24487-91-0

Basic information

• Product Name: 2-Methyl-3-methoxybenzoyl chloride
• Synonyms: Benzoyl chloride, 3-methoxy-2-methyl- (9CI);2-Methyl-3-methoxybenzoyl chloride;2-Methyl-m-anisoyl chloride;3-Methoxy-2-methylbenzoyl chloride;2-Methyl-3-Methoxybe;IHT-FC MMBC
• CAS NO: 24487-91-0
• Molecular Formula: C₉H₉ClO₂
• Molecular Weight: 184.62
• EINECS: 1312995-182-4
• Product Categories: ACIDHALIDE
• Mol File: 24487-91-0.mol

Chemical Properties

• Boiling Point: 257 ºC
• Flash Point: 96 ºC
• Appearance: /
• Density: 1.182
• Vapor Pressure: 0.0149mmHg at 25°C
• Refractive Index: 1.527
• CAS DataBase Reference: 2-Methyl-3-methoxybenzoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-3-methoxybenzoyl chloride(24487-91-0)
• EPA Substance Registry System: 2-Methyl-3-methoxybenzoyl chloride(24487-91-0)

Safety Data

• Hazardous Substances Data: 24487-91-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Methyl-3-methoxybenzoyl chloride is used as an intermediate in the synthesis of Methoxyfenozide-d9 (M262768) and deuterium labelled Methoxyfenozide (M262765). Its unique structure allows it to participate in various chemical reactions, facilitating the creation of complex molecules with specific properties.
Used in Pesticide Industry:
2-Methyl-3-methoxybenzoyl chloride is used as a key component in the production of Methoxyfenozide, which is an insecticide and pesticide. Its role in the synthesis of these compounds contributes to their effectiveness in controlling pests and protecting crops from damage. The compound's reactivity and stability make it an essential part of the formulation process, ensuring the development of efficient and reliable pest control solutions.

InChI:InChI=1/C9H9ClO2/c1-6-7(9(10)11)4-3-5-8(6)12-2/h3-5H,1-2H3

Upstream product

• 55289-06-0 3-methoxy-2-methylbenzoic acid 
• 68-12-2 N,N-dimethyl-formamide 
• 42981-93-1 3-methoxy-2-methylbenzoic acid methyl ester 
• 3260-88-6 1-chloro-3-methoxy-2-methylbenzene 
• 118-69-4 2,6-dichlorotoluene 
• 55289-05-9 methyl 3-hydroxy-2-methylbenzoate 
• 59382-59-1 2-methyl-3-nitro-benzoic acid methyl ester 
• 18583-89-6 methyl 3-amino-2-methylbenzoate 
• 1975-50-4 2-methyl-3-nitrobenzic acid 
• 83-41-0 2,3-dimethylnitrobenzene 
• 95-47-6 o-xylene 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 131-27-1 3-amino-1,5-naphthalenedisulfonic acid 
• 603-80-5 3-hydroxy 2-methylbenzoic acid 

Downstream Products

• 104216-40-2 1-(3-methoxy-2-methyl-phenyl)-propan-1-one 
• 24487-92-1 1-(3-methoxy-2-methylphenyl)ethanone 
• 117498-59-6 (3-Methoxy-2-methyl-phenyl)-thiophen-2-yl-methanone 
• 119086-32-7 N-[2-(3,4-Dimethoxy-phenyl)-2-hydroxy-ethyl]-3-methoxy-2-methyl-benzamide 
• 149653-77-0 (S)-N-(1-azabicyclo[2.2.2]oct-3-yl)-3-methoxy-2-methylbenzamide 
• 603-80-5 3-hydroxy 2-methylbenzoic acid 
• 860732-72-5 2,6-dihydroxy-1,5-dimethyl-9,10-anthraquinone 
• 860731-27-7 2,6-Dimethoxy-1,5-dimethyl-9,10-anthrachinon 
• 551963-98-5 2-(3-methoxy-2-methyl-phenyl)-3-oxa-1-aza-spiro[4.4]non-1-en-4-one 
• 24487-90-9 2-Methyl-3-methoxy-phenylacetylen 
• 24503-52-4 1,3-Dimethyl-2-hydroxy-2-<(2-methyl-3-methoxy-phenyl)-ethinyl>-cyclohexan-carbonsaeure-1-ethylester 
• 740799-69-3 3-methoxy-2-methyl-benzoic acid hydrazide 
• 748155-54-6 RG-120042 
• 748155-55-7 2-methyl-3-methoxybenzoyl anhydride 

Relevant articles and documents

Green preparation process of 2-methyl-3-methoxybenzoyl chloride

The invention discloses a green preparation process of 2-methyl-3-methoxybenzoyl chloride. The green preparation process comprises the following steps: heating and hydrolyzing methyl 2-methyl-3-methoxybenzoate in an alkaline aqueous solution, and distilling off generated methanol while a hydrolysis reaction is carried out; adding an organic solvent into hydrolyzed reaction liquid under the condition of heat preservation for dissolving, and adding an acidic aqueous solution for neutralizing; conducting neutralizing, then preserving heat and conducting layering to obtain a water layer and an organic layer, and washing the organic layer with water; heating the washed organic layer for azeotropic water removal; and adding a catalyst into the organic layer after azeotropic dehydration, carrying out heating, dropwise adding an acylating chlorination reagent, and carrying out a heat-preserved reaction to obtain the 2-methyl-3-methoxybenzoyl chloride. In a neutralization process after hydrolysis is completed, the organic solvent is added, and the product 2-methyl-3-methoxybenzoic acid is transferred into the organic solvent and is transferred to a subsequent reaction in a solution state, so water consumption for post-treatment is reduced, and meanwhile, harm to a working environment and the health of workers in the solid dust drying and feeding process is avoided.

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.

Facile Synthesis of Alkylidene Phthalides by Rhodium-Catalyzed Domino C?H Acylation/Annulation of Benzamides with Aliphatic Carboxylic Acids

The Rh-catalyzed ortho-C(sp2)?H functionalization of 8-aminoquinoline-derived benzamides with aliphatic acyl fluorides generated in situ from the corresponding acids has been developed. This reaction initiated with 8-aminoquinoline-directed ortho-C(sp2)?H acylation, which was accompanied by subsequent intramolecular nucleophilic acyl substitution of amide group to produce alkylidene phthalides This approach exhibits high stereo-selectivity for Z-isomer products, and tolerates a variety of functional groups as well as aliphatic carboxylic acids with diverse structural scaffolds.

Electrochemical intramolecular C-H/N-H functionalization for the synthesis of isoxazolidine-fused isoquinolin-1(2: H)-ones

A general and practical protocol for the construction of isoxazolidine-fused isoquinolin-1(2H)-ones has been described by electrochemical-oxidation-induced intramolecular annulation via amidyl radicals. In an undivided cell, isoquinolinones could be easily generated from various available amides bearing CONHOR groups under metal-free, additive-free and external oxidant-free conditions. Moreover, this transformation proceeded smoothly by using cheap 95% ethanol as the green solvent and could be extended to the gram scale.

Improved synthesis of sterically encumbered heteroaromatic biaryls from aromatic β-keto esters

A protocol for the synthesis of hindered 4-aryl 2-aminopyrimidines from β–keto esters is described. The process employs trifluoroethanol as an essential additive to promote the guanidine condensation reaction, enabling the synthesis of 25 aryl- and heteroaryl substituted aminopyrimidines in good yields and high purities with no column chromatography. The conditions described herein are readily scalable and have been employed in the large-scale synthesis of the clinical A2a/A2bR antagonist AB928.

Cu-Catalyzed C-H Alkenylation of Benzoic Acid and Acrylic Acid Derivatives with Vinyl Boronates

An efficient Cu-catalyzed C-H alkenylation with acyclic and cyclic vinyl boronates was realized for the first time under mild conditions. The scope of the vinyl borons and the compatibility with functional groups including heterocycles are superior than Pd-catalyzed C-H coupling with vinyl borons, providing a reliable access to multisubstituted alkenes and dienes. Subsequent hydrogenation of the product from the internal vinyl borons will lead to installation of secondary alkyls.

Cu(II)-Catalyzed 6π-Photocyclization of Non-6πSubstrates

This research successfully achieved a Cu(II)-catalyzed 6π-photocyclization of non-6πsubstrates. The photoenolization converts ortho-alkylphenyl alkynl ketones into a triene-type intermediate which undergoes the subsequent 6π-photocyclization to give napht

2-methyl-3-methoxybenzoyl chloride synthesizing process

The invention discloses a 2-methyl-3-methoxybenzoyl chloride synthesizing process. According to the present invention, low-cost o-xylene is used as a starting raw material, the product is synthesizedby using a conventional synthesis method comprising nitrification, esterification, reduction, diazotization, methylation, acyl chlorination and other steps, and the total yield is controlled at more than 65%; the esterification of the intermediate product improves the separation degree of the intermediate; the reaction solvent is added in the diazotization step, such that the process parameters are relatively easy to control, and the purity of the intermediate in the diazotization step is more than 96% so as to provide the guarantee for the quality of the subsequent product; and with the synthesis process, the product quality is stable and reliable, and the cost is low.

Rhodium-Catalyzed Alkylation of C?H Bonds in Aromatic Amides with Non-activated 1-Alkenes: The Possible Generation of Carbene Intermediates from Alkenes

The alkylation of C?H bonds (hydroarylation) in aromatic amides with non-activated 1-alkenes using a rhodium catalyst and assisted by an 8-aminoquinoline directing group is reported. The addition of a carboxylic acid is crucial for the success of this reaction. The results of deuterium-labeling experiments indicate that one of deuterium atoms in the alkene is missing, suggesting that the reaction does not proceed through the commonly accepted mechanism for C?H alkylation reactions. Instead the reaction is proposed to proceed through a carbene mechanism. The carbene mechanism is also supported by preliminary DFT calculations.

Synthesis and bioactivities of diamide derivatives containing a phenazine-1-carboxamide scaffold

Taking natural product phenazine-1-carboxamide (PCN) as a lead compound, a series of novel phenazine-1-carboxylic acid diamide derivatives were designed and synthesised. Their structures were confirmed by 1H-NMR and HRMS. The bioassays showed that some of the target compounds exhibited promising in vitro fungicidal activities, and exhibited excellent and selective herbicidal activities. Particularly, compounds c, h, o and s displayed root length inhibition activities against barnyard grass with the rate of more than 80%. Compound c exhibited the best activity among all the target compounds against barnyard grass stalk length with the IC50 value of 0.158?mmol/L, and compound o exhibited the best and wide spectrum inhibition against barnyard grass root length and rape in both root length and stalk length herbicidal activities with its IC50 values of 0.067, 0.048 and 0.059?mmol/L respectively. The analysis of preliminary Structure-Activity Relationships provides the theoretical basis for further design of phenazine-1-carboxylic acid.