2-(Ethylamino)benzoic acid

Base Information

• Chemical Name: 2-(Ethylamino)benzoic acid
• CAS No.: 89-50-9
• Molecular Formula: C9H11 N O2
• Molecular Weight: 165.192
• Hs Code.: 2922499990
• European Community (EC) Number: 201-912-3
• NSC Number: 16162
• UNII: 9UPT2LGS5L
• DSSTox Substance ID: DTXSID5058989
• Nikkaji Number: J79.436H
• Wikidata: Q81988633
• ChEMBL ID: CHEMBL1451886
• Mol file: 89-50-9.mol

Synonyms:2-(Ethylamino)benzoic acid;89-50-9;N-Ethylanthranilic acid;Benzoic acid, 2-(ethylamino)-;Anthranilic acid, N-ethyl-;9UPT2LGS5L;MLS000737796;CHEMBL1451886;EINECS 201-912-3;MFCD00020248;NSC 16162;NSC-16162;N-ethyl anthranilic acid;2-(ethylamino)benzoesyre;UNII-9UPT2LGS5L;2-(Ethylamino)benzoicacid;n-ethyl-o-aminobenzoic acid;Oprea1_837094;SCHEMBL184136;2-(Ethylamino)benzoic acid #;DTXSID5058989;HMS2269D05;NSC16162;BDBM50535053;STK421957;AKOS002664912;NCGC00246752-01;SMR000528165;E79662;EN300-146581;F0436-0020

Chemical Property of 2-(Ethylamino)benzoic acid

Chemical Property:

• Vapor Pressure: 0.000112mmHg at 25°C
• Boiling Point: 322.8°C at 760 mmHg
• Flash Point: 149°C
• PSA: 49.33000
• Density: 1.197g/cm³
• LogP: 1.88960
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 165.078978594
• Heavy Atom Count: 12
• Complexity: 159

Purity/Quality:

96% 1H NMR ^*data from raw suppliers

N-ETHYLANTHRANILIC ACID Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCNC1=CC=CC=C1C(=O)O
• Uses: 2-(Ethylamino)benzoic acid is used as a reactant in the preparation of secondary amines via reductive monoalkylation of primary amines with nitriles.

Technology Process of 2-(Ethylamino)benzoic acid

There total 21 articles about 2-(Ethylamino)benzoic acid 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: 91.0%

anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) + acetonitrile (75-05-8,26809-02-9) → 2-(ethylamino)benzoic acid (89-50-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 26h;

DOI:10.1021/ol047871o

Reference yield: 87.0%

anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) + 2-(2-methoxyethoxy)ethyl ethyl carbonate (214470-03-8) → 2-(ethylamino)benzoic acid (89-50-9)

Guidance literature:

NaY-faujasite; at 150 ℃; for 18h;

Reference yield: 86.0%

ethanamine hydrochloride (557-66-4) + 2-bromobenzoic-acid (88-65-3) → 2-(ethylamino)benzoic acid (89-50-9)

Guidance literature:

With potassium phosphate; copper(l) iodide; 1,1'-bi-2-naphthol; In N,N-dimethyl-formamide; at 25 ℃; for 16h; Inert atmosphere;

DOI:10.1002/adsc.200900065

upstream raw materials:

2,4,6-trimethyl-[1,3,5]triazinane

anthranilic acid

ethyl bromide

potassium anthranilate

Downstream raw materials:

1-(carboxymethyl)-N-ethylanthranilic acid

methyl 2-(ethylamino)benzoate

ethyl 2-(ethylamino)benzoate

1-ethyl-1,2,3,4-tetrahydro-2,4-quinazolinedione

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". supporting information; experimental part. p. 293 - 304. Retrieved 2012/02/01.
• 2、 Zeng, Liang,Fu, Hua,Qiao, Renzhong,Jiang, Yuyang,Zhao, Yufen. "Efficient copper-catalyzed synthesis of N-alkylanthranilic acids via an ortho-substituent effect of the carboxyl group of 2-halobenzoic acids at room temperature". supporting information; experimental part. p. 1671 - 1676. Retrieved 2011/02/25.