2-(4-methoxyphenyl)-N,N-dimethylacetamide

Base Information

• Chemical Name: 2-(4-methoxyphenyl)-N,N-dimethylacetamide
• CAS No.: 19625-79-7
• Molecular Formula: C11H15NO2
• Molecular Weight: 193.246
• Hs Code.: 2924299090
• European Community (EC) Number: 606-345-9
• DSSTox Substance ID: DTXSID80349924
• Nikkaji Number: J1.009.382A
• Wikidata: Q82125505
• Mol file: 19625-79-7.mol

Synonyms:19625-79-7;2-(4-methoxyphenyl)-N,N-dimethylacetamide;Benzeneacetamide,4-methoxy-N,N-dimethyl-;N,N-Dimethyl 4-methoxyphenylacetamide;N,N-DIMETHYL-2-(4-METHOXYPHENYL)-ACETAMIDE;ST042236;TimTec1_002840;SCHEMBL755827;DTXSID80349924;HMS1542B02;N,N-Dimethyl4-methoxyphenylacetamide;AKOS000668595;N,N-Dimethyl-4-methoxybenzeneacetamide;4-Methoxy-N,N-Dimethylbenzene Acetamide;FT-0691244;BRD-K53526905-001-01-9;Z32014544

Chemical Property of 2-(4-methoxyphenyl)-N,N-dimethylacetamide

Chemical Property:

• Vapor Pressure: 0.000308mmHg at 25°C
• Melting Point: 79-81 °C
• Refractive Index: 1.516
• Boiling Point: 320.9 °C at 760 mmHg
• PKA: -0.56±0.70(Predicted)
• Flash Point: 147.9 °C
• PSA: 29.54000
• Density: 1.052 g/cm³
• LogP: 1.32590
• Storage Temp.: Room Temperature
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 193.110278721
• Heavy Atom Count: 14
• Complexity: 184

Purity/Quality:

98%min ^*data from raw suppliers

2-(4-METHOXY PHENYL) N,N-DIMETHYL ACETAMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C(=O)CC1=CC=C(C=C1)OC
• Uses: 4-Methoxy-N,N-dimethylbenzeneacetamide is an intermediate in the synthesis of α-(1-Hydroxycyclohexyl)-4-Methoxy-N,N-Dimethylbenzeneacetamide (H555555) which is a synthetic analogue of the drug Venlafaxine. (Cat# V120000) Venlafaxine is a selective serotonin noradrenaline reuptake inhibitor which has powerful application in the treatment of anxiety and depression.

Technology Process of 2-(4-methoxyphenyl)-N,N-dimethylacetamide

There total 15 articles about 2-(4-methoxyphenyl)-N,N-dimethylacetamide 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: 100.0%

4-Methoxyphenylacetic acid (104-01-8) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → N,N-dimethyl-2-(4-methoxyphenyl)ethanamide (19625-79-7)

Guidance literature:

With sulfur trioxide pyridine complex; In 1,2-dichloro-benzene; at 160 ℃; Schlenk technique; Inert atmosphere;

DOI:10.1246/cl.171216

Reference yield: 97.0%

p-Methoxybenzyl bromide (2746-25-0) + N,N-dimethyl (trimethylsilyl)methanamide (479486-96-9) → N,N-dimethyl-2-(4-methoxyphenyl)ethanamide (19625-79-7)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 65 ℃; for 0.1h;

DOI:10.1021/jo0512406

Reference yield: 94.0%

4-Methoxyphenylacetic acid (104-01-8) + dimethyl amine (124-40-3) → N,N-dimethyl-2-(4-methoxyphenyl)ethanamide (19625-79-7)

Guidance literature:

4-Methoxyphenylacetic acid; dimethyl amine; at 100 ℃; Autoclave;

at 95 - 245 ℃; for 0.0158333h; under 18751.9 Torr; Product distribution / selectivity; Microwave irradiation;

upstream raw materials:

N,N-dimethyl acetamide

para-iodoanisole

4-Methoxyphenylacetic acid

dimethyl amine

Downstream raw materials:

2-(4-methoxy-phenyl)-1-(4-methylsulfanyl-phenyl)ethanone

1,4-di(4-methoxyphenyl)ethanone

methoxybenzene

C₂₅H₂₃NO₄

Refernces

• 1、 Djukanovic, Dimitrije,Filipponi, Paolo,Heinz, Benjamin,Knochel, Paul,Mandrelli, Francesca,Martin, Benjamin,Mostarda, Serena. "Continuous Flow Acylation of (Hetero)aryllithiums with Polyfunctional N,N-Dimethylamides and Tetramethylurea in Toluene". supporting information. p. 13977 - 13981. Retrieved 2021/09/13.
• 2、 Wang, Biyun,Zhao, Xianghu,Liu, Qingyun,Cao, Song. "Direct defluorinative amidation-hydrolysis reaction of gem-difluoroalkenes with N,N-dimethylformamide, and primary and secondary amines". . p. 8546 - 8552. Retrieved 2018/12/01.