4-Methylbenzhydrylamine

Base Information

• Chemical Name: 4-Methylbenzhydrylamine
• CAS No.: 55095-21-1
• Molecular Formula: C14H15 N
• Molecular Weight: 197.28
• Hs Code.: 2921499090
• DSSTox Substance ID: DTXSID10970462
• Nikkaji Number: J346.217J
• Mol file: 55095-21-1.mol

Synonyms:4-methylbenzhydrylamine;pMBHA

Chemical Property of 4-Methylbenzhydrylamine

Chemical Property:

• Vapor Pressure: 0.00031mmHg at 25°C
• Boiling Point: 320.8°C at 760 mmHg
• Flash Point: 151.5°C
• PSA: 26.02000
• Density: 1.04g/cm³
• LogP: 3.74340
• Storage Temp.: 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 197.120449483
• Heavy Atom Count: 15
• Complexity: 176

Purity/Quality:

98%min ^*data from raw suppliers

[(4-methylphenyl)(phenyl)methyl]amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C(C2=CC=CC=C2)N
• General Description: 4-Methylbenzhydrylamine (MBHA) is a key solid-phase support resin widely used in peptide synthesis, particularly for producing C-terminal amides. It is synthesized via benzotriazole-mediated amidoalkylation, yielding high-loading-capacity resin suitable for solid-phase peptide synthesis (SPPS), as demonstrated in the preparation of peptides like Leu-enkephalin. Additionally, MBHA resin serves as a scaffold for synthesizing bioactive peptides, such as penetratin derivatives, which exhibit antifungal properties against pathogens like *Candida albicans* and *Cryptococcus neoformans*. Its utility in Boc-strategy SPPS highlights its importance in peptide chemistry and drug development.

Technology Process of 4-Methylbenzhydrylamine

There total 13 articles about 4-Methylbenzhydrylamine 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: 100.0%

Phenyl N-(4-methylbenzhydryl)carbamate → phenyl-p-tolylmethylamine (55095-21-1)

Guidance literature:

With lithium hydroxide; water; In acetonitrile; at 50 ℃; for 3h;

DOI:10.1055/s-2000-6391

Reference yield: 98.0%

4-methyl-benzophenone-imine (22632-90-2) → phenyl-p-tolylmethylamine (55095-21-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 2h;

DOI:10.1055/s-2002-19328

Reference yield: 67.0%

triphenylborane (960-71-4) + 1-[(4-methylphenyl)methyl]thiolan-1-ium trifluoroborane fluoride → phenyl-p-tolylmethylamine (55095-21-1)

Guidance literature:

Multistep reaction;

DOI:10.1021/ja043632k

upstream raw materials:

(4-methylphenyl)phenylmethanone oxime

4-methyl-benzophenone-imine

triphenylborane

bromobenzene

Downstream raw materials:

4-Methylbenzophenone

C₂₉H₂₆N₂O₃

N-[(4-methylphenyl)(phenyl)methyl]-1-phenyl-4-[(E)-2-(5-phenyl-1,3,4-oxadiazol-2-yl)ethenyl]-1H-pyrazole-3-carboxamide

N-[(4-methylphenyl)(phenyl)methyl]acetamide

Refernces

Preparation of MBHA resin by benzotriazole-mediated amidoalkylation

10.1016/j.tetlet.2008.06.110

The research focuses on the development of a new method for synthesizing MBHA (4-methylbenzhydrylamine) resin, a widely used solid support for the synthesis of carboxamides or peptide C-terminal amides. The study introduces a benzotriazole-mediated amidoalkylation approach to prepare MBHA resin, utilizing N-[(benzotriazol-1yl)(p-tolyl)methyl]formamide or N-[formamido(p-tolyl)methyl]formamide as key reactants. The experiments involved the reaction of these compounds with benzene in the presence of aluminum chloride to achieve the amidoalkylation of unactivated aromatic compounds like benzene. The resulting products were then subjected to hydrolysis to obtain the MBHA resin, which was characterized by its loading capacity determined through Fmoc titration after coupling with Fmoc-Gly-OH. The resin's performance was evaluated by synthesizing a model peptide, Leu-enkephalin, and analyzing the crude product using HPLC and MALDI-TOF. The study demonstrated that the benzotriazole-mediated amidoalkylation method is effective for synthesizing MBHA resin with high loading capacity and good properties as a solid support for solid-phase peptide synthesis (SPPS).

Penetratin and derivatives acting as antifungal agents

10.1016/j.ejmech.2008.02.019

The research presents a comprehensive study on the synthesis, in vitro evaluation, and conformational analysis of penetratin and its derivatives as potential antifungal agents. The research involved the synthesis of penetratin (RQIKIWFQNRRMKWKKeNH2) and its derivatives. The synthesis was carried out manually on a p-methylbenzhydrylamine resin (MBHA) using Boc-strategy and standard methodology. Side chain protecting groups used were Tos for Arg and 2-chloro-Z for Lys. The main focus was on their activity against human pathogenic strains of Candida albicans and Cryptococcus neoformans, as well as clinical isolates of C. neoformans. The experiments involved solid phase peptide synthesis using Boc-strategy, antimicrobial susceptibility testing, and a series of computational methods including EDMC calculations, simulated annealing, and molecular dynamics simulations. The peptides were analyzed for their conformational behavior and molecular electrostatic potentials to identify a topographical template for designing new antifungal compounds. The study identified penetratin and certain derivatives as significantly active against Cryptococcus species, with a detailed exploration of their structure-activity relationships and potential as antifungal agents.