2-iodosylbenzoic acid

• ChemBase ID: 91435
• Molecular Formular: C7H5IO3
• Molecular Mass: 264.01727
• Monoisotopic Mass: 263.92834202
• SMILES: [I](=O)c1c(cccc1)C(=O)O
• Canonical SMILES: O=[I]c1ccccc1C(=O)O
• InChI: InChI=1S/C7H5IO3/c9-7(10)5-3-1-2-4-6(5)8-11/h1-4H,(H,9,10)
• InChIKey: IFPHDUVGLXEIOQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-iodosylbenzoic acid
• IUPAC Traditional name: o-iodosobenzoic acid
• Synonyms: Iodosyl benzoic acid; 2-Iodosobenzoic acid; o-IODOSOBENZOIC ACID; 2-Iodosobenzoic acid; Iodosylbenzoic acid; 2-亚碘酰基苯甲酸

Database IDs

• CAS Number: 304-91-6
• EC Number: 206-159-4
• MDL Number: MFCD00002401
• Beilstein Number: 1939973
• PubChem SID: 24896131; 162078134
• PubChem CID: 67537

CALCULATED PROPERTIES

• Acid pKa: 3.0489004
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.003348205
• LogD (pH = 7.4): -1.0473341
• Log P: 2.4211574
• Molar Refractivity: 48.1196 cm^3
• Polarizability: 19.42996 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 230 °C (dec.)(lit.); ca 230°C dec.

Safety Information

• Storage Condition: 0°C
• Storage Warning: Irritant; Light Sensitive
• RTECS: DH3056550
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: 97%

DETAILS

MP Biomedicals - 02102068

Crystalline
Reagent for chemical cleavage at tryptophyl and tyrosyl residues.

Sigma Aldrich - I8000

Application
For cleavage of tryptophanyl peptide bonds.

REFERENCES

• Mahoney, W.C., Biochemistry , 20 : 443, (1981).
• Reagent for ɑ-hydroxylation of ketones; the by-product benzoic acid is easily removed by base extraction: Tetrahedron Lett., 25, 691 (1984). For an example, see: Org. Synth. Coll., 7, 263 (1990).
• Catalyst for cleavage of toxic phosphates and reactive esters: Tetrahedron Lett., 28, 251 (1987); J. Am. Chem. Soc., 108, 788 (1986); 116, 4471 (1994).
• Probably exists as the cyclized form 1-Hydroxy-1,1-dihydro-1,2-benzodioxol-3(1H)-one; CAS registry no. [161-62-4].
• For a review of polyvalent iodine compounds, see: Chem. Rev., 96, 1123 (1996).