1-(2-Propynyloxy)naphthalene

Base Information

• Chemical Name: 1-(2-Propynyloxy)naphthalene
• CAS No.: 18542-45-5
• Molecular Formula: C13H10O
• Molecular Weight: 182.222
• Hs Code.: 2909309090
• DSSTox Substance ID: DTXSID10171775
• Nikkaji Number: J42.437D
• Wikidata: Q83041926
• Mol file: 18542-45-5.mol

Synonyms:1-(2-Propynyloxy)naphthalene;18542-45-5;1-prop-2-ynoxynaphthalene;1-(2-Propyn-1-yloxy)naphthalene;BRN 2252429;NAPHTHALENE, 1-(2-PROPYNYLOXY)-;1-(Propargyloxy)naphthalene;1-(prop-2-yn-1-yloxy)naphthalene;1propargyloxynaphthalene;naphthyl propargyl ether;propargyl naphthyl ether;1-propargyloxynaphthalene;SCHEMBL2204213;DTXSID10171775;MFCD03787730;AKOS005091827;AB90395;LS-94854;CS-0158538;P2227;T71986;4W-0894

Chemical Property of 1-(2-Propynyloxy)naphthalene

Chemical Property:

• Vapor Pressure: 0.000635mmHg at 25°C
• Refractive Index: 1.6200 to 1.6240
• Boiling Point: 319.4°Cat760mmHg
• Flash Point: 142.9°C
• PSA: 9.23000
• Density: 1.108g/cm³
• LogP: 2.85180
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 182.073164938
• Heavy Atom Count: 14
• Complexity: 225

Purity/Quality:

97% ^*data from raw suppliers

1-(2-Propynyloxy)naphthalene >95.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CCOC1=CC=CC2=CC=CC=C21

Technology Process of 1-(2-Propynyloxy)naphthalene

There total 4 articles about 1-(2-Propynyloxy)naphthalene 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: 97.0%

α-naphthol (90-15-3) + propargyl bromide (106-96-7) → 1-(propargyloxy)naphthalene (18542-45-5)

Guidance literature:

α-naphthol; With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

propargyl bromide; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/acs.orglett.8b03941

Reference yield: 81.0%

dipropargyl ether (6921-27-3) + α-naphthol (90-15-3) → 1-(propargyloxy)naphthalene (18542-45-5)

Guidance literature:

With potassium carbonate; In acetone; toluene; at 20 ℃;

DOI:10.1021/acs.orglett.9b03999

Reference yield:

α-naphthol (90-15-3) + 2-propynyl chloride (624-65-7) → 1-(propargyloxy)naphthalene (18542-45-5)

Guidance literature:

α-naphthol; With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

2-propynyl chloride; In N,N-dimethyl-formamide; for 12h;

DOI:10.1016/j.bmcl.2018.04.045

upstream raw materials:

α-naphthol

propargyl bromide

2-propynyl chloride

dipropargyl ether

Downstream raw materials:

[3-(naphthalen-1-yloxy)prop-1-ynyl](phenyl)selane

[Au(I)(1-propargyloxynaphthalene(-H))(triphenylphosphine)]

1-(2,2-difluoro-2-(phenylthio)ethyl)-4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazole

2-(3-(naphthalen-1-yloxy)prop-1-ynyl)aniline

Refernces

Synthesis and biological studies of some gold(I) complexes containing functionalised alkynes

10.1039/b911234k

The study investigates the synthesis and biological activities of gold(I) alkynyl complexes containing functionalized alkynes. The researchers synthesized three gold(I) complexes ([Au(C≡COCH2Ar)(PPh3)]) using propargyl ethers (7-chloro-(4-propargyloxy)quinoline, 1-propargyloxynaphthalene, and 2-propargyloxybenzophenone) reacting with [AuCl(PPh3)] in the presence of KOH. These complexes were characterized by spectroscopic methods and tested for their biological activity against four human tumour cell lines and Plasmodium falciparum, the malaria-causing parasite. The complexes exhibited antiproliferative effects on cancer cells with IC50 values ranging from 0.4–12 mM, but showed low activity against P. falciparum with IC50 values between 7.2 and 23 mM. The study demonstrates that mononuclear gold(I) compounds can have antiproliferative activity in human cancer cells in vitro, suggesting potential for further research into their use as anti-cancer agents.

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