1-Acetyl-5-bromo-4-chloro-1H-indol-3-yl acetate

Name: 1-Acetyl-5-bromo-4-chloro-1H-indol-3-yl acetate
Brand: ChemScene
Availability: InStock
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CAS No. 3030-06-6
Cat. No. CS-M1903
Molecule weight330.56
Purity≥98%
MDL No.MFCD00040632

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1-Acetyl-5-bromo-4-chloro-1H-indol-3-yl acetate|CS-M1903

Structure of 3030-06-6

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General Information

CAS No. 3030-06-6
Cat. No. CS-M1903
Purity ≥98%
MDL No. MFCD00040632
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₉BrClNO₃
Molecular Weight 330.56
Synonym(s) Indol-3-ol, 1-acetyl-5-bromo-4-chloro-, acetate (ester); Indoxyl, 1-acetyl-5-bromo-4-chloro-, acetate; 3-Acetoxy-1-acetyl-5-bromo-4-chloroindole
SMILES O=C(C)N1C2=CC=C(Br)C(Cl)=C2C(OC(C)=O)=C1

Description

1-Acetyl-5-bromo-4-chloro-1H-indol-3-yl acetate features a halogenated indole core with strategically positioned bromo and chloro substituents, enabling selective cross-coupling reactions. The acetyl group at the 1-position enhances solubility and stability, while the ester functionality at C3 supports downstream derivatization. This compound serves as a key intermediate in the synthesis of bioactive heterocycles and pharmaceutical candidates.

Application

1-Acetyl-5-bromo-4-chloro-1H-indol-3-yl acetate serves as a versatile building block for the synthesis of substituted indole derivatives, leveraging its orthogonal functionalization potential at C3 and C5 positions. The acetyl group at C1 enables direct electrophilic substitution or further derivatization, while the bromo and chloro substituents facilitate palladium-catalyzed cross-coupling reactions. Bench-stable and readily purified by flash chromatography, it functions effectively in late-stage diversification strategies for medicinal chemistry and heterocyclic scaffold development.

Synthesis

Route1
- 3030-10-2
- 108-24-7
- ~%
- In-stock
  
  3030-06-6
References
- Pr.roy. Soc.<B>, , vol. 148, p. 481,491,492

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 48.3
LogP 3.6426
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Indole compounds

Key Words

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1-Acetyl-5-bromo-4-chloro-1H-indol-3-yl acetate

CAS No. 3030-06-6

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