ethyl 4-(methylamino)benzoate

Base Information

• Chemical Name: ethyl 4-(methylamino)benzoate
• CAS No.: 10541-82-9
• Molecular Formula: C10H13 N O2
• Molecular Weight: 179.219
• Hs Code.: 2922499990
• Mol file: 10541-82-9.mol

Synonyms:Benzoicacid, p-(methylamino)-, ethyl ester (7CI,8CI); 4-(Methylamino)benzoic acidethyl ester; 4-Ethoxycarbonyl-N-methylaniline; Ethyl 4-(methylamino)benzoate;Ethyl p-(methylamino)benzoate; NSC 265435

Chemical Property of ethyl 4-(methylamino)benzoate

Chemical Property:

• Vapor Pressure: 0.0018mmHg at 25°C
• Melting Point: >63°C (dec.)
• Boiling Point: 292.7°Cat760mmHg
• Flash Point: 130.8°C
• PSA: 38.33000
• Density: 1.097g/cm³
• LogP: 1.97800
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-(Methylamino)benzoicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-(Methylamino)benzoic Acid Ethyl Ester (cas# 10541-82-9) is a compound useful in organic synthesis.

Technology Process of ethyl 4-(methylamino)benzoate

There total 32 articles about ethyl 4-(methylamino)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: 98.0%

4'-ethoxycarbonyl-N-methyl-4-toluenesulfonanilide (16965-50-7) → ethyl 4-(methylamino)benzoate (10541-82-9)

Guidance literature:

4'-ethoxycarbonyl-N-methyl-4-toluenesulfonanilide; With potassium diphenylphosphine; In tetrahydrofuran; at -78 ℃; for 2h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; water; Inert atmosphere;

DOI:10.1021/ja309642r

Reference yield: 91.0%

4-fluorobenzoic acid ethyl ester (451-46-7) + methylamine hydrochloride (593-51-1) → ethyl 4-(methylamino)benzoate (10541-82-9)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide; at 80 ℃; for 48h;

Reference yield: 90.0%

ethyl p-dimethyaminolbenzoate (10287-53-3) → ethyl 4-(methylamino)benzoate (10541-82-9) + N-(4-ethoxycarbonylphenyl)-N-methylformamide (53892-40-3)

Guidance literature:

With sodium tetrafluoroborate; [Cu(salicylate)₂(NCMe)]₂; tetrabutyl-ammonium chloride; oxygen; In acetonitrile; at 40 ℃; Schlenk technique;

DOI:10.1002/cctc.201901962

upstream raw materials:

1.4-Dimethyl-1-(4'-tolyl)-4-(p-carbaethoxyphenyl)-2-tetrazen

N-methyl-p-aminobenzoic acid

ethyl N-methyl-N-phenylcarbamate

N-(4-ethoxycarbonylphenyl)formamide

Downstream raw materials:

ethyl 4-amino-4-deoxy-N¹⁰-methylpteroate

C₁₆H₂₁NO₄

C₁₄H₁₇NO₂

ethyl p-dimethyaminolbenzoate

Refernces

• 1、 Tayama, Eiji,Kobayashi, Yoshiaki,Toma, Yuka. "Diaza [1,4] Wittig-type rearrangement of N-allylic-N-Boc-hydrazines into γ-amino- N -Boc-enamines". . p. 10570 - 10573. Retrieved 2016.
• 2、 Wang, Hongli,Huang, Yongji,Dai, Xingchao,Shi, Feng. "N -Monomethylation of amines using paraformaldehyde and H2". supporting information. p. 5542 - 5545. Retrieved 2017/07/06.