Lot numbers can be found on the outside label of a product:
6-Iodoquinazoline-2,4(1H,3H)-dione
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CAS No. 16353-27-8
- Cat. No. CS-0060656
- Purity≥98%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
Structure of 16353-27-8
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General Information
- CAS No. 16353-27-8
- Cat. No. CS-0060656
- Purity ≥98%
- MDL No. None
- Storage 4°C, protect from light
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₈H₅IN₂O₂
- Molecular Weight 288.04
- Synonym(s) 6-iodo-1H-quinazoline-2,4-dione
- SMILES O=C(N1)NC2=C(C=C(I)C=C2)C1=O
Description
6-Iodoquinazoline-2,4(1H,3H)-dione features a reactive iodine atom at the C6 position, enabling direct functionalization in cross-coupling reactions. The quinazolinedione core provides enhanced solubility and stability under standard conditions, facilitating integration into medicinal chemistry campaigns targeting kinase inhibitors and bioactive heterocycles.
Application
6-Iodoquinazoline-2,4(1H,3H)-dione serves as a versatile building block for the synthesis of biologically active heterocycles, enabling palladium-catalyzed cross-coupling reactions with broad functional group tolerance. Its iodine substituent facilitates efficient C–C and C–heteroatom bond formation under mild conditions, while the quinazoline-dione core provides structural rigidity and hydrogen-bonding capacity. The compound exhibits excellent bench stability and ease of purification, making it well-suited for iterative synthesis in medicinal chemistry and process development workflows.
Synthesis
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Route1
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590-28-3 -
In-stock
5326-47-6 - ~90%
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In-stock
16353-27-8
References
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Gruenenthal GmbH Patent: US2009/69320 A1, 2009 ; Location in patent: Page/Page column 66 ;
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Route2
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In-stock
5326-47-6
- ~%
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In-stock
16353-27-8
References
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Ono Pharmaceutical Co., Ltd. Patent: US5436233 A1, 1995 ;
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References
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Smits, Rogier A.; Adami, Maristella; Istyastono, Enade P.; Zuiderveld, Obbe P.; Van Dam, Cindy M. E.; De Kanter, Frans J. J.; Jongejan, Aldo; Coruzzi, Gabriella; Leurs, Rob; De Esch, Iwan J. P. Journal of Medicinal Chemistry, 2010 , vol. 53, # 6 p. 2390 - 2400
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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 65.72
- LogP 0.821
- H_Acceptors 2
- H_Donors 2
- Rotatable_Bonds 0
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Key Words
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