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2-(2′-Hydroxyphenyl)benzimidazole

Cat No.:V67229 Purity: ≥98%
2-(2′-Hydroxyphenyl)benzimidazole is the most widely studied excited-state intramolecular proton transfer (ESIPT) molecule with normal and tautomer emissions.
2-(2′-Hydroxyphenyl)benzimidazole
2-(2′-Hydroxyphenyl)benzimidazole Chemical Structure CAS No.: 2963-66-8
Product category: Fluorescent Dye
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5g
Other Sizes
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Product Description
2-(2′-Hydroxyphenyl)benzimidazole is the most widely studied excited-state intramolecular proton transfer (ESIPT) molecule with normal and tautomer emissions. 2-(2′-Hydroxyphenyl)benzimidazole has been used as a fluorescent probe in various systems.
2-(2′-Hydroxyphenyl)benzimidazole (CAS#: 2963-66-8) is a fluorescent compound consisting of a benzimidazole core with a hydroxyphenyl substituent. The compound has a molecular formula of C₁₃H₁₀N₂O and a molecular weight of 210.23 g/mol. It exhibits excited-state intramolecular proton transfer (ESIPT) fluorescence, which results in a large Stokes shift and sensitivity to the local environment. The compound is used as a fluorescent probe for studying proton transfer reactions, as a pH indicator, and as a model compound for investigating ESIPT mechanisms.
Biological Activity I Assay Protocols (From Reference)
Targets
2-(2′-Hydroxyphenyl)benzimidazole does not target a specific protein or enzyme. Its utility as a fluorescent probe is based on its ESIPT properties, which make it sensitive to the local environment and proton transfer reactions.
ln Vitro
The in vitro activity of 2-(2′-Hydroxyphenyl)benzimidazole is characterized by its ESIPT fluorescence, which results in a large Stokes shift and sensitivity to the local environment. The compound is used as a fluorescent probe for studying proton transfer reactions and as a pH indicator.
ln Vivo
2-(2′-Hydroxyphenyl)benzimidazole is not used as a therapeutic agent. Its in vivo utility is limited to research applications as a fluorescent probe. The compound is not intended for systemic therapeutic use.
Enzyme Assay
In vitro assays for 2-(2′-Hydroxyphenyl)benzimidazole involve measuring its fluorescence properties under various conditions to study ESIPT mechanisms and proton transfer reactions. The compound can be used as a fluorescent probe to investigate molecular interactions and environmental effects.
Cell Assay
For in vitro cellular experiments, 2-(2′-Hydroxyphenyl)benzimidazole may be used as a fluorescent probe for imaging applications. Cells are incubated with the compound and analyzed by fluorescence microscopy.
Animal Protocol
In vivo animal experiments with 2-(2′-Hydroxyphenyl)benzimidazole are not typically performed, as the compound is primarily used as a fluorescent probe for in vitro studies. The compound is intended for research use only.
ADME/Pharmacokinetics
Pharmacokinetic properties of 2-(2′-Hydroxyphenyl)benzimidazole have not been characterized, as the compound is a research-use fluorescent probe rather than a drug candidate. The compound has a molecular weight of 210.23 g/mol and should be stored under appropriate conditions.
Toxicity/Toxicokinetics
Toxicological data for 2-(2′-Hydroxyphenyl)benzimidazole has not been systematically evaluated, as the compound is intended for research applications only and not for therapeutic use. Standard laboratory safety precautions should be observed.
References

[1]. Excited state proton transfer of 2-(2'-hydroxyphenyl)benzimidazole and its nitrogen substituted analogues in bovine serum albumin. Photochem Photobiol Sci. 2014 Sep;13(9):1297-304.

Additional Infomation
Structure in the first source
2-(2′-Hydroxyphenyl)benzimidazole is a fluorescent compound exhibiting ESIPT fluorescence, used as a fluorescent probe for studying proton transfer reactions and as a pH indicator. The compound has no clinical or therapeutic applications.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C13H10N2O
Molecular Weight
210.23
Exact Mass
210.079
CAS #
2963-66-8
PubChem CID
18075
Appearance
Light yellow to yellow solid powder
Density
1.289g/cm3
Boiling Point
388.6ºC at 760mmHg
Melting Point
239-243ºC
Flash Point
167.6ºC
Vapour Pressure
0mmHg at 25°C
Index of Refraction
1.726
LogP
2.935
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Heavy Atom Count
16
Complexity
246
Defined Atom Stereocenter Count
0
SMILES
C1=CC=C(C(=C1)C2=NC3=CC=CC=C3N2)O
InChi Key
XWXMGTIHBYFTIE-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H10N2O/c16-12-8-4-1-5-9(12)13-14-10-6-2-3-7-11(10)15-13/h1-8,16H,(H,14,15)
Chemical Name
2-(1H-benzimidazol-2-yl)phenol
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 100 mg/mL (475.67 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.89 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (11.89 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.7567 mL 23.7835 mL 47.5670 mL
5 mM 0.9513 mL 4.7567 mL 9.5134 mL
10 mM 0.4757 mL 2.3783 mL 4.7567 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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