81029-03-0

Basic information

• Product Name: 2,3-DIMETHYL-4-NITROANISOLE
• Synonyms: 3-METHOXY-6-NITRO-O-XYLENE;2,3-DIMETHYL-4-NITROANISOLE;2,3-DIMETHYL-P-NITROANISOLE;1-Methoxy-2,3-dimethyl-4-nitrobenzene;4-Methoxy-2,3-dimethylnitrobenzene;2,3-Dimethyl-p-nitroanisole,98%;3-Methoxy-6-nitro-o-xylene 1-Methoxy-2,3-dimethyl-4-nitrobenzene;2,3-DiMethy-4-nitrolanisole
• CAS NO: 81029-03-0
• Molecular Formula: C₉H₁₁NO₃
• Molecular Weight: 181.19
• EINECS: 279-674-5
• Product Categories: Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 81029-03-0.mol

Chemical Properties

• Melting Point: 70-73 °C(lit.)
• Boiling Point: 314.29°C (rough estimate)
• Flash Point: 141.2 °C
• Appearance: light beige-green powder and chunks
• Density: 1.2375 (rough estimate)
• Vapor Pressure: 0.0017mmHg at 25°C
• Refractive Index: 1.5270 (estimate)
• CAS DataBase Reference: 2,3-DIMETHYL-4-NITROANISOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIMETHYL-4-NITROANISOLE(81029-03-0)
• EPA Substance Registry System: 2,3-DIMETHYL-4-NITROANISOLE(81029-03-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 81029-03-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3-DIMETHYL-4-NITROANISOLE is used as a starting material for the synthesis of conformationally restricted derivatives of lavendustin A. These derivatives have potential applications in the development of new drugs and therapeutic agents, particularly in the treatment of various diseases and disorders.
Used in Chemical Synthesis:
2,3-DIMETHYL-4-NITROANISOLE is also used in the synthesis of 1,4-piperazin-2,5-diones. These compounds are important building blocks in the production of various pharmaceuticals, agrochemicals, and other specialty chemicals. The versatility of 2,3-DIMETHYL-4-NITROANISOLE as a starting material allows for the creation of a wide range of products with diverse applications across different industries.

InChI:InChI=1/C9H11NO3/c1-6-7(2)9(13-3)5-4-8(6)10(11)12/h4-5H,1-3H3

Upstream product

• 2944-49-2 2,3-dimethylanisole 
• 509-14-8 tetranitromethane 

Downstream Products

• 77375-19-0 2,3-dimethyl-4-methoxyaniline 
• 455888-92-3 2,3-bis-bromomethyl-1-methoxy-4-nitro-benzene 
• 474454-40-5 6-methoxy-2-methyl-3-nitrobenzyl acetate 
• 474454-38-1 6-methoxy-2-methyl-3-nitrobenzylidene diacetate 
• 74783-55-4 4-acetamino-1-methoxy-2,3-dimethylbenzene 
• 19499-93-5 2,3-dimethyl-4-nitrophenol 

Relevant articles and documents

A switchable oxidation process leading to two various versatile pharmaceutical intermediates

An efficient high-yielding and environmentally benign switchable oxidation process that can selectively produce two different versatile synthetic intermediates is disclosed. One of the two intermediates, 2,3-dimethoxy-5- methylcyclohexa-2,5-diene-1,4-dione (coenzyme Q0), is obtained by means of a telescoped two-step synthetic protocol that in the first step involves treatment of the substrate (1,2,3-trimethoxy-5-methylbenzene) with hydrogen peroxide in acetic acid with p-toluene sulphonic acid present as a Bronsted acid catalyst, succeeded by a telescoped second step that entails treatment with fuming nitric acid to achieve the target molecule in an excellent isolated yield (88%). If the substrate is treated directly with nitric acid (65%) in glacial acetic acid two different products can be obtained, namely acetic acid 3,4,5-trimethoxybenzyl ester in a superb isolated yield (93%) or, under slightly altered reaction conditions, 1,2,3-trimethoxy-5- (nitromethyl)benzene in a moderate to low yield (35%) and low selectivity. The two pathways leading to the two different products in the nitric acid oxidation protocol were investigated by means of DFT calculations as an aid to elaborate a proposal for the reaction mechanism.

Photochemical nitration by tetranitromethane. Part XXXVII. Adduct formation and the regiochemistry of attack of trinitromethanide ion on radical cations in the photochemical reactions of 2-methyl-, 2,3-dimethyl- and 2,4-Dimethylanisoles

The photolysis of the charge transfer (CT) complex of tetranitromethane and 2-methylanisole 2 in dichloromethane at 20 °C gives the epimeric 1-methoxy-6-methyl-6-nitro-3-trinitromethylcyclohexa-1,4-dienes 8 and 9 in addition to 2-methyl-4-trinitromethylanisole (3) and 2-methyl-4-nitroanisole (4). In acetonitrile the yields of compound 4 and adducts 8 and 9 are significantly higher. Similar reaction of 2,3-dimethylanisole (6) in dichloromethane gave nitro-trinitromethyl adducts 10 and 11, hydroxy-trinitromethyl adducts 12 and 13, 2,3-dimethyl-5-trinitromethylanisole (14), 4-methoxy-2,3-dimethylbenzonitrile N-oxide (15), 2,3-dimethyl-4-trinitromethylanisole (16), 2,3-dimethyl-4-nitroanisole (17), 2,3-dimethyl-4,6-dinitrophenol (18), 3-methoxy-4,5-dimethyl-benzoic acid (19) and the hydroxy dinitro compound (20). The photolysis of the CT complex of 2,4-dimethylanisole (7) with tetranitromethane in dichloromethane gave the epimeric 1-methoxy-4,6-dimethyl-6-nitro-3-trinitromethylcyclohexa-1,4-dienes 21 and 22, together with 4,6-dimethyl-3-trinitromethylanisole (23), 4,6-dimethyl-2-nitrophenol (24), 4,6-dimethyl-2-trinitromethylanisole (25), 4,6-dimethyl-3-nitroanisole (26), 4,6-dimethyl-2-nitroanisole (27) and 4,6-dimethyl-4-nitrocyclohexa-2,5-dienone (28). The modes of formation of the above products are discussed, including the effects of the reaction solvent on those processes. The X-ray crystal structure of 1-methoxy-2-methyl-c-6-nitro-r-3-trinitromethylcyclohexa-1,4-diene (9) is reported. Acta Chemica Scandinavica 1997.