Jump to content

Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Tert-Butyl bromide: Difference between pages

(Difference between pages)
Content deleted Content added
VisualWikitext
Saving copy of the {{chembox}} taken from revid 459810852 of page Tert-Butyl_bromide for the Chem/Drugbox validation project (updated: '').
 
Altered template type. Add: s2cid, series. Removed parameters. Some additions/deletions were parameter name changes. | Use this bot. | #UCB_Other
 
Line 1: Line 1:
⚫
''tert''-Butyl bromide
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid [{{fullurl:Tert-Butyl_bromide|oldid=459810852}} 459810852] of page [[Tert-Butyl_bromide]] with values updated to verified values.}}
{{chembox
{{
| Watchedfields = changed
| verifiedrevid = 458267716
| verifiedrevid =
⚫
| Name=''tert''-Butyl bromide
| Name = ''tert''-Butyl bromide
| ImageFile = Tert-butyl bromide.svg
| ImageFile = Tert-butyl bromide.svg
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 135px
| ImageSize =
| ImageName = Structural formula
| ImageName = Skeletal formula of tert-butyl bromide with all implicit hydrogens shown
| ImageFile1 = Tert-butyl-bromide-3D-balls.png
| ImageFile1 = Tert-butyl-bromide-3D-balls.png
| ImageFile1_Ref = {{chemboximage|correct|??}}
| ImageSize1 = 165px
| ImageSize1 =
| ImageName1 = Ball-and-stick model
| ImageName1 = Ballandstick model
| IUPACName = 2-bromo-2-methylpropane
| PIN = 2-Bromo-2-methylpropane<ref>{{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}}</ref>
| OtherNames = 1,1-dimethylethyl bromide<br/>1-bromo-1,1-dimethylethane<br/>bromotrimethylmethane<br/>trimethylbromomethane<br/>''t''-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
⚫
|Section1={{Chembox Identifiers
⚫
| CASNo_Ref = {{cascite|correct|CAS}}
| EC-number = 208-065-9
| = --
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| = {{|correct|}}
⚫
| = {{|correct|}}
⚫
| ChEMBL = 347644
| PubChem = 24848212
| =
⚫
| SMILES = CC(C)(C)Br
⚫
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 347644
| PubChem = 10485
| PubChem = 10485
⚫
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10053
| ChemSpiderID = 10053
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| = {{|correct|chemspider}}
| EINECS = 208-065-9
⚫
| UNNumber =
⚫
| 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 = 1S/C4H9Br/c1-4(2,3)5/h1-3H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RKSOPLXZQNSWAS-UHFFFAOYSA-N
| StdInChIKey = RKSOPLXZQNSWAS-UHFFFAOYSA-N
⚫
| = {{|correct|chemspider}}
⚫
| RTECS = TX4150000
}}
⚫
| UNNumber =
⚫
|Section2={{Chembox Properties
⚫
}}
| C=4 | H=9 | Br=1
⚫
| Section2 = {{Chembox Properties
⚫
| Appearance = Colorless liquid
| Formula = C<sub>4</sub>H<sub>9</sub>Br
⚫
| Density = 1.22 g <sup></sup> <ref name=crc>[[CRC Handbook of Chemistry and Physics]] 65th Ed.</ref>
| MolarMass = 137.02 g/mol
| MeltingPtK = 256.95
⚫
| Appearance = Colorless liquid
| BoilingPtK = 346.4
⚫
| Density = 1.22 g cm<sup>−3</sup> <ref name=crc>[[CRC Handbook of Chemistry and Physics]] 65th Ed.</ref>
| MeltingPtC = −16.2
| = .
| HenryConstant = 310 nmol Pa<sup>−1</sup> kg<sup>−1</sup>
| BoilingPtC = 73.2
| Solubility =
| =
}}
}}
| Section8 = {{Chembox Related
|={{Chembox
| DeltaHf = −133.4 kJ mol<sup>−1</sup>
| Function = [[alkyl halide]]s
| HeatCapacity = 165.7 J K mol<sup>−1</sup>
| OtherFunctn = [[tert-Butyl chloride]]
}}
}}
|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<sup>−1</sup> <small>(intraperitoneal, rat)</small>|4.4 g kg<sup>−1</sup> <small>(intraperitoneal, mouse)</small>}}
}}
|Section5={{Chembox Related
| OtherFunction_label = alkanes
| OtherFunction = {{Unbulleted list|[[Bromoethane]]|[[n-Propyl bromide|''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 Me<sub>3</sub>CBr (Me = [[methyl]]). The molecule features a [[tert-butyl|''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|di-''tert''-butylcyclopentadiene]]:<ref name=Walter>{{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-(Me<sub>3</sub>C)<sub>3</sub>C<sub>5</sub>H<sub>2</sub>} and Mg{η<sup>5</sup>-1,2,4-(Me<sub>3</sub>C)<sub>3</sub>C<sub>5</sub>H<sub>2</sub>)<sub>2</sub>|year=2018|last1=Reiners|first1=Matthias|last2=Ehrlich|first2=Nico|last3=Walter|first3=Marc D.|series=Inorganic Syntheses|volume=37|page=199|s2cid=105376454 }}</ref>
:C<sub>5</sub>H<sub>6</sub> + 2 NaOH + 2 Me<sub>3</sub>CBr → (Me<sub>3</sub>C)<sub>2</sub>C<sub>5</sub>H<sub>4</sub> + 2 NaBr + 2 H<sub>2</sub>O

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

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)<ref>“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</ref>

==References==
{{Reflist}}

{{DEFAULTSORT:Butyl bromide, tert-}}
[[Category:Bromoalkanes]]
[[Category:Tert-butyl compounds]]
Retrieved from "https://en.wikipedia.org/wiki/Special:ComparePages"