3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol

• ChemBase ID: 34943
• Molecular Formular: C5H4N4O
• Molecular Mass: 136.11146
• Monoisotopic Mass: 136.03851077
• SMILES: n1(nnc2c1nccc2)O
• Canonical SMILES: On1nnc2c1nccc2
• InChI: InChI=1S/C5H4N4O/c10-9-5-4(7-8-9)2-1-3-6-5/h1-3,10H
• InChIKey: FPIRBHDGWMWJEP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol
• IUPAC Systematic name: 3-Hydroxytriazolo[4,5-b]pyridine
• IUPAC Traditional name: 1-hydroxy-7-azabenzotriazole
• Synonyms: [1,2,3]Triazolo[4,5-b]pyridin-3-ol; 1H-[1,2,3]triazolo[4,5-b]pyridine 3-Oxide; HOAt.; 3H-[1,2,3]Triazolo[4,5-b]pyridin-3-ol; 1-Hydroxy-7-azabenzotriazole; HOAt; 3H-[1,2,3]-Triazolo[4,5-b]pyridin-3-ol; 1-Hydroxy-7-azabenzotriazole solution; 3H-[1,2,3]-三唑[4,5-b]吡啶-3-醇; N-羟基-7-偶氮苯并三氮唑 溶液

Database IDs

• CAS Number: 39968-33-7
• MDL Number: MFCD00210053
• Beilstein Number: 1211115
• PubChem SID: 24879800; 160998250; 24866289
• PubChem CID: 181649
• Chemspider ID: 158005
• Wikipedia Title: 1-Hydroxy-7-azabenzotriazole

CALCULATED PROPERTIES

• Acid pKa: 4.878624
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.9290792
• LogD (pH = 7.4): -2.3647661
• Log P: -0.22123325
• Molar Refractivity: 43.9377 cm^3
• Polarizability: 12.874772 Å^3
• Polar Surface Area: 63.83 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 217-218°C
• Flash Point: 136.4 °F; 58 °C
• Density: 0.973 g/mL at 20 °C
• Refractive Index: n20/D 1.4390; n20/D 1.441

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT
• European Hazard Symbols: Toxic (T)
• UN Number: 1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3
• Risk Statements: 61-20/21-36
• Safety Statements: 53-26-36/37-45
• TSCA Listed: false
• GHS Pictograms: GHS02; GHS05; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H302 + H312 + H332-H318-H360D
• GHS Precautionary statements: P201-P280-P305 + P351 + P338-P308 + P313
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 3

Product Information

• Purity: 95+%
• Concentration: ~0.6 M in DMF; 0.5-0.7 M in DMF
• Impurities: <1.0% water
• Empirical Formula (Hill Notation): C5H4N4O

DETAILS

Sigma Aldrich - 41996

Other Notes
Coupling additive for efficient racemization-free coupling in peptide synthesis;1,2,3 segment coupling.4

Sigma Aldrich - 559156

Caution
Material is currently undergoing additional testing for DOT shipping approval. This material will be on back order for an indefinite period of time until testing is complete. In many cases, 157260 may be used as a replacement for this product.
Packaging
200 mL in glass bottle