2-Azidobenzaldehyde

Base Information

• Chemical Name: 2-Azidobenzaldehyde
• CAS No.: 16714-25-3
• Molecular Formula: C7H5N3O
• Molecular Weight: 147.136
• Hs Code.: 2929909090
• European Community (EC) Number: 843-812-8
• DSSTox Substance ID: DTXSID90447122
• Nikkaji Number: J82.537I
• Wikidata: Q82265921
• Mol file: 16714-25-3.mol

Synonyms:ortho-azidobenzaldehyde;2-azido-1-benzaldehyde;Benzaldehyde,2-azido;2-azidobenzenecarbaldehyde;azidobenzaldehyde;o-azidobenzaldehyde;2-azido-benzaldehyde;

Chemical Property of 2-Azidobenzaldehyde

Chemical Property:

• Melting Point: 35 °C
• PSA: 66.82000
• LogP: 1.89366
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 147.043261791
• Heavy Atom Count: 11
• Complexity: 186

Purity/Quality:

99%, ^*data from raw suppliers

2-Azidobenzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C=O)N=[N+]=[N-]
• Use Description: 2-Azidobenzaldehyde is a versatile compound with applications in various fields. In organic chemistry, it serves as a valuable building block for the synthesis of diverse organic molecules, including pharmaceuticals, agrochemicals, and specialty chemicals. Its azido group (N3) is a useful handle for introducing azide functionality into target molecules, which can subsequently be used for click chemistry reactions, allowing for the creation of complex molecular structures. In the field of materials science, 2-Azidobenzaldehyde can find use as a precursor for the preparation of functional polymers, resins, and coatings. Its role is fundamental in advancing chemical synthesis and materials development, with potential applications ranging from drug discovery to the design of advanced materials with tailored properties. Its significance varies within these fields, but it consistently plays a pivotal role in promoting innovation and scientific research.

Technology Process of 2-Azidobenzaldehyde

There total 14 articles about 2-Azidobenzaldehyde 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: 100.0%

2-nitro-benzaldehyde (552-89-6) → 2-azidobenzaldehyde (16714-25-3)

Guidance literature:

With sodium azide; In N,N,N,N,N,N-hexamethylphosphoric triamide; for 8h; Ambient temperature;

DOI:10.1021/jo00112a054

Reference yield: 98.0%

2-azidobenzyl alcohol (20615-76-3) → 2-azidobenzaldehyde (16714-25-3)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 25 ℃;

DOI:10.1016/j.tetlet.2007.03.121

Reference yield: 65.0%

2-nitro-benzaldehyde (552-89-6) → anthranil (271-58-9) + 2-azidobenzaldehyde (16714-25-3)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; for 20h; > 60 deg C;

DOI:10.1016/S0040-4039(97)01272-0

upstream raw materials:

o-aminobenzaldehyde

2-Aminobenzyl alcohol

2-azidobenzyl alcohol

2-nitro-benzaldehyde

Downstream raw materials:

1-(2-azidophenyl)ethan-1-ol

anthranil

1-(2-azidophenyl)-3-cyclopent-1-enylprop-2-yn-1-ol

Refernces

• 1、 Schwan,Davis. "More convenient syntheses 0f o-azidobenzaldehyde and 2-substituted indazoles.". . p. 877 - 878. Retrieved 1968.
• 2、 Kuznetsova, Lyubov I.,Chagarovskiy, Alexey O.,Levina, Irina I.,Rybakov, Victor B.,Ivanova, Olga A.,Trushkov, Igor V.. "A simple synthesis of 2-{2-[(arylmethylidene)amino]-indazol-3-yl}malonate esters". . p. 555 - 561. Retrieved 2020.
• 3、 Abeykoon, Gayan A.,Sahn, James J.,Martin, Stephen F.. "Novel substituted triazolo benzodiazepine scaffolds to explore chemical space". . . Retrieved 2021/02/16.
• 4、 Mazur, Maryna O.,Zhelavskyi, Oleksii S.,Zviagin, Eugene M.,Shishkina, Svitlana V.,Musatov, Vladimir I.,Kolosov, Maksim A.,Shvets, Elena H.,Andryushchenko, Anna Yu,Chebanov, Valentyn A.. "Effective microwave-assisted approach to 1,2,3-triazolobenzo-diazepinones via tandem Ugi reaction/catalyst-free intramolecular azide–alkyne cycloaddition". supporting information. p. 678 - 687. Retrieved 2021/04/09.