2944-49-2

Basic information

• Product Name: 2,3-Dimethylanisole
• Synonyms: 1-Methoxy-2,3-dimethylbenzene;Benzene, 1-methoxy-2,3-dimethyl-;3-METHOXY-O-XYLENE;2,3-DIMETHYLANISOLE;2,3-DIMETHYLANISOLE 97%;1,2-Dimethyl-6-methoxybenzene;2,3-Dimethylphenol methyl ether;1,2-Dimethyl-3-methoxybenzene
• CAS NO: 2944-49-2
• Molecular Formula: C₉H₁₂O
• Molecular Weight: 136.19
• EINECS: 220-948-0
• Product Categories: Aromatic Ethers;Anisoles, Alkyloxy Compounds & Phenylacetates;Ethers;Organic Building Blocks;Oxygen Compounds;Building Blocks;C9;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 2944-49-2.mol
• Article Data: 15

Chemical Properties

• Melting Point: 29 °C(lit.)
• Boiling Point: 195 °C(lit.)
• Flash Point: 155 °F
• Appearance: clear light yellow liquid
• Density: 0.984 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.582mmHg at 25°C
• Refractive Index: n20/D 1.52(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: immiscible
• BRN: 1859736
• CAS DataBase Reference: 2,3-Dimethylanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dimethylanisole(2944-49-2)
• EPA Substance Registry System: 2,3-Dimethylanisole(2944-49-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• Hazardous Substances Data: 2944-49-2(Hazardous Substances Data)

Usage

Description

2,3-Dimethylanisole is a clear light yellow liquid that serves as a versatile starting reagent in the synthesis of various organic compounds, particularly in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
2,3-Dimethylanisole is used as a starting reagent for the synthesis of biphenyl-indanone A, which is a positive allosteric modulator of the metabotropic glutamate receptor subtype 2. This application is significant due to its potential role in the development of novel treatments for neurological and psychiatric disorders.
Additionally, 2,3-Dimethylanisole can be used to produce 2-methoxy-6-methyl-benzaldehyde by heating, which may have further applications in the synthesis of various organic compounds and specialty chemicals.

InChI:InChI=1/C9H12O/c1-7-5-4-6-9(10-3)8(7)2/h4-6H,1-3H3

Upstream product

• 526-75-0 2,3-Dimethylphenol 
• 77-78-1 dimethyl sulfate 
• 17938-69-1 4-iodo-2,3-dimethyl-phenol 
• 74-88-4 methyl iodide 
• 616-38-6 carbonic acid dimethyl ester 
• 562-54-9 potassium methyl sulfate 

Downstream Products

• 854636-88-7 toluene-4-sulfonic acid-[2-(4-methoxy-2,3-dimethyl-benzoyl)-anilide] 
• 38998-17-3 2,3-dimethyl-4-methoxybenzaldehyde 
• 25347-66-4 4,4'-Dimethoxy-2,2',3,3'-tetramethyl-stilben 
• 61808-02-4 2,3-dimethyl-phenetole 
• 124267-93-2 3-Methyl-2-propylphenetole 
• 124267-92-1 2-Methyl-3-propylphenetole 
• 124268-41-3 2-Ethyl-3-propylphenetole 
• 124267-91-0 3-Methyl-2-ethylphenetole 
• 124267-94-3 2,3-Dipropylphenetole 
• 118104-43-1 7,8-dimethyl-6-methoxy-1,2,3,4,4a,9a-hexahydrofluoren-9-one 
• 70264-73-2 1-(bromomethyl)-3-methoxy-2-methylbenzene 
• 50638-48-7 1-bromo-4-methoxy-2,3-dimethylbenzene 
• 89244-40-6 2-(Bromomethyl)-3-methylanisole 
• 69813-89-4 α,α,α',α'-tetrabromo-3-methoxy-o-xylene 

Relevant articles and documents

Impact of N-Alkylamino Substituents on Serotonin Receptor (5-HTR) Affinity and Phosphodiesterase 10A (PDE10A) Inhibition of Isoindole-1,3-dione Derivatives

In this study, a series of compounds derived from 4-methoxy-1H-isoindole-1,3(2H)-dione, potential ligands of phosphodiesterase 10A and serotonin receptors, were investigated as potential antipsychotics. A library of 4-methoxy-1H-isoindole-1,3(2H)-dione derivatives with various amine moieties was synthesized and examined for their phosphodiesterase 10A (PDE10A)-inhibiting properties and their 5-HT1A and 5-HT7 receptor affinities. Based on in vitro studies, the most potent compound, 18 (2-[4-(1H-benzimidazol-2-yl)butyl]-4-methoxy-1H-isoindole-1,3(2H)-dione), was selected and its safety in vitro was evaluated. In order to explain the binding mode of compound 18 in the active site of the PDE10A enzyme and describe the molecular interactions responsible for its inhibition, computer-aided docking studies were performed. The potential antipsychotic properties of compound 18 in a behavioral model of schizophrenia were also investigated.

A Spiroalkylation Method for the Stereoselective Construction of α-Quaternary Carbons and Its Application to the Total Synthesis of (R)-Puraquinonic Acid

Cyclic α-quaternary carbon stereocenters were prepared from biselectrophillic substrates and an easily prepared chiral bicyclic sulfonyl lactam. This was achieved in two steps by spiroalkylation, employing biphasic reaction conditions with a phase-transfer catalyst, followed by reduction and alkylation with a series of alkyl halide electrophiles. The products of this method were isolated in good yields with with high levels of diastereoselectivity. This methodology was employed in the enantioselective total synthesis of (R)-puraquinonic acid (1) for a late-stage installation of the α-quaternary carbon stereocenter. This enabled the shortest synthesis of 1 to date, an eight-pot sequence providing an overall yield of 14%.

From catechol-tocopherol to catechol-hydroquinone polyphenolic antioxidant hybrids

Multidefence antioxidants represent a valuable solution for the protection against oxidative stress. From the planned synthesis of a catechol-tocopherol hybrid, we isolated a catechol-hydroquinone hybrid through a BBr3-mediated benzochromene-fluoren-1-ol transposition. The compound prepared showed a remarkable chain-breaking antioxidant in the catechol portion, while the very sensitive hydroquinone moiety revealed to be an efficient generator of hydroperoxyl radicals.