2-iodobenzoic acid

• ChemBase ID: 11731
• Molecular Formular: C7H5IO2
• Molecular Mass: 248.01787
• Monoisotopic Mass: 247.9334274
• SMILES: c1ccc(c(c1)C(=O)O)I
• Canonical SMILES: OC(=O)c1ccccc1I
• InChI: InChI=1S/C7H5IO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10)
• InChIKey: CJNZAXGUTKBIHP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-iodobenzoic acid
• IUPAC Traditional name: 2-iodobenzoic acid
• Synonyms: 2-Iodo benzoic acid; 2-Iodobenzoic acid; o-Iodobenzoic acid; 2-Iodobenzoic acid; 2-Iodobenzoic acid 98%; 2-Iodobenzoic acid; o-IODOBENZOIC ACID; o-Iodobenzoic Acid; 2-Carboxyphenyl Iodide; NSC 3772; 3-Iodobenzenecarboxylic Acid; NSC 176131; NSC 74693; m-Carboxyiodobenzene; m-Iodobenzoic Acid; 3-Iodobenzoic Acid; 2-碘苯甲酸; 邻碘苯甲酸

Database IDs

• CAS Number: 88-67-5; 618-51-9
• EC Number: 201-850-7
• MDL Number: MFCD00002419
• Beilstein Number: 1861406
• Merck Index: 145030
• PubChem SID: 160975038; 24866223; 24896125; 24880558
• PubChem CID: 6941
• CHEBI ID: 287979
• CHEMBL: 112424
• Chemspider ID: 6675
• Wikipedia Title: 2-Iodobenzoic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.3004298
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.377326
• LogD (pH = 7.4): -0.86623657
• Log P: 2.5597732
• Molar Refractivity: 46.6767 cm^3
• Polarizability: 17.974607 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 159-162°C; 160-162 °C(lit.); 160-164°C; 161-162°C; 161-164 °C; 162°C; 162-163 °C; 162-163°C; 186-187°C
• Density: 2.250

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• Storage Warning: Irritant; IRRITANT, LIGHT SENSITIVE; Light Sensitive
• RTECS: DH2975000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38; 22-37/38-41
• Safety Statements: 26-36/37-60; 26-39
• TSCA Listed: true; 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H315-H318-H335; H302-H315-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95.0% (GC); ≥99%; 97%; 98%; 98+%
• Grade: purum
• Ignition Residue: ≤0.5%
• Purified By: sublimation
• Linear Formula: IC6H4CO2H

DETAILS

MP Biomedicals - 02151350

Light yellow crystals
Reagent for detection of SH-groups in proteins.

MP Biomedicals - 05207875

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 57730

Other Notes
Starting material for the preparation of iodosobenzoate, a useful oxidant. Protecting group for alcohols, the esters are cleaved oxidatively1

Sigma Aldrich - 418463

Packaging
1, 5 g in glass bottle

Sigma Aldrich - I7675

Packaging
25, 100 g in poly bottle

REFERENCES

• Can be used to protect alcohols as their 2-iodobenzoates by DCC coupling. The group is removed by oxidation with chlorine under basic conditions: Tetrahedron Lett., 28, 5005 (1987).
• In the presence of Tetrakis(triphenylphosphine)palladium(0), 10548, and zinc chloride, undergoes cyclization with terminal acetylenes to give isocoumarins: J. Org. Chem., 60, 3711 (1995):
  
• For related reactions, see 4,4-Dimethyl-2-pentyne, L10210, 2-Iodoaniline, A13059 and 2-Iodophenol, A13599.