1-(1,4-Dihydroxy-2-naphthyl)ethanone

Base Information

• Chemical Name: 1-(1,4-Dihydroxy-2-naphthyl)ethanone
• CAS No.: 40420-48-2
• Molecular Formula: C12H10O3
• Molecular Weight: 202.21
• NSC Number: 111552
• DSSTox Substance ID: DTXSID60296785
• Nikkaji Number: J259.036K
• Wikidata: Q82037550
• ChEMBL ID: CHEMBL1382760
• Mol file: 40420-48-2.mol

Synonyms:40420-48-2;1-(1,4-Dihydroxy-2-naphthyl)ethanone;1-(1,4-Dihydroxynaphthalen-2-yl)ethan-1-one;1-(1,4-dihydroxynaphthalen-2-yl)ethanone;NSC111552;MLS000737721;2-Mc-1,4-NHQ;SMR000528515;2-Acetyl-1,4-naphthalenediol;cid_269862;CHEMBL1382760;SCHEMBL10902143;BDBM50642;DTXSID60296785;CKLPUCARSNJTSJ-UHFFFAOYSA-N;HMS2880M16;NSC-111552;1-(1,4-dihydroxy-2-naphthalenyl)ethanone;1-(1,4-Dihydroxy-2-naphthyl)ethanone #;Ethanone, 1-(1,4-dihydroxy-2-naphthyl)-;1-[1,4-bis(oxidanyl)naphthalen-2-yl]ethanone

Chemical Property of 1-(1,4-Dihydroxy-2-naphthyl)ethanone

Chemical Property:

• Vapor Pressure: 3.65E-08mmHg at 25°C
• Boiling Point: 434.7°C at 760 mmHg
• Flash Point: 230.8°C
• Density: 1.33g/cm³
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 202.062994177
• Heavy Atom Count: 15
• Complexity: 251

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=C(C2=CC=CC=C2C(=C1)O)O

Technology Process of 1-(1,4-Dihydroxy-2-naphthyl)ethanone

There total 12 articles about 1-(1,4-Dihydroxy-2-naphthyl)ethanone 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: 77.0%

2-Acetyl-1,4-benzoquinone (1125-55-9) + trimethyl(2-methyl-2-propenyl)stannane (55562-82-8) → 2-acetylnaphthalene-1,4-diol (40420-48-2) + 2-acetyl-3-(2-methylallyl)-1,4-benzenediol

Guidance literature:

In benzene; dissolved acylquione and stannane under Ar; concd.; column chromy. (silica gel); eluted (hexane/ether); NMR; IR; mass spectra; elem. anal.;

DOI:10.1246/bcsj.62.3877

Reference yield: 46.0%

phthalic anhydride (85-44-9) + methyl vinyl ketone (78-94-4,25038-87-3) → 2-acetylnaphthalene-1,4-diol (40420-48-2)

Guidance literature:

phthalic anhydride; methyl vinyl ketone; With chloro-trimethyl-silane; triethylamine; at 20 ℃; Electrochemical reaction;

With hydrogenchloride; at 20 ℃; for 0.5h;

DOI:10.1021/acs.joc.0c02000

Reference yield: 41.0%

2-acetyl-1,4-naphthoquinone (5813-57-0) + trimethyl(allyl)stannane (762-73-2) → 2-acetylnaphthalene-1,4-diol (40420-48-2) + 3-allyl-2-hydroxy-1,4-naphthoquinone (40815-76-7) + 2-acetyl-3-prop-2-enyl-1,4-naphthoquinone (87976-14-5) + 2-acetyl-3-allyl-2,3-epoxy-2,3-dihydro-1,4-naphthoquinone + 3a-acetyl-2-trimethylstannyl-2,3,3a,4,9,9a-hexahydro-1H-cyclopentanaphthalene-4,9-dione (127889-59-2)

Guidance literature:

In dichloromethane; byproducts: 5-acetyl-2H-benzo{h}chromene-6-ol; dissolved acylquinone and allylstannane stood for 20 h under Ar; concd.; column chromy. (silica gel); eluted (hexane/ether); 5-acetyl-2H-benzo(h)chromene-6-ol was obtained with a yield of 3%; NMR; IR; mass spectra; elem. anal.;

DOI:10.1246/bcsj.62.3877

upstream raw materials:

dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonate

methyl vinyl ketone

2-acetyl-1,4-naphthoquinone

allyltributylstanane

Downstream raw materials:

2-Acetyl-3-(2-methoxy-phenylamino)-[1,4]naphthoquinone

2-Acetyl-3-(4-nitro-phenylamino)-[1,4]naphthoquinone

5-<1,2,3,4-Tetrahydro-3-(1-hydroxyethylidene)-1,4-dioxo-2-naphthyl>furan-2-(5H)-one

3-acetyl-2-anilino-1,4-naphthoquinone

Refernces

• 1、 Watanabe,Morimoto,Nogami,Ijichi,Furukawa. "An annulation reaction to naphthalene-1,4-diols using dimethyl phthalide-3-phosphonates". . p. 968 - 970. Retrieved 2007/10/02.