903885-96-1

Basic information

• Product Name: 2,2-DIBROMO-2,3-DIHYDRO-5-METHOXY-1H-INDEN-1-ONE
• Synonyms: 2,2-DIBROMO-2,3-DIHYDRO-5-METHOXY-1H-INDEN-1-ONE
• CAS NO: 903885-96-1
• Molecular Formula: C10H8Br2O2
• Molecular Weight: 319.98
• Mol File: 903885-96-1.mol

Chemical Properties

• Melting Point: 109-110 °C(Solv: ethanol (64-17-5))
• Boiling Point: 372.1±42.0 °C(Predicted)
• Appearance: /
• Density: 1.925±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2,2-DIBROMO-2,3-DIHYDRO-5-METHOXY-1H-INDEN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIBROMO-2,3-DIHYDRO-5-METHOXY-1H-INDEN-1-ONE(903885-96-1)
• EPA Substance Registry System: 2,2-DIBROMO-2,3-DIHYDRO-5-METHOXY-1H-INDEN-1-ONE(903885-96-1)

Safety Data

• Hazardous Substances Data: 903885-96-1(Hazardous Substances Data)

Upstream product

• 5111-70-6 5-methoxy-1-indanone 

Relevant articles and documents

Halogenation of ketones with N-halosuccinimides under solvent-free reaction conditions

Several aryl substituted ketones, cyclic ketones, 1,3-diketones and a β-ketoamide were halogenated with N-halosuccinimides under solvent-free reaction conditions (SFRC) at various temperatures (20-80 °C), whereas less enolized ketones required the presence of an acid catalyst (p-toluenesulfonic acid, PTSA). Bromination of substituted acetophenones obeys first order kinetics v=kBr[ketone] and the following correlation with the keto-enol equilibrium constant: log kBr=0.3pKE+C1, less enolized substrates being more reactive; the moderate positive charge developed in the rate determining step was confirmed by the Hammett correlation (ρ=-0.5). On the other hand, in cyclic ketones an opposite relation was observed: log kBr=-0.6pKE+C2, indicating higher reactivity of substrates with higher enolization constant (KE). The important role of the nature of the solvent (MeCN, MeOH) in preorganization of the ketone-NBS-PTSA mixture prior to SFRC bromination was found.

Directed regioselectivity of bromination of ketones with NBS: solvent-free conditions versus water

The reaction conditions employed directed the site of functionalisation of ketones with NBS: under solvent-free conditions α-bromination was the exclusive process, while in water, ring functionalisation occurred in the case of methoxy substituted aromatic ketones.