4900-63-4

Basic information

• Product Name: 1-METHOXY-4-NITRONAPHTHALENE
• Synonyms: 1-METHOXY-4-NITRONAPHTHALENE;1-Methoxy-4-nitronaphthalin;1-Nitro-4-methoxynaphthalene;methyl4-nitronaphthylether;Naphthalene,1-methoxy-4-nitro-;4-Methoxy-1-nitronaphthalene;1-Methoxy-4-nitronaphthalene,99%;1-Methoxy-4-nitronaphthalene 99%
• CAS NO: 4900-63-4
• Molecular Formula: C₁₁H₉NO₃
• Molecular Weight: 203.19
• EINECS: 225-528-0
• Product Categories: Naphthalene derivatives;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 4900-63-4.mol
• Article Data: 22

Chemical Properties

• Melting Point: 83-85 °C(lit.)
• Boiling Point: 341.49°C (rough estimate)
• Flash Point: 178.3°C
• Appearance: /
• Density: 1.2621 (rough estimate)
• Vapor Pressure: 2.93E-05mmHg at 25°C
• Refractive Index: 1.4950 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-METHOXY-4-NITRONAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHOXY-4-NITRONAPHTHALENE(4900-63-4)
• EPA Substance Registry System: 1-METHOXY-4-NITRONAPHTHALENE(4900-63-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 4900-63-4(Hazardous Substances Data)

Usage

Chemical Properties

yellow to orange crystalline powder

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.

Synthesis Reference(s)

Synthesis, p. 70, 1985 DOI: 10.1055/s-1985-31110

Purification Methods

Purify it by chromatography on silica gel, then recrystallise it from MeOH or EtOH (yellow needles). [Hodgson & Habeshaw J Chem Soc 47 1942, Bunce et al. J Org Chem 52 4214 1987, Beilstein 6 H 616, 6 III 2938.]

InChI:InChI=1/C11H9NO3/c1-15-11-7-6-10(12(13)14)8-4-2-3-5-9(8)11/h2-7H,1H3

Upstream product

• 67-56-1 methanol 
• 605-61-8 1-chloro-4-nitronaphthalene 
• 91569-62-9 ethyl-(4-nitro-[1]naphthyl)-ether 
• 124-41-4 sodium methylate 
• 108-24-7 acetic anhydride 
• 2216-69-5 1-Methoxynaphthalene 
• 605-62-9 4-nitro-1-naphthol 
• 77-78-1 dimethyl sulfate 
• 509-14-8 tetranitromethane 
• 71-23-8 propan-1-ol 
• 64-17-5 ethanol 
• 91-20-3 naphthalene 
• 7697-37-2 nitric acid 
• 141870-15-7 4-methoxy-1-naphthylsulphonic acid 

Downstream Products

• 16430-99-2 1-amino-4-methoxynaphthalene 
• 871887-75-1 4-methoxy-N-phenyl-1-naphthalenamine 
• 108451-00-9 4-Methoxy-1-nitro-2-(p-tolylsulfonylmethyl)naphthalene 
• 73323-53-2 4-Benzyl-1-nitronaphthalene 
• 73323-56-5 cis-2-Benzyl-4-methoxy-1-nitro-1,2-dihydronaphthalene 
• 73323-59-8 trans-2-Benzyl-4-methoxy-1-nitro-1,2-dihydronaphthalene 
• 5961-55-7 4-methoxy-1-naphthalenecarbonitrile 
• 58-27-5 menadione 
• 69798-30-7 2-methyl-4-methoxy-1-naphthylamine 
• 95393-47-8 E-2-methyl-2,3-dihydro-1,4-naphthoquinone-1-oxime 
• 95393-42-3 E-2-methyl-4-methoxy-1-(2H)naphthalenone oxime 
• 77416-45-6 r-1-bromo-1-nitro-t-2-benzyl-1,2,3,4-tetrahydronaphthalen-4-one 
• 77416-44-5 r-1-bromo-1-nitro-t-2-phenethyl-1,2,3,4-tetrahydronaphthalen-4-one 
• 92599-05-8 1-amino-4-methoxynapthalene hydrochloride 

Relevant articles and documents

Regioselective Functionalization of 9,9-Dimethyl-9-silafluorenes by Borylation, Bromination, and Nitration

Despite the utility of 9-silafluorenes as functional materials and as building blocks, methods for efficient functionalization of their backbone are rare, probably because of the presence of easily cleavable C-Si bonds. Although controlling the regioselectivity of iridium-catalyzed direct borylation of C-H bonds is difficult, we found that bromination and nitration of 2-methoxy-9-silafluorene under mild conditions occurred predominantly at the electron-rich position. The resulting product having methoxy and bromo groups can be utilized as a building block for the synthesis of unsymmetrically substituted 9-silafluorene-containing ?-conjugated molecules.

Direct nitration method of electron-enriched aromatic hydrocarbons

The invention discloses a direct nitration method of electron-enriched aromatic hydrocarbons, and belongs to the field of organic synthesis. The direct nitration method is a novel green free radical nitration method; aromatic hydrocarbons are taken as raw materials, acetonitrile, dichloromethane, chloroform, or acetone is taken as a reaction solvent, at room temperature conditions, the raw materials and green nitration reagent tert-butyl nitrite (TBN) are subjected to free radical nitration so as to obtain nitro-aromatic compounds. According to the direct nitration method, no metal is adoptedin reaction, tert-butyl nitrite is directly adopted in nitration reaction. Electron-donating groups such as OMe are introduced, the electron density of aromatic compounds is increased, the nitration reaction possibility is increased. The using amount of tert-butyl nitrite is reduced; only a product and tert-butyl alcohol are generated, environment pollution is reduced. The direct nitration methodis promising in application prospect in the field of nitro-aromatic compound synthesis, green nitration is realized, and a novel idea is provided for large-scale industrialized nitro-aromatic compoundproduction.