40774-43-4

Basic information

• Product Name: trans-2,3-dibromo-1-indanone
• Synonyms: trans-2,3-dibromo-1-indanone
• CAS NO: 40774-43-4
• Molecular Weight: 289.954
• Mol File: 40774-43-4.mol

Chemical Properties

• CAS DataBase Reference: trans-2,3-dibromo-1-indanone(CAS DataBase Reference)
• NIST Chemistry Reference: trans-2,3-dibromo-1-indanone(40774-43-4)
• EPA Substance Registry System: trans-2,3-dibromo-1-indanone(40774-43-4)

Safety Data

• Hazardous Substances Data: 40774-43-4(Hazardous Substances Data)

Upstream product

• 1775-27-5 2-bromoindanone 
• 480-90-0 1H-inden-1-one 

Relevant articles and documents

PHOTOCHEMISTRY OF α-HALOCYCLOALKANONES AND α,α-DIHALOCYCLOALKANONES. IONIC AND RADICAL PHOTOCHEMICAL CARBON-HALOGEN BOND CLEAVAGE

The nature of the photochemical carbon-halogen bond cleavage in α-halo cycloalkanones depends on the halogen atom bonded and on the ring size of the cycloalkanone.In the 2-halo-1-indanone series the amount of radical products increased from iodine to chlorine, while in the case of 2-halo-3,4-dihydro-1(2H)-naphthalenone 43percent for iodo, 32percent for bromo, and 53percent for the chloro derivative were found.On the other hand, photochemical carbon-chlorine bond cleavage in 2,2-dichloro-1-indanone led to only radical products, while the formation of both radical and ionic products inthe ratio 1:1 was observed in the case of 2,2-dibromo-1-indanone.In the 2,2-dihalo-3,4-dihydro-1(2H)-naphthalenone series, the ratio of the radical to ionic products formed strongly depended on the halogen atom bonded: preferential formation of the radical product in the case of the chloro derivative (92percent) in contrast to 94percent of the ionic products in the case of the bromoderivative, was observed.

Electrophilic Additions to Indene and Indenone: Factors Effecting Syn Addition

The electrophiles bromine, bromine chloride, chlorine, acetyl hypochlorite, and acetyl hypobromite all yield substantial cis addition product by reaction with indene (1) in aprotic solvents, showing that the direct syn collapse of ion pairs obtained from bromine and similar electrophiles is readily possible.The cis to trans ratios with the halogens (but not with the acyl hypohalites) vary with solvent polarities.In the low-polarity solvents (hydrocarbons and carbon tetrachloride) much more syn addition occurs at high halogen concentration.Syn addition of the above electrophiles to 1 as well as methyl hypobromite and methyl hypochlorite was also observed in methanol and acetic acid, with the exception of bromination in methanol where only the trans-dibromide was obtained.Bromine and bromine chloride addition to indenone (20) yielded only the trans-dihalides, suggesting that a neighboring keto group stabilizes the bridged bromonium ion.Chlorination of 20 was not stereospecific but yielded more trans-dichloride than did chlorination of 1.