tert-Butyl bromide

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.

tert-Butyl bromide
Names
IUPAC name
2-Bromo-2-methylpropane[1]
Other names
  • 1-Bromo-1,1-dimethylethane
  • Bromotrimethylmethane
  • 1,1-Dimethylethyl bromide
  • Trimethylbromomethane
Identifiers
3D model (JSmol)
1730892
ChEMBL
ChemSpider
ECHA InfoCard 100.007.333
EC Number
  • 208-065-9
RTECS number
  • TX4150000
UNII
UN number 2342
Properties
C4H9Br
Molar mass 137.020 g·mol−1
Appearance Colorless liquid
Density 1.22 g mL−1 (at 20 °C)[2]
Melting point −16.20 °C; 2.84 °F; 256.95 K
Boiling point 73.3 °C; 163.8 °F; 346.4 K
log P 2.574
310 nmol Pa−1 kg−1
1.4279
Thermochemistry
165.7 J K mol−1
Std enthalpy of
formation (ΔfH⦵298)
 −133.4 kJ mol−1
Hazards
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H225
P210
Flash point 16 °C (61 °F; 289 K)
Lethal dose or concentration (LD, LC):
  • 1.25 g kg−1 (intraperitoneal, rat)
  • 4.4 g kg−1 (intraperitoneal, mouse)
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

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 a FCC phase I, which can be observed between 210-250 K. Phase transitions have also been studied at high pressure (up to 300MPa)[5]

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References
  1. "2-Bromo-2-methylpropane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 16 June 2012.
  2. CRC Handbook of Chemistry and Physics 65th Ed.
  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. 37: 199. doi:10.1002/9781119477822.ch8.
  4. “2-Bromo-2-Methylpropane 135615.” H2NC6H4CO2C2H5, Drugs, www.sigmaaldrich.com/catalog/product/aldrich/135615?lang=en®ion=US.
  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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