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Benzyl (trans-4-hydroxycyclohexyl)carbamate
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CAS No. 27489-63-0
- Cat. No. CS-0036513
- Purity≥97%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
Structure of 27489-63-0
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General Information
- CAS No. 27489-63-0
- Cat. No. CS-0036513
- Purity ≥97%
- MDL No. None
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₄H₁₉NO₃
- Molecular Weight 249.31
- Synonym(s) trans-N-Cbz-4-aminocyclohexanol
- SMILES C1=CC=C(C=C1)COC(=N[C@H]2CC[C@@H](CC2)O)O
Description
Benzyl (trans-4-hydroxycyclohexyl)carbamate features a bench-stable, moisture-tolerant carbamate group that enables selective protection of primary amines. The trans-configured cyclohexyl scaffold provides defined stereochemistry and enhanced solubility in organic media. This reagent streamlines amine derivatization workflows while minimizing epimerization risks during synthesis.
Application
Benzyl (trans-4-hydroxycyclohexyl)carbamate serves as a robust, bench-stable protecting group for primary amines, enabling selective N-alkylation and amide coupling reactions. The trans-4-hydroxycyclohexyl moiety offers enhanced stability and facilitates orthogonal deprotection under mild acidic conditions. Its compatibility with diverse reaction environments makes it particularly valuable in the synthesis of complex heterocycles and peptide-based scaffolds.
Synthesis
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References
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Sher, Philip M.; Nirschl, Alexandra A.; Meng, Wei; Washburn, William N. Patent: US2006/111338 A1, 2006 ; Location in patent: Page/Page column 29 ;
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Route2
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In-stock
50910-54-8 -
501-53-1 - ~97%
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In-stock
27489-63-0
References
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Venuti, Michael C.; Jones, Gordon H.; Alvarez, Robert; Bruno, John J. Journal of Medicinal Chemistry, 1987 , vol. 30, # 2 p. 303 - 318
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Route3
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In-stock
27489-62-9 -
501-53-1
- ~98%
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In-stock
27489-63-0
References
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Dehmlow, Henrietta; Ackermann, Jean; Aebi, Johannes; Blum-Kaelin, Denise; Chucholowski, Alexander; Coassolo, Philippe; Hartman, Peter; Kansy, Manfred; Maerki, Hans Peter; Morand, Olivier; Von Der Mark, Elisabeth; Panday, Narendra; Ruf, Armin; Thoma, Ralf; Schulz-Gasch, Tanja Chimia, 2005 , vol. 59, # 3 p. 72 - 76
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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 62.05
- LogP 2.4207
- H_Acceptors 3
- H_Donors 2
- Rotatable_Bonds 3
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Key Words
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