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

Chemical Properties

clear light yellow liquid

Uses

2,3-Dimethylanisole is used as starting reagent in the synthesis of biphenyl-indanone A, a positive allosteric modulator of the metabotropic glutamate receptor subtype 2. It can be used to produce 2-methoxy-6-methyl-benzaldehyde by heating.

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

Downstream Products

• 526-75-0 2,3-Dimethylphenol 
• 14963-97-4 3-methoxyphthalic acid 
• 81029-03-0 4-Methoxy-2,3-dimethylnitrobenzene 
• 854636-88-7 toluene-4-sulfonic acid-[2-(4-methoxy-2,3-dimethyl-benzoyl)-anilide] 
• 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 
• 89244-41-7 (2-Methoxy-6-methylbenzyl)-triphenylphosphonium bromide 
• 55415-95-7 2,3,4,5-Tetrachloro-6-(4-methoxy-2,3-dimethyl-phenylazo)-benzoic acid 
• 526-85-2 2,3,4-trimethylphenol 
• 18102-34-6 2-methoxy-3,4-dimethylphenol 

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.

Design, synthesis and evaluation of a series of 5-methoxy-2,3-naphthalimide derivatives as AcrB inhibitors for the reversal of bacterial resistance

A series of novel 5-methoxy-2,3-naphthalimide derivatives were designed, synthesized and evaluated for their biological activities. In particular, the ability of the compounds to synergize with antimicrobials, to inhibit Nile Red efflux, and to target AcrB was assayed. The results showed that the most of the tested compounds more sensitized the Escherichia coli BW25113 to the antibiotics than the parent compounds 7c and 15, which were able to inhibit Nile Red efflux. Significantly, compound A5 possessed the most potent antibacterial synergizing activity in combination with levofloxacin by 4 times and 16 times at the concentration of 8 and 16 μg/mL, respectively, whilst A5 could effectively abolish Nile Red efflux at 100 μM. Additionally, target effect of A5 was confirmed in the outer- or inner membrane permeabilization assays. Therefore, A5 is an excellent lead compound for further structural optimization.

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.