5367-32-8

Basic information

• Product Name: 3-Methyl-4-nitroanisole
• Synonyms: 3-Methyl-4-nitrophenol methyl ether;4-Methoxy-2-methyl-1-nitrobenzene;Anisole, 3-methyl-4-nitro-;Nitrobenzene, 4-methoxy-6-methyl-;1-METHOXY-3-METHYL-4-NITROBENZENE;2-NITRO-5-METHOXYTOLUENE;3-METHOXY-6-NITROTOLUENE;3-METHYL-4-NITROANISOLE
• CAS NO: 5367-32-8
• Molecular Formula: C₈H₉NO₃
• Molecular Weight: 167.16
• EINECS: 226-357-4
• Product Categories: Aromatic Ethers;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het
• Mol File: 5367-32-8.mol
• Article Data: 14

Chemical Properties

• Melting Point: 48-50 °C(lit.)
• Boiling Point: 135 °C / 0.5mmHg
• Flash Point: >230 °F
• Appearance: yellow to brown powder
• Density: 1.2917 (rough estimate)
• Vapor Pressure: 0.00631mmHg at 25°C
• Refractive Index: 1.5570 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 2328600
• CAS DataBase Reference: 3-Methyl-4-nitroanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-4-nitroanisole(5367-32-8)
• EPA Substance Registry System: 3-Methyl-4-nitroanisole(5367-32-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 5367-32-8(Hazardous Substances Data)

Usage

Chemical Properties

yellow to brown powder

Uses

3-Methyl-4-nitroanisole was used in the preparation of enamine.

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 522, 1980 DOI: 10.1021/jo01291a031

InChI:InChI=1/C8H9NO3/c1-6-5-7(12-2)3-4-8(6)9(10)11/h3-5H,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 2581-34-2 3-methyl-4-nitrophenol 
• 108-39-4 3-methyl-phenol 
• 77-78-1 dimethyl sulfate 
• 509-14-8 tetranitromethane 
• 100-84-5 1-methoxy-3-methyl-benzene 
• 74-88-4 methyl iodide 
• 446-33-3 5-Fluoro-2-nitrotoluene 
• 124-41-4 sodium methylate 
• 74204-00-5 3-bromo-5-methylphenol 
• 58169-99-6 2,3,4,6-tetrabromo-5-methyl-phenol 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 100-17-4 para-methoxynitrobenzene 
• 676-58-4 methylmagnesium chloride 

Downstream Products

• 1882-69-5 5-methoxy-2-nitro-benzoic acid 
• 102-50-1 2-methyl-4-methoxyaniline 
• 21857-42-1 2-(5-methoxy-2-nitrophenyl)ethan-1-ol 
• 109433-96-7 α-phenyl-5-methoxy-2-nitrophenethyl alcohol 
• 32989-62-1 4-methoxy-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene 
• 383860-01-3 5,5'-dimethoxy-2,2'-dinitrobibenzyl 
• 61293-32-1 1-[(E)-2-(5-methoxy-2-nitrophenyl)vinyl]pyrrolidine 
• 61495-08-7 N-(4-methoxy-2-methylphenyl)benzamide 
• 147779-39-3 2-benzoylamino-5-methoxy-benzoic acid 
• 89302-15-8 2-(5-methoxy-2-nitrophenyl)acetonitrile 
• 708-58-7 2-(4-fluoro-2-nitrophenyl)acetonitrile 
• 20357-24-8 5-methoxy-2-nitro-benzaldehyde 
• 82204-34-0 (5-methoxy-2-nitro-phenyl)-pyruvic acid 
• 131761-77-8 ethyl 3-(5-methoxy-2-nitrophenyl)-2-oxopropanoate 

Relevant articles and documents

Discovery of Novel Polycyclic Heterocyclic Derivatives from Evodiamine for the Potential Treatment of Triple-Negative Breast Cancer

Evodiamine (Evo) is a quinazolinocarboline alkaloid found in Evodia rutaecarpa and exhibits moderate antiproliferative activity. Herein, we report using a scaffold-hopping approach to identify a series of novel polycyclic heterocyclic derivatives based on Evo as the topoisomerase I (Top1) inhibitor for the treatment of triple-negative breast cancer (TNBC), which is an aggressive subtype of breast cancer with limited treatment options. The most potent compound 7f inhibited cell growth in a human breast carcinoma cell line (MDA-MB-231) with an IC50 value of 0.36 μM. Further studies revealed that Top1 was the target of 7f, which directly induced irreversible Top1-DNA covalent complex formation or induced an oxidative DNA lesion through an indirect mechanism mediated by reactive oxygen species. More importantly, in vivo studies showed that 7f exhibited potent antitumor activity in a TNBC-patient-derived tumor xenograft model. These results suggest that compound 7f deserves further investigation as a promising candidate for the treatment of TNBC.

Alkylation of nitroarenes with Grignard reagents via oxidative nucleophilic substitution of hydrogen

Alkylation of nitroarenes with Grignard reagents via oxidative nucleophilic substitution of hydrogen (ONSH) can be efficiently executed with potasium permanganate in liquid ammonia as an oxidative system for the σH adducts. The addition of RMgX to ArNO2 of stoichiometry 1:1 is accompanied with a redox process apparently of stoichiometry 2:1. Because of that, real stoichiometry of the reaction between nitroarenes and Grignard reagents is ca. 1:1.5.

Method for preparing aromatic secondary amino compound

Disclosed are (1) a method for preparing an aromatic secondary amino compound which comprises reacting an N-cyclohexylideneamino compound in the presence of a hydrogen moving catalyst and a hydrogen acceptor by the use of a sulfur-free polar solvent and/or a cocatalyst, and (2) a method for preparing an aromatic secondary amino compound which comprises reacting cyclohexanone or a nucleus-substituted cyclohexanone, an amine and a nitro compound corresponding to the amine in a sulfur-free polar solvent in the presence of a hydrogen moving catalyst, a cocatalyst being added or not added. In a further aspect, a method is provided for the preparation of aminodiphenylamine by reacting phenylenediamine and cyclohexanone in the presence of a hydrogen transfer catalyst in a sulfur-free polar solvent while using nitroaniline as a hydrogen acceptor.