Ethyl5-acetoxy-6-bromo-2-(bromomethyl)-1-methyl-1H-indole-3-car-boxylate

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Cat Number

INT110543981

CAS Number

110543-98-1

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Product Detail Description Customer Q&A

CAS Number

110543-98-1

Storage

2-8℃

Synonyms

Ethyl 5-acetoxy-6-broMo-2-broMoMethyl-1-Methylindo;5-acetoxy-6-bromo-2-(bromomethyl)-1-methyl-1H-indole-3-carboxylate;5-Acetoxy-6-bromo-2-(bromomethyL

Molecular Formula

C15H15Br2NO4

Molecular Weight

433.09

Smiles

N1(C)C2=C(C=C(OC(C)=O)C(Br)=C2)C(C(OCC)=O)=C1CBr

Appearance

Brown solid

Melting Point

168-171℃

Boiling Point

530℃

Relative Density

1.67

General Description

Ethyl 5-acetoxy-6-bromo-2-(bromomethyl)-1-methyl-1H-indole-3-carboxylate is a highly functionalized indole intermediate featuring a bromo-indole core with an ethoxycarbonyl group at C-3, an acetoxy group at C-5, two bromine-containing substituents at C-2 (bromomethyl) and C-6 (bromo), and a methyl group on the indole nitrogen. This dense functionalization provides multiple sites for further synthetic elaboration and is characteristic of advanced intermediates in alkaloid total synthesis.

Mechanism of Action

This compound functions as a complex indole intermediate in the synthesis of indole alkaloids and indazole-containing pharmaceuticals. The 2-(bromomethyl) group is a reactive electrophile suitable for intramolecular cyclization (forming the second ring of the indole alkaloid framework) or for coupling with nucleophiles. The acetoxy group at C-5 can be hydrolyzed to the phenol for further O-alkylation or O-acylation. The bromo substituent at C-6 can undergo cross-coupling reactions. The ethyl ester can be hydrolyzed or transesterified.

Application

This compound is used as an advanced intermediate in the synthesis of complex indole alkaloids including those of the ergot family, vincristine analogs, and kinase inhibitors bearing indole cores. The bromomethyl indole moiety is found in certain marketed drugs and in clinical candidates for oncology. It is also used in the synthesis of fluorescent probes and fluorescent protein chromophore analogs.

What is the recommended storage condition for Ethyl5-acetoxy-6-bromo-2-(bromomethyl)-1-methyl-1H-indole-3-car-boxylate?

It should be stored at 2-8°C 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 Ethyl5-acetoxy-6-bromo-2-(bromomethyl)-1-methyl-1H-indole-3-car-boxylate?

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 analytical characterization data is available for Ethyl5-acetoxy-6-bromo-2-(bromomethyl)-1-methyl-1H-indole-3-car-boxylate?

Standard analytical data including HPLC purity profile, NMR confirmation, and physical specifications are included in the COA. Additional characterization data can be arranged upon request.

Can Ethyl5-acetoxy-6-bromo-2-(bromomethyl)-1-methyl-1H-indole-3-car-boxylate be provided with custom specifications for synthetic applications?

Custom specifications including adjusted particle size, solvent residue limits, or additional purity testing can be arranged for qualified customers with defined requirements.

Is Ethyl5-acetoxy-6-bromo-2-(bromomethyl)-1-methyl-1H-indole-3-car-boxylate suitable for use in regulated pharmaceutical processes?

Yes, it is manufactured under quality standards consistent with regulated pharmaceutical applications, including in-process controls and release testing aligned with industry requirements.