6-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one: Properties & Applications
6-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one: Properties & Applications
6-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one is a halogenated indanone derivative widely used as a versatile synthetic building block in organic and medicinal chemistry research.
- IUPAC Name
- 6-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one
- Molecular Formula
- C10H9ClO
- Molecular Weight
- 180.63 g/mol
- CAS Number
- Needs review — not confirmed in source material
- Core Scaffold
- Indanone (2,3-dihydro-1H-inden-1-one) with chloro substituent at C-6 and methyl at C-2
- Functional Groups
- Aromatic ring, ketone carbonyl, aliphatic ring, chloro substituent
- SKU
- C727059
- Supplier
- Aladdin Scientific
Chemical Structure and Identity
6-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one belongs to the indanone family of cyclic ketones. Its core structure consists of a five-membered carbocyclic ring fused to a benzene ring, with a ketone carbonyl at the 1-position. The compound is distinguished by a chlorine atom at the 6-position of the aromatic ring and a methyl group at the 2-position of the aliphatic ring. This combination of substituents imparts unique electronic and steric properties that make it a valuable scaffold in chemical synthesis. The molecular formula is C10H9ClO, giving a molecular weight of approximately 180.63 g/mol. The presence of the electron-withdrawing chloro group on the aromatic ring modulates the reactivity of the carbonyl and facilitates downstream functionalization.
Physicochemical Properties
As a halogenated indanone, 6-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one is expected to be a solid or low-melting solid at ambient temperature, consistent with other members of the indanone series. The compound contains a ketone carbonyl group that is amenable to nucleophilic addition, condensation reactions, and enolization. The chloro substituent on the aromatic ring can participate in cross-coupling reactions (e.g., Suzuki, Buchwald-Hartwig) under appropriate palladium or other transition-metal catalysis. The methyl group at C-2 introduces a stereocenter, making chiral resolution or asymmetric synthesis relevant for certain applications. Solubility is anticipated in common organic solvents such as dichloromethane, ethyl acetate, and DMSO, with limited aqueous solubility. Specific melting point, boiling point, density, and spectroscopic data should be verified against the certificate of analysis supplied with SKU C727059.
Synthesis and Role as a Building Block
Indanone derivatives are well-established intermediates in synthetic organic chemistry. 6-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one can be accessed via Friedel-Crafts acylation strategies applied to suitably substituted arenes, or through cyclization of appropriately functionalized phenylpropionic acid precursors. The halogen handle at C-6 provides a site for further elaboration via metal-catalyzed cross-coupling, nucleophilic aromatic substitution, or halogen-metal exchange, enabling the introduction of diverse substituents. The C-2 methyl group can serve as a handle for enolate chemistry, aldol-type condensations, or Knoevenagel reactions, expanding the structural diversity accessible from this scaffold. These features collectively position the compound as a versatile building block for the preparation of more complex target molecules.
Research and Medicinal Chemistry Applications
Indanone-based scaffolds occupy a prominent place in medicinal chemistry due to their conformational rigidity, balanced lipophilicity, and capacity for diverse substitution. Halogenated indanones in particular have been explored as intermediates in the synthesis of pharmaceutically relevant targets including kinase inhibitors, central nervous system (CNS) active compounds, and anti-inflammatory agents. The chloro substituent in 6-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one facilitates the preparation of biaryl or heteroaryl-substituted analogs through cross-coupling, which is a common strategy in lead optimization campaigns. Researchers in drug discovery, agrochemical development, and materials science may employ this compound as a key intermediate when constructing polycyclic or functionalized ring systems. Specific reported biological activities or target associations for this exact compound are not confirmed in the available source material and should be verified in primary literature before drawing conclusions.
Handling, Storage, and Procurement
As with all halogenated ketone reagents, appropriate laboratory safety precautions should be followed when handling 6-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one. Users should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for specific hazard classifications, personal protective equipment recommendations, and first-aid measures. The compound should be stored in a cool, dry, well-ventilated location, away from moisture and incompatible materials such as strong bases and reducing agents. Purity grade and detailed analytical specifications (HPLC purity, NMR data, residual solvent levels) are available on the product certificate of analysis for SKU C727059. Procurement inquiries can be directed to Aladdin Scientific through standard ordering channels.
常见问题
What is 6-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one used for in research?
This compound is primarily used as a synthetic building block in organic and medicinal chemistry. Its chloro substituent and ketone carbonyl provide complementary reactive handles for cross-coupling reactions, condensations, and further functionalization, making it valuable for the construction of complex target molecules.
Does the C-2 methyl group in this compound create a chiral center?
Yes, the methyl substituent at the 2-position of the indanone ring creates a stereocenter. Researchers requiring enantiopure material should consider asymmetric synthesis strategies or chiral resolution; the racemic form is typically supplied as the standard catalog offering.
What solvents are suitable for dissolving 6-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one?
Based on the physicochemical profile typical of halogenated indanones, this compound is expected to dissolve readily in common organic solvents including dichloromethane, ethyl acetate, THF, and DMSO. Aqueous solubility is expected to be low. Specific solubility data should be confirmed from the Aladdin Scientific product documentation for SKU C727059.
How should this compound be stored to maintain stability?
The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated environment, protected from moisture, light, and strong bases or oxidizing agents. Always refer to the current SDS from Aladdin Scientific for authoritative storage guidance.
Where can I find the purity and analytical data for SKU C727059?
Detailed analytical data including HPLC purity, NMR spectra, and other quality metrics are provided on the Certificate of Analysis (CoA) available from Aladdin Scientific at the time of purchase or upon request through customer service channels.
参考文献
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for indanone chemistry and Friedel-Crafts acylation.
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry. Oxford University Press. General reference for carbonyl chemistry and halogenated aromatic intermediates.
- Aladdin Scientific. Product page for 6-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one, SKU C727059. Aladdin Scientific catalog.
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