Naphtho[1,8-de:4,5-d'e']bis[1,3]dioxin

Base Information

• Chemical Name: Naphtho[1,8-de:4,5-d'e']bis[1,3]dioxin
• CAS No.: 88051-28-9
• Molecular Formula: C12H8O4
• Molecular Weight: 216.193
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID90444732
• Wikidata: Q72493595
• Mol file: 88051-28-9.mol

Synonyms:88051-28-9;Naphtho[1,8-de:4,5-d'e']bis[1,3]dioxin;Naphtho[1,8-de:4,5-d'e']bis([1,3]dioxine);DTXSID90444732;AKOS015856095;FT-0701643;Naphtho[1,8-de,4,5-d'e']bis[1,3]dioxin;5,7,12,14-tetraoxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene

Chemical Property of Naphtho[1,8-de:4,5-d'e']bis[1,3]dioxin

Chemical Property:

• Melting Point: 149-151℃
• PSA: 36.92000
• Density: 1.481
• LogP: 2.29720
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 216.04225873
• Heavy Atom Count: 16
• Complexity: 230

Purity/Quality:

98%min ^*data from raw suppliers

Naphtho[1,8-de:4,5-d'e']bis[1,3]dioxin 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1OC2=C3C(=CC=C4C3=C(C=C2)OCO4)O1

Technology Process of Naphtho[1,8-de:4,5-d'e']bis[1,3]dioxin

There total 2 articles about Naphtho[1,8-de:4,5-d'e']bis[1,3]dioxin 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: 86.0%

chlorobromomethane (74-97-5) + 5,8-dihydroxy-2,3-dihydro-[1,4]naphthoquinone (4988-51-6) → naphtho[1,8-de:4,5-d'e']bis([1,3]dioxine) (88051-28-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 65 - 95 ℃;

DOI:10.1002/ejoc.201501479

Reference yield:

1,4,5,8-Tetrahydroxynaphthalene (5690-27-7) + 1,1-dibromomethane (74-95-3) → naphtho[1,8-de:4,5-d'e']bis([1,3]dioxine) (88051-28-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 100 - 110 ℃; for 22h;

DOI:10.1080/00397910008087120

Reference yield: 99.0%

naphtho[1,8-de:4,5-d'e']bis([1,3]dioxine) (88051-28-9) → 2-bromo-1,8:4,5-bis(methylenedioxy)naphthalene (88051-30-3)

Guidance literature:

With N-Bromosuccinimide; In chloroform; Inert atmosphere;

DOI:10.1002/ejoc.201501479

upstream raw materials:

chlorobromomethane

5,8-dihydroxy-2,3-dihydro-[1,4]naphthoquinone

1,4,5,8-Tetrahydroxynaphthalene

1,1-dibromomethane

Downstream raw materials:

2-bromo-1,8:4,5-bis(methylenedioxy)naphthalene

shikonin

(S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione