2,3-dimethyl-1,4-naphthoquinone

Base Information

• Chemical Name: 2,3-dimethyl-1,4-naphthoquinone
• CAS No.: 2197-57-1
• Molecular Formula: C12H10 O2
• Molecular Weight: 186.21
• Hs Code.: 2914690090
• European Community (EC) Number: 833-888-0
• NSC Number: 36460
• UNII: SY9IO0B44O
• DSSTox Substance ID: DTXSID50176380
• Nikkaji Number: J42.457I
• Wikidata: Q27096888
• Metabolomics Workbench ID: 150836
• ChEMBL ID: CHEMBL354201
• Mol file: 2197-57-1.mol

Synonyms:1,4-Naphthoquinone,2,3-dimethyl- (6CI,7CI,8CI); 2,3-Dimethyl-1,4-naphthoquinone;2,3-Dimethylnaphthoquinone; NSC 36460

Chemical Property of 2,3-dimethyl-1,4-naphthoquinone

Chemical Property:

• Vapor Pressure: 0.000527mmHg at 25°C
• Boiling Point: 312.5°Cat760mmHg
• Flash Point: 116.9°C
• PSA: 34.14000
• Density: 1.174g/cm³
• LogP: 2.40200
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 186.068079557
• Heavy Atom Count: 14
• Complexity: 293

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s): Moderately toxic by ingestion.
• Hazard Codes: Moderately toxic by ingestion.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)C2=CC=CC=C2C1=O)C

Technology Process of 2,3-dimethyl-1,4-naphthoquinone

There total 17 articles about 2,3-dimethyl-1,4-naphthoquinone 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: 66.0%

2,3-dimethylnaphthalene (581-40-8) → 2,3-dimethyl[1,4]naphthoquinone (2197-57-1) + 6,7-dimethyl-1,4-naphthoquinone (2202-79-1)

Guidance literature:

With chromium(VI) oxide; periodic acid; In acetonitrile; at 5 ℃; for 1h;

DOI:10.1016/S0040-4039(01)00432-4

Reference yield: 44.0%

1a,7a-dimethylnaphtho[2,3-b]oxirene-2,7(1aH,7aH)-dione (53948-58-6) → 2,3-dimethyl[1,4]naphthoquinone (2197-57-1) + 2,3-dimethyl-2-hydroxy-1,2,3,4-tetrahydronaphthalin-1,4-dione (77455-20-0) + (2S,3S)-3-Acetyl-3-hydroxy-2-methoxy-2-methyl-indan-1-one (77455-18-6,77455-19-7) + (2R,3S)-3-Acetyl-3-hydroxy-2-methoxy-2-methyl-indan-1-one (77455-18-6,77455-19-7)

Guidance literature:

With methanol; In benzene; Irradiation;

DOI:10.1246/cl.1981.201

Reference yield: 40.0%

dimethyl sulfoxide (67-68-5,8070-53-9) + [1,4]naphthoquinone (130-15-4) → menadione (58-27-5,34524-96-4) + 2,3-dimethyl[1,4]naphthoquinone (2197-57-1)

Guidance literature:

With copper(II) sulfate; at 50 ℃; for 1h;

DOI:10.1080/00397919508015851

upstream raw materials:

diazomethane

2-methyl-1,4-naphthohydroquinone

methanol

1a,7a-dimethylnaphtho[2,3-b]oxirene-2,7(1aH,7aH)-dione

Downstream raw materials:

2,3-dimethyl-1,4-diphenyl-1,4-dihydro-naphthalene-1,4-diol

di(p-tolyl) disulfide

2-methyl-3-p-tolylthiomethyl-1,4-naphthoquinone

2,3-bis-(p-tolylthiomethyl)-1,4-naphthoquinone

Refernces

• 1、 Catir, Mustafa,Kilic, Hamdullah. "Bis(trifluoroacetoxyiodo)benzene-induced activation of tert-butyl hydroperoxide for the direct oxyfunctionalization of arenes to quinones". . p. 2151 - 2154. Retrieved 2007/10/03.
• 2、 Bansal,Thapliyal,Khanna. "Dimethyl sulfoxide and anhydrous copper (II) sulfate as alkylating reagent for 1,4-quinones". . p. 1669 - 1675. Retrieved 2007/10/02.