Lot numbers can be found on the outside label of a product:
2-Methyl-5-nitropyrimidine-4,6-diol
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CAS No. 53925-27-2
- Cat. No. CS-0037967
- Purity≥97%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
Structure of 53925-27-2
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General Information
- CAS No. 53925-27-2
- Cat. No. CS-0037967
- Purity ≥97%
- MDL No. None
- Storage 4°C, stored under nitrogen
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₅H₅N₃O₄
- Molecular Weight 171.11
- Synonym(s) 6-hydroxy-2-methyl-5-nitro-4(3H)-pyrimidinone
- SMILES CC1=NC(=C(C(=N1)O)[N+](=O)[O-])O
Description
2-Methyl-5-nitropyrimidine-4,6-diol features a fused heterocyclic core with strategically positioned nitro and hydroxyl groups, enabling direct incorporation into bioactive scaffolds. The electron-deficient pyrimidine ring enhances reactivity in nucleophilic substitution, while the ortho-hydroxyl arrangement promotes tautomerization and metal chelation. This bench-stable compound serves as a key intermediate for pharmaceuticals and agrochemicals requiring polar, nitrogen-rich motifs.
Application
2-Methyl-5-nitropyrimidine-4,6-diol serves as a versatile building block in heterocyclic synthesis, enabling efficient access to substituted pyrimidines via nucleophilic displacement or reduction. The ortho-diol functionality enhances solubility and facilitates downstream derivatization, while the nitro group provides a handle for reductive transformations. Bench-stable and compatible with standard purification methods, it functions effectively in medicinal chemistry campaigns targeting kinase inhibitors and antiviral scaffolds.
Synthesis
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Route1
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In-stock
1193-24-4 - ~%
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In-stock
53925-27-2
References
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Deninno, Michael P.; Wright, Stephen W.; Etienne, John B.; Olson, Thanh V.; Rocke, Benjamin N.; Corbett, Jeffrey W.; Kung, Daniel W.; Dirico, Kenneth J.; Andrews, Kim M.; Millham, Michele L.; Parker, Janice C.; Esler, William; Van Volkenburg, Maria; Boyer, David D.; Houseknecht, Karen L.; Doran, Shawn D. Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 17 p. 5721 - 5726
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Route2
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7697-37-2 -
In-stock
1194-22-5 - ~%
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In-stock
53925-27-2
References
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DuPont Pharmaceuticals Company Patent: US6342503 B1, 2002 ; Location in patent: Example 101 ; US 6342503 B1
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Route3
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In-stock
1194-22-5
- ~85%
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In-stock
53925-27-2
References
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Beck, James P.; Arvanitis, Argyrios G.; Curry, Matt A.; Rescinito, Joseph T.; Fitzgerald, Larry W.; Gilligan, Paul J.; Zaczek, Robert; Trainor, George L. Bioorganic and Medicinal Chemistry Letters, 1999 , vol. 9, # 7 p. 967 - 972
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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-P280-P302+P352
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Quality Control
Computational Chemistry Data
- TPSA 109.38
- LogP 0.10442
- H_Acceptors 6
- H_Donors 2
- Rotatable_Bonds 1
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Key Words
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