Indole-2-carboxylic acid
Indole-2-carboxylic acid (CAS: 1477-50-5; Formula: C9H7NO2; MW: 161.16) is a valuable organic compound widely employed in chemical synthesis. It serves as a crucial building block in the preparation of various complex molecules, including natural products and their analogues. Its utility spans the fields of bioactive small molecules and cell biology research, making it an essential reagent for advanced organic chemistry.
- IUPAC
- 2-Carboxyindole,2-Indolylformic acid,NSC 16598
- Synonyms
- 2-Carboxyindole2-Indolylformic acidNSC 16598
Synthesis of Natural Products and Analogs
Indole-2-carboxylic acid is a key reactant in the total synthesis of compounds such as (±)-dibromophakellin and its analogues, as well as the pyrrolizidine alkaloid (±)-trachelanthamidine. It is also utilized in the stereoselective preparation of renieramycin G analogues, showcasing its versatility in complex molecular construction.
Preparation of Spirooxindoles
This compound is employed in a multi-step synthesis to prepare spirooxoindolepyrrolidines. The process involves reduction of indole-2-carboxylic acid, followed by oxidation, condensation, further reduction, amidation, and Kharasch radical cyclization.
Advanced Organic Synthesis
Indole-2-carboxylic acid acts as a reactant in various advanced synthetic methodologies, including Pd-catalyzed cyclizations. It is also used in the preparation of specific bis-indolecarboxamide derivatives, such as N,N′-(pentane)diylbis[indolecarboxamide] and N,N′-[phenylenebis(methylene)]bis[indolecarboxamide].
| Molecular weight | 161.16 |
|---|---|
| Empirical formula | C9H7NO2 |
| Assay | 98% |
| Application | • Reactant for total synthesis of (±)-dibromophakellin and analogs1• Reactant for synthesis of the pyrrolizidine alkaloid (±)-trachelanthamidine2• Reactant for stereoselective preparation of renieramycin G analogs3• Reactant for preparation of spirooxoindolepyrrolidines via reduction of indole-2-carboxylic acid followed by oxidation, condensation, reduction, amidation and Kharasch radical cyclization4• Reactant for Pd-catalyzed cyclization5• Reactant for preparation of N,N′-(pentane)diylbis[indolecarboxamide] and N,N′-[phenylenebis(methylene)]bis[indolecarboxamide] derivatives6 |
| Melting point | 202-206 °C(lit.) |
| Protective equipment | Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter |
|---|---|
| Water hazard class (WGK, DE) | 3 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
| Gene Information | human ... SRD5A1(6715)rat ... Grin2a(24409) |
|---|
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is Indole-2-carboxylic acid used for?
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Indole-2-carboxylic acid is used as a reactant in the total synthesis of natural products and their analogues, the preparation of spirooxindoles, and various advanced organic synthesis pathways including Pd-catalyzed cyclizations.
What are the CAS number and chemical formula for Indole-2-carboxylic acid?
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The CAS number for Indole-2-carboxylic acid is 1477-50-5, and its chemical formula is C9H7NO2.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Indole-2-carboxylic acid with an assay of 98%. We do not represent this product as USP, BP, EP, or any other pharmacopoeia grade.
What are the safety precautions for handling Indole-2-carboxylic acid?
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When handling Indole-2-carboxylic acid, it is essential to wear eyeshields and gloves. A type N95 (US) or type P1 (EN143) respirator filter is also recommended. The substance has a WGK Germany classification of 3, indicating a high level of hazard.
How is Indole-2-carboxylic acid packed and shipped?
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Indole-2-carboxylic acid is carefully packed and exported by Tech Serve Solutions, adhering to all necessary regulations for safe transportation of chemical reagents.
How can I request a sample or quote for Indole-2-carboxylic acid?
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To request a sample or quote for Indole-2-carboxylic acid, please contact our sales department through the website or by phone.
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