Lot numbers can be found on the outside label of a product:
5-Bromo-2-nitroaniline
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CAS No. 5228-61-5
- Cat. No. CS-W003590
- Purity≥97%
- MDL No.MFCD09056836
*For research and further manufacturing use only, not for direct human use.
Structure of 5228-61-5
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General Information
- CAS No. 5228-61-5
- Cat. No. CS-W003590
- Purity ≥97%
- MDL No. MFCD09056836
- Storage 4°C, protect from light
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₆H₅BrN₂O₂
- Molecular Weight 217.02
- Synonym(s) 5-bromo-2-nitrobenzenamine
- SMILES NC1=CC(Br)=CC=C1[N+]([O-])=O
Description
5-Bromo-2-nitroaniline features a bromine substituent at the 5-position and a nitro group at the 2-position, creating a highly electron-deficient aromatic core. This combination enables selective coupling reactions in synthetic chemistry, particularly in palladium-catalyzed cross-couplings. The molecule exhibits enhanced stability under standard bench conditions and serves as a key intermediate in the synthesis of functionalized heterocycles and advanced materials.
Application
5-Bromo-2-nitroaniline serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling direct access to substituted anilines via selective reduction. Its bromine and nitro groups provide orthogonal handles for cross-coupling reactions (e.g., Suzuki, Stille) and subsequent functionalization. The compound exhibits good bench stability and is readily purified by recrystallization, facilitating integration into multi-step synthetic sequences.
Synthesis
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Route1
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In-stock
51686-78-3 - ~93%
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In-stock
5228-61-5
References
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ELI LILLY AND COMPANY Patent: WO2004/14900 A1, 2004 ; Location in patent: Page 24; 58 ; WO 2004/014900 A1
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Route2
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586-78-7 - ~81%
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In-stock
5228-61-5
References
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METHYLGENE INC. Patent: WO2007/118137 A1, 2007 ; Location in patent: Page/Page column 109-110 ;
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Route3
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In-stock
593-56-6 -
586-78-7
- ~73%
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In-stock
5228-61-5
References
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METHYLGENE, INC. Patent: WO2005/30704 A1, 2005 ; Location in patent: Page/Page column 138 ;
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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 69.16
- LogP 1.9395
- H_Acceptors 3
- H_Donors 1
- Rotatable_Bonds 1
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Key Words
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