Bromoiodomethane

Bromoiodomethane is a halomethane with the formula BrCH2I. It is a colorless liquid, although older samples appear yellow. The compound has been investigated as a reagent for cyclopropanation by the Simmons-Smith reaction, but diiodomethane and chloroiodomethane are preferred. It also occurs naturally as the result of microbial action.[1]

Bromoiodomethane
Names
Preferred IUPAC name
Bromo(iodo)methane
Other names
  • Bromoiodomethane
  • Bromomethyl iodide
  • Iodobromomethane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.156.567
Properties
CH2BrI
Molar mass 220.835 g·mol−1
Appearance Colourless liquid
Density 2.93 g mL−1
Melting point 1 °C; 34 °F; 274 K
Boiling point 138 to 141 °C (280 to 286 °F; 411 to 414 K)
1.6382
Hazards
GHS pictograms
GHS Signal word Danger
H315, H318, H335
P261, P280, P305+351+338
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Its critical point is at 367.85 °C and 6.3 MPa and refractive index is 1.6382 (20 °C, D).

Additional reading
  • Tarnovsky A. N.; Wall M.; Gustafsson M.; Lascoux N.; Sundström V.; Åkesson E. (March 2002). "Ultrafast Study of the Photodissociation of Bromoiodomethane in Acetonitrile upon 266 nm Excitation". J. Phys. Chem. A. 106 (25): 5999–6005(7). Bibcode:2002JPCA..106.5999T. doi:10.1021/jp014306j. Retrieved 2007-06-29.
  • Liu Y.-J.; Ajitha D.; Krogh J. W.; Tarnovsky A. N.; Lindh R. (December 2005). "Spin-Orbit Ab Initio Investigation of the Photolysis of Bromoiodomethane". ChemPhysChem. 7 (4): 955–963(9). doi:10.1002/cphc.200500654. PMID 16596616. Archived from the original on 2011-08-13. Retrieved 2007-06-29.
  • Zheng, X.; Phillips, D. L. (August 2000). "Photoisomerization reaction of CH2BrI following A-band and B-band photoexcitation in the solution phase: Transient resonance Raman observation of the iso-CH2I-Br photoproduct". J. Chem. Phys. 113 (8): 3194–3203(10). Bibcode:2000JChPh.113.3194Z. doi:10.1063/1.1286920. hdl:10722/42350.
  • Liu K.; Zhao H.; Wang C.; Zhang A.; Ma S.; Li Z. (January 2005). "A theoretical study of bond selective photochemistry in CH2BrI". J. Chem. Phys. 122 (4): 044310. Bibcode:2005JChPh.122d4310L. doi:10.1063/1.1835955. PMID 15740251. Retrieved 2007-06-29.

References
  1. Lim, Y.-K.; Phang, S.-M.; Rahman, N. Abdul; Sturges, W. T.; Malin, G. (2017). "REVIEW: Halocarbon Emissions from Marine Phytoplankton and Climate Change". Int. J. Environ. Sci. Technol.: 1355–1370. doi:10.1007/s13762-016-1219-5. S2CID 99300836.


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