One-pot synthesis of polysubstituted imidazoles in a bronsted acidic deep eutectic solvent

Wang, Liang,Zhong, Xia,Zhou, Min,Zhou, Wei-You,Chen, Qun,He, Ming-Yang

, p. 236 - 238 (2013)

A Bronsted acidic deep eutectic solvent based on choline chloride and p-toluenesulfonic acid was prepared and was found to be effective for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles with high yields. In addition, the deep eutectic solvent is non-toxic, cost-effective and recyclable.

Silica coated magnetic NiFe2O4 nanoparticle supported phosphomolybdic acid; Synthesis, preparation and its application as a heterogeneous and recyclable catalyst for the one-pot synthesis of tri- and tetra-substituted imidazoles under solvent free conditions

Maleki, Behrooz,Eshghi, Hossein,Khojastehnezhad, Amir,Tayebee, Reza,Ashrafi, Samaneh Sedigh,Kahoo, Golnoosh Esmailian,Moeinpour, Farid

, p. 64850 - 64857 (2015)

In this research, a magnetically-recoverable catalyst (NiFe2O4@SiO2-H3PMo12O40) was prepared by supporting phosphomolybdic acid (H3PMo12O40) onto silica-coated NiFe2O4 nanoparticles. The prepared sample was characterized by FT-IR, TEM, SEM and VSM techniques and then the catalytic activity of this catalyst was investigated in the synthesis of tri- and tetra-substituted imidazole derivatives. More importantly, the catalyst was easily isolated from the reaction mixture by a magnetic bar and reused at least ten times without significant degradation in its activity.

Amberlyst A-15: Reusable catalyst for the synthesis of 2,4,5-trisubstituted and 1,2,4,5-Tetrasubstituted-1H-Imidazoles under MW irradiation

Pandit, Shivaji S.,Bhalerao, Swapnil K.,Aher, Uddhav S.,Adhav, Gorakshanath L.,Pandit, Vikram U.

, p. 421 - 426 (2011)

One-pot multi-component condensation of benzyl, aldehydes, ammonium acetate and primary amines were used for synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted-1H-imidazole derivatives underMWradiation using amberlyst A-15 as a catalysts. This catalyst has several advantages (simple work-up, low cost and reusability) . Indian Academy of Sciences.

BF3·SiO2: an efficient reagent system for the one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles

Sadeghi, Bahareh,Mirjalili, Bi Bi Fatemeh,Hashemi, Mohammad M.

, p. 2575 - 2577 (2008)

Silica-supported boron trifluoride (BF3·SiO2) is an efficient, readily available and reusable catalyst for the synthesis of 1,2,4,5-tetrasubstituted imidazoles using benzil, an aromatic aldehyde and an amine in the presence of ammonium acetate. This one-pot procedure is very simple, affording good to excellent yields.

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