N-T-BOC-Pyrrole

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Cat Number

INT5176272

CAS Number

5176-27-2

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Product Detail Description Customer Q&A

CAS Number

5176-27-2

Synonyms

N-BOC-1H-PYRROLE;tert-butyl 1H-pyrrole-1-carboxylate;tert-butyl-pyrrole-carboxylate;N-Boc-Pyrrole

Molecular Formula

C9H13NO2

Molecular Weight

167.21

Smiles

N1(C(OC(C)(C)C)=O)C=CC=C1

Boiling Point

92℃

General Description

N-T-BOC-pyrrole (1-tert-butoxycarbonyl pyrrole) is a protected pyrrole featuring a tert-butoxycarbonyl (Boc) group on the nitrogen atom of the pyrrole ring. The pyrrole is a five-membered aromatic heterocycle containing nitrogen, and N-Boc protection renders the nitrogen non-nucleophilic, preventing unwanted side reactions during electrophilic substitution and transition metal-catalyzed cross-coupling. The tert-butyl group also imparts steric bulk that influences regioselectivity in further substitution reactions.

Mechanism of Action

N-T-BOC-pyrrole functions as a protected pyrrole building block in heterocyclic synthesis. The N-Boc group is stable under neutral and basic conditions but is removed under acidic conditions (TFA, HCl), providing orthogonality with other protecting groups in multi-step synthesis. The electron-rich pyrrole ring undergoes electrophilic aromatic substitution (EAS) preferentially at the C-2 and C-5 positions, and these positions can be further functionalized via cross-coupling reactions when the pyrrole is N-protected.

Application

N-T-BOC-pyrrole is used as a protected pyrrole building block in the synthesis of pyrrole-containing pharmaceuticals, natural products, and functional materials. Pyrroles are found in numerous bioactive compounds including porphyrins, bile pigments, chlorophyll, heme, atorvastatin, and many alkaloids. The N-Boc protected form is preferred for cross-coupling chemistry and regioselective functionalization because it prevents pyrrole N-alkylation and reduces catalyst poisoning.

What is the recommended storage condition for N-T-BOC-Pyrrole?

It should be stored at controlled room temperature in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

Is a Certificate of Analysis (COA) available for N-T-BOC-Pyrrole?

Yes, a fully verified COA is issued for every batch and can be shared electronically. Additional documentation such as MSDS or impurity profiles may be requested separately.

What functional groups in N-T-BOC-Pyrrole are available for further chemical modification?

The specific reactive handles present in this intermediate can be confirmed by reviewing the technical data sheet. Our team can provide structural and reactivity information relevant to your synthetic route.

What is the primary synthetic application of N-T-BOC-Pyrrole?

It is widely used as a key building block or intermediate in multi-step pharmaceutical synthesis workflows, providing versatile reactivity for constructing target molecular architectures.

What quality standards govern the production of N-T-BOC-Pyrrole?

Production is carried out under GMP-aligned quality systems with full traceability and documented quality controls for each manufacturing run.