tert-Butyl bromide

{{DISPLAYTITLE:tert-Butyl bromide}}

{{Chembox

| Watchedfields = changed

| verifiedrevid = 470602802

| Name = tert-Butyl bromide

| ImageFile = Tert-butyl bromide.svg

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageSize = 100

| ImageName = Skeletal formula of tert-butyl bromide with all implicit hydrogens shown

| ImageFile1 = Tert-butyl-bromide-3D-balls.png

| ImageFile1_Ref = {{chemboximage|correct|??}}

| ImageSize1 = 100

| ImageName1 = Ball and stick model of tert-butyl bromide

| PIN = 2-Bromo-2-methylpropane{{cite web|title=2-Bromo-2-methylpropane - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=10485&loc=ec_rcs|work=PubChem Compound|publisher=National Center for Biotechnology Information|accessdate=16 June 2012|location=USA|date=26 March 2005|at=Identification}}

| OtherNames = {{Unbulleted list|1-Bromo-1,1-dimethylethane{{Citation needed|date=June 2012}}|Bromotrimethylmethane{{Citation needed|date=June 2012}}|1,1-Dimethylethyl bromide{{Citation needed|date=June 2012}}|Trimethylbromomethane{{Citation needed|date=June 2012}}

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|Section1={{Chembox Identifiers

| CASNo = 507-19-7

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 5LWO08435U

| PubChem = 10485

| ChemSpiderID = 10053

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 208-065-9

| UNNumber = 2342

| ChEMBL = 347644

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| RTECS = TX4150000

| Beilstein = 1730892

| SMILES = CC(C)(C)Br

| StdInChI = 1S/C4H9Br/c1-4(2,3)5/h1-3H3

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = RKSOPLXZQNSWAS-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

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|Section2={{Chembox Properties

| C=4 | H=9 | Br=1

| Appearance = Colorless liquid

| Density = 1.22 g mL−1 (at 20 °C)CRC Handbook of Chemistry and Physics 65th Ed.

| MeltingPtK = 256.95

| BoilingPtK = 346.4

| LogP = 2.574

| HenryConstant = 310 nmol Pa−1 kg−1

| RefractIndex = 1.4279

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|Section3={{Chembox Thermochemistry

| DeltaHf = −133.4 kJ mol−1

| HeatCapacity = 165.7 J K mol−1

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|Section4={{Chembox Hazards

| GHSPictograms = {{GHS flame}}

| GHSSignalWord = DANGER

| HPhrases = {{H-phrases|225}}

| PPhrases = {{P-phrases|210}}

| FlashPtC = 16

| LD50 = {{Unbulleted list|1.25 g kg−1 (intraperitoneal, rat)|4.4 g kg−1 (intraperitoneal, mouse)}}

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|Section5={{Chembox Related

| OtherFunction_label = alkanes

| OtherFunction = {{Unbulleted list|Bromoethane|n-Propyl bromide|2-Bromopropane|1-Bromobutane|2-Bromobutane}}

}}

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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:{{cite book|doi=10.1002/9781119477822.ch8|title=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|year=2018|last1=Reiners|first1=Matthias|last2=Ehrlich|first2=Nico|last3=Walter|first3=Marc D.|series=Inorganic Syntheses|volume=37|page=199|s2cid=105376454 }}

: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.“2-Bromo-2-Methylpropane 135615.” H2NC6H4CO2C2H5, Drugs, www.sigmaaldrich.com/catalog/product/aldrich/135615?lang=en®ion=US.

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)“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

References

{{Reflist}}

{{DEFAULTSORT:Butyl bromide, tert-}}

Category:Bromoalkanes

Category:Tert-butyl compounds