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
| 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}}
}}
|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}}
}}
|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
}}
|Section3={{Chembox Thermochemistry
| DeltaHf = −133.4 kJ mol−1
| HeatCapacity = 165.7 J K mol−1
}}
|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)}}
}}
|Section5={{Chembox Related
| OtherFunction_label = alkanes
| OtherFunction = {{Unbulleted list|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:{{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-}}