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

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
CAS Number	507-19-7 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1730892
ChEMBL	ChEMBL347644 Y
ChemSpider	10053 Y
ECHA InfoCard	100.007.333
EC Number	208-065-9
PubChem CID	10485
RTECS number	TX4150000
UNII	5LWO08435U Y
UN number	2342
CompTox Dashboard (EPA)	DTXSID5060144
InChI InChI=1S/C4H9Br/c1-4(2,3)5/h1-3H3 Y Key: RKSOPLXZQNSWAS-UHFFFAOYSA-N Y
SMILES CC(C)(C)Br
Properties
Chemical formula	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
Henry's law constant (kH)	310 nmol Pa−1 kg−1
Refractive index (nD)	1.4279
Thermochemistry
Heat capacity (C)	165.7 J K mol−1
Std enthalpy of formation (ΔfH⦵298)	−133.4 kJ mol−1
Hazards
GHS labelling:
Pictograms
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−1 (intraperitoneal, rat) 4.4 g kg−1 (intraperitoneal, mouse)
Related compounds
Related alkanes	Bromoethane n-Propyl bromide 2-Bromopropane 1-Bromobutane 2-Bromobutane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) 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 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]