Lot numbers can be found on the outside label of a product:
tert-Butyl (3-ethynylphenyl)carbamate
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CAS No. 185619-66-3
- Cat. No. CS-0187651
- Purity≥98%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
Structure of 185619-66-3
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General Information
- CAS No. 185619-66-3
- Cat. No. CS-0187651
- Purity ≥98%
- MDL No. None
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₃H₁₅NO₂
- Molecular Weight 217.26
- Synonym(s) Tert-butyl 3-ethynylphenylcarbamate
- SMILES C#CC1=CC(NC(OC(C)(C)C)=O)=CC=C1
Description
tert-Butyl (3-ethynylphenyl)carbamate features a sterically hindered tert-butyl carbamate protecting group that stabilizes the pendant alkyne, enabling reliable copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. This bench-stable reagent integrates seamlessly into bioconjugation workflows and modular synthesis strategies.
Application
tert-Butyl (3-ethynylphenyl)carbamate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to functionalized phenylacetylene derivatives. The protected amine and terminal alkyne functionalities offer orthogonal reactivity, facilitating copper-catalyzed azide-alkyne cycloaddition (CuAAC) and Pd-catalyzed cross-coupling reactions. Its bench-stable tert-butyl carbamate group allows straightforward deprotection under mild acidic conditions, making it ideal for constructing complex scaffolds in medicinal chemistry and materials science applications.
Synthesis
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Route1
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In-stock
24424-99-5 -
54060-30-9 - ~99%
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In-stock
185619-66-3
References
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Liu, Gang; Xin, Zhili; Pei, Zhonghua; Hajduk, Philip J.; Abad-Zapatero, Cele; Hutchins, Charles W.; Zhao, Hongyu; Lubben, Thomas H.; Ballaron, Stephen J.; Haasch, Deanna L.; Kaszubska, Wiweka; Rondinone, Cristina M.; Trevillyan, James M.; Jirousek, Michael R. Journal of Medicinal Chemistry, 2003 , vol. 46, # 20 p. 4232 - 4235
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Route2
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In-stock
24424-99-5
- ~%
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In-stock
185619-66-3
References
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Macdonald, Gregor; Lewis, Norman J.; Taylor, Richard J. K. Chemical Communications, 1996 , # 23 p. 2647 - 2648
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Route3
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In-stock
626-01-7 - ~%
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In-stock
185619-66-3
References
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Macdonald, Gregor; Lewis, Norman J.; Taylor, Richard J. K. Chemical Communications, 1996 , # 23 p. 2647 - 2648
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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 38.33
- LogP 3.0149
- H_Acceptors 2
- H_Donors 1
- Rotatable_Bonds 1
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Key Words
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