2-Acetyl-6-methoxynaphthalene

Base Information

• Chemical Name: 2-Acetyl-6-methoxynaphthalene
• CAS No.: 3900-45-6
• Molecular Formula: C13H12O2
• Molecular Weight: 200.237
• Hs Code.: 29145000
• European Community (EC) Number: 223-453-8
• NSC Number: 105564
• UNII: 61VBH3537C
• DSSTox Substance ID: DTXSID60192278
• Nikkaji Number: J30.385B
• Wikidata: Q27263377
• Mol file: 3900-45-6.mol

Synonyms:2-Acetyl-6-methoxynaphthalene;3900-45-6;1-(6-Methoxynaphthalen-2-yl)ethanone;1-(6-Methoxy-2-naphthyl)ethanone;6'-Methoxy-2'-acetonaphthone;6-Methoxy-2-acetylnaphthalene;Ethanone, 1-(6-methoxy-2-naphthalenyl)-;NSC 105564;MFCD00021643;1-(6-Methoxy-2-naphthyl)ethan-1-one;6'-Methoxy-2'-acetonaphthone (Naproxen Impurity L);Acetylnerolin;1-(6-methoxynaphthalen-2-yl)ethan-1-one;UNII-61VBH3537C;61VBH3537C;EINECS 223-453-8;1-(6-Methoxy-2-naphthalenyl)ethanone;NSC-105564;1-(6-methoxy-2-naphthyl)-1-ethanone;EC 223-453-8;1-(6-Methoxynaphthalen-2-yl)ethanone (Acetylnerolin);2'-Acetonaphthone, 6'-methoxy- (6CI,7CI,8CI);1-(2-Methoxynaphthalen-6-yl)ethanone;Naproxen impurity L;NSC105564;Naproxen EP Impurity L;6-Methoxy-2-Acetonaphthone;NCIOpen2_002197;2-acetyl-6-methoxynapthalene;6-methoxy-2-acetonaphthalene;SCHEMBL246511;DTXSID60192278;6-Methyoxy-2-acetonaphthone,(S);BCP27069;STR07278;AC1237;STL183262;1-(6-methoxy-2naphthyl)-1-ethanone;1-(6-Methoxy-2-naphthyl)ethanone #;6'-Methoxy-2'-acetonaphthone, 98%;AKOS000119504;CS-O-10938;CS-W019877;FS-3053;1-(6-methoxy-naphthalen-2-yl)-ethanone;AC-23635;NAPROXEN IMPURITY L [EP IMPURITY];SY014453;6-METHOXY-2-NAPHTHYL METHYL KETONE;AM20060253;FT-0621181;1-(2-METHOXYNAPHTHALEN-6-YL)ETHANONE;EN300-20337;NAPROXEN SODIUM IMPURITY L [EP IMPURITY];AE-641/00011040;W-106460;Q27263377;Z104477778;2-Acetyl-6-methoxynaphthalene 100 microg/mL in Acetonitrile;Naproxen impurity L, European Pharmacopoeia (EP) Reference Standard;6-Methoxy-2-naphthyl Methyl Ketone;6-Acetyl-2-methoxynaphthalene

Chemical Property of 2-Acetyl-6-methoxynaphthalene

Chemical Property:

• Appearance/Colour: Light yellow-beige powder.
• Vapor Pressure: 0.009Pa at 25℃
• Melting Point: 107-109 °C(lit.)
• Refractive Index: 1.5906 (estimate)
• Boiling Point: 343.4 °C at 760 mmHg
• Flash Point: 158.9 °C
• PSA: 26.30000
• Density: 1.118 g/cm³
• LogP: 3.05100
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 760mg/L at 27℃
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 200.083729621
• Heavy Atom Count: 15
• Complexity: 237

Purity/Quality:

99%, ^*data from raw suppliers

6''-Methoxy-2''-acetonaphthone(NaproxenImpurityL) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-36/37/38
• Safety Statements: 37/39-26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC2=C(C=C1)C=C(C=C2)OC
• Uses: Naproxen impurity L. Naproxen impurity L. Naproxen USP Related Compound L

Technology Process of 2-Acetyl-6-methoxynaphthalene

There total 85 articles about 2-Acetyl-6-methoxynaphthalene 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: 98.0%

2-ethynyl-6-methoxynaphthalene (129113-00-4) → 6-methoxy-2-acetylnaphthalene (3900-45-6)

Guidance literature:

With water; In neat (no solvent); at 100 ℃; for 4h; Green chemistry;

DOI:10.1016/j.apcata.2015.07.038

Reference yield: 97.0%

1-(6-methoxy-2-naphthyl)ethanol (108781-65-3,119341-64-9,125712-80-3,77301-42-9) → 6-methoxy-2-acetylnaphthalene (3900-45-6)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium tert-butylate; copper(I) triflate; 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole; In N,N-dimethyl-formamide; at 25 ℃; for 0.5h; Catalytic behavior;

DOI:10.1016/j.tet.2014.11.015

Reference yield: 91.0%

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid (22204-53-1) → 6-methoxy-2-acetylnaphthalene (3900-45-6)

Guidance literature:

With iron(III) chloride; oxygen; In N,N-dimethyl-formamide; at 110 ℃;

DOI:10.1039/d0ob01790f

upstream raw materials:

6-methoxy-2-naphthoyl chloride

methylzinc iodide

2-Methoxynaphthalene

acetyl chloride

Downstream raw materials:

3t-[2]furyl-1-(6-methoxy-[2]naphthyl)-propenone

(E)-1-(2-methoxynaphthalen-6-yl)-3-(4-methoxyphenyl)prop-2-en-1-one

methyl 6-methoxy-2-naphthylacetate

naproxen

Refernces

• 1、 Hodala, Janardhan L.,Halgeri, Anand B.,Shanbhag, Ganapati V.. "Enhancement in activity and shape selectivity of zeolite BEA by phosphate treatment for 2-methoxynaphthalene acylation". . p. 90579 - 90586. Retrieved 2016.
• 2、 Botella,Corma,Sastre. "Al-ITQ-7, a Shape-Selective Zeolite for Acylation of 2-Methoxynaphthalene". . p. 81 - 90. Retrieved 2001.
• 3、 Heinichen,Hoelderich. "Acylation of 2-methoxynaphthalene in the presence of modified zeolite HBEA". . p. 408 - 414. Retrieved 1999.
• 4、 Gildersleeve, Jeff,Varvak, Alex,Atwell, Shane,Evans, Doug,Schultz, Peter G.. "Development of a High-Throughput Screen for Protein Catalysts: Application to the Directed Evolution of Antibody Aldolases". . p. 5971 - 5973. Retrieved 2003.
• 5、 Kumaraguru, Thenkrishnan,Devi, Avala Vedamayee,Siddaiah, Vidavalur,Rajdeo, Kishor,Fadnavis, Nitin W.. "Regioselective acylation of 2-methoxy naphthalene catalyzed by supported 12-Phosphotungstic acid". . p. 55 - 61. Retrieved 2014.
• 6、 Harvey, Gillian,Maeder, Georg. "THE SHAPE-SELECTIVE ACYLATION OF 2-METHOXYNAPHTHALENE, CATALYZED BY ZEOLITES Y, BETA AND ZSM-12". . p. 862 - 868. Retrieved 1992.
• 7、 Chen, Yukun,Li, Weirong,Luo, Yixin,Qi, Xiaotian,Xi, Xiaoxiang,Xu, Minghao,Yuan, Weiming,Zhao, Hongping,Zheng, Songlin. "From Esters to Ketones via a Photoredox-Assisted Reductive Acyl Cross-Coupling Strategy". supporting information. . Retrieved 2021/12/06.
• 8、 Gangadurai, Chinnakuzhanthai,Illa, Giri Teja,Reddy, D. Srinivasa. "FeCl3-catalyzed oxidative decarboxylation of aryl/heteroaryl acetic acids: Preparation of selected API impurities". . p. 8459 - 8466. Retrieved 2020/11/05.