Lot numbers can be found on the outside label of a product:
2,3-dihydro-1,4-benzodioxine-6-carboxylic acid
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CAS No. 4442-54-0
- Cat. No. CS-W002623
- Purity≥97%
- MDL No.MFCD00463509
*For research and further manufacturing use only, not for direct human use.
Structure of 4442-54-0
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General Information
- CAS No. 4442-54-0
- Cat. No. CS-W002623
- Purity ≥97%
- MDL No. MFCD00463509
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₉H₈O₄
- Molecular Weight 180.16
- Synonym(s) None
- SMILES OC(=O)c1ccc2c(c1)OCCO2
Description
1,4-Benzodioxane-6-carboxylic acid features a rigid, electron-rich benzodioxane core that enhances metabolic stability and solubility. The carboxylic acid moiety enables direct conjugation or derivatization in synthetic routes. This scaffold serves as a key building block in medicinal chemistry, particularly for CNS-targeted compounds and bioactive heterocycles.
Application
1,4-Benzodioxane-6-carboxylic acid serves as a versatile building block for bioactive heterocycles, offering a rigid, electron-rich scaffold with predictable reactivity. Its carboxylic acid group enables straightforward derivatization via amide coupling, esterification, or decarboxylative functionalization. The benzodioxane core provides enhanced metabolic stability and favorable pharmacokinetic properties, making it a practical choice for medicinal chemistry campaigns targeting CNS-active compounds and kinase inhibitors.
Synthesis
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Route1
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In-stock
29668-44-8 - ~96%
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In-stock
4442-54-0
References
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Walker, Daniel P.; Wishka, Donn G.; Piotrowski, David W.; Jia, Shaojuan; Reitz, Steven C.; Yates, Karen M.; Myers, Jason K.; Vetman, Tatiana N.; Margolis, Brandon J.; Jacobsen, E. Jon; Acker, Brad A.; Groppi, Vincent E.; Wolfe, Mark L.; Thornburgh, Bruce A.; Tinholt, Paula M.; Cortes-Burgos, Luz A.; Walters, Rodney R.; Hester, Matthew R.; Seest, Eric P.; Dolak, Lester A.; Han, Fusen; Olson, Barbara A.; Fitzgerald, Laura; Staton, Brian A.; Raub, Thomas J.; Hajos, Mihaly; Hoffmann, William E.; Li, Kai S.; Higdon, Nicole R.; Wall, Theron M.; Hurst, Raymond S.; Wong, Erik H.F.; Rogers, Bruce N. Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 24 p. 8219 - 8248
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Route2
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In-stock
![6-Iodo-2,3-dihydrobenzo[b][1,4]dioxine|CS-0063836](https://file.chemscene.com/productPIC/CS-0063836.gif)
57744-67-9 -
109-77-3 - ~51%
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In-stock
4442-54-0
References
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Yang, Daoshan; Yang, Haijun; Fu, Hua Chemical Communications, 2011 , vol. 47, # 8 p. 2348 - 2350
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Route3
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590-29-4
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In-stock
![6-Bromo-2,3-dihydrobenzo[b][1,4]dioxine|CS-W002191](https://file.chemscene.com/productPIC/CS-W002191.gif)
52287-51-1 - ~93%
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In-stock
4442-54-0
References
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Korsager, Signe; Taaning, Rolf H.; Skrydstrup, Troels Journal of the American Chemical Society, 2013 , vol. 135, # 8 p. 2891 - 2894
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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 : H302-H315-H319-H335
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Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 55.76
- LogP 1.156
- H_Acceptors 3
- H_Donors 1
- Rotatable_Bonds 1
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Key Words
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