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{{chembox {{chembox
| Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 402344255 | verifiedrevid = 420021562
| ImageFile1 = Diethylaluminium cyanide.png | ImageFile1 = Diethylaluminium cyanide.png
| ImageName1 = | ImageSize1 = 170
| ImageAlt1 = Skeletal formula of diethylaluminium cyanide
| ImageFile2 =
| ImageSize2 = | ImageFile2 =
| ImageName2 = | ImageSize2 = 190
| ImageAlt2 = Ball-and-stick model of the diethylaluminium cyanide molecule
| IUPACName = diethylalumanylformonitrile | IUPACName = diethylalumanylformonitrile
| OtherNames = Cyanodiethyl Aluminum<br />(cyano-κC)diethyl-Aluminum<br />(cyano-C)diethyl-Aluminum<br />Cyanodiethyl-(7CI,8CI) Aluminum <br /> Cyanodiethylallane <br /> Cyanodiethylaluminum <br /> Diethylaluminum Cyanide | OtherNames = {{ubl|Cyanodiethyl aluminium|(Cyano-κC)diethyl-aluminium|(Cyano-C)diethyl-aluminium|Cyanodiethyl-(7CI,8CI) aluminium|Cyanodiethylallane|Cyanodiethylaluminium|Diethylaluminium Cyanide}}
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| SMILES =
⚫ | CASNo_Ref = {{cascite|correct|??}}
⚫ | InChI =
| InChIKey =
| CASNo = 5804-85-3 | CASNo = 5804-85-3
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | CASNo_Ref = {{cascite}}
⚫ | ChemSpiderID = 10491962
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EC_number = 227-359-8
⚫ | ChemSpiderID =
| PubChem = | PubChem = 16683962
| StdInChI=1S/2C2H5.CN.Al/c3*1-2;/h2*1H2,2H3;;
| RTECS =
| StdInChIKey = KWMUAEYVIFJZEB-UHFFFAOYSA-N
| SMILES = CC(CC)C#N
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = {{chem2|(CH3CH2)2AlCN}}
| Formula = {{chem|C|4|H|10|Al|C|N}} <br/> {{chem|]|2|Al|C|N}}
| C=5|H=10|Al=1|N=1
| MolarMass = 111.12 g/mol
| Appearance = colorless liquid | Appearance = Dark brown, clear liquid (1.0 mol/L in toluene)<ref name = "MSDS" />
| Density = 0.864 g/cm<sup>3</sup> at (25 °C) liquid | Density = 0.864 g/cm<sup>3</sup> at (25 °C) (liquid)
| Solubility = Benzene, Toluene, diisopropyl ether | Solubility = Reacts with water
| SolubleOther = Benzene, Toluene, diisopropyl ether
| MeltingPt = | MeltingPt =
| BoilingPt = 162 °C/0.02 mmHg (435.15 K) °F)
| pKa = | BoilingPtC = 162
| BoilingPt_notes = at 0.02&nbsp;mmHg
| pKb =
| Viscosity = | pKa =
⚫ | pKb =
| Viscosity =
}} }}
| Section3 = {{Chembox Structure |Section3={{Chembox Structure
| MolShape = | MolShape =
| Dipole = | Dipole =
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| MainHazards = | MainHazards =
| NFPA-H = | NFPA-H =
| NFPA-F = | NFPA-F =
| NFPA-R = | NFPA-R =
| FlashPt = | FlashPtC = 7
| FlashPt_notes = closed cup<ref name = "MSDS" />
| RPhrases =
| GHS_ref=
| SPhrases =
| GHSPictograms = {{GHS06}}{{GHS09}}
⚫ }}
| GHSSignalWord = Danger
⚫ | Section8 = {{Chembox Related
| HPhrases = {{H-phrases|300|310|330|400}}
| Function =
| PPhrases = {{P-phrases|260|262|264|270|271|273|280|284|301+316|302+352|304+340|316|320|321|330|361+364|391|403+233|405|501}}
| OtherFunctn =
| OtherCpds =
}} }}
⚫ |Section8={{Chembox Related
| OtherFunction_label =
| OtherFunction =
| OtherCompounds =
⚫ }}
}} }}
'''Diethylaluminum cyanide''' is the ] with formula ((C<sub>2</sub>H<sub>5</sub>)<sub>2</sub>AlCN)<sub>n.</sub> This compound is usually handled as a solution in toluene. This compound is a ] for the ] of α,β-unsaturated ]s.<ref>{{cite journal | last1= Nagata | first1= W | title= Alkylaluminum cyanides as potent reagents for hydrocyanation | journal= Tetrahedron Letters |year= 1966 |volume= 7 | issue= 18 |pages= 1913–1918 | doi=10.1016/S0040-4039(00)76271-X }}</ref> '''Diethylaluminium cyanide''' ("Nagata's reagent")<ref>{{cite journal|last1=Nagata|first1=W|title = Diethylaluminum cyanide|journal= Organic Syntheses|date=1988|volume=VI|page=307|doi=10.15227/orgsyn.052.0090}}</ref> is the ] with formula {{chem2|((C2H5)2AlCN)_{''n''}|}}. This colorless compound is usually handled as a solution in toluene. It is a ] for the ] of α,β-unsaturated ]s.<ref name = "MSDS">{{cite web|url = http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=AU&language=en&productNumber=276863&brand=ALDRICH&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Faldrich%2F276863%3Flang%3Den|title = MSDS - 276863|publisher = ]|access-date = December 9, 2012}}</ref><ref>{{cite journal|last1 = Nagata|first1 = W.|title = Alkylaluminum cyanides as potent reagents for hydrocyanation|journal = ]|year = 1966|volume = 7|issue = 18|pages = 1913–1918|doi=10.1016/S0040-4039(00)76271-X}}</ref><ref name = "Uhl 1995" /><ref>{{cite journal|last1 = Wade|first1 = K.|last2 = Wyatt|first2 = B. K.|title = Reactions of organoaluminium compounds with cyanides. Part III. Reactions of trimethylaluminium, triethylaluminium, dimethylaluminium hydride, and diethylaluminium hydride with dimethylcyanamide|journal = ]|pages = 1121–1124|year = 1969|doi = 10.1039/J19690001121}}</ref><ref>{{cite journal|last1 = Coates|first1 = G. E.|last2 = Mukherjee|first2 = R. N.|title = 35. Dimethylaluminium cyanide and its gallium, indium, and thallium analogues; beryllium and methylberyllium cyanide|journal = ]|pages = 229–232|year = 1963|doi = 10.1039/JR9630000229}}</ref>
<ref>http://www.sigmaaldrich.com/catalog/ProductDetail.dolang=en&N4=276863|ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC</ref> <ref>{{cite journal|last1= Uhl|first1= Werner|last2= SchüTz|first2= Uwe|last3= Hiller|first3= Wolfgang|last4= Heckel|first4= Maximilian|title= Synthese und Kristallstruktur des trimeren 2Al?CN|journal= Zeitschrift für anorganische und allgemeine Chemie|volume= 621|pages= 823–828|year= 1995 | doi = 10.1002/zaac.19956210521 }}</ref><ref>{{cite journal | last1=Wade | first1=K. | last2=Wyatt | first2=B. K. | title=Reactions of organoaluminium compounds with cyanides. Part III. Reactions of trimethylaluminium, triethylaluminium, dimethylaluminium hydride, and diethylaluminium hydride with dimethylcyanamide | journal=Journal of the Chemical Society A: Inorganic, Physical, Theoretical | pages=1121–1124 | year=1969 | doi = 10.1039/J19690001121 }}</ref><ref>{{cite journal | last1= Coates | first1= G. E. | last2= Mukherjee | first2= R. N. | title= 35. Dimethylaluminium cyanide and its gallium, indium, and thallium analogues; beryllium and methylberyllium cyanide | journal= Journal of the Chemical Society (Resumed) | pages= 229–232 | year= 1963 | doi = 10.1039/JR9630000229 }}</ref>


== Synthesis == == Synthesis ==
Diethylaluminum cyanide was originally produced in 1966. It is generated by the treatment of ] with a slight excess of ]. The product is typically stored in ampoules because it is highly toxic. It dissolves in ], ], ] and ]. It undergoes ] readily and is not compatible with ]. Diethylaluminium cyanide was originally generated by treatment of ] with a slight excess of ]. The product is typically stored in ampoules because it is highly toxic. It dissolves in ], ], ] and ]. It undergoes ] readily and is not compatible with ].


:Et<sub>3</sub>Al + HCN → Et<sub>2</sub>AlCN + Et-H :{{chem2|''n'' Et3Al + ''n'' HCN → (Et2AlCN)_{''n''} + ''n'' EtH}}


== Structure == == Structure ==
Diethylaluminum cyanide has not been examined by ], although other diorganoaluminum cyanides have had their crystal structures determined. Diorganylaluminum cyanides have the general formula (R<sub>2</sub>AlCN)<sub>''n''</sub>, and they exist as cyclic ]s (''n'' = 3) or tetramers (''n'' = 4). In these oligomers one finds AlCN---Al linkages. Diethylaluminium cyanide has not been examined by ], although other diorganoaluminium cyanides have been. Diorganylaluminium cyanides have the general formula {{chem2|(R2AlCN)_{''n''}|}}, and they exist as cyclic ]s (''n'' = 3) or tetramers (''n'' = 4). In these oligomers, one finds AlCN---Al linkages. One compound similar to diethylaluminium cyanide is bis<nowiki>aluminium cyanide, {{chem2|((Me3Si)2CH)2AlCN}}, which has been shown crystallographically to exist as a trimer with the following structure:<ref name = "Uhl 1995">{{ cite journal|title = Synthese und Kristallstruktur des trimeren <sub>2</sub>Al—CN|first1 = Werner|last1 = Uhl|first2 = Uwe|last2 = Schütz|first3 = Wolfgang|last3 = Hiller|first4 = Maximilian|last4 = Heckel|journal = ]|year = 1995|volume = 621|issue = 5|pages = 823–828|doi = 10.1002/zaac.19956210521}}</ref>


⚫ :aluminium cyanide]]
A compound similar to diethylaluminum cyanide is bis(trimethylsilyl)methyl]aluminium cyanide, ((Me<sub>3</sub>Si)<sub>2</sub>CH)<sub>2</sub>AlCN, which has been shown crystallographically to exist as a trimer with the following structure:<ref>{{ cite journal | title = Synthese und Kristallstruktur des trimeren <sub>2</sub>Al—CN | first1 = Werner | last1 = Uhl | first2= Uwe | last2= Schütz | first3= Wolfgang | last3= Hiller | first4= Maximilian | last4 = Heckel | journal = ] | year = 1995 | volume = 621 | issue = 5 | pages = 823–828 | doi = 10.1002/zaac.19956210521 }}</ref>


⚫ Bis(''tert''-butyl)aluminium cyanide, {{chem2|^{''t''}Bu2AlCN}} exists as a tetramer in the crystalline phase:<ref>{{cite journal|title = Hydroalumination of nitriles and isonitriles|first1 = W.|last1 = Uhl|first2 = M.|last2 = Matar|journal = ]|year = 2004|volume = 59|issue = 11–12|pages = 1214–1222|doi = 10.1515/znb-2004-11-1239|s2cid = 99001626|url = http://www.znaturforsch.com/ab/v59b/59b1214.pdf}}</ref><ref>{{cite journal|title = Synthese und Kristallstruktur des trimeren <nowiki></nowiki><sub>2</sub>Al—CN|first1 = W.|last1 = Uhl|first2 = U.|last2 = Schütz|first3 = W.|last3 = Hiller|first4 = M.|last4 = Heckel|journal = ]|year = 2005|volume = 60|issue = 2|pages = 155–163|url = http://www.znaturforsch.com/ab/v60b/60b0155.pdf}}</ref>
⚫ :aluminium cyanide]]

⚫ More recently, bis(hydrocarbyl)aluminium cyanides have been structurally characterized, such as bis(''tert''-butyl)aluminium cyanide, tBu<sub>2</sub>AlCN, which forms a tetramer in the crystalline phase:<ref>{{ cite journal | title = Hydroalumination of Nitriles and Isonitriles | first1 = Werner | last1 = Uhl | first2= Madhat | last2= Matar | journal = Z. Naturforsch., B: Chem. Sci. | year = 2004 | volume = 59 | issue = 11/12 | pages = 1214–1222 | url = http://www.znaturforsch.com/ab/v59b/59b1214.pdf }}</ref><ref>{{ cite journal | title = Synthese und Kristallstruktur des trimeren <nowiki></nowiki><sub>2</sub>Al—CN | first1 = Werner | last1 = Uhl | first2= Uwe | last2= Schütz | first3= Wolfgang | last3= Hiller | first4= Maximilian | last4 = Heckel | journal = Z. Naturforsch., B: Chem. Sci. | year = 2005 | volume = 60 | issue = 2 | pages = 155–163 | url = http://www.znaturforsch.com/ab/v60b/60b0155.pdf }}</ref>


:] :]


== Uses == == Uses ==
Diethylaluminum cyanide is used for hydrocyanation of α,β- unsaturated ketones. The reaction is influenced by the ] of the solvent. This effect arises from the Lewis acidic qualities of the reagent.<ref>{{OrgSynth | collvol = 6 | collvolpages = 436 | year = 1988 | title = Diethylaluminum cyanide | author = W. Nagata and M. Yoshioka | prep = cv6p0436}}</ref> Diethylaluminium cyanide is used for the stoichiometric ] of α,β-unsaturated ketones. The reaction is influenced by the ] of the solvent. This effect arises from the Lewis acidic qualities of the reagent.<ref>{{OrgSynth|collvol = 6|collvolpages = 436|year = 1988|title = Diethylaluminum cyanide|author1 = Nagata, W.|author2 = Yoshioka, M.|prep = cv6p0436}}</ref>
The purpose of this reaction is to generate alkylnitriles which are precursors to amines, amides, carboxylic acids and esters. The purpose of this reaction is to generate alkylnitriles, which are precursors to amines, amides, carboxylic acids esters and aldehydes.
:] :]

== References == ==References==
{{Reflist}} {{Reflist}}


==External links==
*{{Commons category-inline}}

{{Aluminium compounds}}


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