3-Azido-7-hydroxycoumarin

Base Information

• Chemical Name: 3-Azido-7-hydroxycoumarin
• CAS No.: 817638-68-9
• Molecular Formula: C9H5N3O3
• Molecular Weight: 203.157
• Hs Code.: 2932209090
• Mol file: 817638-68-9.mol

Synonyms:3-Azido-7-hydroxy-chromen-2-one;

Chemical Property of 3-Azido-7-hydroxycoumarin

Chemical Property:

• Melting Point: 118-120℃
• PSA: 100.19000
• LogP: 1.89316
• Storage Temp.: -20°C
• Solubility.: DMSO (Slightly)

Purity/Quality:

99%min ^*data from raw suppliers

3-Azido-7-hydroxycoumarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: This special UV active chromophore is ideal for imaging purposes after conjugation to biomolecules. It emits fluorescence only after the click reaction when its electron system is expanded. Therefore no background signal is expected for the unreacted compound. λabs 404 nm (after click reaction), λem 477 nm (after click reaction ). 3-Azido-7-hydroxycoumarin, is a Fluorescent dye that has shown to quickly and efficiently label proteins in bicarbonate buffered solns. ( Abs/Em = 404/477 nm )

Technology Process of 3-Azido-7-hydroxycoumarin

There total 6 articles about 3-Azido-7-hydroxycoumarin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 52.2%

3-acetamido-2-oxo-2H-chromen-7-yl acetate (69019-75-6) → 3-azido-7-hydroxycoumarin (817638-68-9)

Guidance literature:

3-acetamido-2-oxo-2H-chromen-7-yl acetate; With hydrogenchloride; In ethanol; water; for 1h; Reflux;

With sodium nitrite; In ethanol; water; Cooling with ice;

With sodium azide; In ethanol; water; for 1h;

DOI:10.1021/ml5004298

Reference yield: 33.0%

N-acetylglycine (543-24-8) + 2,4-Dihydroxybenzaldehyde (95-01-2) → 3-azido-7-hydroxycoumarin (817638-68-9)

Guidance literature:

N-acetylglycine; 2,4-Dihydroxybenzaldehyde; With sodium acetate; acetic anhydride; for 8h; Reflux;

With hydrogenchloride; In ethanol; water; for 1h; Further stages; Reflux;

DOI:10.1016/j.tetlet.2008.11.107

Reference yield: 25.0%

3-acetylamino-7-hydroxy-2H-1-benzopyran-2-one (79418-42-1) → 3-azido-7-hydroxycoumarin (817638-68-9)

Guidance literature:

3-acetylamino-7-hydroxy-2H-1-benzopyran-2-one; With hydrogenchloride; In ethanol; water; for 1h; Reflux;

With sodium nitrite; In ethanol; water; at 0 ℃; for 0.333333h;

With sodium azide; In ethanol; water; at 0 ℃; for 0.25h;

DOI:10.1002/chem.201404502

upstream raw materials:

3-acetamido-2-oxo-2H-chromen-7-yl acetate

2,4-Dihydroxybenzaldehyde

N-acetylglycine

3-amino-7-hydroxy-2H-chromen-2-one

Refernces

• 1、 Ivanova, Irina M.,Nepogodiev, Sergey A.,Saalbach, Gerhard,O'Neill, Ellis C.,Urbaniak, Michael D.,Ferguson, Michael A.J.,Gurcha, Sudagar S.,Besra, Gurdyal S.,Field, Robert A.. "Fluorescent mannosides serve as acceptor substrates for glycosyltransferase and sugar-1-phosphate transferase activities in Euglena gracilis membranes". . p. 26 - 38. Retrieved 2017.
• 2、 Hems, Edward S.,Wagstaff, Ben A.,Saalbach, Gerhard,Field, Robert A.. "CuAAC click chemistry for the enhanced detection of novel alkyne-based natural product toxins". . p. 12234 - 12237. Retrieved 2018.
• 3、 Ngororabanga, Jean Marie Vianney,Okerio, Jaspher,Mama, Neliswa. "Synthesis of fluorescent poly(coumarin-triazoles) via a CuAAC 'click' reaction". . p. 89 - 93. Retrieved 2017/06/27.