2461-42-9

Basic information

• Product Name: 2-[(1-Naphthyloxy)methyl]oxirane
• Synonyms: NAPHTHYL GLYCIDYL ETHER;1-(2,3-epoxypropoxy)-naphthalen;1-naphthylglycidylether;ether,2,3-epoxypropyl1-naphthyl;glycidyl1-naphthylether;1-(ALPHA-NAPHTHALENOXY)-2,3-EPOXYPROPANE;1-NAPHTHOL GLYCIDYL ETHER;2-[(1-NAPHTHYLOXY)METHYL]OXIRANE
• CAS NO: 2461-42-9
• Molecular Formula: C₁₃H₁₂O₂
• Molecular Weight: 200.23
• EINECS: 219-555-7
• Product Categories: Aromatics Compounds;Aromatics;Heterocycles;Intermediates
• Mol File: 2461-42-9.mol
• Article Data: 79

Chemical Properties

• Melting Point: 95 °C
• Boiling Point: 163-167
• Flash Point: 152 °C
• Appearance: Light purple oil
• Density: 1.192 g/cm³
• Vapor Pressure: 0.000191mmHg at 25°C
• Refractive Index: 1.628
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: 2-[(1-Naphthyloxy)methyl]oxirane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(1-Naphthyloxy)methyl]oxirane(2461-42-9)
• EPA Substance Registry System: 2-[(1-Naphthyloxy)methyl]oxirane(2461-42-9)

Safety Data

• Hazardous Substances Data: 2461-42-9(Hazardous Substances Data)

Usage

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.

Chemical Properties

2-[(1-Naphthyloxy)methyl]oxirane is Light Purple Oil

Uses

2-[(1-Naphthyloxy)methyl]oxirane is used in the preparation of Naftopidil (N213500) and propranolol (P831800).

Contact allergens

Glycidyl ethers are used as reactive diluents for epoxy resins. Alpha-naphthyl glycidyl ether is formed by adding epichlorhydrin and NaOH to alpha-naphthol. Contact dermatitis was reported in workers of a chemical plant.

Synthesis

The α-naphthol and epichlorohydrin are heated and reacted, and after etherification, 1-chloro-3-(1-naphthyloxy)-2-propanol is generated, and then hydrogen chloride is removed under the action of sodium hydroxide to obtain 2-[ (1-Naphthyloxy)methyl]oxirane.

InChI:InChI=1/C13H12O2/c1-2-6-12-10(4-1)5-3-7-13(12)15-9-11-8-14-11/h1-7,11H,8-9H2/t11-/m0/s1

Upstream product

• 30165-97-0 3-hydroxy-4-(N-morpholino)-1,2,5-thiadiazole 
• 106-89-8 epichlorohydrin 
• 30389-33-4 5-hydroxycarbostyril 
• 90-15-3 α-naphthol 
• 115314-14-2 (2s)-(+)-glycidyl 3-nitrobenzenesulfonate 
• 865-47-4 potassium tert-butylate 
• 3132-64-7 1,2-Epoxy-3-bromopropane 
• 75-31-0 isopropylamine 
• 20009-25-0 allyl naphthyl ether 
• 150855-02-0 1-Benzyloxy-3-(naphthalen-1-yloxy)-propan-2-ol 
• 3019-88-3 sodium naphtholate 
• 36112-95-5 3-(1-naphthyloxy)propane-1,2-diol 
• 118712-54-2 glycidyl p-toluenesulfonate 
• 96-23-1 1,3-Dichloro-2-propanol 

Downstream Products

• 41510-06-9 dl-N-3-(1-Naphthoxy)-2-hydroxypropylmorpholine 
• 20804-76-6 3-hydroxy-4-(1-naphthyloxy)butanenitrile 
• 102654-83-1 3-(1-naphthyloxy)-1-(4-phenylpiperazinyl)propan-2-ol 
• 112551-82-3 1-(4-(2-chlorophenyl)piperazinyl)-3-(1-naphthyloxy)-propan-2-ol 
• 57149-07-2 naftopidil 
• 65919-73-5 3-[4-(p-chlorophenyl)-4-ethoxycarbonylpiperidino]-1-(1-naphthoxy)-2-propanol 
• 65919-69-9 1-(1-naphthoxy)-3-(4-phenylpiperidino)-2-propanol 
• 2007-11-6 N-[2-hydroxy-3-(1-naphthalenyloxy)propyl]-N-(1-methylethyl)acetamide 

Relevant articles and documents

Drug repurposing and rediscovery: Design, synthesis and preliminary biological evaluation of 1-arylamino-3-aryloxypropan-2-ols as anti-melanoma agents

Malignant melanoma (MM) presents as the highest morbidity and mortality type in skin cancer. Herein, inspired by the previously reported anti-melanoma effect of propranolol, a widely applied β adrenergic receptor antagonist as cardiovascular drug, we set out to exploit its potential as anti-melanoma therapy based on the drug repurposing strategy. Structural optimization of propranolol yielded 5m, which exhibits dramatically improved potency on human melanoma cell growth (1.98–3.70 μM), compared to propranolol (59.5–75.8 μM). Further investigation demonstrated that 5m could inhibit colony formation of melanoma cell line (completely abolished at 2 μM for 5m, partially inhibited at 50 μM for propranolol), induce cell apoptosis and cell cycle arrest in the G2/M phase (both observed at 1 μM). Preliminary mechanism study indicated that 5m could disrupt the cellular microtubule network, which suggested tubulin as a potential target. Docking study provided a structural insight into the interaction between 5m and tubulin. In summary, our study presents a drug repurposing case that redirects a cardiovascular agent to an anti-melanoma agent.

One pot synthesis of (±)/(S)-atenolol and (±)/(S)-propranolol by employing polymer supported reagent

(±)/(S)-Atenolol and (±)/(S)-propranolol were synthesized by using reaction of (±)/(S)-epichlorohydrin with polymer supported phenoxide anion followed by reaction with isopropylamine.

Relationship of nonspecific antiarrhythmic and negative inotropic activity with physicochemical parameters of propranolol analogues

in an attempt to separate the nonspecific antiarrhythmic activity of propranolol from its negative inotropic effects, analogues containing hydrophilic and lipophylic substituents on the nitrogen and on the naphthyl ring were prepared and tested in an isolated tissue preparation. Though it had been predicted that analogues containing a very hydrophilic group on the nitrogen would have the highest antiarrhythmic/negative inotropic effect ratio, it was found that both effects increased identically when the lipophilicity of either the nitrogen or ring substituent was increased.

Synthetic method of propranolol hydrochloride

The invention belongs to the field of medicines, and particularly relates to a synthetic method of propranolol hydrochloride. The preparation method comprises the following steps: by taking epoxy chloropropane and methyl naphthol as raw materials and acetonitrile as a solvent, firstly reacting in tetramethylammonium hydroxide to obtain an intermediate product, then reacting the intermediate product with isopropylamine in the presence of a metal salt Ni/alpha-Al2O3 catalyst to obtain propranolol, and finally salinizing to obtain the propranolol hydrochloride. The method can significantly improve the yield and purity of the propranolol hydrochloride.

Facile microwave-assisted synthesis and antitubercular evaluation of novel aziridine derivatives

Novel 2-(aryloxymethyl)aziridines and 2-((3-aryl-1-phenylallyloxy)methyl)aziridine derivatives were prepared via ring-opening reaction of epoxides. The synthesized derivatives were characterized by using elemental analysis (EA), FT-IR, 13C NMR, and 1H NMR. The in vitro antitubercular activities of the synthesized compounds were evaluated against Mycobacterium tuberculosis H37Rv (MTB H37Rv) strain using MTT-MABA assay. All the aziridine derivatives exhibited improved persuasive antitubercular activity against MTB H37Rv in comparison with standard drugs. Among the tested compounds, 2-(naphthalene-1-yloxy) methyl aziridine (5b), 2-(naphthalene-2-yloxy)methylaziridine (5c), 2-(m-tolyloxymethyl)aziridine (5e), 2-(3-(4-methoxyphenyl)-1-phenylalloxy)methylaziridine (12b) and 2-(3-(2-chlorophenyl)-1-phenylallyloxy)methylaziridine (12c) revealed promising activity against MTB H37Rv. Specifically, compound 5b and 12 b showed three-times more active (MIC = 0.5 μg/mL) than the standard drugs ethambutol (MIC = 1.56 μg/mL) and ciprofloxacin (MIC = 1.56 μg/mL).