1-Methoxy-4-nitronaphthalene

Base Information

• Chemical Name: 1-Methoxy-4-nitronaphthalene
• CAS No.: 4900-63-4
• Molecular Formula: C11H9NO3
• Molecular Weight: 203.197
• Hs Code.: 2909309090
• European Community (EC) Number: 225-528-0
• NSC Number: 65626
• DSSTox Substance ID: DTXSID20197663
• Nikkaji Number: J150.112G
• Wikidata: Q83070461
• Mol file: 4900-63-4.mol

Synonyms:1-Methoxy-4-nitronaphthalene;4900-63-4;Naphthalene, 1-methoxy-4-nitro-;Methyl 4-nitronaphthyl ether;4-methoxy-1-nitronaphthalene;1-Nitro-4-methoxynaphthalene;1-methoxy-4-nitro-naphthalene;EINECS 225-528-0;MFCD00003926;AI3-26493;NSC65626;NCIOpen2_003101;SCHEMBL589908;DTXSID20197663;1-Methoxy-4-nitronaphthalene, 99%;BBL101408;GEO-01717;NSC 65626;NSC-65626;STL555204;AKOS005258353;MS-20212;CS-0061976;FT-0635475;EN300-181915;W17449;A827642;W-200388;Z1401082072

Chemical Property of 1-Methoxy-4-nitronaphthalene

Chemical Property:

• Vapor Pressure: 2.93E-05mmHg at 25°C
• Melting Point: 83-85oC(lit.)
• Refractive Index: 1.4950 (estimate)
• Boiling Point: 367.2°Cat760mmHg
• Flash Point: 178.3°C
• PSA: 55.05000
• Density: 1.274g/cm³
• LogP: 3.27980
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 203.058243149
• Heavy Atom Count: 15
• Complexity: 239

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-Methoxy-4-nitronaphthalene ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=C(C2=CC=CC=C21)[N+](=O)[O-]
• Uses: 1-Methoxy-4-nitronaphthalene is used as a reagent in the synthesis of UMI-77 (U700850); a small molecule inhibitor of Mcl-1 which blocks and attenuates pancreatic cell cancer growth. Also an anticancer agent.

Technology Process of 1-Methoxy-4-nitronaphthalene

There total 36 articles about 1-Methoxy-4-nitronaphthalene 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: 85.0%

ammonium thiocyanate (1147550-11-5) + 1-Methoxynaphthalene (2216-69-5) → 1-methoxy-4-nitronaphthalene (4900-63-4) + 1-methoxy-4-thiocyanato naphthalene (66231-77-4)

Guidance literature:

With oxygen; Nitrogen dioxide; trifluoroacetic acid; In acetonitrile; at 15 ℃; for 3h;

DOI:10.1002/cctc.201600785

Reference yield: 83.0%

1-Methoxynaphthalene (2216-69-5) → 1-methoxy-4-nitronaphthalene (4900-63-4) + 2-nitro-1-methoxynaphthalene (4900-62-3)

Guidance literature:

With Iron(III) nitrate nonahydrate; In 1,2-dichloro-ethane; at 25 ℃; for 5h; regioselective reaction;

DOI:10.1021/acs.joc.9b00598

Reference yield: 80.0%

4-methoxy-1-naphthoic acid (13041-62-8) → 1-methoxy-4-nitronaphthalene (4900-63-4)

Guidance literature:

With Nitrogen dioxide; In dichloromethane; at 22 ℃; for 3h;

DOI:10.3891/acta.chem.scand.50-0885

upstream raw materials:

methanol

1-chloro-4-nitronaphthalene

ethyl-(4-nitro-[1]naphthyl)-ether

sodium methylate

Downstream raw materials:

1-amino-4-methoxynaphthalene

4-methoxy-N-phenyl-1-naphthalenamine

4-Methoxy-1-nitro-2-(p-tolylsulfonylmethyl)naphthalene

4-Benzyl-1-nitronaphthalene

Refernces

• 1、 Antoniak, Damian,Barbasiewicz, Micha?. "Corey-Chaykovsky Cyclopropanation of Nitronaphthalenes: Access to Benzonorcaradienes and Related Systems". supporting information. p. 9320 - 9325. Retrieved 2019/11/19.
• 2、 Murai, Masahito,Nishinaka, Naoki,Kimura, Mizuki,Takai, Kazuhiko. "Regioselective Functionalization of 9,9-Dimethyl-9-silafluorenes by Borylation, Bromination, and Nitration". . . Retrieved 2019/05/08.