Description

tert-Butyl 3-formyl-1H-indole-1-carboxylate (CAS No. 57476-50-3) is a high-purity, synthetic organic compound with the molecular formula C₁₄H₁₅NO₃. This indole derivative features a formyl group at the 3-position and a Boc (tert-butoxycarbonyl) protecting group at the 1-position, making it a versatile intermediate in pharmaceutical and agrochemical synthesis. Its IUPAC name is tert-butyl 3-formylindole-1-carboxylate, and it is characterized by excellent stability under standard storage conditions. This compound is supplied as a crystalline solid with ≥95% purity (HPLC), ensuring reliable performance in demanding research applications. Ideal for use in medicinal chemistry, it serves as a key precursor for the development of indole-based bioactive molecules, including kinase inhibitors and serotonin receptor modulators.

Properties

• CAS Number: 57476-50-3
• Complexity: 334
• IUPAC Name: tert-butyl 3-formylindole-1-carboxylate
• InChI: InChI=1S/C14H15NO3/c1-14(2,3)18-13(17)15-8-10(9-16)11-6-4-5-7-12(11)15/h4-9H,1-3H3
• InChI Key: GDYHUGFAKMUUQL-UHFFFAOYSA-N
• Exact Mass: 245.10519334
• Molecular Formula: C14H15NO3
• Molecular Weight: 245.27
• SMILES: CC(C)(C)OC(=O)N1C=C(C2=CC=CC=C21)C=O
• Topological: 48.3
• Monoisotopic Mass: 245.10519334
• Synonyms: 57476-50-3, tert-butyl 3-formyl-1H-indole-1-carboxylate, DTXSID10377477, DTXCID10328505, 827-428-8, 1-Boc-3-Formylindole, tert-butyl 3-formylindole-1-carboxylate, 3-formyl-indole-1-carboxylic acid tert-butyl ester, MFCD00049230, 3-FORMYLINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER, 1H-INDOLE-1-CARBOXYLIC ACID, 3-FORMYL-, 1,1-DIMETHYLETHYL ESTER, 1H-Indole-3-carboxaldehyde, N-BOC protected, tert-butyl 3-formylindolecarboxylate, TERT-BUTYL3-FORMYL-1H-INDOLE-1-CARBOXYLATE, 1-(tert-Butoxycarbonyl)-3-formyl-1H-indole, N-Boc-indole-3-carboxaldehyde, SCHEMBL3533644, CHEMBL3622755, 1-t-butoxycarbonyl-3-formylindole, GDYHUGFAKMUUQL-UHFFFAOYSA-N, ALBB-016768, BCP26869, AB2740, SBB059070, AKOS005071300, MB00438, 1-(tert-butyloxycarbonyl)-3-formylindole, BP-11116, SY081294, DB-001926, CS-0031417, ST51043359, 9P-905, EN300-119402, 3-formyl-indole-1-carboxylic acid t-butyl ester, 3-formyl-indole-1-carboxylic acid-tert-butylester, F2158-2278, Z1741974671

Application

tert-Butyl 3-formyl-1H-indole-1-carboxylate is widely used as a building block in the synthesis of indole-containing pharmaceuticals, particularly in the development of kinase inhibitors and CNS-active compounds. Its reactive formyl group enables facile derivatization via condensation or nucleophilic addition reactions. The Boc protecting group enhances solubility and allows selective deprotection under mild acidic conditions, making it valuable for multi-step synthetic routes. Researchers employ this compound in the construction of complex heterocycles for drug discovery programs.

Safety and Hazards

GHS Hazard Statements

• H302 (33.3%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (66.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (33.3%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (66.7%)

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