5-methoxy-2-methylnaphthoquinone

Base Information

• Chemical Name: 5-methoxy-2-methylnaphthoquinone
• CAS No.: 22266-99-5
• Molecular Formula: C12H10 O3
• Molecular Weight: 202.21
• Mol file: 22266-99-5.mol

Synonyms:1,4-Naphthoquinone,5-methoxy-2-methyl- (8CI); 2-Methyl-5-methoxy-1,4-naphthoquinone;5-Methoxy-2-methyl-1,4-naphthoquinone

Chemical Property of 5-methoxy-2-methylnaphthoquinone

Chemical Property:

• Vapor Pressure: 6.68E-06mmHg at 25°C
• Boiling Point: 377.6°Cat760mmHg
• Flash Point: 170.7°C
• PSA: 43.37000
• Density: 1.228g/cm³
• LogP: 2.02050

Purity/Quality:

5-Methoxy-2-methyl-1,4-naphthoquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 5-Methoxy-2-methyl-1,4-naphthoquinone is an intermediate in the synthesis of Plumbagin-d3 (P627002). Plumbagin-d3 is labelled Plumbagin (P627000) which induces apoptosis in cancer cells. It also inhibits NADPH oxidase 4 in a time- and dose-dependent manner.

Technology Process of 5-methoxy-2-methylnaphthoquinone

There total 22 articles about 5-methoxy-2-methylnaphthoquinone 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: 99.0%

5-hydroxy-2-methyl-1,4-naphthoquinone (481-42-5) + methyl iodide (74-88-4) → 2-methyl-5-methoxy-1,4-naphthoquinone (22266-99-5)

Guidance literature:

With silver(l) oxide; In dichloromethane; at 20 ℃; for 48h; Inert atmosphere;

DOI:10.1039/c4md00111g

Reference yield: 72.0%

1-Hydroxy-5-methoxy-2-methylnaphthalin (79795-25-8) → 2-methyl-5-methoxy-1,4-naphthoquinone (22266-99-5)

Guidance literature:

With salcomine; oxygen; In N,N-dimethyl-formamide; for 3h; Ambient temperature;

DOI:10.1055/s-1986-31669

Reference yield: 70.0%

7-methoxy-3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile (94930-41-3) + methacrylic acid methyl ester (80-62-6,114512-63-9,143476-91-9,25188-98-1,9011-14-7) → 2-methyl-5-methoxy-1,4-naphthoquinone (22266-99-5)

Guidance literature:

7-methoxy-3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile; With lithium tert-butoxide; In tetrahydrofuran; at -78 - -60 ℃; for 0.416667h; Inert atmosphere;

methacrylic acid methyl ester; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.5b02920

upstream raw materials:

4-hydroxy-5-methoxy-2-methyl-naphthalene

1-Hydroxy-5-methoxy-2-methylnaphthalin

5-methoxynaphthoquinone

dimethyl sulfoxide

Downstream raw materials:

5-hydroxy-2-methyl-1,4-naphthoquinone

5-methoxy-2-methyl-3-(4-(trifluoromethyl)benzylamino)naphthalene-1,4-dione

5-methoxy-3-(4-methoxybenzylamino)-2-methylnaphthalene-1,4-dione

3-(allylamino)-5-methoxy-2-methylnaphthalene-1,4-dione

Refernces

• 1、 Likhitwitayawuid, Kittisak,Kaewamatawong, Rawiwun,Ruangrungsi, Nijsiri,Krungkrai, Jerapan. "Antimalarial naphthoquinones from Nepenthes thorelii". . p. 237 - 241. Retrieved 1998.
• 2、 Kamikawa, Tadao,Kubo, Isao. "Synthesis of 2-Alkyl-1,4-naphthoquinones via an ortho-Directive Metalation". . p. 431 - 433. Retrieved 1986.
• 3、 Bao, Na,Ou, Jinfeng,Shi, Wei,Li, Na,Chen, Li,Sun, Jianbo. "Highly Efficient Synthesis and Structure–Activity Relationships of a Small Library of Substituted 1,4-Naphthoquinones". supporting information. p. 2254 - 2258. Retrieved 2018/06/04.