3-(4-Chlorobutyl)indole-5-carbonitrile
[CAS# 143612-79-7]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: 3-(4-Chlorobutyl)indole-5-carbonitrile
• Synonyms: 3-(4-chlorobutyl)-1H-indole-5-carbonitrile
• Molecular Formula: C₁₃H₁₃ClN₂
• Molecular Weight: 232.71
• CAS Registry Number: 143612-79-7
• EC Number: 801-938-0
• SMILES: C1=CC2=C(C=C1C#N)C(=CN2)CCCCCl

Properties

• Density: 1.22
• Melting point: 99-100 °C

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H302+H312+H332-H302-H312-H315-H319-H332-H400-H410
• Safety Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P321-P330-P332+P317-P337+P317-P362+P364-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410

Discovery and Applications

3-(4-Chlorobutyl)indole-5-carbonitrile is a chemical compound that has garnered attention in the fields of organic chemistry and pharmaceuticals due to its unique structure and potential applications. This compound, with the formula C13H13ClN2, consists of an indole core substituted with a 4-chlorobutyl group and a cyano group at the 5-position. Its distinctive structure makes it a valuable subject for research and development.

The discovery of 3-(4-chlorobutyl)indole-5-carbonitrile is part of broader research into indole derivatives and their potential applications. Indole is a heterocyclic compound with significant biological activity, and its derivatives have been explored for various uses in medicinal chemistry. The introduction of a 4-chlorobutyl group and a cyano group to the indole ring enhances the compound's potential as a bioactive agent.

Synthesis of 3-(4-chlorobutyl)indole-5-carbonitrile typically involves the reaction of indole with a 4-chlorobutyl halide and a cyanation agent. The synthesis requires careful control of reaction conditions to obtain a high yield of the desired product. Techniques such as chromatography and spectroscopy are used to purify and characterize the compound.

One of the primary applications of 3-(4-chlorobutyl)indole-5-carbonitrile is in medicinal chemistry. The compound's structure suggests potential activity in various biological systems. Research has indicated that indole derivatives can exhibit a range of pharmacological effects, including anti-inflammatory, anticancer, and antimicrobial activities. The presence of the 4-chlorobutyl and cyano groups may further modulate these activities, making 3-(4-chlorobutyl)indole-5-carbonitrile a candidate for drug development.

In particular, this compound has been investigated for its potential as an anticancer agent. The indole nucleus is a common motif in many known anticancer drugs, and the addition of substituents such as 4-chlorobutyl and cyano groups can enhance the compound's ability to interact with biological targets involved in cancer progression. Preclinical studies may focus on evaluating its effectiveness in inhibiting tumor growth or inducing apoptosis in cancer cells.

Additionally, 3-(4-chlorobutyl)indole-5-carbonitrile is of interest in the study of neuroactive compounds. The indole structure is related to neurotransmitters such as serotonin, and derivatives like this compound could potentially influence neurological pathways. Research may explore its effects on neurotransmitter systems and its potential as a treatment for neurological disorders.

The compound's cyano group also provides opportunities for further chemical modifications. The cyano group can be converted into various functional groups through additional chemical reactions, allowing for the development of analogs with altered biological activities. This versatility makes 3-(4-chlorobutyl)indole-5-carbonitrile a valuable starting point for designing new pharmaceuticals.

In summary, 3-(4-chlorobutyl)indole-5-carbonitrile is a significant compound in organic and medicinal chemistry, with potential applications in drug development and biomedical research. Its structure and substituents offer opportunities for exploring its biological activities and developing new therapeutic agents.

References

2014. Vilazodone. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-22-0038