5446-96-8

Basic information

• Product Name: 2-Butoxybenzoic acid methyl ester
• Synonyms: 2-Butoxybenzoic acid methyl ester
• CAS NO: 5446-96-8
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.2536
• Mol File: 5446-96-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 292.5°Cat760mmHg
• Flash Point: 118.3°C
• Appearance: /
• Density: 1.036g/cm³
• CAS DataBase Reference: 2-Butoxybenzoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butoxybenzoic acid methyl ester(5446-96-8)
• EPA Substance Registry System: 2-Butoxybenzoic acid methyl ester(5446-96-8)

Safety Data

• Hazardous Substances Data: 5446-96-8(Hazardous Substances Data)

Upstream product

• 606-45-1 2-methoxybenzoic acid methyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 2372-45-4 sodium butanolate 
• 109-65-9 1-bromo-butane 
• 119-36-8 methyl salicylate 
• 4766-57-8 tetra(n-butoxy)silane 
• 610-97-9 o-iodo-methyl-benzoic acid 

Downstream Products

• 2200-81-9 2-butoxybenzoic acid 
• 1187944-13-3 C₁₂H₁₅IO₃ 
• 911282-14-9 C₃₄H₄₄N₄O₇ 
• 911282-13-8 C₃₄H₄₂N₄O₉ 
• 911282-10-5 [5-(5-acetylamino-2-butoxy-benzoylamino)-2,4-diethoxy-phenyl]-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 911282-11-6 5-acetylamino-N-(5-amino-2,4-diethoxy-phenyl)-2-butoxy-benzamide 
• 911281-97-5 5-acetylamino-2-butoxy-benzoic acid methyl ester 
• 911282-08-1 5-acetylamino-2-butoxy-benzoic acid 
• 911282-07-0 5-amino-2-butoxybenzoic acid methyl ester 
• 911282-06-9 2-butoxy-5-nitro-benzoic acid methyl ester 
• 31792-00-4 2-butoxy-N-hydroxybenzamide 
• 90233-45-7 2-butoxy-benzoic acid butylamide 

Relevant articles and documents

Ligand-free Cu(ii)-catalyzed aerobic etherification of aryl halides with silanes: An experimental and theoretical approach

Owing to their wide occurrence in nature and immense applications in various fields, the synthesis of aryl alkyl ethers has remained a focus of interest. In contrast to the conventional/traditional methods of etherification, herein, we have reported a more efficient method, which is better yielding and more general in application. The etherification of aryl halides by alkoxy/phenoxy silanes was catalyzed by copper acetate in the presence of cesium carbonate and oxygen in DMF at 145 °C. All the as-synthesized compounds were characterized via the 1H-NMR and 13C-NMR spectroscopic techniques. Density functional theory calculations using the B3LYP functional were performed to elucidate the reaction mechanism. The C-O coupling reaction between 2-nitroiodobenzene and tetramethoxysilane was used as a model reaction. The activation energy barriers for the generation of catalytic species (31.6 kcal mol-1) and the σ-bond metathesis (16.0 kcal mol-1), oxidative addition/reductive elimination (20.3 kcal mol-1), halogen atom transfer (19.2 kcal mol-1) and single electron transfer (SET) (29.5 kcal mol-1) mechanisms for the C-O coupling reaction were calculated. Calculations for the key reaction steps were repeated with the B3PW91, PBEH1PBE, wB97XD, CAM-B3LYP and mPW1LYP functionals. The formation of catalytic species via a single electron transfer reaction between tetramethoxysilane and copper acetate, formation of methoxy radicals and methoxylation of copper showed an overall energy barrier of 31.6 kcal mol-1, and therefore is the rate determining step.

Facile alkoxyl exchange of 2-methoxybenzoates via nucleophilic aromatic substitution with sodium alkoxides in dimethylformamide

Methyl 2-methoxybenzoate undergoes facile nuclear-methoxyl displacement by treatment with sodium butexide or isopropoxide in dimethylformamide.