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tert-Butyl bromide

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tert-Butyl bromide
Skeletal formula of tert-butyl bromide with all implicit hydrogens shown
Skeletal formula of tert-butyl bromide with all implicit hydrogens shown
Ball and stick model of tert-butyl bromide
Ball and stick model of tert-butyl bromide
Names
Preferred IUPAC name 2-Bromo-2-methylpropane
Other names
  • 1-Bromo-1,1-dimethylethane
  • Bromotrimethylmethane
  • 1,1-Dimethylethyl bromide
  • Trimethylbromomethane
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1730892
ChEMBL
ChemSpider
ECHA InfoCard 100.007.333 Edit this at Wikidata
EC Number
  • 208-065-9
PubChem CID
RTECS number
  • TX4150000
UNII
UN number 2342
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H9Br/c1-4(2,3)5/h1-3H3Key: RKSOPLXZQNSWAS-UHFFFAOYSA-N
SMILES
  • CC(C)(C)Br
Properties
Chemical formula C4H9Br
Molar mass 137.020 g·mol
Appearance Colorless liquid
Density 1.22 g mL (at 20 °C)
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
Henry's law
constant (kH) 		310 nmol Pa kg
Refractive index (nD) 1.4279
Thermochemistry
Heat capacity (C) 165.7 J K mol
Std enthalpy of
formation (ΔfH298) 		−133.4 kJ mol
Hazards
GHS labelling:
Pictograms GHS02: Flammable
Signal word Danger
Hazard statements H225
Precautionary statements P210
Flash point 16 °C (61 °F; 289 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
  • 1.25 g kg (intraperitoneal, rat)
  • 4.4 g kg (intraperitoneal, mouse)
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
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.

Reactions

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

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.

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)

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{η-1,2,4-(Me3C)3C5H2)2. Inorganic Syntheses. Vol. 37. p. 199. doi:10.1002/9781119477822.ch8. S2CID 105376454.
  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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