Lot numbers can be found on the outside label of a product:
1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium iodide
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CAS No. 14134-81-7
- Cat. No. CS-0153894
- Purity≥97%
- MDL No.MFCD00227166
*For research and further manufacturing use only, not for direct human use.
Structure of 14134-81-7
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General Information
- CAS No. 14134-81-7
- Cat. No. CS-0153894
- Purity ≥97%
- MDL No. MFCD00227166
- Storage 4°C, sealed storage, away from moisture
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₃H₁₈IN
- Molecular Weight 315.20
- Synonym(s) 3H-Indolium, 1-ethyl-2,3,3-trimethyl-, iodide
- SMILES [I-].C=1C=CC2=C(C1)[N+](=C(C)C2(C)C)CC
Description
This indolium salt features a cationic core with three methyl groups at the 3-position, enhancing steric protection and electronic stability. The ethyl substitution at the 1-position introduces a mild electron-donating effect, while the iodide counterion ensures high solubility in polar solvents. Designed for synthetic applications requiring stable, bench-ready heterocyclic electrophiles.
Application
1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium iodide serves as a stable, bench-ready indolium salt that facilitates electrophilic functionalization in late-stage diversification. Its robust cationic core enables efficient coupling with nucleophiles under mild conditions, offering high functional group tolerance and ease of purification. This reagent functions as a key building block for indole-based scaffolds in medicinal chemistry and natural product synthesis.
Synthesis
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Route1
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In-stock
1640-39-7 -
75-03-6 - ~96%
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In-stock
14134-81-7
References
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Lindsey, Jonathan S.; Brown, Philip A.; Siesel, David A. Tetrahedron, 1989 , vol. 45, # 15 p. 4845 - 4866
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Route2
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563-80-4
- ~%
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In-stock
14134-81-7
References
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MICHIGAN TECHNOLOGICAL UNIVERSITY; BI, Lanrong Patent: WO2014/63033 A2, 2014 ;
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Route3
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59-88-1
- ~%
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In-stock
14134-81-7
References
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Levitz, Andrew; Ladani, Safieh Tork; Hamelberg, Donald; Henary, Maged Dyes and Pigments, 2014 , vol. 105, p. 238 - 249
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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-P330-P362+P364-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 3.01
- LogP 0.1066
- H_Acceptors 0
- H_Donors 0
- Rotatable_Bonds 1
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Key Words
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