Di-tert-butylzinc

Di-tert-butylzinc is a compound with the formula ZnC₈H₁₈. This compound is used as a meta activating reagent in the syntheses of N,N-dimethyl-3-iodoaniline from N,N-dimethylaniline.[1]

Di-tert-butylzinc

Names
IUPAC name Bis(dimethylethyl)zinc
Other names Di-tert-butylzinc
Identifiers
CAS Number	16636-96-7
3D model (JSmol)	Interactive image
ChemSpider	10750751
PubChem CID	545313
CompTox Dashboard (EPA)	DTXSID20337885
InChI InChI=1S/2C4H9.Zn/c2*1-4(2)3;/h2*1-3H3; Key: KYHHMFUFEIHUHB-UHFFFAOYSA-N InChI=1/2C4H9.Zn/c2*1-4(2)3;/h2*1-3H3;/rC8H18Zn/c1-7(2,3)9-8(4,5)6/h1-6H3 Key: KYHHMFUFEIHUHB-UUODNYSZAB
SMILES CC(C)(C)[Zn]C(C)(C)C
Properties
Chemical formula	C8H18Zn
Molar mass	179.61 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Synthesis

Di-tert-butylzinc is obtained from the reaction between tert-butyllithium and zinc chloride.[2]

2 (CH₃)₃CLi + ZnCl₂ → Zn(C(CH₃)₃)₂ + 2 LiCl

References

1. Armstrong, David R.; Clegg, William; Dale, Sophie H.; Hevia, Eva; Hogg, Lorna M.; Honeyman, Gordon W.; Mulvey, Robert E. (2006). "Directedmeta-Metalation Using Alkali-Metal-Mediated Zincation". Angewandte Chemie International Edition. 45 (23): 3775–8. doi:10.1002/anie.200600720. PMID 16671139.
2. Mulvey, Robert E.; Garden, Jennifer A. (2014), "Di-tert-butylzinc", Encyclopedia of Reagents for Organic Synthesis, Chichester, UK: John Wiley & Sons, Ltd, doi:10.1002/047084289x.rn01774, ISBN 978-0-470-84289-8