Lot numbers can be found on the outside label of a product:
5-Hydroxyisobenzofuran-1,3-dione
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CAS No. 27550-59-0
- Cat. No. CS-W022391
- Purity≥95%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
Structure of 27550-59-0
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General Information
- CAS No. 27550-59-0
- Cat. No. CS-W022391
- Purity ≥95%
- MDL No. None
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₈H₄O₄
- Molecular Weight 164.12
- Synonym(s) 5-hydroxy-2-benzofuran-1,3-dione
- SMILES O=C1OC(C2=C1C=CC(O)=C2)=O
Description
5-Hydroxyisobenzofuran-1,3-dione features a reactive ortho-quinone moiety flanked by a hydroxyl group, enabling direct participation in nucleophilic addition and cycloaddition processes. This bench-stable scaffold integrates readily into complex molecular architectures under mild conditions.
Application
5-Hydroxyisobenzofuran-1,3-dione serves as a versatile synthon in medicinal chemistry, enabling efficient access to substituted isobenzofuranone scaffolds. Its hydroxyl group facilitates direct derivatization and acts as a handle for orthogonal functionalization, while the quinone core supports electrophilic substitution and cycloaddition reactions. The compound exhibits sufficient bench stability for routine handling and purification, making it a practical building block for complex heterocyclic systems in API development.
Synthesis
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Route1
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In-stock
610-35-5 - ~99%
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In-stock
27550-59-0
References
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Dhanya, Raveendra-Panickar; Sidique, Shyama; Sheffler, Douglas J.; Nickols, Hilary Highfield; Herath, Ananda; Yang, Li; Dahl, Russell; Ardecky, Robert; Semenova, Svetlana; Markou, Athina; Conn, P. Jeffrey; Cosford, Nicholas D. P. Journal of Medicinal Chemistry, 2011 , vol. 54, # 1 p. 342 - 353
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Route2
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89-08-7 - ~%
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In-stock
27550-59-0
References
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IVOCLAR VIVADENT AG; BOCK, Thorsten; FISCHER, Urs Karl; LAMPARTH, Iris; MOSZNER, Norbert; RHEINBERGER, Volker Patent: US2013/90404 A1, 2013 ;
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Route3
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64139-21-5 - ~%
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In-stock
27550-59-0
References
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Baeyer Chemische Berichte, 1877 , vol. 10, p. 1079
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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 63.6
- LogP 0.7028
- H_Acceptors 4
- H_Donors 1
- Rotatable_Bonds 0
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Key Words
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