1,4,7,10,13,16-Hexaoxacyclooctadecane-2-methanamine

Base Information

• Chemical Name: 1,4,7,10,13,16-Hexaoxacyclooctadecane-2-methanamine
• CAS No.: 83585-61-9
• Molecular Formula: C13H27 N O6
• Molecular Weight: 293.36
• Hs Code.: 2932999099
• European Community (EC) Number: 624-669-9
• DSSTox Substance ID: DTXSID70408130
• Nikkaji Number: J1.117.203B
• Mol file: 83585-61-9.mol

Synonyms:83585-61-9;2-Aminomethyl-18-crown-6;1,4,7,10,13,16-Hexaoxacyclooctadecane-2-methanamine;1,4,7,10,13,16-hexaoxacyclooctadec-2-ylmethanamine;2-(aminomethyl)-18-crown-6;2-amino-methyl-18-crown-6;SCHEMBL1247208;DTXSID70408130;2-Aminomethyl-18-crown-6, 95%;AKOS015894749;(1,4,7,10,13,16-Hexaoxacyclooctadecan-2-yl)methanamine

Chemical Property of 1,4,7,10,13,16-Hexaoxacyclooctadecane-2-methanamine

Chemical Property:

• Vapor Pressure: 4.85E-08mmHg at 25°C
• Refractive Index: n20/D 1.479(lit.)
• Boiling Point: 135 °C/0.08 mmHg(lit.)
• PKA: 9.11±0.29(Predicted)
• Flash Point: 113 °C
• PSA: 81.40000
• Density: 1.126 g/mL at 25 °C(lit.)
• LogP: 0.12720
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 293.18383758
• Heavy Atom Count: 20
• Complexity: 207

Purity/Quality:

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

2-Aminomethyl-18-crown-6 95% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCCOCCOC(COCCOCCO1)CN
• Uses: 2-Aminomethyl-18-crown-6 (AM-18-C-6) can be used to prepare: AM-18-C-6 bonded Merrifield peptide resin, which is used to study the absorption and the isotopic effect of magnesium. Schiff base of gossypol with aminomethyl crown ether for complexation of monovalent cations. Crown tagged triarylphosphine by reacting with triphenylphosphine carboxylic acid. These tagged triarylphosphine reagents are used in Mitsunobu and Heck reactions for the removal of phosphine derived by-products. 1,16-hexadecanoyl-bis-(2-aminomethyl)-18-crown-6 (bola A-16), which is utilized as a vesicular carrier in a drug delivery system.

Technology Process of 1,4,7,10,13,16-Hexaoxacyclooctadecane-2-methanamine

There total 5 articles about 1,4,7,10,13,16-Hexaoxacyclooctadecane-2-methanamine 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: 43.0%

tetraethylene glycol di(p-toluenesulfonate) (37860-51-8) + 1-amino-3-(2-hydroxy-ethoxy)-propan-2-ol (114012-79-2) → 2-(aminomethyl)-18-crown-6 (83585-61-9)

Guidance literature:

With sodium t-butanolate; In 1,4-dioxane; tert-butyl alcohol; at 40 ℃; for 2.5h;

DOI:10.1021/jo00147a025

Reference yield: 40.0%

2-[1-Aminomethyl-2-(2-hydroxy-ethoxy)-ethoxy]-ethanol (83585-69-7) + triethylene glycol di-(p-toluenesulfonate) (19249-03-7) → 2-(aminomethyl)-18-crown-6 (83585-61-9)

Guidance literature:

With sodium t-butanolate; In 1,4-dioxane; tert-butyl alcohol; at 40 ℃; for 2.5h;

DOI:10.1021/jo00147a025

Reference yield:

1-chloro-3-(2-hydroxyethoxy)-2-propanol (18371-74-9) → 2-(aminomethyl)-18-crown-6 (83585-61-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / 26percent aq. NH₃, K₂CO₃ / 55 h / Ambient temperature

2: 43 percent / tert-BuONa / dioxane; 2-methyl-propan-2-ol / 2.5 h / 40 °C

With ammonium hydroxide; potassium carbonate; sodium t-butanolate; In 1,4-dioxane; tert-butyl alcohol;

DOI:10.1021/jo00147a025

upstream raw materials:

tetraethylene glycol di(p-toluenesulfonate)

1-amino-3-(2-hydroxy-ethoxy)-propan-2-ol

2-[1-Aminomethyl-2-(2-hydroxy-ethoxy)-ethoxy]-ethanol

triethylene glycol di-(p-toluenesulfonate)

Downstream raw materials:

(E)-N-(2-(1,4,7,10,13-Pentaoxa-16-azacyclooctadecan-16-yl)ethyl)-2-(3-hydroxy-4-(4-methoxyphenyl)-5-oxofuran-2(5H)-ylidene)-2-(4-methoxyphenyl)acetamide

1-(2-(trifluoromethylcarbonyl)phenylaminocarbonyl)-1'-((18-crown-6)methylaminocarbonyl)ferrocene

Refernces

• 1、 Maeda, Hirokazu,Kikui, Takashi,Nakatsuji, Yohji,Okahara, Mitsuo. "Synthesis of Aminomethyl Crown Ethers". . p. 5167 - 5171. Retrieved 2007/10/02.