Pentakis(dimethylamido)tantalum

Names
IUPAC name

Tantalum(V) dimethylazanide

Other names

Pentakis(dimethylamino)tantalum(V), Tantalum dimethylamide

Identifiers

CAS Number

* 19824-59-0

3D model (JSmol)

* Interactive image

ChemSpider |

* 124019

PubChem CID

* 140614

InChI

* InChI=1S/5C2H6N.Ta/c5*1-3-2;/h5*1-2H3;/q5*-1;+5

Key: VSLPMIMVDUOYFW-UHFFFAOYSA-N

SMILES

* C[N-]C.C[N-]C.C[N-]C.C[N-]C.C[N-]C.[Ta+5]

Properties

Chemical formula

| C10H30N5Ta
Molar mass | 401.333 g·mol−1
Appearance  | orange powder (xtl)
Melting point | 100 °C
Hazards
GHS labelling:

Pictograms

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Chemical compound

Pentakis(dimethylamido)tantalum is an organometallic compound of tantalum. It is a colorless solid that is soluble in organic solvents. It hydrolyzes readily to release dimethylamine.

## Synthesis and structure

[edit]

Ta(NMe2)5 is prepared by treating TaCl5 with lithium dimethylamide.[1] The preparation is similar to that for tetrakis(dimethylamido)titanium.

The compound has idealized D3h symmetry (ignoring the organic substituents).

## Applications to organic synthesis

[edit]

Main article: Organotantalum chemistry

The complex effects C-alkylation of secondary amines with 1-alkenes [2] and hydroaminoalkylation of olefins to form alkylamines.[3]

Hydroaminoalkylation Reaction Scheme

## References

[edit]

1. ^ Bradley, D. C.; Thomas, I. M. (1962-07-01). "Metallo-Organic Compounds Containing Metal–Nitrogen Bonds: Part Iii. Dialkylamino Compounds of Tantalum". Canadian Journal of Chemistry. 40 (7): 1355–1360\. doi:10.1139/v62-207. ISSN 0008-4042.1355-1360&rft.date=1962-07-01&rft_id=info:doi/10.1139/v62-207&rft.issn=0008-4042&rft.aulast=Bradley&rft.aufirst=D.+C.&rft.au=Thomas,+I.+M.&rft_id=https://doi.org/10.1139%2Fv62-207&rfr_id=info:sid/en.wikipedia.org:Pentakis(dimethylamido)tantalum" class="Z3988">
2. ^ Clerici, Mario G.; Maspero, Federico (1980-01-01). "CatalyticC-Alkylation of Secondary Amines with Alkenes". Synthesis. 1980 (4): 305–306\. doi:10.1055/s-1980-29002. ISSN 0039-7881. S2CID 94579838.305-306&rft.date=1980-01-01&rft_id=https://api.semanticscholar.org/CorpusID:94579838#id-name=S2CID&rft.issn=0039-7881&rft_id=info:doi/10.1055/s-1980-29002&rft.aulast=Clerici&rft.aufirst=Mario+G.&rft.au=Maspero,+Federico&rfr_id=info:sid/en.wikipedia.org:Pentakis(dimethylamido)tantalum" class="Z3988">
3. ^ Herzon, Seth B.; Hartwig, John F. (2007-05-01). "Direct, Catalytic Hydroaminoalkylation of Unactivated Olefins with N-Alkyl Arylamines". Journal of the American Chemical Society. 129 (21): 6690–6691\. doi:10.1021/ja0718366. ISSN 0002-7863. PMC 2590937. PMID 17474747.6690-6691&rft.date=2007-05-01&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2590937#id-name=PMC&rft.issn=0002-7863&rft_id=info:pmid/17474747&rft_id=info:doi/10.1021/ja0718366&rft.aulast=Herzon&rft.aufirst=Seth+B.&rft.au=Hartwig,+John+F.&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2590937&rfr_id=info:sid/en.wikipedia.org:Pentakis(dimethylamido)tantalum" class="Z3988">

* v
* t
* e

Tantalum compounds

Tantalum(II)|

* TaB2

Tantalum(III)|

* TaAl3
* TaAs
* TaN
* TaCl3

| Organotantalum(III)|

* Ta(SiOtBu)3

|

Tantalum(IV)|

* TaS2
* TaSe2
* TaI4
* TaC
* TaTe2
* Ta4HfC5

Tantalum(V)|

* TaF5
* TaCl5
* TaBr5
* TaI5
* Ta2O5
* LiTaO3
* NdTaO4
* LuTaO4
* K2TaF7
* H2TaF7
* K2Ta2O3F6

| Organotantalum(V)|

* Ta2(OC2H5)10
* TaC5H15
* TaCl2(CH3)3
* Ta(C2H6N)5
* TaCp2H3

|

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