Editing Decaborane

{{chembox
| Watchedfields  = changed
| verifiedrevid  = 429598903
| Name           = Decaborane
| ImageFile      = Decaborane(14)-from-xtal-view-1-tilt-3D-bs-17.png
| ImageClass = bg-transparent
| ImageSize      = 
| ImageName      = The three-dimensional structure of decaborane
| ImageFile1     = Decaborane.png
| OtherNames     = decaborane<br/>decaboron tetradecahydride
| Section1       = {{Chembox Identifiers
| ChemSpiderID = 21241886
| PubChem = 6328162
| SMILES = [H]1[BH]234[BH]156[BH]278[BH]39([H]4)[BH]712[BH]853[BH]645[BH]311[BH]922[BH]14([H]5)[H]2
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| InChI =1/B10H14/c11-5-1-2-3(1,5)7(2,9(3,5,11)13-7)8(2)4(1,2)6(1,5)10(4,8,12-6)14-8/h1-10H
| InChIKey = XAMMYYSPUSIWAS-UHFFFAOYAD
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/B10H14/c11-5-1-2-3(1,5)7(2,9(3,5,11)13-7)8(2)4(1,2)6(1,5)10(4,8,12-6)14-8/h1-10H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XAMMYYSPUSIWAS-UHFFFAOYSA-N
| CASNo = 17702-41-9
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4O04290A2J
| EINECS = 241-711-8
  }}
| Section2       = {{Chembox Properties
| B = 10 | H = 14
| MolarMass = 122.22 g/mol
| Appearance = White crystals
| Odor = bitter, [[chocolate]]-like or burnt [[rubber]]<ref name=PGCH/>
| Solvent = other solvents
| SolubleOther = Slightly, in cold water. [http://www.inchem.org/documents/icsc/icsc/eics0712.htm]
| MeltingPtC = 97-98
| BoilingPtC = 213
| VaporPressure = 0.2 mmHg<ref name=PGCH/>
| Density = 0.94 g/cm<sup>3</sup><ref name=PGCH/>
  }}
| Section7       = {{Chembox Hazards
| AutoignitionPtC = 149
| AutoignitionPt_notes = 
| PEL = TWA 0.3 mg/m<sup>3</sup> (0.05 ppm) [skin]<ref name=PGCH>{{PGCH|0175}}</ref>
| FlashPtF = 176<ref name=PGCH/>
| IDLH = 15 mg/m<sup>3</sup><ref name=PGCH/>
| REL = TWA 0.3 mg/m<sup>3</sup> (0.05 ppm) ST 0.9 mg/m<sup>3</sup> (0.15 ppm) [skin]<ref name=PGCH/>
| MainHazards = may ignite spontaneously on exposure to air<ref name=PGCH/>
| LC50 = 276 mg/m<sup>3</sup> (rat, 4 hr)<br/>72 mg/m<sup>3</sup> (mouse, 4 hr)<br/>144 mg/m<sup>3</sup> (mouse, 4 hr)<ref>{{IDLH|17702419|Decaborane}}</ref>
| GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}}{{GHS08}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|228|301|310|316|320|330|335|336|370|372}}
| PPhrases = {{P-phrases|210|240|241|260|261|262|264|270|271|280|284|301+310|302+350|304+340|305+351+338|307+311|310|312|314|320|321|322|330|332+313|337+313|361|363|370+378|403+233|405|501}}
| NFPA-H = 3
| NFPA-F = 2
| NFPA-R = 2
| NFPA-S = W
}}
}}
'''Decaborane''', also called '''decaborane(14)''', is the [[inorganic compound]] with the [[chemical formula]] [[Boron|B]]<sub>10</sub>[[Hydrogen|H]]<sub>14</sub>.  It is classified as a [[Boranes|borane]] and more specifically a [[boron hydride cluster]]. This white crystalline compound is one of the principal boron hydride clusters, both as a reference structure and as a precursor to other boron hydrides.  It is toxic and volatile, giving off a foul odor, like that of burnt rubber or chocolate.

==Handling, properties and structure==
The physical characteristics of decaborane(14) resemble those of [[naphthalene]] and [[anthracene]], all three of which are volatile colorless solids. [[Sublimation (physics)|Sublimation]] is the common method of purification. Decaborane is highly flammable, and burns with a bright green flame like other [[boron hydrides]]. It is not sensitive to moist air, although it hydrolyzes in boiling water, releasing hydrogen and giving a solution of [[boric acid]]. It is soluble in cold water as well as a variety of non-polar and moderately polar [[solvent]]s.<ref name=IS/>

In decaborane, the B<sub>10</sub> framework resembles an incomplete [[octadecahedron]]. Each boron atom has one "radial" hydride, and four boron atoms near the open part of the cluster feature extra bridging hydrides. In the language of cluster chemistry, the structure is classified as "nido".

==Synthesis and reactions==
It is commonly synthesized via the [[pyrolysis]] of smaller boron hydride [[Atom cluster|clusters]]. For example, pyrolysis of [[diborane|B<sub>2</sub>H<sub>6</sub>]] or [[Pentaborane(9)|B<sub>5</sub>H<sub>9</sub>]] gives decaborane, with loss of H<sub>2</sub>.<ref>{{Greenwood&Earnshaw}}</ref>  On a laboratory scale, sodium borohydride is treated with boron trifluoride to give NaB<sub>11</sub>H<sub>14</sub>, which is acidified to release borane and hydrogen gas.<ref name=IS>Gary B. Dunks, Kathy Palmer-Ordonez, Eddie Hedaya "Decaborane(14)" Inorg. Synth. 1983, vol. 22, pp. 202–207.  {{doi|10.1002/9780470132531.ch46}}</ref>

It reacts with Lewis bases (L) such as [[acetonitrile|CH<sub>3</sub>CN]] and [[diethyl sulfide|Et<sub>2</sub>S]], to form adducts:<ref name=LJT>{{cite book|title=Inorganic Syntheses|author=Charles R. Kutal |author2=David A. Owen |author3=Lee J. Todd |chapter=''closo'' -1,2-Dicarbadodecaborane(12): &#91; ''1,2-Dicarbaclovododecaborane(12'' )&#93; |year=1968 |volume=11|pages=19–24|doi=10.1002/9780470132425.ch5|isbn=978-0-470-13170-1 }}</ref><ref name=MFH>{{cite book|chapter=Icosahedral Carboranes and Intermediates Leading to the Preparation of Carbametallic Boron Hydride Derivatives |author=M. Frederick Hawthorne |author2=Timothy D. Andrews |author3=Philip M. Garrett |author4=Fred P. Olsen |author5=Marten Reintjes |author6=Fred N. Tebbe |author7=Les F. Warren |author8=Patrick A. Wegner |author9=Donald C. Young |title=Inorganic Syntheses|year=1967 |volume=10|pages=91–118|doi=10.1002/9780470132418.ch17|isbn=978-0-470-13241-8}}</ref>
:B<sub>10</sub>H<sub>14</sub> + 2 L → B<sub>10</sub>H<sub>12</sub>L<sub>2</sub> + H<sub>2</sub>

These species, which are classified as "arachno" clusters, in turn react with [[acetylene]] to give the "closo" [[ortho-carborane]]:
:B<sub>10</sub>H<sub>12</sub>·2L + C<sub>2</sub>H<sub>2</sub> → C<sub>2</sub>B<sub>10</sub>H<sub>12</sub> + 2 L + H<sub>2</sub>

Decaborane(14) is a weak [[Brønsted acid]]. Monodeprotonation generates the [[anion]] [B<sub>10</sub>H<sub>13</sub>]<sup>−</sup>, with again a nido structure.

In the [[Brellochs reaction]], decaborane is converted to arachno-CB<sub>9</sub>H<sub>14</sub><sup>−</sup>:
:B<sub>10</sub>H<sub>14</sub> +  CH<sub>2</sub>O  + 2 OH<sup>−</sup>  +  H<sub>2</sub>O  →  CB<sub>9</sub>H<sub>14</sub><sup>−</sup>  +  B(OH)<sub>4</sub><sup>−</sup>  +  H<sub>2</sub>

==Possible applications==
Decaborane has no significant commercial applications, although the compound has often been investigated. It and its derivatives were investigated as an additive to special high-performance [[rocket fuel]]s. Its derivates were investigated as well, e.g. ethyl decaborane.{{cn|date=May 2024}}

Decaborane is an effective reagent for the [[reductive amination]] of ketones and aldehydes.<ref>{{cite journal|author1=Jong Woo Bae|author2=Seung Hwan Lee|author3=Young Jin Cho|author4= Cheol Min Yoon|journal=J. Chem. Soc., Perkin Trans. 1|year=2000|pages=145–146|title=A reductive amination of carbonyls with amines using decaborane in methanol|issue=2|doi=10.1039/A909506C}}</ref>

Decaborane has been assessed for low energy [[ion implantation]] of boron in the manufacture of [[semiconductor]]s. It has also been considered for [[plasma (physics)|plasma]]-assisted [[chemical vapor deposition]] for the manufacture of boron-containing [[thin film]]s. In fusion research, the [[neutron]]-absorbing nature of boron has led to the use of these thin boron-rich films to "boronize" the walls of the [[tokamak]] vacuum vessel to reduce recycling of particles and impurities into the plasma and improve overall performance.<ref>{{cite web |url=http://www.nifs.ac.jp/psi/abstract/p1-05.html |archive-url=https://web.archive.org/web/20040530120541/http://www.nifs.ac.jp/psi/abstract/p1-05.html |archive-date=2004-05-30 |author1=Nakano, T. |author2=Higashijima, S. |author3=Kubo, H. |author4=Yagyu, J. |author5=Arai, T. |author6=Asakura, N. |author7=Itami, K. |title=Boronization effects using deuterated-decaborane (B<sub>10</sub>D<sub>14</sub>) in JT-60U |work=15th PSI Gifu, P1-05 |publisher=National Institute for Fusion Science |location=Sokendai, Japan }}</ref> It has been evaluated in the context of [[nuclear fusion]].<ref>{{Cite news|url=https://www.nextbigfuture.com/2018/03/lpp-fusion-has-funds-try-to-reach-nuclear-fusion-net-gain-milestone.html|title=LPP Fusion has funds try to reach nuclear fusion net gain milestone {{!}} NextBigFuture.com|last=Wang|first=Brian|date=2018-03-27|work=NextBigFuture.com|access-date=2018-03-27|language=en-US}}</ref>

==Safety==
Decaborane, like [[Pentaborane(9)|pentaborane]], is a powerful toxin affecting the [[central nervous system]], although decaborane is less toxic than pentaborane. It can be absorbed through skin.

Purification by sublimation require a dynamic vacuum to remove evolved gases.  Crude samples explode near 100&nbsp;°C.<ref name=MFH/>

It forms an explosive mixture with [[carbon tetrachloride]], which caused an often-mentioned explosion in a manufacturing facility.<ref>{{ cite web | publisher = [[UCLA]] | url = http://www.chem.ucla.edu/dept/Faculty/hawthorne/lecture/lecture2.htm | title = Condensed version of the 79th Faculty Research Lecture Presented by Professor M. Frederick Hawthorne }}</ref>

In crystalline form, it reacts violently with [[red fuming nitric acid|red]] and [[Nitric acid#Anhydrous nitric acid|white fuming nitric acid]] which has a use as rocket fuel oxidizer, producing an extremely powerful detonation.<ref>{{cite web |quote=YouTube video name: 'The Most DESTRUCTIVE Chemical Reaction from two NON-explosive components' |title= The Most DESTRUCTIVE Chemical Reaction from two NON-explosive components |website= [[YouTube]] |date=21 December 2023 |url=https://www.youtube.com/watch?v=DnOQsC9MGbc }}</ref>


==References==
{{reflist}}

==Further reading==
* {{ cite web | publisher = NIST | work = WebBook | title = Decaborane(14) | url = http://webbook.nist.gov/cgi/cbook.cgi?ID=17702-41-9&Units=SI }}
* {{ cite web | work = National Pollutant Inventory | url = http://www.npi.gov.au/substances/boron/index.html | title = Boron and Compounds | publisher = Australian Government }}
* {{ cite web | url = https://www.organic-chemistry.org/chemicals/reductions/decaborane.shtm | title = Decaborane | publisher = Organic Chemistry Portal }}
* {{ cite web | publisher = WebElements | url = http://www.webelements.com/compounds/boron/decaborane_14.html | title = Boron compounds: decaborane (14) }}
* {{cite web | publisher = Centers for Disease Control and Prevention | url = https://www.cdc.gov/niosh/npg/npgd0175.html | title = NIOSH Pocket Guide to Chemical Hazards - Decaborane }}

{{boron compounds}}
{{Hydrides by group}}

[[Category:Boranes]]
[[Category:Rocket fuels]]
[[Category:Foul-smelling chemicals]]