Lot numbers can be found on the outside label of a product:
6-Bromo-3-nitro-4-quinolinol
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CAS No. 853908-50-6
- Cat. No. CS-B0352
- Purity≥95%
- MDL No.MFCD09800413
*For research and further manufacturing use only, not for direct human use.
Structure of 853908-50-6
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General Information
- CAS No. 853908-50-6
- Cat. No. CS-B0352
- Purity ≥95%
- MDL No. MFCD09800413
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₉H₅BrN₂O₃
- Molecular Weight 269.05
- Synonym(s) 6-bromo-3-nitro-quinolin-4-ol
- SMILES OC1=C([N+]([O-])=O)C=NC2=CC=C(Br)C=C21
Description
6-Bromo-3-nitro-4-quinolinol offers a strategically positioned bromine and nitro group on a quinolinol scaffold, enabling direct functionalization in cross-coupling and cyclization reactions. The electron-deficient ring system enhances reactivity in transition-metal-catalyzed transformations, while the phenolic OH facilitates coordination and derivatization under mild conditions. This scaffold provides access to advanced heterocyclic architectures in medicinal chemistry and materials science.
Application
6-Bromo-3-nitro-4-quinolinol serves as a versatile building block for the synthesis of substituted quinoline derivatives. The bromo group enables palladium-catalyzed cross-coupling reactions, while the nitro function provides a handle for selective reduction and further functionalization. Its stability under standard bench conditions facilitates purification and integration into multi-step syntheses targeting pharmaceutical intermediates and agrochemical scaffolds.
Synthesis
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Route1
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1201643-75-5 - ~62%
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In-stock
853908-50-6
References
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PIRAMAL LIFE SCIENCES LIMITED; KUMAR, Sanjay; VISHWAKARMA, Ram; MUNDADA, Ramswaroop; DEORE, Vijaykumar; KUMAR, Pramod; SHARMA, Somesh Patent: WO2011/1212 A1, 2011 ; Location in patent: Page/Page column 37-38 ; WO 2011/001212 A1
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Route2
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853908-49-3 - ~60%
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In-stock
853908-50-6
References
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INTELLIKINE, LLC; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WILSON, Troy, Edward; CAMPBELL, Simon, Fraser Patent: WO2012/116237 A2, 2012 ; Location in patent: Page/Page column 119 ; WO 2012/116237 A2
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Route3
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In-stock
145369-94-4 - ~51%
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In-stock
853908-50-6
References
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Zhang, Wenjuan; Li, Zhi; Zhou, Meng; Wu, Feng; Hou, Xueyan; Luo, Hao; Liu, Hao; Han, Xuan; Yan, Guoyi; Ding, Zhenyu; Li, Rui Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 3 p. 799 - 807
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Safety Information
Download SDS|
GHS Pictogram :
N/A
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GHS No : N/A
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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 : H315-H319-H335
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Precautionary Statements : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 76.26
- LogP 2.6111
- H_Acceptors 4
- H_Donors 1
- Rotatable_Bonds 1
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Key Words
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