1-Hydroxybenzotriazole
- Iupac Name：1-hydroxybenzotriazole
- CAS No.: 2592-95-2
- Molecular Weight：135.126
- Modify Date.: 2022-11-25 01:17
- Introduction:
1-Hydroxybenzotriazole, with the chemical formula C6H5N3O and CAS registry number 2592-95-2, is a compound known for its applications in peptide synthesis and as a coupling reagent in organic chemistry. This white crystalline powder is characterized by its hydroxybenzotriazole functional group, which enhances the efficiency of peptide bond formation. It is commonly used in the synthesis of peptides and proteins, as it improves the yield and purity of the desired products. 1-Hydroxybenzotriazole is also used as a stabilizer for reactive intermediates and as an additive in polymerization reactions. Overall, this compound plays a crucial role in various chemical processes, particularly in the field of peptide chemistry.
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1. Names and Identifiers
- 1.1 Name
- 1-Hydroxybenzotriazole
- 1.2 Synonyms
1,2,3-Benzotriazol-1-ol 1H-1,2,3-Benzotriazole, 1-hydroxy- 1H-Benzo[d][1,2,3]triazol-1-ol 1H-Benzotriazol-1-ol 1-HOB 1-hydroxy benzotriazole 1-HYDROXY-1,2,3-BENZOTRIAZOLE 1-hydroxy-1H-1,2,3-benzotriazole 1-HYDROXY-1-H-BENZOTRIAZOLE 1-HYDROXYBENZOTRIAZOL 1-Hydroxybenzotriazole 〔HBT〕 1-hydroxybenzotriazole anhydrous 1-HYDROXYLBENZOTRIAZOLE 1-Methyl-2-pyrrolidinone 1-Oxy-benztriazol Benzazimidol BENZOTRIAZOL-1-OL EINECS 219-989-7 HBT HOBT HOBt solution HOBTA hydroxybenzotriazole MFCD00005805 N-hydroxy-benzotriazole N-Hydroxybenzotrizole
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- 1.3 CAS No.
- 2592-95-2
- 1.4 CID
- 75771
- 1.5 EINECS(EC#)
- 219-989-7
- 1.6 Molecular Formula
- C6H5N3O (isomer)
- 1.7 Inchi
- InChI=1S/C6H5N3O/c10-9-6-4-2-1-3-5(6)7-8-9/h1-4,10H
- 1.8 InChIkey
- ASOKPJOREAFHNY-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- C1=CC=C2C(=C1)N=NN2O
- 1.10 Isomers Smiles
- C1=CC=C2C(=C1)N=NN2O
2. Properties
- 2.1 Density
- 1.51
- 2.1 Melting point
- 156-159℃
- 2.1 Boiling point
- 344.6 °C at 760 mmHg
- 2.1 Refractive index
- n20/D 1.488
- 2.1 Flash Point
- 162.2 °C
- 2.1 Precise Quality
- 135.04300
- 2.1 PSA
- 61.80000
- 2.1 logP
- 0.66350
- 2.1 Appearance
- white to light yellow powder
- 2.2 Chemical Properties
- white to light yellow powder
- 2.3 Color/Form
- White to off-white crystalline powder
- 2.4 pKa
- 7.39±0.58(Predicted)
- 2.5 Water Solubility
- 8.4 [ug/mL]
- 2.6 Stability
- Stable, but possible risk of explosion if heated under confinement. Flammable.
- 2.7 StorageTemp
- Inert atmosphere,2-8°C
3. Use and Manufacturing
- 3.1 GHS Classification
- Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 115 companies from 6 notifications to the ECHA C&L Inventory.
H203 (98.26%): Explosive; fire, blast or projection hazard [Danger Explosives]
Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.
Precautionary Statement Codes
P210, P230, P240, P250, P280, P370+P380, P372, P373, P401, and P501
- 3.2 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.] 1-Hydroxybenzotriazole Preparation Products And Raw materials Preparation Products
- 3.3 Usage
- additive for oligonucleotide couplings and in racemization-free peptide couplings
4. Safety and Handling
- 4.1 Hazard Codes
- F
- 4.1 Risk Statements
- R11;R5
- 4.1 Safety Statements
- S16;S33;S7/9
- 4.1 Packing Group
- III
- 4.1 Hazard Class
- 4.1
- 4.1 Hazard Declaration
- H203
- 4.1 RIDADR
- 1325
- 4.1 Caution Statement
- P210, P230, P240, P250, P280, P370+P380, P372, P373, P401, P501
- 4.1 RTECS
- DM1288000
- 4.1 Safety
-
Hazard Codes:?
F,?
Xi,?
T
Risk Statements: 11-5-36/38-36/37/38-36-20/21-61?
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 eyes.?
R20/21:Harmful by inhalation and in contact with skin.?
R61:May cause harm to the unborn child.
Safety Statements: 16-33-7/9-26-45-53-15?
S16:Keep away from sources of ignition.?
S33:Take precautionary measures against static discharges.?
S7:Keep container tightly closed.?
S9:Keep container 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 the label whenever possible.)?
S53:Avoid exposure - obtain special instructions before use.?
S15:Keep away from heat.
RIDADR: 1325
RTECS: DM1288000
HazardClass: 4.1
PackingGroup: III
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- 4.2 Specification
-
?1-Hydroxybenzotriazole (CAS NO.2592-95-2) is also named as 1-Hydroxy-1H-benzotriazole hydrate ; 1-Hydroxybenzotriazole hydrate ; 4-26-00-00095 (Beilstein Handbook Reference) ; BRN 0004515 ; Benzazimidol hydrate ; CCRIS 2605 ; N-Hydroxybenzotriazole hydrate?.?1-Hydroxybenzotriazole (CAS NO.2592-95-2) is?white to light yellow powder. It reacts with activated acyl groups to form activated molecules that are referred to as activated esters. These esters are insoluble (like the N-hydroxysuccinimide esters) and react with amines at ambient temperature to give amides.
- 4.3 Toxicity
-
| Organism |
Test Type |
Route |
Reported Dose (Normalized Dose) |
Effect |
Source |
| rat |
LDLo |
oral |
5gm/kg (5000mg/kg) |
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) |
Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 679, 1992. |
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5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Explosives, Division 1.3
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Danger |
| Hazard statement(s) | H203 Explosive; fire, blast or projection hazard |
| Precautionary statement(s) | |
| Prevention | P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking. P230 Keep wetted with \u2026 P234 Keep only in original packaging. P240 Ground and bond container and receiving equipment. P250 Do not subject to grinding/shock/friction/\u2026. P280 Wear protective gloves/protective clothing/eye protection/face protection. |
| Response | P370+P372+P380+P373 In case of fire: Explosion risk. Evacuate area. DO NOT fight fire when fire reaches explosives. |
| Storage | P401 Store in accordance with\u2026 |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
2592-95-2Total: 18 Synthesis Route
8. Other Information
- 8.0 Chemical Properties
- white to light yellow powder
- 8.1 Uses
- additive for oligonucleotide couplings and in racemization-free peptide couplings
- 8.2 Uses
- 1-Hydroxybenzotriazole (HOBT) is used in preparation method of carbon fiber/polyamide composite powder material for laser sintering.
- 8.3 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.]
- 8.4 Mesh Entry Terms
- 1-hydroxybenzotriazole
- 8.5 Manufacturing Info
- 1H-Benzotriazole, 1-hydroxy-: ACTIVE
- 8.6 Use Classification
- Corrosion inhibitors -> Transformation products
9. Computational chemical data
- Molecular Weight: 135.126g/mol
- Molecular Formula: C6H5N3O
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 135.043261791
- Monoisotopic Mass: 135.043261791
- Complexity: 130
- Rotatable Bond Count: 0
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 3
- Topological Polar Surface Area: 50.9
- Heavy Atom Count: 10
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADcYBjIAAAAAAAAAAAAAAAAAAAAWAAAAAwAAAAAAAAAFgB8AAAHAAMCAAACAiBFgAwwLAQAACiASRiQACCBAQgEgA4mCAwdJgIYKKAkZGAIABggAAIyAcQAAAAAAAAAAAAACAAAAAAAAAAQAAAAAAAAA==
10. Question & Answer
-
Introduction 1-Hydroxybenzotriazole plays a crucial role in organic chemistry, especially in peptide synthesis. This compound, with the chemical formula C6H5N3O, is known for its ability to improve th..
-
1-Hydroxybenzotriazole (HOBT), also known as 1-Hydroxybenzotriazole, is a white or grayish-white crystalline solid at room temperature and pressure. It is commonly used as an organic synthesis and pha..
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