1,1-Dibromoethane - CAS 557-91-5
Catalog number: 557-91-5
Category: Main Product
Molecular Formula:
Molecular Weight:
clear colourless to brownish liquid
1,1-Dibromethan; 1,1-dibromo-ethan; CH3CHBr2; Ethane,1,1-dibromo-; Ethylidene dibromide; ethylidenedibromide
Data not available, please inquire.
Boiling Point:
104.7ºC at 760mmHg
Melting Point:
Canonical SMILES:
Physical Description:
1,1-Dibromoethane, stabilized 99% (100g)
1.Photodissociation of dibromoethanes at 248 nm: an ignored channel of Br2 elimination.
Lee HL1, Lee PC, Tsai PY, Lin KC, Kuo HH, Chen PH, Chang AH. J Chem Phys. 2009 May 14;130(18):184308. doi: 10.1063/1.3130768.
Br(2) molecular elimination is probed in the photodissociation of 1,1- and 1,2-C(2)H(4)Br(2) isomeric forms at 248 nm by using cavity ring-down absorption spectroscopy. Their photodissociation processes differ markedly from each other. The quantum yield of the Br(2) fragment in 1,2-dibromoethane is 0.36+/-0.18, in contrast to a value of 0.05+/-0.03 in 1,1-dibromoethane. The vibrational population ratios of Br(2)(v=1)/Br(2)(v=0) are 0.8+/-0.1 and 0.5+/-0.2 for 1,2- and 1,1-dibromoethanes, respectively. The Br(2) yield densities are found to increase by a factor of 35% and 190% for 1,2- and 1,1-dibromoethanes within the same temperature increment. In the ab initio potential energy calculations, the transition state (TS) along the adiabatic ground state surface may correlate to the Br(2) products. The TS energy for 1,2-dibromoethane is well below the excitation energy at 483 kJ/mol, whereas that for 1,1-dibromoethane is slightly above. Such a small TS energy barrier impedes the photodissociation of the ground state 1,1-dibromoethane such that the production yield of Br(2) may become relatively low, but rise rapidly with the temperature.
2.Mutagenicity of halogenated alkanes and their derivatives.
Rosenkranz HS. Environ Health Perspect. 1977 Dec;21:79-84.
The ability of a series of haloalkanes, haloethanols and haloacetaldehydes to induce mutations in Salmonella typhrimurium and preferentially to inhibit the growth of DNA polymerase-deficient E. coli (pol A(+)/pol A(-)) was investigated. For the haloalkanes investigated, the order of reactivities towards the E. coli pol A(+)/pol A(-), was: 1,1,2,2-tetrabromoethane > 1,1-dibromoethane > 1,1,2,2-tetrachlorethane > 1,2-dibromoethane = 1,5 dibromopentane > 1,2-dibromo-2-methylpropane > 1-bromo-2-chloroethane > 1,2-dichloroethane. In the standard Salmonella mutagenicity assay the order of these substances was 1,2-dibromoethane = 1,5-dibromopentane > 1,2-dibromo-2-methylpropane >/= 1-bromo-2-chloroethane > 1,1,2,2-tetrachloroethane = 1,1-dibromoethane > 1,2-dichloroethane. 1,1,2,2-Tetrabromoethane was negative in the standard assay but strongly mutagenic when tested in suspension. It would appear that the discrepancy between the two procedures is due to the fact that bactericidal mutagens cannot be scored reliably in the standard Salmonella assay.
3.Case of the missing isomer: pathways for molecular elimination in the photoinduced decomposition of 1,1-dibromoethane.
Kalume A1, George L, Cunningham N, Reid SA. J Phys Chem A. 2013 Nov 21;117(46):11915-23. doi: 10.1021/jp403114s. Epub 2013 Jul 26.
We report an experimental and computational study of the photodecomposition pathways of a prototypical gem-dihalide, 1,1-dibromoethane (1,1-EDB), in the condensed phase. Following photolysis of the matrix isolated parent compound in Ar at 5 K, photoproducts are observed corresponding to Br2 elimination (+ C2H4 or C2H2) and HBr elimination (+ vinyl bromide). The elimination products are observed in the matrix as complexes. In contrast to our recent studies of the photolysis of matrix isolated polyhalomethanes, no evidence for the iso-1,1-EDB species is found, although studies of the matrix isolated 1,1-dibromo-2,2,2-trifluoroethane analogue show that the isomer is the dominant photoproduct. These results are examined in the light of theoretical studies that have characterized in detail the 1,1-EDB potential energy surface (PES). For Br2 elimination, a pathway from the isomer on the singlet PES is found which involves a simultaneous Br2 loss with 1,2-hydrogen shift; this pathway lies lower in energy than a concerted three-center elimination from the parent 1,1-EDB.
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