Lot numbers can be found on the outside label of a product:
2,2'-Azanediyldibenzoic acid
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CAS No. 579-92-0
- Cat. No. CS-0453838
- Purity≥98%
- MDL No.MFCD00012303
*For research and further manufacturing use only, not for direct human use.
Structure of 579-92-0
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General Information
- CAS No. 579-92-0
- Cat. No. CS-0453838
- Purity ≥98%
- MDL No. MFCD00012303
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₄H₁₁NO₄
- Molecular Weight 257.25
- Synonym(s) None
- SMILES O=C(O)C=1C=CC=CC1NC=2C=CC=CC2C(=O)O
Description
2,2'-Azanediyldibenzoic acid features a rigid, conjugated backbone with two carboxylic acid groups positioned ortho to a central azo linkage. This architecture enables robust coordination in metal-organic frameworks and facilitates integration into functional polymers. The molecule exhibits enhanced thermal stability and solubility in polar aprotic solvents, supporting its use in advanced materials synthesis under standard conditions.
Application
2,2'-Azanediyldibenzoic acid serves as a versatile bifunctional building block for the synthesis of conjugated polymers and functionalized ligands. Its dual carboxylic acid groups enable robust coupling reactions with diamines or diols, facilitating the construction of stable amide or ester linkages. The central azo linkage provides structural rigidity and enhances electronic delocalization, making it valuable in materials chemistry and coordination chemistry applications. Bench-stable and readily purified by recrystallization, it functions efficiently in standard peptide-like coupling protocols.
Synthesis
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Route1
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118-92-3 -
118-91-2 - ~85%
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In-stock
579-92-0
References
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Kamal, Ahmed; Srinivas; Ramulu; Ramesh; Kumar, P. Praveen Bioorganic and Medicinal Chemistry Letters, 2004 , vol. 14, # 15 p. 4107 - 4111
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Route2
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118-92-3
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In-stock
88-65-3 - ~93%
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In-stock
579-92-0
References
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Jahromi, Amin Haghighat; Fu, Yuan; Miller, Kali A.; Nguyen, Lien; Luu, Long M.; Baranger, Anne M.; Zimmerman, Steven C. Journal of Medicinal Chemistry, 2013 , vol. 56, # 23 p. 9471 - 9481
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Route3
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![Methyl 2-{[2-(Methoxycarbonyl)phenyl]amino}benzoate|CS-0764261](https://file.chemscene.com/productPIC/CS-0764261.gif)
34069-89-1 - ~78%
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In-stock
579-92-0
References
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Csuk, Rene; Barthel, Alexander; Raschke, Christian Tetrahedron, 2004 , vol. 60, # 27 p. 5737 - 5750
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H315-H319-H335
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Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 86.63
- LogP 2.8266
- H_Acceptors 3
- H_Donors 3
- Rotatable_Bonds 4
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