Tert-Butyl_bromide

<i>tert</i>-Butyl bromide

tert-Butyl bromide

Chemical compound

tert-Butyl bromide (also referred to as 2-bromo-2-methylpropane) is an organic compound with the formula Me3CBr (Me = methyl). The molecule features a tert-butyl group attached to a bromide substituent. This organobromine compound is used as a standard reagent in synthetic organic chemistry. It is a colorless liquid.

Quick Facts Names, Identifiers ...

Reactions

It is used to introduce tert-butyl groups. Illustrative is the tert-butylation of cyclopentadiene to give di-tert-butylcyclopentadiene:[3]

C5H6 + 2 NaOH + 2 Me3CBr → (Me3C)2C5H4 + 2 NaBr + 2 H2O

Other aspects

tert-Butyl bromide used to study the massive deadenylation of adenine based-nucleosides induced by halogenated alkanes (alkyl halides) under physiological conditions. 2-Bromo-2-methylpropane causes the massive deguanylation of guanine based-nucleosides and massive deadenylation of adenine based-nucleosides.[4]

Phase transition from orthorhombic Pmn21 phase III at low temperatures (measurements from 95 K), to a disordered rhombohedral phase II at 205-213 K. Phase II can exist from 213-223 K, partly coincident with an FCC phase I, which can be observed between 210-250 K. Phase transitions have also been studied at high pressure (up to 300MPa)[5]

References

  1. [1]
    "2-Bromo-2-methylpropane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 16 June 2012.
  2. [2]
    CRC Handbook of Chemistry and Physics 65th Ed.
  3. [3]
    Reiners, Matthias; Ehrlich, Nico; Walter, Marc D. (2018). Synthesis of 1,3,5-Tri-tert-Butylcyclopenta-1,3-diene and Its Metal Complexes Na{1,2,4-(Me3C)3C5H2} and Mg{η5-1,2,4-(Me3C)3C5H2)2. Inorganic Syntheses. Vol. 37. p. 199. doi:10.1002/9781119477822.ch8. S2CID 105376454.
  4. [4]
    “2-Bromo-2-Methylpropane 135615.” H2NC6H4CO2C2H5, Drugs, www.sigmaaldrich.com/catalog/product/aldrich/135615?lang=en®ion=US.
  5. [5]
    “2-Bromo-2-Methylpropane Structures.” The Cambridge Crystallographic Data Centre (CCDC), www.ccdc.cam.ac.uk/structures/search?id=doi:10.5517/ccvcqmj&sid=DataCite
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