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4-Azidobenzyl alcohol

Cat No.:V54655 Purity: ≥98%
4-Azidobenzyl alcohol is a dot chemical reagent containing an Azide (N3) moiety.
4-Azidobenzyl alcohol
4-Azidobenzyl alcohol Chemical Structure CAS No.: 31499-54-4
Product category: ADC Linker
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
4-Azidobenzyl alcohol is a dot chemical reagent containing an Azide (N3) moiety. 4-Azidobenzyl alcohol is a click chemical reagent. It has an Azide (N3) moiety and could undergo CuAAc (copper-catalyzed azide-alkyne cycloaddition reaction) with compounds bearing an Alkyne group. SPAAC (Strain-promoted alkyne-azide cycloaddition) may also happen with compounds bearing a BCN or DBCO group.
4-Azidobenzyl alcohol (CAS 31499-54-4) is a click chemistry reagent containing an azide (N3) moiety. Its molecular formula is C7H7N3O with a molecular weight of 149.2 g/mol. The compound features an azide group at the para (4-) position of the aromatic ring and a primary alcohol group. It can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions with molecules bearing alkyne groups. It can also undergo strain-promoted azide-alkyne cycloaddition (SPAAC) reactions with molecules containing DBCO or BCN groups.
Biological Activity I Assay Protocols (From Reference)
Targets
As a click chemistry reagent, 4-Azidobenzyl alcohol does not have a defined biological target. Its role is to serve as a chemical tool for bioconjugation and functionalization. The azide group enables bioorthogonal reactions with alkyne-bearing molecules, while the alcohol group provides a handle for further derivatization. The compound is commonly used in the development of photoaffinity labels, bioconjugates, and functionalized materials for chemical biology research.
ln Vitro
In cell-free biochemical systems, this compound is used as a click chemistry reagent for the labeling and modification of biomolecules. The azide group undergoes CuAAC reactions with molecules bearing alkyne groups. It can also undergo SPAAC reactions with molecules containing DBCO or BCN groups. The alcohol group can be further functionalized to attach various moieties. The compound serves as a protective group in organic synthesis.
ln Vivo
This compound does not exhibit direct cellular activity as it is a chemical reagent for bioconjugation. Biomolecules labeled with 4-Azidobenzyl alcohol can be delivered into cells for various functional studies. The azide functionality allows for subsequent click chemistry labeling within cells, enabling the study of biomolecule localization, trafficking, and interactions. The compound can be used to create photoaffinity labels for target identification.
Enzyme Assay
The standard procedure for using this compound involves click chemistry reactions between the azide group and alkyne-bearing molecules. The CuAAC reaction is typically performed in aqueous buffer with copper sulfate, sodium ascorbate, and a ligand such as TBTA. The SPAAC reaction is performed with DBCO or BCN-containing molecules without copper catalysis. The efficiency of labeling is assessed by mass spectrometry, HPLC, or TLC analysis. The alcohol group can be activated for further functionalization.
Cell Assay
No cell-based experimental protocols are directly applicable to this compound as it is a chemical reagent. Biomolecules labeled with 4-Azidobenzyl alcohol can be evaluated in cell culture experiments. Typical protocols include treating cells with azide-containing biomolecules followed by click chemistry labeling with fluorescent or affinity tags. The labeled biomolecules can be analyzed by fluorescence microscopy, flow cytometry, or Western blotting.
Animal Protocol
4-Azidobenzyl alcohol is not administered to animals as it is a chemical reagent for synthesis. Biomolecules labeled with this compound may be evaluated in animal models for various applications. Typical studies involve administration of labeled biomolecules to animals via appropriate routes. The azide functionality can be used for in vivo click chemistry labeling if suitable bioorthogonal reaction conditions are available.
ADME/Pharmacokinetics
As a chemical reagent, this compound does not have established pharmacokinetic properties. The compound is used in vitro for bioconjugation and labeling. Its stability, solubility, and reactivity are relevant for its use in chemical synthesis. The compound is typically stored at room temperature or 4°C. It has a melting point of 28-38°C. It is not intended for therapeutic use.
Toxicity/Toxicokinetics
The compound is not intended for therapeutic use and lacks established toxicity profiles. Standard laboratory safety precautions should be observed when handling this chemical reagent. The compound contains an azide group, which can be potentially explosive when heated or subjected to shock. Appropriate safety measures should be taken. The compound is for research use only and is not for human therapeutic applications.
References

[1]. Recent applications of click chemistry in drug discovery. Expert Opin Drug Discov. 2019 Aug;14(8):779-789.

Additional Infomation
4-Azidobenzyl alcohol is a research-grade chemical supplied for click chemistry and chemical biology applications. It is not an approved pharmaceutical and has no clinical trial history. The compound is a click chemistry reagent containing an azide group. It is commonly used in the development of photoaffinity labels, bioconjugates, and functionalized materials. This product is intended for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C7H7N3O
Molecular Weight
149.14998
Exact Mass
149.058
CAS #
31499-54-4
PubChem CID
11171062
Appearance
Light yellow to yellow solid powder
LogP
2
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
2
Heavy Atom Count
11
Complexity
157
Defined Atom Stereocenter Count
0
SMILES
N(C1C=CC(CO)=CC=1)=[N+]=[N-]
InChi Key
GEKVUCLUCOBNIE-UHFFFAOYSA-N
InChi Code
InChI=1S/C7H7N3O/c8-10-9-7-3-1-6(5-11)2-4-7/h1-4,11H,5H2
Chemical Name
(4-azidophenyl)methanol
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 : ~250 mg/mL (~1676.16 mM)
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.7047 mL 33.5233 mL 67.0466 mL
5 mM 1.3409 mL 6.7047 mL 13.4093 mL
10 mM 0.6705 mL 3.3523 mL 6.7047 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:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
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:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
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
  • Click the “Calculate” button
  • 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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