3-Azido-5-hydroxybenzoic acid

Base Information

• Chemical Name: 3-Azido-5-hydroxybenzoic acid
• CAS No.: 66761-27-1
• Molecular Formula: C7H5N3O3
• Molecular Weight: 179.135
• Hs Code.: 2929909090
• DSSTox Substance ID: DTXSID50985338
• Wikidata: Q82972849
• Mol file: 66761-27-1.mol

Synonyms:3-azido-5-hydroxybenzoic acid;DTXSID50985338;Benzoic acid, 4-azido-2-hydroxy-

Chemical Property of 3-Azido-5-hydroxybenzoic acid

Chemical Property:

• Melting Point: 190-193°C (dec.)
• PSA: 107.28000
• LogP: 1.48496
• Storage Temp.: Amber Vial, -20°C Freezer
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 179.03309103
• Heavy Atom Count: 13
• Complexity: 249

Purity/Quality:

97% ^*data from raw suppliers

4-Azidosalicylic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C=C1N=[N+]=[N-])O)C(=O)O
• Uses: 4-azidosalicylic acid is a aryl azide which can be used for the photofunctionalization.

Technology Process of 3-Azido-5-hydroxybenzoic acid

There total 5 articles about 3-Azido-5-hydroxybenzoic 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: 97.6%

4-Aminosalicylic acid (65-49-6) → 4-carboxy-3-hydroxyphenyl azide (66761-27-1)

Guidance literature:

4-Aminosalicylic acid; With sulfuric acid; sodium nitrite; In water; at 0 ℃; for 1h;

With sodium azide; In water; at 0 ℃; for 1h;

Reference yield: 37.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 3-azidophenol (51642-25-2) → 4-carboxy-3-hydroxyphenyl azide (66761-27-1)

Guidance literature:

With triethylamine; magnesium chloride; In acetonitrile; at 70 - 80 ℃; for 7h; Inert atmosphere;

DOI:10.1021/acs.joc.0c00901

Reference yield:

4-carboxy-3-hydroxy-benzenediazonium; hydrogen sulfate → 4-carboxy-3-hydroxyphenyl azide (66761-27-1)

Guidance literature:

With sodium azide; In water; at 0 - 20 ℃;

DOI:10.1016/S0040-4039(01)00131-9

upstream raw materials:

4-Aminosalicylic acid

sodium p-aminosalicylate

formaldehyd

3-azidophenol

Downstream raw materials:

methyl 4-azido-2-hydroxybenzoate

6-(4-azido-2-hydroxybenzamido)-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

succinimide 4-azidosalicylate

4-azidosalicoyl chloride