1-adamantyl 4-[(2,5-dihydroxyphenyl)methylamino]benzoate

Base Information

• Chemical Name: 1-adamantyl 4-[(2,5-dihydroxyphenyl)methylamino]benzoate
• CAS No.: 241127-58-2
• Molecular Formula: C24H27 N O4
• Molecular Weight: 393.483
• Mol file: 241127-58-2.mol

Synonyms:Adaphostin;NSC 680410

Chemical Property of 1-adamantyl 4-[(2,5-dihydroxyphenyl)methylamino]benzoate

Chemical Property:

• Vapor Pressure: 2.73E-15mmHg at 25°C
• Boiling Point: 606.2°Cat760mmHg
• Flash Point: 320.4°C
• PSA: 70.00000
• Density: 1.33g/cm³
• LogP: 4.99130
• Storage Temp.: Desiccate at +4°C
• Solubility.: DMSO: soluble20mg/mL, clear

Purity/Quality:

97% ^*data from raw suppliers

Adaphostin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Novel antitumor agent that induces apoptosis in tumor cells through inhibition of the tyrosine kinase BCR/ABL.

Technology Process of 1-adamantyl 4-[(2,5-dihydroxyphenyl)methylamino]benzoate

There total 7 articles about 1-adamantyl 4-[(2,5-dihydroxyphenyl)methylamino]benzoate 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: 96.0%

1-adamantyl 4-aminobenzoate (241127-66-2) → Adaphostin (241127-58-2)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethanol; for 2h; under 982.607 Torr;

DOI:10.1016/j.bmcl.2021.128270

Reference yield: 90.0%

4-[[(2,5-dihydroxyphenyl)methylene]amino]benzoic acid 1-adamantyl ester → Adaphostin (241127-58-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 1.75h; under 982.581 Torr;

DOI:10.1016/j.bmc.2004.12.003

Reference yield:

1-adamantanol p-nitrobenzoate (968-84-3) → Adaphostin (241127-58-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / H₂ / Pd/C / ethanol / 3 h / 1551.44 Torr

2: 86 percent / NaHCO₃ / ethanol / 20 h / 20 °C

3: 90 percent / H₂ / Pd/C / ethanol / 1.75 h / 982.58 Torr

With hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In ethanol;

DOI:10.1016/j.bmc.2004.12.003

upstream raw materials:

1-adamantyl 4-aminobenzoate

2,5-Dihydroxybenzaldehyde

1-adamantanol p-nitrobenzoate

1-adamanthanol