55289-06-0

Basic information

• Product Name: 3-Methoxy-2-methylbenzoic acid
• Synonyms: 3-METHOXY-O-TOLUIC ACID;3-METHOXY-2-METHYLBENZOIC ACID;2-Methyl-3-Methoxy Benzoic Acid;3-Methoxy-o-toluic acid~2-Methyl-m-anisic acid;2-Methyl-m-anisicacid;Methoxy-2-Methylbenzoic
• CAS NO: 55289-06-0
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: 1533716-785-6
• Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Acids & Esters;Anisoles, Alkyloxy Compounds & Phenylacetates;intermediate
• Mol File: 55289-06-0.mol
• Article Data: 23

Chemical Properties

• Melting Point: 147.0 to 151.0 °C
• Boiling Point: 297 °C at 760 mmHg
• Flash Point: 119.9 °C
• Appearance: /
• Density: 1.168 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.83±0.10(Predicted)
• Water Solubility: Soluble in methanol. Insoluble in water.
• BRN: 510395
• CAS DataBase Reference: 3-Methoxy-2-methylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methoxy-2-methylbenzoic acid(55289-06-0)
• EPA Substance Registry System: 3-Methoxy-2-methylbenzoic acid(55289-06-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 55289-06-0(Hazardous Substances Data)

Usage

Description

3-Methoxy-2-methylbenzoic acid, also known as methyl gallate, is an organic compound belonging to the class of benzoic acids. It is characterized by the presence of a methoxy group at the 3rd position and a methyl group at the 2nd position on the benzene ring. 3-Methoxy-2-methylbenzoic acid exhibits various chemical properties and reactivity, making it a versatile building block in organic synthesis and a potential candidate for pharmaceutical and chemical applications.

Uses

Used in Pharmaceutical Industry:
3-Methoxy-2-methylbenzoic acid is used as a Corey-Bakshi-Shibata oxazaborolidine catalyst for asymmetric reduction and asymmetric synthesis. It plays a crucial role in the development of pharmaceutical compounds with specific stereochemistry, which is essential for their biological activity and efficacy.
Used in Chemical Synthesis:
3-Methoxy-2-methylbenzoic acid is used in the asymmetric reduction of prochiral ketones, a key step in the synthesis of various chiral compounds. This application is vital for the production of enantiomerically pure compounds, which are often required in the pharmaceutical, agrochemical, and fragrance industries.
Used in Enantioselective Synthesis:
3-Methoxy-2-methylbenzoic acid is employed in the enantioselective synthesis of α-hydroxy acids, α-amino acids, C2 symmetrical ferrocenyl diols, and propargyl alcohols. These chiral building blocks are essential for the development of new drugs, agrochemicals, and other specialty chemicals with improved selectivity and performance.
Used in Desymmetrizing Reduction:
3-Methoxy-2-methylbenzoic acid is also used in desymmetrizing reduction, leading to the production of (S)-4-hydroxycyclohexenone. This process is important for the synthesis of complex molecules with specific stereochemistry, which are often found in natural products and have potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 586-38-9 3-Methoxybenzoic acid 
• 74-88-4 methyl iodide 
• 3260-88-6 1-chloro-3-methoxy-2-methylbenzene 
• 124-38-9 carbon dioxide 
• 603-80-5 3-hydroxy 2-methylbenzoic acid 
• 118-69-4 2,6-dichlorotoluene 
• 74-96-4 ethyl bromide 
• 10533-44-5 trisodium 1,3,5-naphthalenetrisulfonate 
• 77-78-1 dimethyl sulfate 
• 75-26-3 isopropyl bromide 
• 7499-08-3 3-chloro-2-methylbenzoic acid 
• 87-60-5 3-chloro-2-methylbenzenamine 
• 3260-87-5 3-chloro-o-cresol 
• 83-42-1 6-chloro-2-nitrotoluene 

Downstream Products

• 24487-91-0 3-methoxy-2-methylbenzoyl chloride 
• 857652-06-3 2-bromomethyl-3-methoxybenzoic acid 
• 95330-29-3 3-methoxy-2,N-dimethylbanzamide 
• 897948-59-3 C₁₂H₁₅NO₂ 
• 163336-50-3 N-(3-methoxy-2-methylbenzoyl)-N'-tert-butylhydrazine 
• 42981-93-1 3-methoxy-2-methylbenzoic acid methyl ester 
• 366453-22-7 4-methoxyisoindolin-1-one 
• 366453-21-6 4-hydroxyisoindolin-1-one 
• 71887-28-0 methyl 2-(bromomethyl)-3-methoxybenzoate 
• 211503-45-6 4-(3-methoxy-2-methylphenyl)butanoic acid 
• 15159-14-5 6-methoxy-5-methyl-α-tetralone 

Relevant articles and documents

Preparation method of 6-chloro-2-methoxytoluene and synthesis process of methoxyfenozide

The invention relates to the field of insecticides, in particular to a preparation method of 6-chloro-2-methoxytoluene and a synthesis process of methoxyfenozide. The preparation method of the 6-chloro-2-methoxytoluene comprises the following steps: in a solvent, mixing 2, 6-dichlorotoluene with sodium methoxide, and carrying out a substitution reaction to prepare a first reaction solution containing 3-chloro-2-sodium methylphenolate and the 6-chloro-2-methoxytoluene; and dropwise adding dimethyl sulfate into the first reaction solution, carrying out etherification reaction, removing 3-chloro-2-sodium methylphenolate to obtain a second reaction solution, and carrying out post-treatment to obtain the 6-chloro-2-methoxytoluene. The synthesis process of the methoxyfenozide comprises the following steps: preparing 3-methoxy-2-methyl benzoic acid by taking 6-chloro-2-methoxytoluene as an intermediate; using 3-methoxy-2-methyl benzoic acid and 3, 5-dimethyl benzoic acid as intermediates, and preparing to obtain the methoxyfenozide. According to the synthesis process disclosed by the invention, the yield and the purity of methoxyfenozide can be remarkably improved.

2-methyl-3-methoxybenzoic acid and preparation method thereof

The invention belongs to the field of compound synthesis, and discloses 2-methyl-3-methoxybenzoic acid and a preparation method thereof, wherein the 2-methyl-3-methoxybenzoic acid is prepared from thefollowing raw materials: 2-methyl-3-chloroanisole, methylbenzene, tetrahydrofuran, magnesium chips, an initiator and a carboxylating agent. According to the invention, the preparation method solves the problems of large pollution hazard, high cost and low yield in the existing 2-methyl-3-methoxybenzoic acid preparation method; and the yield of the intermediate 2-methyl-3-chloroanisole of 2-methyl-3-methoxybenzoic acid obtained in the preparation method can reach 90-91%, the yield of 2-methyl-3-methoxybenzoic acid prepared from 2-methyl-3-chloroanisole is about 88%, the reaction is easy to control, the pollution is small, and the cost is low.

Preparation method of 2-methyl-3-methoxybenzoic acid

The invention relates to a preparation method of 2-methyl-3-methoxybenzoic acid. The preparation method comprises the following specific steps: A, adding a proper amount of a sodium methoxide solution, 2,6-dichlorotoluene, dimethylformamide and cuprous salt into a reaction kettle; stirring and raising the temperature; controlling the temperature to 80 DEG C to 150 DEG C and reacting to obtain 2-methyl-3-chloroanisole; B, adding a proper amount of tetrahydrofuran and magnesium into the other reaction kettle; controlling the temperature to be 30 DEG C to 60 DEG C; adding a mixed solution of bromoethane and the 2-methyl-3-chloroanisole; after reacting for 20min to 40min, controlling the temperature to be 40 DEG C to 60 DEG C and dropwise adding the 2-methyl-3-chloroanisole; after dropwise adding, keeping heat and reacting for 1.5h to 2.5h; then cooling to -15 DEG C to -5 DEG C; adding dry ice by batches; controlling the temperature to be 0 DEG C to 20 DEG C, keeping the heat and reactingfor 2h to 4h; then recycling the tetrahydrofuran; adjusting the pH (Potential of Hydrogen) value to separate out white powder, namely the 2-methyl-3-methoxybenzoic acid. The preparation method of the2-methyl-3-methoxybenzoic acid, provided by the invention, is simple in route and high in yield.