2-Iodo-5-nitrobenzoic acid

Base Information

• Chemical Name: 2-Iodo-5-nitrobenzoic acid
• CAS No.: 19230-50-3
• Molecular Formula: C7H4 I N O4
• Molecular Weight: 293.018
• Hs Code.: 2916399090
• European Community (EC) Number: 886-519-0
• DSSTox Substance ID: DTXSID10397276
• Nikkaji Number: J2.238.284E
• Wikidata: Q82198487
• Mol file: 19230-50-3.mol

Synonyms:2-Iodo-5-nitrobenzoic acid;19230-50-3;Benzoic acid, 2-iodo-5-nitro-;2-iodo-5-nitro-benzoic acid;MFCD00234256;2-Iodo-5-nitrobenzoicacid;5-nitro-2-iodobenzoic acid;2-iodo-5-nitro benzoic acid;AC-907/25004610;SCHEMBL3550116;DTXSID10397276;JSSFIFUXHORXJX-UHFFFAOYSA-N;TD1238;AKOS000149229;AC-28700;DS-16219;SY040815;CS-0041122;FT-0687134;EN300-39535;J-012426;Z239685228

Chemical Property of 2-Iodo-5-nitrobenzoic acid

Chemical Property:

• Vapor Pressure: 6.36E-07mmHg at 25°C
• Melting Point: 197-198 °C
• Refractive Index: 1.702
• Boiling Point: 394.2°C at 760 mmHg
• PKA: 2.16±0.10(Predicted)
• Flash Point: 192.2°C
• PSA: 83.12000
• Density: 2.156g/cm³
• LogP: 2.42080
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 292.91851
• Heavy Atom Count: 13
• Complexity: 227

Purity/Quality:

99.90% ^*data from raw suppliers

2-Iodo-5-nitrobenzoicAcid ^*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+](=O)[O-])C(=O)O)I
• Uses: 2-iodo-5-nitrobenzoic acid is a useful reactant for the synthesis of 2-?Arylquinazolines and Tetracyclic Isoindolo[1,?2-?a]?quinazoline.

Technology Process of 2-Iodo-5-nitrobenzoic acid

There total 12 articles about 2-Iodo-5-nitrobenzoic 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: 89.0%

2-amino-5-nitro-benzoic acid (616-79-5) → 2-iodo-5-nitro-benzoic acid (19230-50-3)

Guidance literature:

2-amino-5-nitro-benzoic acid; With hydrogenchloride; sodium hydroxide; In water; at 0 - 70 ℃; for 0.166667h; Inert atmosphere;

With sodium nitrite; In water; at 0 ℃; for 0.5h; Inert atmosphere;

With potassium iodide; In water; at 0 - 23 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.orglett.9b03557

Reference yield: 85.0%

2-Iodobenzoic acid (88-67-5) → 2-iodo-5-nitro-benzoic acid (19230-50-3)

Guidance literature:

With sulfuric acid; nitric acid; at 0 - 135 ℃; for 1.83333h;

DOI:10.1021/jo050440e

Reference yield:

N-(4-nitro-2-(trifluoromethyl)phenyl)acetamide (395-68-6) → 2-iodo-5-nitro-benzoic acid (19230-50-3)

Guidance literature:

Multi-step reaction with 3 steps

1: aq.-ethanolic NaOH

2: acetic acid; sulfuric acid; aqueous sodium nitrite solution; aqueous potassium iodide solution

3: H₂SO₄

With sodium hydroxide; sulfuric acid; acetic acid; potassium iodide; sodium nitrite;

DOI:10.1039/jr9510003459

upstream raw materials:

2-Iodobenzoic acid

1-iodo-4-nitro-2-(trifluoromethyl)benzene

2-amino-5-nitro-benzoic acid

sulfuric acid

Downstream raw materials:

2-(2-Fluoro-phenylsulfanyl)-5-nitro-benzoic acid

2-(3-Methoxyphenylthio)-5-nitrobenzoesaeure

tert-butyl 2-iodo-5-nitrobenzoate

2-iodo-5-nitrobenzamide

Refernces

• 1、 Subramanian, Venkataraman,Batchu, Venkateswara Rao,Barange, Deepak,Pal, Manojit. "Synthesis of isocoumarins via Pd/C-mediated reactions of o-iodobenzoic acid with terminal alkynes". . p. 4778 - 4783. Retrieved 2005.
• 2、 Chand-Thakuri, Pratibha,Landge, Vinod G.,Kapoor, Mohit,Young, Michael C.. "One-Pot C-H Arylation/Lactamization Cascade Reaction of Free Benzylamines". . p. 6626 - 6644. Retrieved 2020/07/14.
• 3、 Ballaschk, Frederic,Kirsch, Stefan F.. "Oxidation of secondary alcohols using solid-supported hypervalent iodine catalysts". supporting information. p. 5896 - 5903. Retrieved 2019/11/11.