Methyl 4-(diethylamino)benzoate

Base Information

• Chemical Name: Methyl 4-(diethylamino)benzoate
• CAS No.: 91563-80-3
• Molecular Formula: C12H17 N O2
• Molecular Weight: 207.27
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID90408192
• Wikidata: Q82213573
• Mol file: 91563-80-3.mol

Synonyms:methyl 4-(diethylamino)benzoate;METHYL 4-DIETHYLAMINOBENZOATE;91563-80-3;4-Diethylaminobenzoic acid methyl ester;SCHEMBL65794;DTXSID90408192;NRZLHHHHUNKJOP-UHFFFAOYSA-N;METHYL4-DIETHYLAMINOBENZOATE;ADAL1200432;STK426308;AKOS003278241;AS-61648;CS-0321859;4-(N,N-diethylamino)benzoic acid methyl ester;Benzoic acid, 4-(diethylamino)-, methyl ester;D93194

Chemical Property of Methyl 4-(diethylamino)benzoate

Chemical Property:

• Vapor Pressure: 0.000531mmHg at 25°C
• Refractive Index: 1.533
• Boiling Point: 312.4°Cat760mmHg
• Flash Point: 117.1°C
• PSA: 29.54000
• Density: 1.045g/cm³
• LogP: 2.31940
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 207.125928785
• Heavy Atom Count: 15
• Complexity: 194

Purity/Quality:

99% ^*data from raw suppliers

METHYL-4-DIETHYLAMINOBENZOATE 98.00% ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-37

MSDS Files:

Useful:

• Canonical SMILES: CCN(CC)C1=CC=C(C=C1)C(=O)OC

Technology Process of Methyl 4-(diethylamino)benzoate

There total 7 articles about Methyl 4-(diethylamino)benzoate 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: 65.0%

methanol (67-56-1) + 4-(diethylamino)benzoic acid (5429-28-7) → 4-diethylamino-benzoic acid methyl ester (91563-80-3)

Guidance literature:

With thionyl chloride; for 5h; Reagent/catalyst;

DOI:10.1080/00304948.2017.1260396

Reference yield:

acetonitrile (75-05-8,26809-02-9) + 4-methoxycarbonyl aniline (619-45-4) → 4-diethylamino-benzoic acid methyl ester (91563-80-3) + methyl 4-(ethylamino)benzoate (79663-14-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 48h; under 760.051 Torr;

DOI:10.1039/c1ob06303k

Reference yield:

4-nitrobenzoic acid methyl ester (619-50-1) → 4-diethylamino-benzoic acid methyl ester (91563-80-3) + methyl 4-(ethylamino)benzoate (79663-14-2)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; ammonium acetate; hydrogen / methanol / 24 h / 20 °C / 760.05 Torr

2: palladium 10% on activated carbon; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr

With palladium 10% on activated carbon; ammonium acetate; hydrogen; In methanol;

DOI:10.1039/c1ob06303k

upstream raw materials:

diazomethane

4-(diethylamino)benzoic acid

4-bromo-N,N-diethylaniline

4-nitrobenzoic acid methyl ester

Downstream raw materials:

4-Dipentafluorethylamino-perfluorcyclohexan-carbonsaeure-⁽¹⁾

4-Diaethylamino-benzoesaeure-hydrazid

Benzaldehyd-(4-diaethylamino-benzoyl)-hydrazon

Refernces

• 1、 Ikawa, Takashi,Fujita, Yuki,Mizusaki, Tomoteru,Betsuin, Sae,Takamatsu, Haruki,Maegawa, Tomohiro,Monguchi, Yasunari,Sajiki, Hironao. "Selective N-alkylation of amines using nitriles under hydrogenation conditions: Facile synthesis of secondary and tertiary amines". . p. 293 - 304. Retrieved 2012/02/01.