5-Chloro-2-indanone: Properties, Handling & Lab Use Guide

5-Chloro-2-indanone is a halogenated bicyclic ketone serving as a versatile synthetic intermediate in medicinal chemistry and organic synthesis research.

CAS Number

4743-17-3

Molecular Formula

C₉H₇ClO

Molecular Weight

166.60 g/mol

Appearance

White to off-white crystalline solid

Functional Class

Halogenated cyclic ketone; synthetic intermediate

Storage Condition

Store in a cool, dry, well-ventilated area away from light and incompatible materials

Aladdin SKU

C194857

Chemical Identity and Physical Properties

5-Chloro-2-indanone (CAS 4743-17-3) belongs to the indanone family of bicyclic compounds, featuring a fused cyclopentanone ring appended to a chloro-substituted benzene ring. Its molecular formula is C₉H₇ClO with a molecular weight of approximately 166.60 g/mol. The compound typically presents as a white to off-white crystalline solid at room temperature. The chlorine substituent at the 5-position of the aromatic ring significantly modulates the compound's electronic properties compared to the parent 2-indanone, increasing electrophilicity at certain reaction sites and altering spectroscopic signatures. These electronic effects make 5-Chloro-2-indanone a useful building block in multi-step synthetic sequences. Researchers should confirm purity by HPLC or GC analysis upon receipt and prior to use in sensitive reactions.

Synthetic Applications and Research Uses

5-Chloro-2-indanone is primarily employed as a synthetic intermediate in medicinal chemistry, agrochemical research, and materials science. The activated carbonyl group permits a broad range of chemical transformations including nucleophilic addition, reductive amination, condensation reactions (e.g., aldol and Knoevenagel condensations), and formation of oximes, hydrazones, and imines. The aryl chloride moiety provides a handle for transition-metal-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Heck, and Buchwald–Hartwig couplings, enabling rapid diversification of the scaffold. These combined reactive sites make the compound especially valuable for constructing pharmacophore-rich heterocyclic frameworks used in drug discovery programs. Researchers exploring indanone-based scaffolds for CNS drug candidates or kinase inhibitor programs may find 5-Chloro-2-indanone a convenient starting material.

Safe Handling, Storage, and Disposal

Researchers must treat 5-Chloro-2-indanone as a potential irritant. Standard personal protective equipment (PPE) — including nitrile gloves, safety goggles, and a laboratory coat — should be worn when handling the compound. Operations generating dust or aerosols must be conducted in a fume hood to prevent inhalation exposure. The compound should be stored in a tightly sealed container in a cool (typically 2–8 °C or as specified on the CoA), dry, and well-ventilated area, protected from direct light and heat sources. Keep away from strong oxidizers, strong bases, and reactive metals. Waste containing 5-Chloro-2-indanone must be segregated and disposed of in accordance with local, national, and institutional regulations governing halogenated organic waste. Always consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific before use.

Quality, Purity, and Verification Recommendations

For research reproducibility, the purity of 5-Chloro-2-indanone should be verified prior to use in critical assays or multi-step syntheses. Recommended analytical methods include gas chromatography (GC) with a flame ionization detector (FID), high-performance liquid chromatography (HPLC) with UV detection, and nuclear magnetic resonance (NMR) spectroscopy (¹H and ¹³C) for structural confirmation. Melting point determination provides a rapid identity check. Aladdin Scientific's product C194857 is supplied with a Certificate of Analysis (CoA) that specifies the purity, lot number, and analytical data. Researchers should retain the CoA for regulatory and publication documentation. If the material has been stored for an extended period, re-analysis before use is strongly recommended, particularly because prolonged storage of halogenated ketones can occasionally lead to decomposition or color development.

Frequently asked questions

What is the recommended storage temperature for 5-Chloro-2-indanone?

5-Chloro-2-indanone should be stored in a cool, dry, and well-ventilated location away from light and heat. Refrigerated storage (2–8 °C) is commonly recommended for halogenated ketones to maximize shelf life; however, always defer to the conditions specified on the Aladdin Scientific Certificate of Analysis (CoA) for lot-specific guidance.

What types of chemical reactions can 5-Chloro-2-indanone undergo?

5-Chloro-2-indanone is bifunctionally reactive. The ketone carbonyl participates in nucleophilic additions, reductive aminations, aldol and Knoevenagel condensations, and imine/oxime formation. Simultaneously, the aryl chloride group is amenable to palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Heck, and Buchwald–Hartwig couplings, making the compound highly versatile for scaffold diversification.

What PPE is required when handling 5-Chloro-2-indanone in the laboratory?

Minimum PPE includes nitrile gloves, chemical splash goggles, and a laboratory coat. Dust-generating or weighing operations should be performed inside a certified fume hood. Consult the current SDS for 5-Chloro-2-indanone (available from Aladdin Scientific) for complete hazard and first-aid information before beginning work.

How can I confirm the identity and purity of 5-Chloro-2-indanone upon receipt?

Identity and purity can be confirmed by comparing ¹H NMR and ¹³C NMR spectra against literature or internal reference spectra, running GC-FID or HPLC-UV analysis, and checking the melting point against reported values. The Certificate of Analysis supplied with Aladdin Scientific product C194857 provides lot-specific analytical data to facilitate incoming QC.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (General reference for ketone reactivity and cross-coupling reactions.)
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (Canonical reference for nucleophilic addition to carbonyls and aromatic substitution.)
3. Aladdin Scientific. Certificate of Analysis for 5-Chloro-2-indanone, SKU C194857. (Lot-specific purity and analytical data; contact Aladdin Scientific for current CoA.)

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.