Methyl 2-(3-amino-4-hydroxyphenyl)acetate

Base Information

• Chemical Name: Methyl 2-(3-amino-4-hydroxyphenyl)acetate
• CAS No.: 78587-72-1
• Molecular Formula: C9H11 N O3
• Molecular Weight: 181.191
• Hs Code.: 2922509090
• European Community (EC) Number: 881-778-6
• DSSTox Substance ID: DTXSID60363067
• Wikidata: Q82146620
• ChEMBL ID: CHEMBL1372098
• Mol file: 78587-72-1.mol

Synonyms:methyl 2-(3-amino-4-hydroxyphenyl)acetate;78587-72-1;methyl 3-amino-4-hydroxyphenylacetate;MLS000736201;SCHEMBL287469;CHEMBL1372098;DTXSID60363067;HMS2660I07;MFCD04125316;methyl-3-amino-4-hydroxyphenylacetate;AKOS005070314;CS-W000711;methyl(3-amino-4-hydroxyphenyl)acetate;methyl (3-amino-4-hydroxyphenyl)acetate;SMR000338451;methyl-2-(3-amino-4-hydroxyphenyl)acetate;FT-0648715;EN300-7388097;3X-0844;A865009;J-521822;Z1201622979

Chemical Property of Methyl 2-(3-amino-4-hydroxyphenyl)acetate

Chemical Property:

• Melting Point: 102-105°
• PSA: 72.55000
• LogP: 1.27110
• Storage Temp.: 2-8°C
• XLogP3: 0.6
• 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%min ^*data from raw suppliers

3-?Amino-?4-?hydroxy-?benzeneaceticacidmethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CC1=CC(=C(C=C1)O)N
• Uses: 3-?Amino-?4-?hydroxy-?benzeneacetic acid methyl ester is used as reagent for the preparation of benzoxazole derivatives.

Technology Process of Methyl 2-(3-amino-4-hydroxyphenyl)acetate

There total 6 articles about Methyl 2-(3-amino-4-hydroxyphenyl)acetate 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%

methyl (4-hydroxy-3-nitrophenyl)acetate (61873-93-6) → methyl (3-amino-4-hydroxyphenyl)acetate (78587-72-1)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In ethanol; ethyl acetate; for 72h;

Reference yield:

4-hydroxy-3-nitrophenylacetic acid (10463-20-4) → methyl (3-amino-4-hydroxyphenyl)acetate (78587-72-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / HCl / Heating

2: 92 percent / H₂ / Pd/C / ethyl acetate

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethyl acetate;

DOI:10.1016/j.bmcl.2005.03.014

Reference yield:

4-hydroxyphenylacetate (156-38-7) → methyl (3-amino-4-hydroxyphenyl)acetate (78587-72-1)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid; nitric acid / 1 h / 0 °C

2: sulfuric acid / 70 °C / Reflux

3: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 2 h / 20 °C

With sulfuric acid; palladium 10% on activated carbon; hydrogen; nitric acid; acetic acid; In tetrahydrofuran; methanol;

upstream raw materials:

methyl (4-hydroxy-3-nitrophenyl)acetate

4-hydroxy-3-nitrophenylacetic acid

4-hydroxyphenylacetate

4-methoxy-phenyl acetic acid methyl ester

Downstream raw materials:

Methyl 3-p-methoxyphenyl-2H-1,4-benzoxazin-2-one-6-acetate

methyl 2-(3-(3,5-dimethylisoxazole-4-carboxamido)-4-hydroxyphenyl)acetate

methyl 2-(4-nitrophenyl)benzoxazole-5-acetate

methyl 2-(2-(4-aminophenyl)benzo[d]oxazol-5-yl)acetate

Refernces

• 1、 -. "COMPOUNDS AND METHODS". Page/Page column 104. . Retrieved 2013/03/26.
• 2、 Xiao, Zhu-Ping,Wang, Ying-Chun,Du, Gao-Yu,Wu, Jun,Luo, Tao,Yi, Shou-Fu. "Efficient reducing system based on iron for conversion of nitroarenes to anilines". experimental part. p. 661 - 665. Retrieved 2011/03/19.