5-(Phenylazo)salicylic acid

Base Information

• Chemical Name: 5-(Phenylazo)salicylic acid
• CAS No.: 3147-53-3
• Molecular Formula: C13H10 N2 O3
• Molecular Weight: 242.234
• Hs Code.: 2927000090
• European Community (EC) Number: 233-406-3,221-569-3
• NSC Number: 163392
• UNII: 0JGZ1HX6EX
• DSSTox Substance ID: DTXSID70877100
• Nikkaji Number: J1.627.233G,J30.159K
• ChEMBL ID: CHEMBL1834961
• Mol file: 3147-53-3.mol

Synonyms:3147-53-3;2-Hydroxy-5-(phenyldiazenyl)benzoic acid;5-(Phenylazo)salicylic acid;Phenylazosalicylic Acid;Benzoic acid, 2-hydroxy-5-(phenylazo)-;2-hydroxy-5-phenyldiazenylbenzoic acid;2-hydroxy-5-phenyldiazenyl benzoic acid;(E)-2-hydroxy-5-(phenyldiazenyl)benzoic acid;0JGZ1HX6EX;2-Hydroxy-5-(phenylazo)benzoic Acid;380360-42-9;CHEMBL1834961;Salicylic acid, 5-(phenylazo)-;EINECS 221-569-3;EINECS 233-406-3;NSC-163392;2-hydroxy-5-[(E)-phenyldiazenyl]benzoic acid;2-Hydroxy-5-(phenyldiazenyl)benzoic Acid (Phenylazosalicylic Acid);C13H10N2O3.Na;C13-H10-N2-O3.Na;Mesalamine Impurity I;10143-07-4;Benzoic acid, 2-hydroxy-5-(phenylazo)-, monosodium salt;NSC 163392;UNII-0JGZ1HX6EX;5-(Phenylazo)Salicylicacid;SCHEMBL137145;CK-46A;SCHEMBL15339774;DTXSID70877100;5-[(E)-Phenylazo]salicylic acid;AMY38797;BCP26299;BDBM50355010;NSC 45521;NSC163392;STL139171;AKOS005134022;AKOS024333040;AKOS025401127;CS-W014141;FS-6631;MESALAZINE IMPURITY I [EP IMPURITY];FT-0673722;PHENYLAZOSALICYLIC ACID [EP IMPURITY];D87835;A846155;J-509654;2-hydroxy-5-[(1E)-2-phenyldiazen-1-yl]benzoic acid;BENZOIC ACID, 2-HYDROXY-5-(2-PHENYLDIAZENYL)-;2-Hydroxy-5-(2-phenyldiazenyl)benzoic Acid

Chemical Property of 5-(Phenylazo)salicylic acid

Chemical Property:

• Vapor Pressure: 9.81E-08mmHg at 25°C
• Melting Point: 220.5 °C
• Boiling Point: 418°Cat760mmHg
• PKA: 2.71±0.10(Predicted)
• Flash Point: 206.6°C
• PSA: 82.25000
• Density: 1.3g/cm³
• LogP: 3.50580
• Storage Temp.: 2-8°C
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 242.06914219
• Heavy Atom Count: 18
• Complexity: 313

Purity/Quality:

95%min. ^*data from raw suppliers

5-(PHENYLAZO)SALICYLIC ACID Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)N=NC2=CC(=C(C=C2)O)C(=O)O
• Uses: Mesalazine (M258100) impurity.

Technology Process of 5-(Phenylazo)salicylic acid

There total 12 articles about 5-(Phenylazo)salicylic 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: 56.0%

sodium salicylate (54-21-7) + aniline (62-53-3) → 2-hydroxy-5-phenylazo-benzoic acid (3147-53-3)

Guidance literature:

aniline; With hydrogenchloride; sodium nitrite; In water; at 0 - 5 ℃; for 0.75h;

sodium salicylate; In water; at 0 - 5 ℃; for 2h; Alkaline conditions;

DOI:10.4314/bcse.v28i3.17

Reference yield: 33.0%

aniline (62-53-3) + salicylic acid (69-72-7,25496-36-0,8052-31-1) → 5‐[(E)‐2‐phenyl‐1‐diazenyl]‐2‐hydroxybenzoic acid (3147-53-3)

Guidance literature:

aniline; With hydrogenchloride; sodium nitrite; In water; at 5 ℃;

salicylic acid; With sodium hydroxide; In water;

DOI:10.1016/S0022-328X(01)01024-5

Reference yield:

benzene diazonium chloride (100-34-5) + salicylic acid (69-72-7,25496-36-0,8052-31-1) → 2-hydroxy-5-phenylazo-benzoic acid (3147-53-3)

Guidance literature:

With sodium hydroxide;

DOI:10.1007/BF03192422

upstream raw materials:

benzene diazonium chloride

salicylic acid

benzenediazonium nitrate

aniline

Downstream raw materials:

2-hydroxy-5-phenylazo-benzoic acid ethyl ester

5-Aminosalicylic Acid

aniline

4-[(3-carboxyl-4-hydroxy)phenylazo]benzenesulfonic acid

Refernces

• 1、 Baigacheva, E. V.,Gogolishvili, V. O.,Gusev, V. Yu.. "Azo Derivatives of Pyrocatechol, Resorcinol, and Salicylic Acid as Collectors for Sulfide Ore Flotation". . p. 1734 - 1744. Retrieved 2020/02/25.
• 2、 Harveer, Kaur,Jasmeen, Sidana. "Synthesis, characterization and radical scavenging activity of aromatic amine conjugates of 5-Aminosalicylic acid". . p. 475 - 480. Retrieved 2015/02/02.