Lot numbers can be found on the outside label of a product:
Methyl 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate
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CAS No. 478375-42-7
- Cat. No. CS-0041217
- Purity≥97%
- MDL No.MFCD13195752
*For research and further manufacturing use only, not for direct human use.
Structure of 478375-42-7
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General Information
- CAS No. 478375-42-7
- Cat. No. CS-0041217
- Purity ≥97%
- MDL No. MFCD13195752
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₅H₂₁BO₄
- Molecular Weight 276.14
- Synonym(s) 3-(2-Methoxy-2-oxoethyl)phenylboronic acid,pinacol ester
- SMILES COC(=O)CC1=CC(=CC=C1)B1OC(C)(C)C(C)(C)O1
Description
Methyl 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate features a boronate ester group flanked by a methyl acrylate moiety, enabling efficient Suzuki-Miyaura coupling under mild conditions. This bench-stable reagent integrates readily into complex molecule synthesis, offering predictable regioselectivity and compatibility with diverse functional groups.
Application
Methyl 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group exhibits high stability, excellent functional group tolerance, and reliable coupling efficiency under standard conditions. It facilitates the construction of biaryl and substituted aryl motifs commonly found in pharmaceutical and agrochemical scaffolds, enabling efficient C–C bond formation with aryl halides or pseudohalides. The methyl ester functionality provides additional handle for downstream transformations, enhancing its utility in synthetic sequences.
Synthesis
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References
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Kranich, Remo; Busemann, Anke S.; Bock, Daniel; Schroeter-Maas, Sabine; Beyer, Diana; Heinemann, Bo; Meyer, Michael; Schierhorn, Katrin; Zahlten, Rainer; Wolff, Gerhard; Aydt, Ewald M. Journal of Medicinal Chemistry, 2007 , vol. 50, # 6 p. 1101 - 1115
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Route2
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In-stock
73183-34-3 -
147283-87-2 - ~90%
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In-stock
478375-42-7
References
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Robichaud, Joel; Oballa, Renata; Prasit, Peppi; Falgueyret, Jean-Pierre; Percival, M. David; Wesolowski, Gregg; Rodan, Sevgi B.; Kimmel, Donald; Johnson, Colena; Bryant, Cliff; Venkatraman, Shankar; Setti, Eduardo; Mendonca, Rohan; Palmer, James T. Journal of Medicinal Chemistry, 2003 , vol. 46, # 17 p. 3709 - 3727
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Route3
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In-stock
1878-67-7 - ~%
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In-stock
478375-42-7
References
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MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG Patent: US2011/257172 A1, 2011 ;
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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 44.76
- LogP 1.7013
- H_Acceptors 4
- H_Donors 0
- Rotatable_Bonds 3
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Key Words
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