5-Iodosalicylic acid

Base Information

• Chemical Name: 5-Iodosalicylic acid
• CAS No.: 119-30-2
• Molecular Formula: C7H5IO3
• Molecular Weight: 264.019
• Hs Code.: 29182990
• European Community (EC) Number: 204-313-5
• NSC Number: 2789
• DSSTox Substance ID: DTXSID10152281
• Nikkaji Number: J49.714B
• Wikidata: Q72484639
• ChEMBL ID: CHEMBL3278559
• Mol file: 119-30-2.mol

Synonyms:Salicylicacid, 5-iodo- (6CI,7CI,8CI);2-Hydroxy-5-iodobenzoic acid;5-Iodo-2-hydroxybenzoic acid;6-Hydroxy-3-iodobenzoicacid;NSC 2789;

Chemical Property of 5-Iodosalicylic acid

Chemical Property:

• Appearance/Colour: white to slightly beige powder
• Vapor Pressure: 3.56E-06mmHg at 25°C
• Melting Point: 189-191 °C(lit.)
• Boiling Point: 371.4 °C at 760 mmHg
• PKA: 2.67±0.10(Predicted)
• Flash Point: 178.4 °C
• PSA: 57.53000
• Density: 2.155 g/cm³
• LogP: 1.69500
• Storage Temp.: Store below +30°C.
• Sensitive.: Light Sensitive
• Solubility.: Solubility in methanol is almost transparent.
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 263.92834
• Heavy Atom Count: 11
• Complexity: 160

Purity/Quality:

99% ^*data from raw suppliers

2-Hydroxy-5-iodobenzoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1I)C(=O)O)O
• Uses: 2-hydroxy-5-iodobenzoic acid is a reagent in various organic chemical reactions leading to pharmaceutical compounds. It is involved in the synthesis of labeled benzamide analogs for tumor imaging as well as the synthesis of the dye, Congo Red, for biological analyses.

Technology Process of 5-Iodosalicylic acid

There total 19 articles about 5-Iodosalicylic 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: 100.0%

methyl 5-iodosalicylate (4068-75-1) → 2-hydroxy-5-iodobenzoic acid (119-30-2)

Guidance literature:

With lithium hydrochloride monohydrate; water; In tetrahydrofuran; at 20 ℃; for 16h;

Reference yield: 95.0%

salicylic acid (69-72-7,25496-36-0,8052-31-1) → 2-hydroxy-5-iodobenzoic acid (119-30-2)

Guidance literature:

With N-chloro-N-(benzenesulfonyl)benzenesulfonamide; potassium iodide; In N,N-dimethyl-formamide; at 25 - 30 ℃;

DOI:10.1021/acs.joc.1c01642

Reference yield: 82.0%

salicylic acid (69-72-7,25496-36-0,8052-31-1) → 2-hydroxy-5-iodobenzoic acid (119-30-2) + 2-hydroxy-3-iodobenzoic acid (520-79-6)

Guidance literature:

salicylic acid; With sulfuric acid; In acetonitrile; at 20 ℃; for 0.0833333h;

With N-iodo-succinimide; In acetonitrile; at 20 ℃; for 1.5h; regioselective reaction;

DOI:10.1080/00397911.2019.1711415

upstream raw materials:

5-Aminosalicylic Acid

methyl 5-iodosalicylate

3-carboxylato-4-hydroxybenzenediazonium

salicylic acid

Downstream raw materials:

ethyl 2-hydroxy-5-iodobenzoate

2,4,6-Triiodophenol

2-hydroxy-5-iodo-3-nitro-benzoic acid

2,5-dihydroxybenzoic acid.

Refernces

• 1、 Brenans,Girod. "-". . p. 1852. Retrieved 1928.
• 2、 Palav, Amey,Misal, Balu,Chaturbhuj, Ganesh. "NCBSI/KI: A Reagent System for Iodination of Aromatics through in Situ Generation of I-Cl". . p. 12467 - 12474. Retrieved 2021/08/24.
• 3、 Wu, Yong-Qi,Lu, Hai-Jia,Zhao, Wen-Ting,Zhao, Hong-Yi,Lin, Zi-Yun,Zhang, Dong-Feng,Huang, Hai-Hong. "A convenient and efficient H2SO4-promoted regioselective monobromination of phenol derivatives using N-bromosuccinimide". supporting information. p. 813 - 822. Retrieved 2020/02/15.