Chemistry:Tert-Butyl bromide

tert-Butyl bromide

Names
Preferred IUPAC name 2-Bromo-2-methylpropane
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

Tracking categories (test):

• SizeSet

|Section1=! colspan=2 style="background: #f8eaba; text-align: center;" |Identifiers

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CAS Number

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• 507-19-7 ^Y

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3D model (JSmol)

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• Interactive image

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Beilstein Reference

| 1730892 |-

| ChEMBL

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• ChEMBL347644 ^Y

|- | ChemSpider

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• 10053 ^Y

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| EC Number

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• 208-065-9

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PubChem CID

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• 10485

|- | RTECS number

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• TX4150000

|- | UNII

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• 5LWO08435U ^Y

|- | UN number | 2342 |-

| colspan="2" |

InChI

• InChI=1S/C4H9Br/c1-4(2,3)5/h1-3H3 ^Y

  Key: RKSOPLXZQNSWAS-UHFFFAOYSA-N ^Y

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| colspan="2" |

SMILES

• CC(C)(C)Br

|- |Section2=! colspan=2 style="background: #f8eaba; text-align: center;" |Properties

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Chemical formula

| C₄H₉Br

|- | Molar mass

| 137.020 g·mol⁻¹

|- | Appearance | Colorless liquid |-

| Density | 1.22 g mL⁻¹ (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

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| log P | 2.574 |-

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Henry's law
constant (k_H)

| 310 nmol Pa⁻¹ kg⁻¹ |-

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Refractive index (n_D)

| 1.4279 |- |Section3=! colspan=2 style="background: #f8eaba; text-align: center;" |Thermochemistry

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Heat capacity (C)

| 165.7 J K mol⁻¹ |-

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Std enthalpy of
formation (Δ_fH^⦵₂₉₈)

| −133.4 kJ mol⁻¹ |- |Section4=! colspan=2 style="background: #f8eaba; text-align: center;" |Hazards

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| GHS pictograms | |- | GHS Signal word |DANGER

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GHS hazard statements

| H225 |-

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GHS precautionary statements

| P210 |-

| Flash point | 16 °C (61 °F; 289 K)

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| colspan=2 style="text-align:left; background-color:#f1f1f1;" | Lethal dose or concentration (LD, LC): |-

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LD₅₀ (median dose)

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• 1.25 g kg⁻¹ (intraperitoneal, rat)
• 4.4 g kg⁻¹ (intraperitoneal, mouse)

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|- |Section5=! colspan=2 style="background: #f8eaba; text-align: center;" |Related compounds

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Related alkanes

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• Bromoethane
• n-Propyl bromide
• 2-Bromopropane
• 1-Bromobutane
• 2-Bromobutane

|- }} 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)