Ethyl 4-amino-3-hydroxybenzoate

Base Information

• Chemical Name: Ethyl 4-amino-3-hydroxybenzoate
• CAS No.: 87081-52-5
• Molecular Formula: C9H11 N O3
• Molecular Weight: 181.191
• Hs Code.: 2922509090
• European Community (EC) Number: 888-934-2
• DSSTox Substance ID: DTXSID80509783
• Wikidata: Q82367642
• Mol file: 87081-52-5.mol

Synonyms:ethyl 4-amino-3-hydroxybenzoate;87081-52-5;ethyl4-amino-3-hydroxybenzoate;SCHEMBL6471721;DTXSID80509783;MFCD01320538;AKOS010053630;CCG-306045;TS-02530;CS-0261606;FT-0722186;EN300-79206;F87525;Z594210704

Chemical Property of Ethyl 4-amino-3-hydroxybenzoate

Chemical Property:

• Melting Point: 90-94 °C
• Boiling Point: 370.6±27.0 °C(Predicted)
• PKA: 8.99±0.10(Predicted)
• PSA: 72.55000
• Density: 1.253±0.06 g/cm3(Predicted)
• LogP: 1.73230
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 181.07389321
• Heavy Atom Count: 13
• Complexity: 184

Purity/Quality:

98.5% ^*data from raw suppliers

Ethyl4-Amino-3-hydroxybenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC(=C(C=C1)N)O
• Uses: Ethyl 4-Amino-3-hydroxybenzoate is used as a reagent in the synthesis of cytotoxic N-mustard derivatives of Hoechst 33258 analogs.

Technology Process of Ethyl 4-amino-3-hydroxybenzoate

There total 3 articles about Ethyl 4-amino-3-hydroxybenzoate 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: 100.0%

ethyl 3-hydroxy-4-nitro-benzoate (717-01-1) → ethyl 4-amino-3-hydroxybenzoate (87081-52-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃;

DOI:10.1021/jm048984g

Reference yield:

3-hydroxy-4-nitro-benzoic acid (619-14-7) → ethyl 4-amino-3-hydroxybenzoate (87081-52-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / sulphuric acid / 2 h / Heating

2: 100 percent / H₂ / Pd/C / ethanol / 20 °C

With sulfuric acid; hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1021/jm048984g

Reference yield:

ethanol (64-17-5) + 4-aminosalicylic acid (2374-03-0) → ethyl 4-amino-3-hydroxybenzoate (87081-52-5)

Guidance literature:

With sulfuric acid;

upstream raw materials:

ethyl 3-hydroxy-4-nitro-benzoate

ethanol

4-aminosalicylic acid

3-hydroxy-4-nitro-benzoic acid

Downstream raw materials:

3-hydroxy-4-[2-(2'-pyridinecarboxamido)acetylamino]benzoic acid

Refernces

• 1、 Anderluh, Petra ?tefani?,Anderluh, Marko,Ila?, Janez,Mravljak, Janez,Dolenc, Marija Sollner,Stegnar, Mojca,Kikelj, Danijel. "Toward a novel class of antithrombotic compounds with dual function. Discovery of 1,4-benzoxazin-3(4H)-one derivatives possessing thrombin inhibitory and fibrinogen receptor antagonistic activities". . p. 3110 - 3113. Retrieved 2007/10/03.
• 2、 Carato, Pascal,Yous, Said,Depreux, Patrick. "Synthesis of 6-chloromethyl benzothiazolin-2-one and of 6-chloromethyl benzoxazolin-2-one". . p. 69 - 74. Retrieved 2007/10/03.