2-Iodobenzoic acid

Base Information

• Chemical Name: 2-Iodobenzoic acid
• CAS No.: 88-67-5
• Molecular Formula: C7H5IO2
• Molecular Weight: 248.02
• Hs Code.: 29163900
• European Community (EC) Number: 201-850-7,695-036-2
• NSC Number: 3772
• UNII: 7Q00V80J7Q
• DSSTox Substance ID: DTXSID6058976
• Nikkaji Number: J38.418F
• Wikipedia: 2-Iodobenzoic_acid
• Wikidata: Q2535469
• Metabolomics Workbench ID: 66949
• ChEMBL ID: CHEMBL112424
• Mol file: 88-67-5.mol

Synonyms:2-(Iodo-(125)I)-benzoic acid;USAF EK-572;o-Iodobenzoic acid;Benzoic acid, o-iodo-;Kyselina o-jodbenzoova [Czech];benzoic acid, 2-iodo-;

Chemical Property of 2-Iodobenzoic acid

Chemical Property:

• Appearance/Colour: white crystal powder
• Vapor Pressure: 0.000205mmHg at 25°C
• Melting Point: 160-164 2 °C
• Boiling Point: 313.9 °C at 760 mmHg
• PKA: 2.85(at 25℃)
• Flash Point: 143.6 °C
• PSA: 37.30000
• Density: 1.999 g/cm³
• LogP: 1.98940
• Storage Temp.: Refrigerator
• Sensitive.: Light Sensitive
• Solubility.: Soluble in dimethyl sulfoxide and methanol
• Water Solubility.: sparingly soluble
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 247.93343
• Heavy Atom Count: 10
• Complexity: 136

Purity/Quality:

99% ^*data from raw suppliers

2-Iodobenzoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41-36/37/38-20/21/22
• Safety Statements: 26-39-24/25-22-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Benzoic Acid Derivatives
• Canonical SMILES: C1=CC=C(C(=C1)C(=O)O)I
• General Description: **2-Iodobenzoic acid** is a chemical compound used as a reagent in organic synthesis, particularly in Cu-catalyzed coupling-cyclization reactions to form isocoumarins under greener conditions. It serves as a key substrate in ultrasound-mediated reactions, where it reacts with terminal alkynes in the presence of a CuI–K2CO3-PEG 400 system, demonstrating high regioselectivity and sustainability by avoiding toxic solvents and palladium catalysts. Its applications extend to pharmaceutical research, contributing to the synthesis of biologically active heterocycles. *(No relevant pharmacological conclusions from the first abstract; focus is on synthetic utility.)*

Technology Process of 2-Iodobenzoic acid

There total 102 articles about 2-Iodobenzoic 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%

C21H15IO3 → 2-Iodobenzoic acid (88-67-5)

Guidance literature:

With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid; In water; acetonitrile; at 20 ℃; for 1h; Irradiation;

DOI:10.1021/acscatal.7b02117

Reference yield: 100.0%

1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione (61717-82-6) → 2-Iodobenzoic acid (88-67-5)

Guidance literature:

With iodine; trifluoroacetic acid; 1,3,5-trimethyl-benzene; In acetonitrile;

DOI:10.1021/jo9007892

Reference yield: 99.0%

2-iodobenzaldehyde (26260-02-6) → 2-Iodobenzoic acid (88-67-5)

Guidance literature:

With potassium permanganate; tetrabutylammomium bromide; water; In dichloromethane; acetone; at 20 ℃; for 24h;

DOI:10.1002/ejoc.202001120

upstream raw materials:

m-iodonitrobenzene

potassium cyanide

ortho-methylphenyl iodide

1,2-Diiodobenzene

Downstream raw materials:

o-iodo-methyl-benzoic acid

1-acetoxy-1,2-benziodoxol-3-one

Ν-(quinolinyl)-o-aminobenzoic acid

benzene-1,2-dicarboxylic acid

Refernces

Potential psychotropic and anthistamine agents: 1- and 3-alkyl-9-(3-dimethylaminopropylidene)- thioxanthenes and 3-alkyl-11-piperazino-10,11-dihydrodibenzo[b,f]thiepins

10.1135/cccc19823134

The research explores the synthesis and pharmacological properties of various thioxanthene and dibenzo[b,f]thiepin derivatives. The study involves the use of chemicals such as 3-methylthiophenol, 3-ethylthiophenol, 2-iodobenzoic acid, (2-iodophenyl)acetic acid, potassium hydroxide, copper, sulfuric acid, polyphosphoric acid, 3-dimethylaminopropylmagnesium chloride, and various piperazine derivatives. These chemicals are used in a series of reactions to produce compounds with potential antihistamine and psychotropic activities. The synthesized compounds are tested for their pharmacological effects, including antihistamine activity, central depressant effects, cataleptic activity, and antireserpine activity. The research aims to investigate the impact of substituents in unusual positions on the pharmacological profiles of these compounds, with potential applications in treating conditions like gastric hyperacidity, ulcers, and central nervous system disorders.

Cu-catalyzed coupling-cyclization in PEG 400 under ultrasound: A highly selective and greener approach towards isocoumarins

10.1039/c3ra40969d

The study explores a CuI–K2CO3-PEG 400 catalytic system for the ultrasound-mediated coupling-cyclization of o-iodobenzoic acid with terminal alkynes to synthesize 3-substituted isocoumarins. This method is highlighted as a greener and more selective alternative to traditional approaches. The CuI acts as the catalyst, K2CO3 serves as the base, and PEG 400 functions both as a solvent and a ligand, facilitating the formation of isocoumarins with high regioselectivity. The process avoids the use of expensive or toxic palladium catalysts and harmful organic solvents, making it a more sustainable and practical option for producing isocoumarins, which have significant pharmacological interest.