2-[(1-Naphthyloxy)methyl]oxirane

• CAS: 2461-42-9
• Catalog Number: ACM2461429
• Category: Main Products
• Molecular Weight: 200.23
• Molecular Formula: C₁₃H₁₂O₂
• 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
• IUPAC Name: α-Naphthyl Glycidyl Ether
• Boiling Point: 163-167
• Flash Point: 152ºC
• Density: 1.192 g/cm³
• Appearance: Light purple oil
• Exact Mass: 200.08400

Case Study

Conversion of 2-[(1-Naphthyloxy)methyl]oxirane to the Corresponding Cyclic Carbonate Using a COF-Salen-Co Catalyst

Li, He, et al. Journal of Materials Chemistry A 7.10 (2019): 5482-5492.

This study reported experimental results showing that the bulky epoxide 2-[(1-naphthyloxy)methyl]oxirane (molecular footprint ~0.8 × 0.9 nm2) can be efficiently converted to its cyclic carbonate by catalytic coupling with CO2 using a crystalline COF-salen-Co material. The catalyst employed was COF-salen-Co(III), synthesized via an in-situ method that forms the salen skeleton directly within the COF framework.
Experimental Procedure: The reaction was conducted in a high-pressure stainless-steel autoclave (15 mL). A typical procedure involved charging the reactor with COF-salen-Co catalyst (4 mg, 8 μmol Co), tetrabutylammonium bromide (TBAB) as a co-catalyst (26 mg, 80 μmol), and the substrate 2-[(1-Naphthyloxy)methyl]oxirane. The system was purged with CO2 and then pressurized to 2 MPa. The reaction proceeded at 100 °C with vigorous stirring (550 rpm) for a defined period. Post-reaction, the mixture was cooled, depressurized, and diluted with ethyl acetate. The catalyst was separated via centrifugation.
Key Results: Under the described conditions, COF-salen-Co demonstrated exceptional efficacy in converting the challenging bulky substrate. Analysis confirmed a 94% conversion of 2-[(1-Naphthyloxy)methyl]oxirane to its corresponding cyclic carbonate, with a calculated turnover frequency (TOF) of 296 h-1.

Custom Q&A

What is the molecular formula of the compound?

The molecular formula of the compound is C13H12O2.

What are the synonyms of the compound?

The synonyms of the compound are:
Glycidyl 1-naphthyl ether
2-[(1-Naphthyloxy)methyl]oxirane
2-((Naphthalen-1-yloxy)methyl)oxirane
Naphthyl glycidyl ether

What is the molecular weight of the compound?

The molecular weight of the compound is 200.23 g/mol.

When was the compound created and last modified?

The compound was created on March 26, 2005, and last modified on October 21, 2023.

What is the IUPAC name of the compound?

The IUPAC name of the compound is 2-(naphthalen-1-yloxymethyl)oxirane.

What is the InChI of the compound?

The InChI of the compound is: InChI=1S/C13H12O2/c1-2-6-12-10(4-1)5-3-7-13(12)15-9-11-8-14-11/h1-7,11H,8-9H2.

What is the InChIKey of the compound?

The InChIKey of the compound is: QYYCPWLLBSSFBW-UHFFFAOYSA-N.

What is the canonical SMILES of the compound?

The canonical SMILES of the compound is: C1C(O1)COC2=CC=CC3=CC=CC=C32.

What is the CAS number of the compound?

The CAS number of the compound is 2461-42-9.

What is the XLogP3 value of the compound?

The XLogP3 value of the compound is 3.3.

Synthetic Use

Upstream Synthesis Route 1

• 90-15-3
• 106-89-8

• 2461-42-9

Reference: [1]Location in patent: experimental part
Narsaiah, A. Venkat; Wadavrao, Sachin B.; Reddy, A. Ramesh; Yadav
[Synthesis, 2011, # 3, p. 485 - 489]
[2]Pollard; Ingwalson
[Journal of the American Chemical Society, 1955, vol. 77, p. 3402]

Downstream Synthesis Route 1

• 2461-42-9
• 35386-24-4

• 57149-07-2

Reference: [1] Patent: US2015/353473, 2015, A1, . Location in patent: Paragraph 0179-0181

Downstream Synthesis Route 2

• 2461-42-9
• 75-31-0

• 318-98-9

Reference: [1] Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 8, p. 2246 - 2250

Downstream Synthesis Route 3

• 2461-42-9
• 10576-12-2

• 67435-09-0

Reference: [1]Patent: DE2651083,1978,

* For details of the synthesis route, please refer to the original source to ensure accuracy.