[(Octadecyloxy)methyl]oxirane

Base Information

• Chemical Name: [(Octadecyloxy)methyl]oxirane
• CAS No.: 16245-97-9
• Deprecated CAS: 111955-43-2
• Molecular Formula: C21H42 O2
• Molecular Weight: 326.563
• Hs Code.: 2910900090
• European Community (EC) Number: 240-359-2
• DSSTox Substance ID: DTXSID70884879
• Nikkaji Number: J286.847D
• Mol file: 16245-97-9.mol

Synonyms:Octadecyl glycidyl ether;[(octadecyloxy)methyl]oxirane;16245-97-9;2-(octadecoxymethyl)oxirane;stearylglycidyl ether;((Octadecyloxy)methyl)oxirane;Oxirane, ((octadecyloxy)methyl)-;EINECS 240-359-2;Oxirane, 2-((octadecyloxy)methyl)-;Oxirane, [(octadecyloxy)methyl]-;Oxirane, 2-[(octadecyloxy)methyl]-;octadecylglycidyl ether;stearyl glycidyl ether;n-octadecyl glycidyl ether;Octadecyl glycidyl ether, n-;SCHEMBL148242;1,2-epoxy-3-octadecyloxypropane;DTXSID70884879;rac-1,2-epoxy-3-octadecyloxypropane

Chemical Property of [(Octadecyloxy)methyl]oxirane

Chemical Property:

• Vapor Pressure: 1.15E-06mmHg at 25°C
• Boiling Point: 413.4°C at 760 mmHg
• Flash Point: 127.4°C
• PSA: 21.76000
• Density: 0.885g/cm³
• LogP: 6.66330
• XLogP3: 8.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 19
• Exact Mass: 326.318480578
• Heavy Atom Count: 23
• Complexity: 230

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCCCOCC1CO1
• General Description: [(Octadecyloxy)methyl]oxirane, also known as glycidyl octadecyl ether or stearyl glycidyl ether, is a hydrophobic epoxide compound derived from octadecanol and epichlorohydrin. It serves as a key intermediate in synthesizing amphiphilic chitosan derivatives (e.g., NOSCS) for micellar drug delivery, as well as in the production of long-chain alkanolamine surfactants (e.g., D-MEA and M-DEA) with applications in foaming, emulsification, and wetting. Its reactivity, particularly in ring-opening reactions, enables the introduction of hydrophobic octadecyl chains into polymeric or surfactant structures, enhancing their self-assembly and functional properties.

Technology Process of [(Octadecyloxy)methyl]oxirane

There total 15 articles about [(Octadecyloxy)methyl]oxirane 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%

1-octadecanol (112-92-5) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → octadecyl glycidyl ether (16245-97-9)

Guidance literature:

With sodium hydroxide; Aliquat 336; In cyclohexane; Heating;

Reference yield: 100.0%

(2R,3R)-2,3-Bis-benzoyloxy-3-carboxy-propionate((R)-2-hydroxy-3-octadecyloxy-propyl)-dimethyl-sulfonium; (140427-69-6) → octadecyl glycidyl ether (16245-97-9)

Guidance literature:

With sodium hydroxide; In dichloromethane;

Reference yield: 71.0%

sodium octadecylate + 1,2-Epoxy-3-bromopropane (3132-64-7,82584-73-4) → octadecyl glycidyl ether (16245-97-9)

Guidance literature:

In N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1016/0040-4039(96)01218-X

upstream raw materials:

(2R,3R)-2,3-Bis-benzoyloxy-3-carboxy-propionate((R)-2-hydroxy-3-octadecyloxy-propyl)-dimethyl-sulfonium;

Toluene-4-sulfonic acid 1-hydroxymethyl-2-octadecyloxy-ethyl ester

1-octadecanol

epichlorohydrin

Downstream raw materials:

batyl alcohol

(2R,3R)-2,3-Bis-benzoyloxy-3-carboxy-propionate(2-hydroxy-3-octadecyloxy-propyl)-dimethyl-sulfonium;

2-<2-<2-hydroxy-3-(octadecyloxy)propyloxy>ethoxy>ethyl trityl ether

2-O-methyl-1-O-octadecyl-3-<2-(2-trityloxyethoxy)ethyl>ether