4-Amino-5-chloro-2-ethoxybenzoic acid

Base Information

• Chemical Name: 4-Amino-5-chloro-2-ethoxybenzoic acid
• CAS No.: 108282-38-8
• Molecular Formula: C9H10ClNO3
• Molecular Weight: 215.636
• Hs Code.: 2922509090
• European Community (EC) Number: 600-861-8
• DSSTox Substance ID: DTXSID40441418
• Nikkaji Number: J1.637.257I
• Wikidata: Q72471271
• Mol file: 108282-38-8.mol

Synonyms:4-amino-5-chloro-2-ethoxybenzoic acid;108282-38-8;2-ETHOXY-4-AMINO-5-CHLOROBENZOIC ACID;4-Amino-5-Chloro-2-Ethoxy benzoic acid;Benzoic acid, 4-amino-5-chloro-2-ethoxy-;MFCD03840527;4-amino-5-chloro-2-ethoxy-benzoic Acid;SCHEMBL99475;XWGYOMHQGQZRLC-UHFFFAOYSA-;AMY8758;DTXSID40441418;XWGYOMHQGQZRLC-UHFFFAOYSA-N;BCP07327;2-ethoxy-4-amino5-chlorobenzoic acid;4-Amino-5-chloro-2-ethoxybenzoicacid;AKOS015888128;CS-W014885;SB78933;4-ammo-5-chloro-2-ethoxy benzoic acid;AS-11809;SY035527;FT-0642648;A801835;4-Amino-5-chloro-2-ethoxybenzoic acid, AldrichCPR;4-amino-5-chloro-2-ethoxy-benzoic acid;4-Amino-5-chloro-2-ethoxy benzoic acid;InChI=1/C9H10ClNO3/c1-2-14-8-4-7(11)6(10)3-5(8)9(12)13/h3-4H,2,11H2,1H3,(H,12,13)

Chemical Property of 4-Amino-5-chloro-2-ethoxybenzoic acid

Chemical Property:

• Appearance/Colour: white crystal powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 165-169 °C
• Refractive Index: 1.6
• Boiling Point: 377.708 °C at 760 mmHg
• PKA: 4.50±0.10(Predicted)
• Flash Point: 182.232 °C
• PSA: 72.55000
• Density: 1.376 g/cm³
• LogP: 2.60030
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 215.0349209
• Heavy Atom Count: 14
• Complexity: 212

Purity/Quality:

99% ^*data from raw suppliers

4-Amino-5-chloro-2-ethoxybenzoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=CC(=C(C=C1C(=O)O)Cl)N
• Uses: Methyl 4-Amino-5-chloro-2-methoxybenzoate is used in preparation of phenoxymethylpyridine derivatives as immunomodulators.

Technology Process of 4-Amino-5-chloro-2-ethoxybenzoic acid

There total 8 articles about 4-Amino-5-chloro-2-ethoxybenzoic 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: 99.0%

4-Acetylamino-5-chloro-2-ethoxy-benzoic acid methyl ester (4235-43-2) → 4-amino-5-chloro-2-ethoxybenzoic acid (108282-38-8)

Guidance literature:

With sodium hydroxide; water; In ethanol; for 5h; Heating;

DOI:10.1021/jm00106a023

Reference yield: 96.3%

ethyl 2-ethoxy-4-phthalimido-5-chlorobenzoate → 4-amino-5-chloro-2-ethoxybenzoic acid (108282-38-8)

Guidance literature:

With hydrazine hydrate; sodium hydroxide; In ethanol; at 80 ℃; for 3h;

Reference yield:

methyl 4-acetamido-2-hydroxybenzoate (4093-28-1) → 4-amino-5-chloro-2-ethoxybenzoic acid (108282-38-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 98.4 percent / K₂CO₃ / dimethylformamide / 24 h / 20 - 30 °C

2: NCS / dimethylformamide / 3 h / 70 °C

3: 86.9 percent / 4N NaOH / methanol / 2 h / Heating

With sodium hydroxide; N-chloro-succinimide; potassium carbonate; In methanol; N,N-dimethyl-formamide;

DOI:10.1248/cpb.46.42

upstream raw materials:

4-Acetylamino-5-chloro-2-ethoxy-benzoic acid methyl ester

methyl 4-acetamido-2-hydroxybenzoate

methyl 4-acetamido-2-ethoxybenzoate

4-Aminosalicylic acid

Downstream raw materials:

methyl 4-amino-5-chloro-2-ethoxybenzoate

(S)-6-{2-[(4-amino-5-chloro-2-ethoxy-benzoylamino)-methyl]-morpholin-4-yl}-hexanoic acid ethyl ester

(R)-6-(2-((4-amino-5-chloro-2-ethoxy-benzoylamino)-methyl)-morpholino)-hexanoic acid ethyl ester

(R)-quinuclidin-3-yl 6-((R)-2-((4-amino-5-chloro-2-ethoxybenzamido)methyl)morpholino)hexanoate

Refernces

• 1、 Deng, Xin,Zhao, Xinxin,Han, Jing,Wang, Jingjie,Huang, Wenlong,Qian, Hai,Ge, Liang. "Synthesis and biological evaluation of berberine derivatives as IBS modulator". scheme or table. p. 489 - 493. Retrieved 2012/08/29.
• 2、 Kato,Morie,Kon,Yoshida,Karasawa,Matsumoto. "Novel benzamides as selective and potent gastrokinetic agents. 2.1 Synthesis and structure-activity relationships of 4-amino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]methyl] benzamide citrate (AS-4370) and related compounds". . p. 616 - 624. Retrieved 2007/10/02.