5-Chloro-1-indanone
[CAS# 42348-86-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic ketone
• Name: 5-Chloro-1-indanone
• Molecular Formula: C₉H₇ClO
• Molecular Weight: 166.60
• CAS Registry Number: 42348-86-7
• EC Number: 610-016-5
• SMILES: C1CC(=O)C2=C1C=C(C=C2)Cl

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Melting point: 93-98 °C
• Index of Refraction: 1.600, Calc.^*
• Boiling Point: 288.5±29.0 °C (760 mmHg), Calc.^*, 124-125 °C (3 mmHg)
• Flash Point: 129.4±15.4 °C, Calc.^*
• Water solubility: insoluble

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

5-Chloro-1-indanone is a significant organic compound that has attracted attention due to its utility in various chemical syntheses and its potential applications in medicinal chemistry. The discovery of 5-chloro-1-indanone can be traced back to research aimed at developing new derivatives of indanone, a bicyclic compound known for its diverse biological activities. This compound features a chloro substituent at the 5-position of the indanone ring, which influences its reactivity and properties.

The synthesis of 5-chloro-1-indanone typically involves the chlorination of indanone derivatives or can be achieved through multi-step synthetic routes starting from simpler precursors. The methods often leverage classical organic chemistry techniques, including Friedel-Crafts reactions, nucleophilic substitutions, or the use of chlorinating agents, which provide access to this valuable intermediate.

5-Chloro-1-indanone has several applications, particularly in the field of organic synthesis. One of its primary uses is as an intermediate in the synthesis of various pharmaceutical compounds. The presence of the chloro group allows for further functionalization, enabling the creation of complex molecules with potential therapeutic properties. Researchers have been exploring its derivatives for their biological activities, including anti-inflammatory, analgesic, and anti-cancer effects.

Additionally, 5-chloro-1-indanone can be used in the development of agrochemicals, as its derivatives may exhibit herbicidal or pesticidal activities. The compound's ability to serve as a building block in the synthesis of more complex structures makes it valuable in the design of new agricultural products.

In the realm of materials science, 5-chloro-1-indanone and its derivatives have been investigated for their potential use in the development of advanced materials, including polymers and dyes. The chemical structure of 5-chloro-1-indanone lends itself to modifications that can lead to materials with specific optical or electronic properties, thus broadening its application spectrum.

Research on 5-chloro-1-indanone continues to expand, with ongoing studies focusing on its biological activities and potential uses in various fields. Its structural features and the presence of the chloro substituent make it a versatile compound that holds promise for further exploration in synthetic chemistry and material science.

References

2006. Weak hydrogen-, halogen- and stacking π-π bonding in crystalline 5-chloro-1-indanone. An analysis by using X-ray diffraction, vibrational spectroscopy and theoretical methods. Chemical Physics, 330(1-2).
DOI: 10.1016/j.chemphys.2005.07.015

2011. Metal-Free Relay Oxidation: Valuable Synthesis of Acylsilane and Ketones under Aerobic Oxidation. Synlett, (18).
DOI: 10.1055/s-0031-1289907

2011. 5-Hy-droxy-indan-1-one. Acta Crystallographica. Section E, Structure Reports Online, 67(4).
DOI: 10.1107/s1600536811010956