Lot numbers can be found on the outside label of a product:
2-Bromo-4-nitroimidazole
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CAS No. 65902-59-2
- Cat. No. CS-D0919
- Purity≥97%
- MDL No.MFCD09038915
*For research and further manufacturing use only, not for direct human use.
Structure of 65902-59-2
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General Information
- CAS No. 65902-59-2
- Cat. No. CS-D0919
- Purity ≥97%
- MDL No. MFCD09038915
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₃H₂BrN₃O₂
- Molecular Weight 191.97
- Synonym(s) 2-Bromo-5-nitro-1H-imidazole
- SMILES O=[N+](C1=CNC(Br)=N1)[O-]
Description
2-Bromo-4-nitroimidazole is a halogenated imidazole featuring a nitro group at the para position, offering enhanced electrophilicity and stability under standard conditions. This electron-deficient heterocycle facilitates selective coupling reactions in synthetic medicinal chemistry and serves as a key intermediate for bioactive compound development.
Application
2-Bromo-4-nitroimidazole serves as a versatile building block in heterocyclic synthesis, enabling direct functionalization at the 2-position via palladium-catalyzed cross-coupling reactions. Its bromine moiety exhibits high reactivity in Suzuki, Stille, and Negishi couplings, while the nitro group provides strong electron-withdrawing character that stabilizes adjacent intermediates. The compound demonstrates excellent bench stability and facilitates efficient purification, making it well-suited for iterative synthesis of bioactive imidazole derivatives and pharmaceutical scaffolds.
Synthesis
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Route1
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In-stock
6154-30-9 - ~62%
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In-stock
65902-59-2
References
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SHIKOKU CHEMICALS CORPORATION Patent: EP2141151 A1, 2010 ; Location in patent: Page/Page column 8 ;
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Route2
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683276-47-3 - ~66%
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In-stock
65902-59-2
References
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Otsuka Pharmaceutical Company, Limited Patent: EP1553088 A1, 2005 ; Location in patent: Page/Page column 48-49 ;
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Route3
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5213-49-0
- ~30%
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In-stock
65902-59-2
References
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Suwinski, Jerzy; Salwinska, Ewa; Watras, Jan; Widel, Maria Polish Journal of Chemistry, 1982 , vol. 56, # 10-12 p. 1261 - 1272
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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
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Precautionary Statements : P264-P270-P280-P302+P352-P330-P362+P364-P501
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Quality Control
Computational Chemistry Data
- TPSA 71.82
- LogP 1.0804
- H_Acceptors 3
- H_Donors 1
- Rotatable_Bonds 1
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Key Words
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