pyridin-2-ol

• ChemBase ID: 75304
• Molecular Formular: C5H5NO
• Molecular Mass: 95.0993
• Monoisotopic Mass: 95.03711379
• SMILES: n1c(cccc1)O
• Canonical SMILES: Oc1ccccn1
• InChI: InChI=1S/C5H5NO/c7-5-3-1-2-4-6-5/h1-4H,(H,6,7)
• InChIKey: UBQKCCHYAOITMY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: pyridin-2-ol
• IUPAC Traditional name: 2-pyridone
• Synonyms: pyridin-2-ol; 2-Hydroxypyridine; 2-Hydroxypyridine; 2-Pyridinone; 2(1H)-Pyridone; 2-Pyridinol; 2(1H)-吡啶酮; 2-吡啶醇; 2-羟基吡啶

Database IDs

• CAS Number: 72762-00-6; 142-08-5
• EC Number: 205-520-3
• MDL Number: MFCD00006268
• Beilstein Number: 105757; 105786
• PubChem SID: 162040222; 24895704; 24880131
• PubChem CID: 8871

CALCULATED PROPERTIES

• Acid pKa: 11.70069
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.0461084
• LogD (pH = 7.4): 1.0464396
• Log P: 1.0464656
• Molar Refractivity: 26.1955 cm^3
• Polarizability: 10.03658 Å^3
• Polar Surface Area: 33.12 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off White Solid
• Melting Point: 102-111°C; 104-108 °C; 105-107 °C(lit.); 105-107°C; 105-107°C
• Boiling Point: 280-281 °C(lit.); 280-281°C; 280-281°C
• Flash Point: 210°C(410°F)
• Density: 1.39

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: UV1144050
• European Hazard Symbols: Toxic (T)
• UN Number: UN2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: III
• Risk Statements: 25-36/37/38
• Safety Statements: 26-36/37-45; 26-45
• TSCA Listed: 是
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338; P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Product Information

• Purity: ≥97.0% (HPLC); 95+%; 97%; 98+%
• Grade: purum
• Impurities: ~1% water
• Empirical Formula (Hill Notation): C5H5NO

DETAILS

MP Biomedicals - 02151309

For preparation of activated esters of peptides and acylated amino acids.

MP Biomedicals - 05215559

MP Biomedicals Rare Chemical collection

Sigma Aldrich - H56800

Packaging
25, 100 g in poly bottle
Application
Catalyst for generating β-oxopropyl carbonates from cyclic carbonates and alcohols1 and in the aminolysis of a polyglutamate.2

Sigma Aldrich - 56380

Other Notes
Educt for the preparation of 1-(alkenyl)-2-pyridones, useful in Diels-Alder-reactions1

REFERENCES

• Bifunctional catalyst for a wide variety of acylation reactions. See, for example: J. Chem. Soc. (C), 89 (1969).
• Reacts with SOCl₂ to form di-2-pyridyl sulfite, a useful reagent for in situ formation of N-sulfinylamines, nitriles, isocyanides and carbodiimides under mild conditions: Tetrahedron Lett., 27, 1925 (1986).
• For use of 2-pyridyl esters as active esters in peptide coupling, see: J. Chem. Soc.(C), 2896 (1971); Chem. Ber., 118, 468 (1985). The group can be introduced on to the N-protected peptide using DCC in pyridine, and is displaced by the amino-residue under mild conditions. For peptide reagents, see Appendix 6. Similar methodology has also been used in an improved preparation of trichloroethyl esters: Synthesis, 24 (1979).