Lot numbers can be found on the outside label of a product:
Methyl 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
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CAS No. 625470-33-9
- Cat. No. CS-0176527
- Purity≥98%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
Structure of 625470-33-9
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General Information
- CAS No. 625470-33-9
- Cat. No. CS-0176527
- Purity ≥98%
- MDL No. None
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₄H₁₈BClO₄
- Molecular Weight 296.55
- Synonym(s) None
- SMILES O=C(OC)C1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1Cl
Description
Methyl 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate delivers a boronate ester group flanked by a chlorinated aromatic ring and an ester functionality. This bench-stable reagent integrates seamlessly into Suzuki-Miyaura coupling reactions, enabling efficient C–C bond formation under standard conditions. The tetramethylcyclopentadienylboron moiety enhances stability and reactivity, while the ortho-chloro substituent offers downstream functionalization potential.
Application
Methyl 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The pendant chloro group enables sequential functionalization via palladium-catalyzed coupling or nucleophilic substitution, while the pinacol boronate moiety offers excellent stability, ease of handling, and compatibility with diverse reaction conditions. Its orthogonal reactivity profile facilitates efficient construction of biaryl and heteroaryl scaffolds in medicinal chemistry and materials science applications.
Synthesis
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References
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PFIZER PRODUCTS INC. Patent: WO2004/99146 A1, 2004 ; Location in patent: Page 69 ; WO 2004/099146 A1
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References
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Subramanyam, Chakrapani; Duplantier, Allen J.; Dombroski, Mark A.; Chang, Shang-Poa; Gabel, Christopher A.; Whitney-Pickett, Carrie; Perregaux, David G.; Labasi, Jeff M.; Yoon, Kwansik; Shepard, Richard M.; Fisher, Michael Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 18 p. 5475 - 5479
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Route3
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In-stock
21739-92-4 - ~%
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In-stock
625470-33-9
References
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Subramanyam, Chakrapani; Duplantier, Allen J.; Dombroski, Mark A.; Chang, Shang-Poa; Gabel, Christopher A.; Whitney-Pickett, Carrie; Perregaux, David G.; Labasi, Jeff M.; Yoon, Kwansik; Shepard, Richard M.; Fisher, Michael Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 18 p. 5475 - 5479
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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 : H315-H319-H335
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Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 44.76
- LogP 2.4258
- H_Acceptors 4
- H_Donors 0
- Rotatable_Bonds 2
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Key Words
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