2-(4-(adaMantan-1-yl)phenoxy)acetic acid

Base Information

• Chemical Name: 2-(4-(adaMantan-1-yl)phenoxy)acetic acid
• CAS No.: 52804-26-9
• Molecular Formula: C18H22O3
• Molecular Weight: 286.371
• Hs Code.: 2918990090
• Mol file: 52804-26-9.mol

Synonyms:[4-(Adamantan-1-yl)phenoxy]acetic acid; Acetic acid, 2-(4-tricyclo[3.3.1.1~3,7~]dec-1-ylphenoxy)-

Chemical Property of 2-(4-(adaMantan-1-yl)phenoxy)acetic acid

Chemical Property:

• Vapor Pressure: 1.47E-08mmHg at 25°C
• Melting Point: 168-170℃ (acetic acid water )
• Boiling Point: 441.1°C at 760 mmHg
• Flash Point: 159.7°C
• PSA: 46.53000
• Density: 1.226g/cm³
• LogP: 3.61780
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

98%,99%, ^*data from raw suppliers

[4-(1-Adamantyl)phenoxy]acetic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(4-(adaMantan-1-yl)phenoxy)acetic acid

There total 7 articles about 2-(4-(adaMantan-1-yl)phenoxy)acetic acid 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%

(4-adamantyl-1-yl-phenoxy) acetic acid ethyl ester (52804-25-8) → (4-adamantan-1-yl-phenoxy)acetic acid (52804-26-9)

Guidance literature:

With lithium hydroxide; In 1,4-dioxane;

DOI:10.1016/j.bmcl.2007.09.005

Reference yield:

adamantane (281-23-2) + 2-phenoxyacetic acid (122-59-8) → 1-adamantanol (700-57-2) + (4-adamantan-1-yl-phenoxy)acetic acid (52804-26-9)

Guidance literature:

With sulfuric acid; trifluoroacetic anhydride; Yield given. Multistep reaction; 1) 65 deg C, 3 h, 2) 80 deg C, 1.5 h;

Reference yield:

4-adamantylphenol (29799-07-3) → (4-adamantan-1-yl-phenoxy)acetic acid (52804-26-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 94.6 percent / potassium carbonate / dimethylformamide / 20 °C

2: 61.3 percent / lithium hydroxide monohydrate / tetrahydrofuran; H₂O / 20 °C

With lithium hydroxide; potassium carbonate; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1021/jm0610292

upstream raw materials:

adamantane

2-phenoxyacetic acid

(4-adamantyl-1-yl-phenoxy) acetic acid ethyl ester

4-adamantylphenol

Downstream raw materials:

methyl 3-(2-(4-adamantan-1-ylphenoxy)acetamido)benzoate

2-[2-(4-adamantan-1-ylphenoxy)acetylamino]benzoic acid methyl ester

4-[2-(4-adamantan-1-ylphenoxy)acetylamino]benzoic acid methyl ester

3-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-4-hydroxy-benzoic acid methyl ester

Refernces

• 1、 Naik, Ravi,Ban, Hyun Seung,Jang, Kyusic,Kim, Inhyub,Xu, Xuezhen,Harmalkar, Dipesh,Shin, Seong-Ah,Kim, Minkyoung,Kim, Bo-Kyung,Park, Jaehyung,Ku, Bonsu,Oh, Sujin,Won, Misun,Lee, Kyeong. "Methyl 3-(3-(4-(2,4,4-Trimethylpentan-2-yl)phenoxy)-propanamido)benzoate as a Novel and Dual Malate Dehydrogenase (MDH) 1/2 Inhibitor Targeting Cancer Metabolism". . p. 8631 - 8646. Retrieved 2017/11/03.
• 2、 Takahashi, Eiki,Hirano, Noriyuki,Nagahara, Takashi,Yoshikawa, Satoru,Momen, Shinobu,Yokokawa, Hiroshi,Hayashi, Ryoji. "Discovery of potent transient receptor potential vanilloid 1 antagonists: Design and synthesis of phenoxyacetamide derivatives". . p. 3154 - 3156. Retrieved 2013/06/26.