2-methoxy-N,N-dimethylbenzamide

Base Information

• Chemical Name: 2-methoxy-N,N-dimethylbenzamide
• CAS No.: 7291-34-1
• Molecular Formula: C10H13NO2
• Molecular Weight: 179.219
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID20457198
• Nikkaji Number: J284.159B
• Wikidata: Q82279953
• Mol file: 7291-34-1.mol

Synonyms:2-methoxy-N,N-dimethylbenzamide;7291-34-1;N,N-dimethyl-(2-methoxy-phenyl)-formamide;2-methoxy-N,N-dimethyl-benzamide;N,N-dimethyl-2-methoxy-benzamide;Benzamide, 2-methoxy-N,N-dimethyl-;SCHEMBL2541558;N,N-Dimethyl-2-methoxybenzamide;DTXSID20457198;MFCD01611815;AKOS003558516;CS-0261320;EN300-78128;F78410

Chemical Property of 2-methoxy-N,N-dimethylbenzamide

Chemical Property:

• Melting Point: 74-75 °C
• Boiling Point: 316.9±25.0 °C(Predicted)
• PKA: -0.81±0.70(Predicted)
• PSA: 29.54000
• Density: 1.062±0.06 g/cm3(Predicted)
• LogP: 1.39700
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 180

Purity/Quality:

95% ^*data from raw suppliers

2-Methoxy-N,N-dimethylbenzamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C(=O)C1=CC=CC=C1OC

Technology Process of 2-methoxy-N,N-dimethylbenzamide

There total 9 articles about 2-methoxy-N,N-dimethylbenzamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

2-bromoanisole (578-57-4) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2-methoxy-N,N-dimethylbenzamide (7291-34-1)

Guidance literature:

With sodium methylate; nickel diacetate; In 1,4-dioxane; at 110 ℃;

DOI:10.1021/ol702058e

Reference yield: 85.0%

N,N-dimethyl acetamide (127-19-5,116057-81-9) + 2-Methoxybenzoic acid (579-75-9) → 2-methoxy-N,N-dimethylbenzamide (7291-34-1)

Guidance literature:

With 1,1'-carbonyldiimidazole; at 160 - 165 ℃; for 1h;

DOI:10.3184/174751913X13602686612047

Reference yield: 78.0%

4-iodoanisol (529-28-2) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2-methoxy-N,N-dimethylbenzamide (7291-34-1)

Guidance literature:

With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; trichlorophosphate; at 135 ℃; for 6h; Inert atmosphere;

DOI:10.1021/jo200754v

upstream raw materials:

dimethyl amine

2-Methoxybenzoyl chloride

2-bromoanisole

N,N-dimethyl-formamide

Downstream raw materials:

1-(2-methoxyphenyl)-3-phenylprop-2-yn-1-one

5-methoxy-3-phenylsulfanyl-1,4-naphthoquinone

N,N-diisopropyl-4-(2-methoxybenzoyl)nicotinamide

(+/-)-phyllodulcin 3'-benzyl-8-methyl ether

Refernces

Ortho-Lithiated Tertiary Benzamides. Chain Extension via o-Toluamide Anion and General Synthesis of Isocoumarins Including Hydrangenol and Phyllodulcin

10.1021/jo00179a002

The research focuses on the synthesis of 3-aryl-3,4-dihydroisocoumarin derivatives, including the natural products hydrangenol and phyllodulcin, using a benzamide directed ortho metalation strategy. The purpose of the study was to develop an efficient and general method for synthesizing these compounds, which are of pharmacological interest due to their potential antifungal and sweetening properties. The researchers utilized various benzamides, such as N,N-diethyl-2-methylbenzamide and N,N-dimethyl-2-methoxybenzamide, along with reagents like lithium diisopropylamide (LDA) and sec-butyl lithium, to achieve the desired metalation and subsequent reactions. The conclusions drawn from the study indicate that the benzamide directed metalation approach is a powerful and adaptable method for synthesizing alkoxy-substituted isocoumarins, which are difficult to prepare by classical routes.