| Identification | More | [Name]
1-Hydroxybenzotriazole | [CAS]
2592-95-2 | [Synonyms]
1H-BENZOTRIAZOLE, 1-HYDROXY-
1-HOB
1-HYDROXY-1,2,3-BENZOTRIAZOLE
1-HYDROXY-1-H-BENZOTRIAZOLE
1-HYDROXYBENZOTRIAZOL
1-HYDROXYBENZOTRIAZOLE
1-hydroxybenzotriazole anhydrous
1-HYDROXYLBENZOTRIAZOLE
BENZOTRIAZOL-1-OL
HBT
HOBT
HOBTA
HYDROXYBENZOTRIAZOLE
N-HYDROXYBENZOTRIAZOLE
1H-1,2,3-Benzotriazol-1-ol
1H-Benzotriazol-1-ol
Benzazimidol
1-Hydroxybenzotrizole
HOBt(anhydrous)
1-HYDROXYBENZOTRIAZOLE SOLUTION & | [EINECS(EC#)]
219-989-7 | [Molecular Formula]
C6H5N3O | [MDL Number]
MFCD00005805 | [Molecular Weight]
135.12 | [MOL File]
2592-95-2.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow powder | [Melting point ]
156-159°C | [Boiling point ]
149-150 °C | [density ]
1 g/cm3 | [vapor pressure ]
0.009Pa at 25℃ | [refractive index ]
n20/D 1.488 | [Fp ]
95 °C | [storage temp. ]
Store at RT. | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
7.39±0.58(Predicted) | [color ]
White to off-white crystalline powder | [Stability:]
Stable, but possible risk of explosion if heated under confinement. Flammable. | [Water Solubility ]
4.201g/L at 29℃ | [Detection Methods]
HPLC,NMR | [LogP]
0.146 at 25℃ | [CAS DataBase Reference]
2592-95-2(CAS DataBase Reference) | [NIST Chemistry Reference]
1H-benzotriazole, 1-hydroxy-(2592-95-2) | [Storage Precautions]
Heat sensitive | [EPA Substance Registry System]
2592-95-2(EPA Substance) |
| Questions And Answer | Back Directory | [Synthesis]
In a dry reaction flask, hydrazine hydrate (1.2 mL, 25 mmol) was added to a solution of o-nitrochlorobenzene (5 mmol) in 1-heptanol (10 mL), and the solution was stirred at 110–120 °C for 5 hours. After the reaction was complete, the reaction mixture was neutralized with 40% NaOH aqueous solvent, and excess hydrazine and 1-heptanol were removed under reduced pressure. The resulting residue was adjusted to pH 3.2–3.5 with 1M hydrochloric acid. The precipitate was collected by filtration, washed with cooled 5% sodium chloride aqueous solution, and finally purified by recrystallization of the precipitate in dichloromethane and methanol to obtain the target product molecule.
 Figure 1. Synthetic Route of 1-Hydroxybenzotriazole (HOBT) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS02 | [Signal word ]
Warning | [Hazard statements ]
H228 | [Precautionary statements ]
P210 | [Hazard Codes ]
F,Xi,T | [Risk Statements ]
R11:Highly Flammable.
R5:Heating may cause an explosion.
R36/38:Irritating to eyes and skin .
R36/37/38:Irritating to eyes, respiratory system and skin .
R36:Irritating to the eyes.
R20/21:Harmful by inhalation and in contact with skin .
R61:May cause harm to the unborn child. | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S33:Take precautionary measures against static discharges .
S7/9:Keep container tightly closed and in a well-ventilated place .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S53:Avoid exposure-obtain special instruction before use .
S15:Keep away from heat . | [RIDADR ]
1325 | [RTECS ]
DM1288000 | [TSCA ]
TSCA listed | [REACH Registrations]
Active | [HazardClass ]
4.1 | [PackingGroup ]
III | [HS Code ]
29339900 | [Toxicity]
rat,LDLo,oral,5gm/kg (5000mg/kg),Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 679, 1992. |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow powder | [Uses]
additive for oligonucleotide couplings and in racemization-free peptide couplings | [Definition]
ChEBI: 1-Hydroxybenzotriazole is a member of benzotriazoles. | [Flammability and Explosibility]
Notclassified | [Biological Activity]
hydroxy benzotriazole, abbreviated hobt, is anorganic compoundthat is a derivative of benzotriazole. hobt, as a commercial product, is a white crystalline powder contains some water (~11.7% wt as the hobt monohydrate crystal). it is mainly used to suppress the racemization of single-enantiomerchiral molecules and to improve the efficiency ofpeptide synthesis. automated peptide synthesisinvolves the condensation of the amino group of protected amino acidswith the activated ester. hobt can be used to produce activated esters such as n-hydroxysuccinimide ester. these esters are insoluble and react with amines at ambient temperature to give amides [1]. hobt is also used for the synthesis of amides from carboxylic acidsaside from amino acids. these substrates may not be convertible to theacyl chlorides [2]. for instance amide derivatives of ionophoric antibiotics have been prepared in this way [3]. | [target]
racemization | [Purification Methods]
Crystallise HOBt from aqueous EtOH or water. [Boyle & Jones J Chem Soc Perkin Trans II 160 1973, Tomita & Ikawa J Pharm Soc Jpn 75 449 1955, Beilstein 26 III/IV 95.] | [References]
[1]. knig w, geiger r. eineneuemethodezursynthese von peptiden: aktivierung der carboxylgruppemitdicyclohexylcarbodiimidunterzusatz von 1‐hydroxy‐benzotriazolen[j]. chemischeberichte, 1970, 103(3): 788-798.
[2]. myers a g, yang b h, chen h. transformation of pseudoephedrine amides into highly enantiomerically enriched aldehydes, alcohols, and ketones[j]. organic syntheses, 2000: 29-29.
[3]. owicki d, huczyński a, ratajczak-sitarz m, et al. structural and antimicrobial studies of a new n-phenylamide of monensin a complex with sodium chloride[j]. journal of molecular structure, 2009, 923(1): 53-59. |
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