Glycidyl 1-naphthyl ether

Base Information

• Chemical Name: Glycidyl 1-naphthyl ether
• CAS No.: 2461-42-9
• Molecular Formula: C13H12O2
• Molecular Weight: 200.237
• Hs Code.: 2910900090
• European Community (EC) Number: 219-555-7
• NSC Number: 632
• UNII: 07FN14F351
• DSSTox Substance ID: DTXSID501030986
• Nikkaji Number: J216.102H
• Wikidata: Q27236303
• ChEMBL ID: CHEMBL1929345
• Mol file: 2461-42-9.mol

Synonyms:alpha-naphthyl glycidyl ether;glycidyl 1-naphthyl ether

Chemical Property of Glycidyl 1-naphthyl ether

Chemical Property:

• Appearance/Colour: Light purple oil
• Vapor Pressure: 0.000191mmHg at 25°C
• Melting Point: 95 °C
• Refractive Index: 1.628
• Boiling Point: 338.6 °C at 760 mmHg
• Flash Point: 152 °C
• PSA: 21.76000
• Density: 1.192 g/cm³
• LogP: 2.61740
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 200.083729621
• Heavy Atom Count: 15
• Complexity: 217

Purity/Quality:

99% ^*data from raw suppliers

a-Naphthyl Glycidyl Ether ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Chemical Classes: Plastics & Rubber -> Glycidyl Ethers
• Canonical SMILES: C1C(O1)COC2=CC=CC3=CC=CC=C32
• Description: Glycidyl ethers are used as reactive diluents for epoxy resins. Alpha-naphtyl glycidyl ether is formed by adding epichlorhydrin and sodium hydroxide to alpha-naphtol. Contact dermatitis was reported in workers of a chemical plant.
• Uses: 2-[(1-Naphthyloxy)methyl]oxirane is used in the preparation of Naftopidil (N213500) and propranolol (P831800).

Technology Process of Glycidyl 1-naphthyl ether

There total 18 articles about Glycidyl 1-naphthyl ether 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: 96.5%

α-naphthol (90-15-3) + (2s)-(+)-glycidyl 3-nitrobenzenesulfonate (115314-14-2) → 3-(1-naphthyloxy)-1,2-epoxypropane (2461-42-9)

Guidance literature:

With cesium fluoride; In water; N,N-dimethyl-formamide;

Reference yield: 96.0%

α-naphthol (90-15-3) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → 3-(1-naphthyloxy)-1,2-epoxypropane (2461-42-9)

Guidance literature:

With sodium hydroxide; tetrabutylammomium bromide; potassium carbonate; at 116 ℃; for 0.0333333h; Irradiation;

DOI:10.1080/00304949809355263

Reference yield: 69.0%

α-naphthol (90-15-3) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → 3-(1-naphthyloxy)-1,2-epoxypropane (2461-42-9) + 1-chloro-3-(1-naphthoxy)-2-propanol (20133-93-1)

Guidance literature:

With sodium hydroxide; In water; for 6h; Heating;

DOI:10.1016/j.tet.2006.08.067

upstream raw materials:

1,3-Dichloro-2-propanol

α-naphthol

epichlorohydrin

glycidyl p-toluenesulfonate

Downstream raw materials:

1-(1-hydroxy-2-propylamino)-3-(1-naphthoxy)-2-propanol

1-<2-(2,4-Dichlorphenyloxy)-aethylamino>-3-(1-naphthoxy)-2-propanol

1-(1,1-Dimethyl-3-phenyl-propylamino)-3-(naphthalen-1-yloxy)-propan-2-ol

1-[Benzyl-(1-methyl-prop-2-ynyl)-amino]-3-(naphthalen-1-yloxy)-propan-2-ol

Refernces

• 1、 Faudone, Giuseppe,Bischoff-Kont, Iris,Rachor, Lea,Willems, Sabine,Zhubi, Rezart,Kaiser, Astrid,Chaikuad, Apirat,Knapp, Stefan,Fürst, Robert,Heering, Jan,Merk, Daniel. "Propranolol Activates the Orphan Nuclear Receptor TLX to Counteract Proliferation and Migration of Glioblastoma Cells". . p. 8727 - 8738. Retrieved 2021.
• 2、 Simon et al.. "-". . . Retrieved 1968.
• 3、 Gella, I. M.. "EPOXYALKYLATION OF α-NAPHTHOL UNDER INTERPHASE CATALYSIS CONDITIONS". . p. 430 - 431. Retrieved 1986.
• 4、 -. "NAFTOPIDIL MONOHYDROCHLORIDE DIHYDRATE AND USE THEREOF FOR PREPARATION OF NAFTOPIDIL". Paragraph 0024-0025. . Retrieved 2021/07/27.