| Revision as of 12:27, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,055 edits Saving copy of the {{chembox}} taken from revid 459810852 of page Tert-Butyl_bromide for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 03:14, 11 February 2024 edit Maxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,058 edits Altered template type. Add: s2cid, series. Removed parameters. Some additions/deletions were parameter name changes. | Use this bot. | #UCB_Other |
| Line 1: |
Line 1: |
|
⚫ |
{{DISPLAYTITLE:''tert''-Butyl bromide}} |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
|
|
{{chembox |
|
{{Chembox |
|
|
| Watchedfields = changed |
|
| verifiedrevid = 458267716 |
|
| verifiedrevid = 470602802 |
| ⚫ |
| 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 = 100 |
|
| 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 = 100 |
|
| ImageName1 = Ball-and-stick model |
|
| ImageName1 = Ball and stick model of tert-butyl bromide |
|
| 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 |
|
| CASNo = 507-19-7 |
|
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
⚫ |
| UNII_Ref = {{fdacite|correct|FDA}} |
| ⚫ |
| ChEMBL = 347644 |
|
|
| PubChem = 24848212 |
|
| UNII = 5LWO08435U |
| ⚫ |
| 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}} |
|
| 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 = 1S/C4H9Br/c1-4(2,3)5/h1-3H3 |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChIKey = RKSOPLXZQNSWAS-UHFFFAOYSA-N |
|
| StdInChIKey = RKSOPLXZQNSWAS-UHFFFAOYSA-N |
|
⚫ |
| StdInChIKey_Ref = {{stdinchicite|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 mL<sup>−1</sup> (at 20 °C)<ref name=crc>] 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>] 65th Ed.</ref> |
|
|
| MeltingPtC = −16.2 |
|
| LogP = 2.574 |
|
|
| HenryConstant = 310 nmol Pa<sup>−1</sup> kg<sup>−1</sup> |
|
| BoilingPtC = 73.2 |
|
|
| Solubility = |
|
| RefractIndex = 1.4279 |
|
}} |
|
}} |
|
| Section8 = {{Chembox Related |
|
|Section3={{Chembox Thermochemistry |
|
|
| DeltaHf = −133.4 kJ mol<sup>−1</sup> |
|
| Function = ]s |
|
|
|
| HeatCapacity = 165.7 J K mol<sup>−1</sup> |
|
| OtherFunctn = ] |
|
|
}} |
|
}} |
|
|
|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|]|]|]|]|]}} |
|
|
}} |
|
}} |
|
}} |
|
|
'''''tert''-Butyl bromide''' (also referred to as '''2-bromo-2-methylpropane''') is an ] with the formula Me<sub>3</sub>CBr (Me = ]). The molecule features a ] group attached to a ] substituent. This ] 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 ]:<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 ] based-nucleosides induced by halogenated alkanes (]) under ] conditions. 2-Bromo-2-methylpropane causes the massive deguanylation of ] 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-}} |
|
|
] |
|
|
] |