Lot numbers can be found on the outside label of a product:
7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline
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CAS No. 851985-81-4
- Cat. No. CS-0061111
- Purity≥97%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
Structure of 851985-81-4
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General Information
- CAS No. 851985-81-4
- Cat. No. CS-0061111
- Purity ≥97%
- MDL No. None
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₅H₁₈BNO₂
- Molecular Weight 255.12
- Synonym(s) Quinoline-7-boronic acid picol ester
- SMILES CC1(C)C(C)(C)OB(C2=CC3=C(C=CC=N3)C=C2)O1
Description
7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline is a bench-stable boronate ester that integrates seamlessly into cross-coupling reactions. The quinoline scaffold provides a rigid, electron-deficient platform for transition metal catalysis, while the tetramethyl-dioxaborolane moiety enables efficient Suzuki-Miyaura coupling under mild conditions. This reagent delivers high functional group tolerance and predictable regiochemistry in complex molecule assembly.
Application
7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline serves as a robust boronate building block for palladium-catalyzed cross-coupling reactions. Its stability under ambient conditions and compatibility with diverse functional groups enable efficient construction of biaryl architectures. The tetramethyl-substituted dioxaborolane moiety enhances shelf life and minimizes protodeboronation, facilitating reliable coupling in Suzuki-Miyaura protocols. This reagent is particularly valuable for assembling quinoline-based scaffolds in medicinal chemistry and materials science applications.
Synthesis
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Route1
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163485-84-5 -
In-stock
73183-34-3 - ~80%
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In-stock
851985-81-4
References
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PFIZER INC.; BROWN, Matthew Frank; CHE, Ye; MARFAT, Anthony; MELNICK, Michael Joseph; MONTGOMERY, Justin Ian; REILLY, Usa Patent: WO2011/73845 A1, 2011 ; Location in patent: Page/Page column 87 ; WO 2011/073845 A1
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References
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PROGENICS PHARMACEUTICALS, INC. Patent: WO2009/155527 A2, 2009 ; Location in patent: Page/Page column 135 ; WO 2009/155527 A2
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Route3
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In-stock
580-20-1 - ~%
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In-stock
851985-81-4
References
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PFIZER INC.; BROWN, Matthew Frank; CHE, Ye; MARFAT, Anthony; MELNICK, Michael Joseph; MONTGOMERY, Justin Ian; REILLY, Usa Patent: WO2011/73845 A1, 2011 ; WO 2011/073845 A1
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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 31.35
- LogP 2.534
- H_Acceptors 3
- H_Donors 0
- Rotatable_Bonds 1
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Key Words
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