Description

Tert-butyl 2-nitrobenzoate (CAS No. 55666-41-6) is a high-purity organic compound with the molecular formula C₁₁H₁₃NO₄. This ester derivative of 2-nitrobenzoic acid features a tert-butyl group, enhancing its stability and solubility for synthetic applications. Ideal for researchers in organic chemistry, pharmaceuticals, and material science, this compound is rigorously tested to meet stringent quality standards (≥95% purity by HPLC/GC). It is supplied as a crystalline solid with excellent shelf stability under recommended storage conditions (2-8°C, inert atmosphere). Tert-butyl 2-nitrobenzoate is a versatile building block for nucleophilic substitution reactions, catalytic transformations, and the synthesis of complex nitroaromatic scaffolds.

Key Specifications:
– CAS: 55666-41-6
– Molecular Weight: 223.23 g/mol
– Appearance: Off-white to pale yellow crystalline powder
– Melting Point: 45-50°C (lit.)
– Purity: ≥95% (HPLC)
– Storage: Store in a cool, dry place under inert gas

Properties

• CAS Number: 55666-41-6
• Complexity: 277
• IUPAC Name: tert-butyl 2-nitrobenzoate
• InChI: InChI=1S/C11H13NO4/c1-11(2,3)16-10(13)8-6-4-5-7-9(8)12(14)15/h4-7H,1-3H3
• InChI Key: DRGCBGCMYGTVIB-UHFFFAOYSA-N
• Exact Mass: 223.08445790
• Molecular Formula: C11H13NO4
• Molecular Weight: 223.22
• SMILES: CC(C)(C)OC(=O)C1=CC=CC=C1[N+](=O)[O-]
• Topological: 72.1
• Monoisotopic Mass: 223.08445790
• Synonyms: Tert-butyl 2-nitrobenzoate, 55666-41-6, DTXSID10406635, DTXCID20357487, 2-NITRO-BENZOIC ACID TERT-BUTYL ESTER, tert-Butyl2-nitrobenzoate, AB1297, MFCD06291302, t-butyl nitrobenzoate, t-butyl 2-nitrobenzoate, SCHEMBL4748764, DRGCBGCMYGTVIB-UHFFFAOYSA-N, AKOS002723484, MB03772, AS-44558, CS-0208740

Application

Tert-butyl 2-nitrobenzoate serves as a key intermediate in pharmaceutical synthesis, particularly for nitroaromatic prodrug development. Its tert-butyl ester group facilitates selective deprotection under mild acidic conditions, enabling controlled release of 2-nitrobenzoic acid in targeted drug delivery systems. Researchers also employ this compound in palladium-catalyzed cross-coupling reactions to construct biaryl structures for agrochemicals and OLED materials. The nitro group offers additional reactivity for reduction to amines or conversion to other functional groups in multistep syntheses.

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