tert-Butyl bromide

From Wikipedia, the free encyclopedia
tert-Butyl bromide
Skeletal formula of tert-butyl bromide with all implicit hydrogens shown
Ball and stick model of tert-butyl bromide
Names
Preferred IUPAC name
2-Bromo-2-methylpropane[1]
Other names
  • 1-Bromo-1,1-dimethylethane[citation needed]
  • Bromotrimethylmethane[citation needed]
  • 1,1-Dimethylethyl bromide[citation needed]
  • Trimethylbromomethane[citation needed]
Identifiers
3D model (JSmol)
1730892
ChEMBL
ChemSpider
ECHA InfoCard 100.007.333 Edit this at Wikidata
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 GHS02: Flammable
GHS Signal word Danger
GHS hazard statements
 H225
P210
Flash point 16 °C (61 °F; 289 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
  • 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).
checkY  (what is checkY☒N ?)
Infobox references

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:[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]

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
Retrieved from ""