Lot numbers can be found on the outside label of a product:
(4-Bromopyridin-2-yl)methanol
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CAS No. 131747-45-0
- Cat. No. CS-W018599
- Purity≥95%
- MDL No.MFCD09800557
*For research and further manufacturing use only, not for direct human use.
Structure of 131747-45-0
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General Information
- CAS No. 131747-45-0
- Cat. No. CS-W018599
- Purity ≥95%
- MDL No. MFCD09800557
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₆H₆BrNO
- Molecular Weight 188.02
- Synonym(s) 4-Bromopyridine-2-methanol
- SMILES BrC1=CC(=NC=C1)CO
Description
(4-Bromopyridin-2-yl)methanol features a brominated pyridine ring linked to a primary alcohol group, enabling direct functionalization in cross-coupling and derivatization workflows. The pendant hydroxymethyl moiety supports facile oxidation to aldehyde or carboxylic acid derivatives, while the electron-deficient pyridine ring enhances reactivity in nucleophilic substitution reactions under standard conditions.
Application
(4-Bromopyridin-2-yl)methanol serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the pyridine ring and side-chain hydroxymethyl group. It functions as a key intermediate in cross-coupling reactions, particularly Suzuki-Miyaura and Negishi transformations, due to its stable bromide handle and compatible aldehyde precursor. The molecule exhibits excellent bench stability and facilitates straightforward purification, making it ideal for modular synthesis of bioactive heterocycles and pharmaceutical scaffolds.
Synthesis
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Route1
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In-stock
30766-03-1 - ~51%
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In-stock
131747-45-0
References
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Gruenenthal GmbH Patent: US2009/69320 A1, 2009 ; Location in patent: Page/Page column 77; 78 ;
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Route2
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In-stock
29681-42-3 - ~94%
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In-stock
131747-45-0
References
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GILEAD SCIENCES, INC.; SELCIA LIMITED; APPLEBY, Todd; FLIRI, Hans, G.; KEATS, Andrew, J.; LAZARIDES, Linos; MACKMAN, Richard, L.; PETTIT, Simon, N.; POULLENNEC, Karine, G.; SANVOISIN, Jonathan; STEADMAN, Victoria, A.; WATT, Gregory, M. Patent: WO2012/78915 A1, 2012 ; Location in patent: Page/Page column 95-96 ;
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Route3
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100367-74-6 - ~61%
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In-stock
131747-45-0
References
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Jones, Roderick C.; Canty, Allan J.; Deverell, Jeremy A.; Gardiner, Michael G.; Guijt, Rosanne M.; Rodemann, Thomas; Smith, Jason A.; Tolhurst, Vicki-Anne Tetrahedron, 2009 , vol. 65, # 36 p. 7474 - 7481
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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 33.12
- LogP 1.3364
- H_Acceptors 2
- H_Donors 1
- Rotatable_Bonds 1
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Key Words
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