| Identification | More | [Name]
1-Hydroxy-7-azabenzotriazole | [CAS]
39968-33-7 | [Synonyms]
3H-[1,2,3]-TRIAZOLO[4,5-B]PYRIDIN-3-OL
3H-1,2,3-TRIAZOLO[4,5-B]PYRIDINE, 3-HYDROXY-
7-AZA-1-HYDROXYBENZOTRIAZOLE
HOAT
1-HYDROXY-7-AZABENZOTRIAZOLE 0.5 TO &
1-HYDROXY-7-AZABENZOTRIAZOLE SOLUTION, 0.5M IN DMF
HOAT [1-HYDROXY-7-AZABENZOTRIAZOLE]
1-Hydroxy-7-Azabenzotriazole99%Puriss
[1,2,3]Triazolo[4,5-b]pyridin-3-ol
1H-[1,2,3]triazolo[4,5-b]pyridine 3-Oxide
1-Hydroxy-7-azabenzotriazole solution
1-Hydroxy-7-azabenotriazole
1-Hydroxy-7-azabenzotriazole (HOAt)
1-HYDROXY-7-AZABENZOTRIAZOL
HO-EPCP
1-Hydroxy-7-azabenzotriazole solution, 0.6 M in DMF
[1,2,3]Triazolo[4,5-β]pyridin-3-ol
1H-[1,2,3]triazolo[4,5-β]pyridine 3-Oxide
3H-[1,2,3]-Triazolo[4,5-b]pyridin-3-ol, HOAt
1-Hydroxy-7-azabenzotriazole ,98% | [EINECS(EC#)]
609-760-3 | [Molecular Formula]
C5H4N4O | [MDL Number]
MFCD00210053 | [Molecular Weight]
136.11 | [MOL File]
39968-33-7.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear, colorless liquid | [Melting point ]
213-216°C | [Boiling point ]
250.36°C (rough estimate) | [density ]
0.973 g/mL at 20 °C
| [refractive index ]
n20/D 1.441
| [Fp ]
213-216°C | [storage temp. ]
Store at RT. | [solubility ]
>6.8mg/mL in DMSO | [form ]
Powder | [pka]
5.85±0.58(Predicted) | [color ]
White to yellow | [Decomposition ]
213-216 ºC | [Detection Methods]
HPLC | [InChI]
InChI=1S/C5H4N4O/c10-9-5-4(7-8-9)2-1-3-6-5/h1-3,10H | [InChIKey]
FPIRBHDGWMWJEP-UHFFFAOYSA-N | [SMILES]
C12N(O)N=NC1=CC=CN=2 | [CAS DataBase Reference]
39968-33-7(CAS DataBase Reference) | [EPA Substance Registry System]
39968-33-7(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T,Xi,F,Xn,E | [Risk Statements ]
R61:May cause harm to the unborn child.
R20/21:Harmful by inhalation and in contact with skin .
R36:Irritating to the eyes.
R5:Heating may cause an explosion.
R36/37/38:Irritating to eyes, respiratory system and skin .
R11:Highly Flammable.
R41:Risk of serious damage to eyes.
R37/38:Irritating to respiratory system and skin .
R22:Harmful if swallowed.
R2:Risk of explosion by shock, friction, fire or other sources of ignition. | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S16:Keep away from sources of ignition-No smoking .
S39:Wear eye/face protection .
S35:This material and its container must be disposed of in a safe way .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 1993 3/PG 3
| [WGK Germany ]
1
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [PackingGroup ]
Ⅱ | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Description]
HOAt (also known as 1-Hydroxy-7-azabenzotriazole) is a benzotriazole compound commonly used as a coupling reagent for amino acids and peptides. HOAt is also used as a solid-phase synthesis reagent for chiral peptide nucleic acids. | [Chemical Properties]
Clear, colorless liquid | [Uses]
1-Hydroxy-7-azabenzotriazole can be used as antibacterial, anti-aging and flame-retardant dendritic polyacrylate emulsion. | [Application]
HOAt is a triazole derivative used in amide coupling chemistry as an additive in combination with coupling agents. The most used coupling reagents with HOAt are the carbodiimides EDCI, DCC and DIC. HOAt is comparable to HOBt but gives a better performance. It has faster reaction rates, reduced racemisation, higher yields and visual indication of the reaction endpoint by colour change of the reaction mixture from yellow to colourless. The increased efficiency of HOAt compared to HOBt is related to the stabilisation of the activated intermediate via anchimeric effect, due to the formation of a hydrogen bond with the N atom in position 7 of the benzotriazole. As is HOBt, HOAt is explosive and is therefore required to be handled carefully. | [General Description]
HOAt is a commonly used peptide bond forming agent that may become an impurity in drug synthesis, but is not mutagenic. HOAt can be used for peptide fragment polycondensation and can also inhibit the racemization of peptide polycondensation. | [reaction suitability]
reaction type: Addition Reactions | [Precautions]
3-Hydroxy-3H-1,2,3-triazolo[4,5-b]pyridine is stable, not hygroscopic, and can be stored indefinitely. HOAt (3-Hydroxy-3H-1,2,3-triazolo[4,5-b]pyridine) solutions in DMF (0.3 M) can be stored in an inert atmosphere for weeks. Syntheses of peptides carried out with freshly prepared and 4-week-old solutions show similar quality to the crude product. Violent decomposition may occur when dried at elevated temperatures.
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