tert-Butyl bromide

*tert*-Butyl bromide
Names
	Preferred IUPAC name 2-Bromo-2-methylpropane
	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 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1730892
ChEMBL	ChEMBL347644 ;
ChemSpider	10053 ;
ECHA InfoCard	100.007.333
EC Number	208-065-9;
PubChem CID	10485;
RTECS number	TX4150000;
UNII	5LWO08435U ;
UN number	2342
CompTox Dashboard (EPA)	DTXSID5060144 ;
	InChI InChI=1S/C4H9Br/c1-4(2,3)5/h1-3H3 Key: RKSOPLXZQNSWAS-UHFFFAOYSA-N ;
	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)
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). verify (what is ?) 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 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]

References

^ "2-Bromo-2-methylpropane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 16 June 2012.
^ CRC Handbook of Chemistry and Physics 65th Ed.
^ 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.
^ “2-Bromo-2-Methylpropane 135615.” H2NC6H4CO2C2H5, Drugs, www.sigmaaldrich.com/catalog/product/aldrich/135615?lang=en®ion=US.
^ “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

[1] "2-Bromo-2-methylpropane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 16 June 2012.

[crc-2] CRC Handbook of Chemistry and Physics 65th Ed.

[Walter-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

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