Description

tert-Butyl 3,4-dihydroquinoline-1(2H)-carboxylate (CAS No. 123387-53-1) is a high-purity synthetic organic compound with the molecular formula C₁₄H₁₉NO₂. This Boc-protected tetrahydroquinoline derivative is widely utilized in pharmaceutical research, medicinal chemistry, and as a versatile intermediate in organic synthesis. The compound features a tert-butyloxycarbonyl (Boc) protecting group, which enhances stability and facilitates selective deprotection during multi-step synthetic processes. With a molecular weight of 233.31 g/mol, it is supplied as a crystalline solid or powder, typically with ≥95% purity (HPLC). Ideal for N-heterocycle functionalization, this reagent is rigorously tested for consistency and is available in research (1 kg) quantities. Store under inert atmosphere at 2-8°C to maintain optimal stability.

Properties

• CAS Number: 123387-53-1
• Complexity: 282
• IUPAC Name: tert-butyl 3,4-dihydro-2H-quinoline-1-carboxylate
• InChI: InChI=1S/C14H19NO2/c1-14(2,3)17-13(16)15-10-6-8-11-7-4-5-9-12(11)15/h4-5,7,9H,6,8,10H2,1-3H3
• InChI Key: GVSRWAIRQCMAHG-UHFFFAOYSA-N
• Exact Mass: 233.141578849
• Molecular Formula: C14H19NO2
• Molecular Weight: 233.31
• SMILES: CC(C)(C)OC(=O)N1CCCC2=CC=CC=C21
• Topological: 29.5
• Monoisotopic Mass: 233.141578849
• Synonyms: 123387-53-1, tert-Butyl 3,4-dihydroquinoline-1(2H)-carboxylate, 1-BOC-1,2,3,4-Tetrahydroquinoline, Tert-butyl 3,4-dihydro-2H-quinoline-1-carboxylate, 1(2H)-Quinolinecarboxylic acid, 3,4-dihydro-, 1,1-dimethylethyl ester, MFCD19684135, tert-Butyl3,4-dihydroquinoline-1(2H)-carboxylate, SCHEMBL3127747, SCHEMBL19639057, SCHEMBL19639063, DTXSID20442802, GVSRWAIRQCMAHG-UHFFFAOYSA-N, AKOS013101942, BS-14731, DB-373468, CS-0154709, 1-tertbutoxycarbonyl-1,2,3,4-tetrahydroquinoline, tert-butyl 3,4-dihydro-1(2H)-quinolinecarboxylate, 1,1-Dimethylethyl 3,4-dihydro-1(2H)-quinolinecarboxylate, 3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

Application

This Boc-protected tetrahydroquinoline serves as a key building block in the synthesis of bioactive alkaloids and pharmaceutical compounds. Researchers employ it in palladium-catalyzed cross-coupling reactions for quinoline ring functionalization. The compound is particularly valuable in developing CNS-active molecules due to the privileged tetrahydroquinoline scaffold. Its Boc group allows for orthogonal protection strategies in peptide-mimetic and combinatorial chemistry applications.

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