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1-Hydroxybenzotriazole

CAS：2592-95-2
MW:135.126
MF：C6H5N3O

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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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

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: 219-989-7

1.6 Molecular Formula: C6H5N3O

1.7 Inchi: InChI=1S/C6H5N3O/c10-9-6-4-2-1-3-5(6)7-8-9/h1-4,10H

1.8 InChkey: 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 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 Description

1-Hydroxybenzotriazole, with the chemical formula C6H5N3O, has the CAS number 2592-95-2. It appears as a white to off-white crystalline powder with no distinct odor. The basic structure of 1-Hydroxybenzotriazole consists of a benzene ring fused with a triazole ring, with a hydroxyl group attached to the benzene ring. This compound is soluble in water and organic solvents. Safety information regarding 1-Hydroxybenzotriazole is not available.

Applicable Fields

Chemical Synthesis: 1-Hydroxybenzotriazole is commonly used as an additive in chemical synthesis reactions. Its purpose in this field involves its ability to act as a coupling agent, facilitating the formation of amide bonds between amino acids or peptides. The mechanism of action in chemical synthesis involves the activation of carboxylic acids, enabling them to react with amines and form stable amide bonds.

Storage

Conditions: Store in a cool and dry place.

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3.2 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

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3.3 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.] 1-Hydroxybenzotriazole Preparation Products And Raw materials Preparation Products

3.4 Usage: additive for oligonucleotide couplings and in racemization-free peptide couplings

4. Safety and Handling

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.

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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

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

Mass spectrum (electron ionization)

7. Synthesis Route

2592-95-2Total: 18 Synthesis Route

88-73-3

2592-95-2 428 Suppliers

98-95-3 66 Suppliers

2592-95-2 428 Suppliers

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8. Precursor and Product

precursor:

64-17-5

2216-12-8

98-95-3

2217-65-4

95-14-7

91-23-6

22713-34-4

2075-46-9

product:

2867-65-4

82911-71-5

90298-76-3

73941-88-5

89028-37-5

95-14-7

54769-36-7

22713-34-4

73941-89-6

9. Computed Properties

Molecular Weight：135.126g/mol
Molecular Formula：C₆H₅N₃O
Compound Is Canonicalized：True
XLogP3-AA：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.Other Information

Chemical Properties: white to light yellow powder

Uses: additive for oligonucleotide couplings and in racemization-free peptide couplings

Uses: 1-Hydroxybenzotriazole (HOBT) is used in preparation method of carbon fiber/polyamide composite powder material for laser sintering.

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.]

Mesh Entry Terms: 1-hydroxybenzotriazole

Manufacturing Info: 1H-Benzotriazole, 1-hydroxy-: ACTIVE

Use Classification: Corrosion inhibitors -> Transformation products

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12. Related Questions

: What Makes 1-Hydroxybenzotriazole Essential in Organic Chemistry?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..; What is 1-Hydroxybenzotriazole (HOBT) and how is it synthesized?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..

13. Realated Product Infomation