Lot numbers can be found on the outside label of a product:
Methyl 5-bromo-1H-indole-2-carboxylate
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CAS No. 210345-56-5
- Cat. No. CS-0036684
- Purity≥97%
- MDL No.MFCD01854034
*For research and further manufacturing use only, not for direct human use.
Structure of 210345-56-5
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General Information
- CAS No. 210345-56-5
- Cat. No. CS-0036684
- Purity ≥97%
- MDL No. MFCD01854034
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₀H₈BrNO₂
- Molecular Weight 254.08
- Synonym(s) Methyl 5-bromoindole-2-carboxyate
- SMILES COC(=O)C1=CC2=C(C=CC(=C2)Br)N1
Description
Methyl 5-bromo-1H-indole-2-carboxylate features a brominated indole core with a methyl ester at the 2-position, enabling direct functionalization in cross-coupling and heterocyclic synthesis. The electron-deficient aryl bromide facilitates palladium-catalyzed transformations, while the bench-stable ester group supports sequential derivatization under standard conditions.
Application
Methyl 5-bromo-1H-indole-2-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling direct functionalization at the C5 position via palladium-catalyzed cross-coupling reactions. The methyl ester group provides compatibility with standard deprotection and derivatization protocols, while the bromine substituent offers high reactivity in Suzuki, Stille, and Negishi couplings. Bench-stable and readily purified by flash chromatography, it functions effectively in the construction of complex indole-based scaffolds relevant to medicinal chemistry and materials science.
Synthesis
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Route1
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67-56-1 -
In-stock
7254-19-5 - ~93%
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In-stock
210345-56-5
References
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La Regina, Giuseppe; Sarkar, Taradas; Bai, Ruoli; Edler, Michael C.; Saletti, Roberto; Coluccia, Antonio; Piscitelli, Francesco; Minelli, Lara; Gatti, Valerio; Mazzoccoli, Carmela; Palermo, Vanessa; Mazzoni, Cristina; Falcone, Claudio; Scovassi, Anna Ivana; Giansanti, Vincenzo; Campiglia, Pietro; Porta, Amalia; Maresca, Bruno; Hamel, Ernest; Brancale, Andrea; Novellino, Ettore; Silvestri, Romano Journal of Medicinal Chemistry, 2009 , vol. 52, # 23 p. 7512 - 7527
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Route2
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In-stock
7254-19-5
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In-stock
210345-56-5
References
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EP1460064 A1, ; Page 35 ; EP 1460064 A1
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References
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Tullberg, Erik; Schacher, Felix; Peters, Dan; Frejd, Torbjoern Synthesis, 2006 , # 7 p. 1183 - 1189
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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 42.09
- LogP 2.717
- H_Acceptors 2
- H_Donors 1
- Rotatable_Bonds 1
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Key Words
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