Lot numbers can be found on the outside label of a product:
tert-Butyl 7-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate
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CAS No. 188576-49-0
- Cat. No. CS-0112266
- Purity≥98%
- MDL No.MFCD08275036
*For research and further manufacturing use only, not for direct human use.
Structure of 188576-49-0
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General Information
- CAS No. 188576-49-0
- Cat. No. CS-0112266
- Purity ≥98%
- MDL No. MFCD08275036
- Storage -20°C, sealed storage, away from moisture
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₄H₁₉NO₃
- Molecular Weight 249.31
- Synonym(s) 2-tert-butoxycarbonyl-7-hydroxy-1,2,3,4-tetrahydroisoquinoline
- SMILES O=C(N1CC2=C(C=CC(O)=C2)CC1)OC(C)(C)C
Description
tert-Butyl 7-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate is a bench-stable, moisture-tolerant intermediate featuring a hydroxylated isoquinoline core. This derivative integrates readily into synthetic sequences requiring regioselective functionalization at the 7-position. The tert-butyl ester group enables straightforward deprotection under mild acidic conditions, facilitating access to the corresponding carboxylic acid for further derivatization.
Application
tert-Butyl 7-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate serves as a versatile intermediate in the synthesis of isoquinoline-based scaffolds, enabling efficient functionalization at the C7 position. The hydroxyl group facilitates derivatization via etherification, esterification, or oxidation to quinone derivatives, while the protected carboxylic acid allows for selective deprotection and coupling reactions. Its bench-stable nature and compatibility with standard synthetic protocols make it well-suited for medicinal chemistry campaigns targeting CNS-active compounds and kinase inhibitors.
Synthesis
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Route1
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30798-64-2 -
In-stock
24424-99-5 - ~93%
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In-stock
188576-49-0
References
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Middleton, Donald S.; Maw, Graham N.; Challenger, Clare; Jessiman, Alan; Johnson, Patrick S.; Million, William A.; Nichols, Carly L.; Price, Jenny A.; Trevethick, Michael Bioorganic and Medicinal Chemistry Letters, 2006 , vol. 16, # 4 p. 905 - 910
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Route2
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188576-56-9 -
In-stock
24424-99-5
- ~73%
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In-stock
188576-49-0
References
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Ajinomoto Co., Inc. Patent: EP2311810 A1, 2011 ; Location in patent: Page/Page column 20 ;
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Route3
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In-stock
39989-39-4 - ~%
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In-stock
188576-49-0
References
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Ueno, Hiroshi; Yokota, Katsuyuki; Hoshi, Jun-Ichi; Yasue, Katsutaka; Hayashi, Mikio; Uchida, Itsuo; Aisaka, Kazuo; Hase, Yasunori; Katoh, Susumu; Cho, Hidetsura Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 1 p. 185 - 189
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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 49.77
- LogP 2.6854
- H_Acceptors 3
- H_Donors 1
- Rotatable_Bonds 0
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Key Words
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