Lot numbers can be found on the outside label of a product:
tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline-1-carboxylate
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CAS No. 837392-67-3
- Cat. No. CS-W011890
- Purity≥98%
- MDL No.MFCD12408237
*For research and further manufacturing use only, not for direct human use.
Structure of 837392-67-3
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General Information
- CAS No. 837392-67-3
- Cat. No. CS-W011890
- Purity ≥98%
- MDL No. MFCD12408237
- Storage -20°C, sealed storage, away from moisture
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₉H₂₈BNO₄
- Molecular Weight 345.25
- Synonym(s) 2,3-Dihydro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylic Acid tert-Butyl E
- SMILES O=C(N1CCC2=C1C=CC(B3OC(C)(C)C(C)(C)O3)=C2)OC(C)(C)C
Description
tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline-1-carboxylate features a boronate ester group enabling efficient Suzuki-Miyaura coupling. The tetramethyl-substituted dioxaborolane moiety ensures high stability and reactivity under standard conditions. This bench-stable reagent integrates readily into complex molecular architectures, particularly in the synthesis of indoline-based pharmaceuticals and functional materials.
Application
tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline-1-carboxylate serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The indoline core provides a rigid, nitrogen-containing heterocyclic scaffold relevant to medicinal chemistry, while the boronate ester enables efficient, mild coupling with aryl and vinyl halides. The tert-butyl carbamate group offers stability and ease of purification, and the tetramethyl-substituted dioxaborolane enhances shelf life and functional group tolerance. This reagent facilitates rapid diversification of indoline frameworks in target-oriented synthesis.
Synthesis
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References
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Axten, Jeffrey M.; Medina, Jesus R.; Feng, Yanhong; Shu, Arthur; Romeril, Stuart P.; Grant, Seth W.; Li, William Hoi Hong; Heerding, Dirk A.; Minthorn, Elisabeth; Mencken, Thomas; Atkins, Charity; Liu, Qi; Rabindran, Sridhar; Kumar, Rakesh; Hong, Xuan; Goetz, Aaron; Stanley, Thomas; Taylor, J. David; Sigethy, Scott D.; Tomberlin, Ginger H.; Hassell, Annie M.; Kahler, Kirsten M.; Shewchuk, Lisa M.; Gampe, Robert T. Journal of Medicinal Chemistry, 2012 , vol. 55, # 16 p. 7193 - 7207
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Route2
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In-stock
22190-33-6 - ~%
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In-stock
837392-67-3
References
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WO2011/119663 A1, ; WO 2011/119663 A1
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Route3
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In-stock
24424-99-5 - ~%
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In-stock
837392-67-3
References
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WO2011/119663 A1, ; WO 2011/119663 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 : 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 48
- LogP 3.2834
- H_Acceptors 4
- H_Donors 0
- Rotatable_Bonds 1
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Key Words
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