1-Hydroxy-7-azabenzotriazole

Base Information

• Chemical Name: 1-Hydroxy-7-azabenzotriazole
• CAS No.: 39968-33-7
• Molecular Formula: C5H4N4O
• Molecular Weight: 136.113
• Hs Code.: 29332990
• European Community (EC) Number: 433-840-5,609-760-3
• UNII: TX8XYH09H0
• DSSTox Substance ID: DTXSID0075239
• Nikkaji Number: J658.842E
• Wikipedia: 1-Hydroxy-7-azabenzotriazole
• Wikidata: Q4545784
• Mol file: 39968-33-7.mol

Synonyms:1-hydroxy-7-azabenzotriazole;7-aza-1-hydroxybenzotriazole

Chemical Property of 1-Hydroxy-7-azabenzotriazole

Chemical Property:

• Appearance/Colour: Clear, colorless liquid
• Vapor Pressure: 3.25E-06mmHg at 25°C
• Melting Point: 213-216 °C
• Refractive Index: n20/D 1.441
• Boiling Point: 376.8 °C at 760 mmHg
• PKA: 5.85±0.58(Predicted)
• Flash Point: 181.7 °C
• PSA: 63.83000
• Density: 1.74 g/cm³
• LogP: 0.06360
• Storage Temp.: Store at RT.
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 136.03851076
• Heavy Atom Count: 10
• Complexity: 131

Purity/Quality:

99% ^*data from raw suppliers

1-Hydroxy-7-azabenzotriazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, Xi, F, Xn, E
• Hazard Codes: T,Xi,F,Xn,E
• Statements: 61-20/21-36-5-36/37/38-11-41-37/38-22-2-36/37
• Safety Statements: 53-45-37/39-26-16-39-35-36-36/37-28-15

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(N=C1)N(N=N2)O
• Description: 1-Hydroxy-7-azabenzotriazole (HOAT) belongs to the category of organic compounds, specifically benzotriazoles. HOAT consists of a benzotriazole ring structure with a hydroxyl group attached to one of the aromatic rings.
• Uses: HOAT is primarily used as a peptide coupling reagent in organic synthesis and as a corrosion inhibitor for mild steel in acidic environments. HOAT acts as a corrosion inhibitor for mild steel in sulfuric acid by adsorbing onto the steel surface and forming a protective layer. It inhibits both cathodic and anodic processes of corrosion.It is also used in various fields including biological, chemical, and pharmaceutical industries.
• References: [1] Thermal hazard and pyrolysis mechanism investigation using thermal analysis coupled with quantum-chemical DFT simulation for 1-hydroxy-7-azabenzotriazole; DOI 10.1007/s10973-023-12068-6; [2] A combination of experiment and theoretical methods to study the novel and low-cost corrosion inhibitor 1-hydroxy-7-azabenzotriazole for mild steel in 1 M sulfuric acid; DOI 10.1039/C8RA06145A; [3] Blind crystal structure prediction of a novel second polymorph of 1-hy-droxy-7-azabenzotriazole; DOI 10.1107/S0108768106012584

Technology Process of 1-Hydroxy-7-azabenzotriazole

There total 13 articles about 1-Hydroxy-7-azabenzotriazole 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: 88.0%

C24H28N4O6S*2ClH + (S)-2-Hydroxy-3-methylbutanoic acid (17407-55-5) + HATU (200731-31-3,148893-10-1) → 1-hydroxy-7-aza-benzotriazole (39968-33-7) + C29H36N4O8S

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 16h;

Reference yield: 25.9%

3-methoxy-2-nitropyridine (20265-37-6) → 1-hydroxy-7-aza-benzotriazole (39968-33-7)

Guidance literature:

With hydrazine hydrate; Heating;

DOI:10.1016/0040-4020(96)00743-0

Reference yield:

C8H7BrN4O2 (1551373-17-1) → 1-hydroxy-7-aza-benzotriazole (39968-33-7) + 2-Bromopropionic acid (598-72-1,10327-08-9)

Guidance literature:

With water;

DOI:10.1002/jlcr.3111

upstream raw materials:

3-methoxy-2-nitropyridine

3-methoxy-3H-[1,2,3]triazolo[4,5-b]pyridine

sodium thiophenolate

morpholine

Downstream raw materials:

3-(2-(1-Z-pentenyl)phenyl)-E-acrylic acid hydroxyazo benzotriazolyl ester

Z-Aib-OAt

3-[benzo[1,3]dioxol-5-yl-([1,2,3]triazolo[4,5-b]pyridin-3-yloxycarbonyl)-methyl]-1-methyl-1H-indole-6-carboxylic acid benzyl ester

Refernces

A comparison of catalysts to promote imidazolide couplings including the identification of 2-hydroxy-5-nitropyridine as a new, safe, and effective catalyst

10.1021/op0580062

The research aimed to evaluate and compare the safety and catalytic effectiveness of five catalysts in promoting imidazolide couplings, a reaction type crucial for amide bond formation in pharmaceutical synthesis. The catalysts tested were 1-hydroxybenzotriazole (HOBt), 6-chloro-1-hydroxybenzotriazole (Cl-HOBt), 1-hydroxy-7-azabenzotriazole (HOAt), 2-hydroxypyridine (HOPy), and the newly identified 2-hydroxy-5-nitropyridine (NO2-HOPy). The study assessed reaction rate enhancement, shock sensitivity, and differential scanning calorimetry (DSC) data. The findings indicated that NO2-HOPy emerged as a safe, effective, and readily available alternative to the commonly used HOBt, offering a favorable balance between catalytic performance and safety. The research concluded that NO2-HOPy is a promising catalyst for imidazolide couplings, particularly given its lack of shock sensitivity and relatively high decomposition onset temperature, making it a safer option compared to the more hazardous HOAt.