4-[2-(Dimethylamino)ethoxy]benzonitrile

Base Information

• Chemical Name: 4-[2-(Dimethylamino)ethoxy]benzonitrile
• CAS No.: 24197-95-3
• Molecular Formula: C11H14N2O
• Molecular Weight: 190.245
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID70338145
• Nikkaji Number: J1.876.055J
• Wikidata: Q72468926
• ChEMBL ID: CHEMBL4587959
• Mol file: 24197-95-3.mol

Synonyms:4-[2-(dimethylamino)ethoxy]benzonitrile;24197-95-3;4-(2-(Dimethylamino)ethoxy)benzonitrile;4-(2-Dimethylaminoethoxy)benzonitrile;AE-641/00336014;SCHEMBL4087894;CHEMBL4587959;DTXSID70338145;ZAA19795;MFCD05738937;AKOS000189245;BS-24895;CS-0204927;FT-0731797;4-[2-(N,N-Dimethylamino)ethoxy]benzonitrile;EN300-49309;F53565;Z54752697

Chemical Property of 4-[2-(Dimethylamino)ethoxy]benzonitrile

Chemical Property:

• Vapor Pressure: 0.000396mmHg at 25°C
• Boiling Point: 115-117/0.1mm
• PKA: 8.59±0.28(Predicted)
• Flash Point: 145.5oC
• PSA: 36.26000
• Density: 1.06g/cm3
• LogP: 1.49868
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 190.110613074
• Heavy Atom Count: 14
• Complexity: 199

Purity/Quality:

99%, ^*data from raw suppliers

4-[2-(Dimethylamino)ethoxy]benzonitrile ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCOC1=CC=C(C=C1)C#N

Technology Process of 4-[2-(Dimethylamino)ethoxy]benzonitrile

There total 7 articles about 4-[2-(Dimethylamino)ethoxy]benzonitrile 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: 97.0%

2-(dimethylamino)ethyl chloride (107-99-3) → 4-(2-(dimethylamino)ethoxy)-benzonitrile (24197-95-3)

Guidance literature:

4-cyanophenol; With potassium hydroxide; In acetone; for 1h; Heating / reflux;

2-(dimethylamino)ethyl chloride; In acetone; for 8h; Heating / reflux;

Reference yield: 91.0%

2-(N,N-dimethylamino)ethanol (108-01-0) + 4-cyano-N,N,N-trimethylanilinium trifluoromethansulfonate → 4-(2-(dimethylamino)ethoxy)-benzonitrile (24197-95-3)

Guidance literature:

2-(N,N-dimethylamino)ethanol; With potassium tert-butylate; In tetrahydrofuran; N,N-dimethyl-formamide; at 25 ℃; for 0.166667h; Inert atmosphere; Schlenk technique;

4-cyano-N,N,N-trimethylanilinium trifluoromethansulfonate; In tetrahydrofuran; N,N-dimethyl-formamide; at 25 ℃; for 3h; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201712618

Reference yield: 80.3%

4-Cyanochlorobenzene (623-03-0) + 2-(N,N-dimethylamino)ethanol (108-01-0) → 4-(2-(dimethylamino)ethoxy)-benzonitrile (24197-95-3)

Guidance literature:

2-(N,N-dimethylamino)ethanol; With sodium methylate; In methanol; at 20 - 135 ℃; for 3.25h;

4-Cyanochlorobenzene; In methanol; at 120 - 125 ℃; for 4h; Product distribution / selectivity;

upstream raw materials:

2-(dimethylamino)ethyl chloride

(2-chloroethyl)dimethylamine hydrochloride

4-cyanophenol

4-Cyanochlorobenzene

Downstream raw materials:

4-<2-(dimethylamino)ethoxy>benzylamine

Refernces

• 1、 Wang, Dong-Yu,Yang, Ze-Kun,Wang, Chao,Zhang, Ao,Uchiyama, Masanobu. "From Anilines to Aryl Ethers: A Facile, Efficient, and Versatile Synthetic Method Employing Mild Conditions". supporting information. p. 3641 - 3645. Retrieved 2018/03/13.
• 2、 -. "METHOD FOR PREPARING 4-[2-(DIMETHYLAMINO)ETHOXY]BENZYLAMINE AS ITOPRIDE HYDROCLORIDE SALT MEDIATE". Page/Page column 8. . Retrieved 2008/06/13.