4-Amino-3-hydroxynaphthalene-1-carboxylic acid

Base Information

• Chemical Name: 4-Amino-3-hydroxynaphthalene-1-carboxylic acid
• CAS No.: 103907-14-8
• Molecular Formula: C11H9 N O3
• Molecular Weight: 203.197
• DSSTox Substance ID: DTXSID90595970
• Nikkaji Number: J35.795B
• Wikidata: Q82491086
• Mol file: 103907-14-8.mol

Synonyms:103907-14-8;4-Amino-3-hydroxynaphthalene-1-carboxylic acid;4-Amino-3-hydroxy-1-naphthoic acid;1-Naphthalenecarboxylicacid,4-amino-3-hydroxy-(9CI);4-amino-3-hydroxy-1-naphthalenecarboxylic acid;SCHEMBL6036421;DTXSID90595970;GUIYTBZJABAZKU-UHFFFAOYSA-N;DA-21265

Chemical Property of 4-Amino-3-hydroxynaphthalene-1-carboxylic acid

Chemical Property:

• Boiling Point: 477.2±45.0 °C(Predicted)
• PKA: 4.84±0.10(Predicted)
• PSA: 83.55000
• Density: 1.485±0.06 g/cm3(Predicted)
• LogP: 2.40700
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 203.058243149
• Heavy Atom Count: 15
• Complexity: 256

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CC(=C2N)O)C(=O)O

Technology Process of 4-Amino-3-hydroxynaphthalene-1-carboxylic acid

There total 7 articles about 4-Amino-3-hydroxynaphthalene-1-carboxylic 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: 15.0%

3-hydroxy-1-naphthalenecarboxylic acid (19700-42-6) → 4-amino-3-hydroxy-1-naphthalenecarboxylic acid (103907-14-8)

Guidance literature:

3-hydroxy-1-naphthalenecarboxylic acid; With 4-diazobenzenesulfonic acid; sodium hydrogencarbonate; at 60 ℃;

With sodium hydrogensulfite; at 50 ℃; for 0.5h; Further stages.;

DOI:10.1021/jm010283l

Reference yield:

3-nitro-1-naphthoic acid (4507-84-0) → 4-amino-3-hydroxy-1-naphthalenecarboxylic acid (103907-14-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 90 percent / 10percent aq. NaOH; H₂ / 10percent Pd/C / 4 h / 20 °C / 2585.81 Torr

2.1: 74 percent / aq. H₂SO₄; NaNO₂ / 10 °C

3.1: p-diazoniumbenzenesulfonate; aq. NaHCO₃ / 60 °C

3.2: 15 percent / NaHSO₃ / 0.5 h / 50 °C

With 4-diazobenzenesulfonic acid; sulfuric acid; hydrogen; sodium hydrogencarbonate; sodium nitrite; 10percent Pd/C;

DOI:10.1021/jm010283l

Reference yield:

3-nitro-1,8-naphthalic anhydride (3027-38-1) → 4-amino-3-hydroxy-1-naphthalenecarboxylic acid (103907-14-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: aq. NaOH; HgO; glacial AcOH / 72 h / Heating

1.2: aq. HCl / 4 h / Heating

2.1: 90 percent / 10percent aq. NaOH; H₂ / 10percent Pd/C / 4 h / 20 °C / 2585.81 Torr

3.1: 74 percent / aq. H₂SO₄; NaNO₂ / 10 °C

4.1: p-diazoniumbenzenesulfonate; aq. NaHCO₃ / 60 °C

4.2: 15 percent / NaHSO₃ / 0.5 h / 50 °C

With sodium hydroxide; 4-diazobenzenesulfonic acid; sulfuric acid; hydrogen; sodium hydrogencarbonate; acetic acid; mercury(II) oxide; sodium nitrite; 10percent Pd/C;

DOI:10.1021/jm010283l

upstream raw materials:

4-diazobenzenesulfonic acid

3-hydroxy-1-naphthalenecarboxylic acid

3-nitro-1-naphthoic acid

3-nitro-1,8-naphthalic anhydride

Downstream raw materials:

4-Carboxy-1,2-naphthochinon

1-amino-2-naphthol