2,3-Naphtho-15-crown-5

Base Information

• Chemical Name: 2,3-Naphtho-15-crown-5
• CAS No.: 17454-47-6
• Molecular Formula: C18H22O5
• Molecular Weight: 318.37
• Hs Code.: 2932999099
• European Community (EC) Number: 805-679-4
• DSSTox Substance ID: DTXSID30375051
• Nikkaji Number: J649.103K
• Wikidata: Q82163594
• Mol file: 17454-47-6.mol

Synonyms:2,3-Naphtho-15-crown-5;17454-47-6;2,3,5,6,8,9,11,12-Octahydronaphtho[2,3-b][1,4,7,10,13]pentaoxacyclopentadecine;2,5,8,11,14-pentaoxatricyclo[13.8.0.017,22]tricosa-1(23),15,17,19,21-pentaene;Naphtho-15-crown-5;SCHEMBL23657991;DTXSID30375051;BDTDDXDRCOLVNJ-UHFFFAOYSA-N;AKOS015907749;Naphtho[2,3-b]-1,4,7,10,13-pentaoxacyclopentadecin,2,3,5,6,8,9,11,12-octahydro-;CS-0203389;FT-0637554;J-011003;2,3-Naphtho-15-crown-5, Selectophore(TM), >=99.0%;2,5,8,11,14-Pentaoxa-tricyclo[13.8.0.0*17,22*]tricosa-1(15),16,18,20,22-pentaene;2,5,8,11,14-pentaoxatricyclo[13.8.0.0^{17,22]tricosa-1(23),15,17,19,21-pentaene

Chemical Property of 2,3-Naphtho-15-crown-5

Chemical Property:

• Vapor Pressure: 3.93E-09mmHg at 25°C
• Melting Point: 116-118 °C
• Refractive Index: 1.524
• Boiling Point: 486.2 °C at 760 mmHg
• Flash Point: 203 °C
• PSA: 46.15000
• Density: 1.116g/cm³
• LogP: 2.66080
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 318.14672380
• Heavy Atom Count: 23
• Complexity: 295

Purity/Quality:

98%min ^*data from raw suppliers

2,3-Naphtho-15-crown-5 Selectophore ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCCOC2=CC3=CC=CC=C3C=C2OCCOCCO1
• Uses: 2,3-Naphtho-15-crown-5 can be prepared to be used as a recognizable dry glue and adhesives.

Technology Process of 2,3-Naphtho-15-crown-5

There total 5 articles about 2,3-Naphtho-15-crown-5 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: 90.0%

2-(2-{3-[2-(2-hydroxyethoxy)ethoxy]naphthalen-2-yloxy}ethoxy)ethanol (89011-99-4) → 2,3-naphtho-15-crown-5 (17454-47-6)

Guidance literature:

With sodium hydroxide; p-toluenesulfonyl chloride; In 1,4-dioxane;

Reference yield: 51.0%

tetraethylene glycol di(p-toluenesulfonate) (37860-51-8) + 2,3-naphthalenediol (92-44-4) → 2,3-naphtho-15-crown-5 (17454-47-6)

Guidance literature:

2,3-naphthalenediol; With tetrabutylammomium bromide; sodium hydroxide; In benzene; at 60 ℃; for 0.5h;

tetraethylene glycol di(p-toluenesulfonate); In benzene; for 15h; Heating;

DOI:10.1039/c005284c

Reference yield:

C28H40O8 (89011-98-3) → 2,3-naphtho-15-crown-5 (17454-47-6)

Guidance literature:

Multi-step reaction with 2 steps

1: conc. HCl / CH₂Cl₂; methanol / 1 h / Ambient temperature

2: 90 percent / NaOH, p-toluenesulfonyl chloride / dioxane

With hydrogenchloride; sodium hydroxide; p-toluenesulfonyl chloride; In 1,4-dioxane; methanol; dichloromethane;

upstream raw materials:

2-(2-{3-[2-(2-hydroxyethoxy)ethoxy]naphthalen-2-yloxy}ethoxy)ethanol

C₂₈H₄₀O₈

2,3-naphthalenediol

tetraethylene glycol di(p-toluenesulfonate)

Downstream raw materials:

3,3-diphenyl-9,10,12,13,15,16,18,19-octahydro-3H-[1,4,7,10,13]pentaoxacyclopentadeca[2′,3′:4,5]benzo[f]chromene

naphthalene

β-naphthol

2,3-naphthalenediol

Refernces

• 1、 Czech, B.,Czech, A.,Bartsch, R. A.. "Application of the Okahara Cyclization to the Preparation of Crown Ethers with Aromatic Units". . p. 341 - 343. Retrieved 2007/10/02.