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.
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Preferred IUPAC name
2-Bromo-2-methylpropane[1] | |
Other names
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Identifiers | |
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3D model (JSmol)
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1730892 | |
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ChemSpider |
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ECHA InfoCard | 100.007.333 |
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PubChem CID
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UNII |
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UN number | 2342 |
CompTox Dashboard (EPA)
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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 |
Henry's law
constant (kH) |
310 nmol Pa−1 kg−1 |
Refractive index (nD)
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1.4279 |
Thermochemistry | |
Heat capacity (C)
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165.7 J K mol−1 |
Std enthalpy of
formation (ΔfH⦵298) |
−133.4 kJ mol−1 |
Hazards | |
GHS labelling: | |
Danger | |
H225 | |
P210 | |
Flash point | 16 °C (61 °F; 289 K) |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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Related compounds | |
Related alkanes
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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
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It is used to introduce tert-butyl groups. Illustrative is the tert-butylation of cyclopentadiene to give di-tert-butylcyclopentadiene:[3]
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]