Lot numbers can be found on the outside label of a product:
2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
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CAS No. 1003575-43-6
- Cat. No. CS-W006140
- Purity≥97%
- MDL No.MFCD11044430
*For research and further manufacturing use only, not for direct human use.
Structure of 1003575-43-6
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General Information
- CAS No. 1003575-43-6
- Cat. No. CS-W006140
- Purity ≥97%
- MDL No. MFCD11044430
- Storage 4°C, protect from light
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₂H₁₇BFNO₂
- Molecular Weight 237.08
- Synonym(s) 3-Amino-4-fluorophenylboronic Acid Pinacol Ester
- SMILES NC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1F
Description
2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline features a boronate ester group enabling reliable Suzuki-Miyaura coupling under mild conditions. The fluorine substituent enhances electronic modulation and metabolic stability in bioactive molecule synthesis. This bench-stable reagent combines high functional group tolerance with excellent handling properties, streamlining access to complex arylated scaffolds in medicinal chemistry and materials science applications.
Application
2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The ortho-fluoro substituent enables directed ortho-metalation and facilitates downstream functionalization, while the stable pinacol boronate group ensures excellent bench stability and compatibility with a wide range of coupling partners. This reagent functions effectively in both small-molecule synthesis and heterocyclic scaffold construction, offering predictable regioselectivity and high yields under standard reaction conditions.
Synthesis
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Route1
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In-stock
1218791-09-3 - ~99%
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In-stock
1003575-43-6
References
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CGI PHARMACEUTICALS, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., Jr.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; LEE, Seung, H.; KROPF, Jeffrey, E.; MITCHELL, Scott, A.; ORTWINE, Daniel; RENNELLS, William, M.; SCHMITT, Aaron, C.; XU, Jianjun; YOUNG, Wendy, B.; ZHAO, Zhongdong; ZHICHKIN, Pavel, E. Patent: WO2010/56875 A1, 2010 ; Location in patent: Page/Page column 205 ;
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References
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SELEXAGEN THERAPEUTICS, INC.; VERNIER, Jean-michel; HOPKINS, Stephanie; BOUNAUD, Pierre-Yves; O'CONNOR, Patrick; MATTHEWS, David; BENDER, Steve Patent: WO2012/125981 A2, 2012 ; Location in patent: Page/Page column 128 ; WO 2012/125981 A2
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References
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Yamamoto, Tetsuya; Morita, Tomoyuki; Takagi, Jun; Yamakawa, Tetsu Organic Letters, 2011 , vol. 13, # 21 p. 5766 - 5769
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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
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Precautionary Statements : P264-P270-P330-P501
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Quality Control
Computational Chemistry Data
- TPSA 44.48
- LogP 1.7071
- H_Acceptors 3
- H_Donors 1
- Rotatable_Bonds 1
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Key Words
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