Diethylzinc

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Diethylzinc
Formula	C4H10Zn
Molecular mass	123.50 g/mol
Boiling point	117 °C
Freezing point	-28 °C
Density	1.498 g/cm3
CAS number	557-20-0
SMILES	CCZnCC

Diethylzinc (C₂H₅)₂Zn, is an organozinc compound comprised of zinc bonded to two ethyl groups. It is an important reagent in organic chemistry and available commercially as solutions of hexanes, heptane or toluene.

Contents 1 Synthesis 2 Reactions 3 Other uses 4 External links 5 References

[edit] Synthesis

Edward Frankland prepared the compound in 1864 from zinc and diethyl mercury ^[1]. A classic synthesis consists of the reaction between ethyl iodide and ethyl bromide with a zinc / copper couple ^[2].

[edit] Reactions

Diethylzinc reacts violently with water and easily catches fire (pyrophoric) when in contact with air. It must therefore be handled under a nitrogen blanket.

Diethylzinc is used in organic synthesis as a nucleophilic ethyl synthon in addition reactions to carbonyl groups (for example in the asymmetric addition to benzaldehyde ^[3]) and imines ^[4]

With diiodomethane it forms a Simmons-Smith reagent ^{[5] [6]}

[edit] Other uses

In microelectronics, diethylzinc is used as a doping agent.

[edit] External links

• Diethylzinc, 15 wt.% solution in hexane MSDS commercial supplier
• Diethylzinc purum MSDS commercial supplier
• Diethylzinc MSDS commercial supplier
• Links to external chemical sources

[edit] References

1. ^ Frankland and Duppa, J. Chem. Soc. 17, 31 (1864).
2. ^ Organic Syntheses, Coll. Vol. 2, p.184 (1943); Vol. 12, p.86 (1932) Article
3. ^ Organic Syntheses, Coll. Vol. 10, p.635 (2004); Vol. 79, p.139 (2002). Article
4. ^ Organic Syntheses, Vol. 83, p.5 (2005) Article.
5. ^ Organic Syntheses, Coll. Vol. 10, p.613 (2004); Vol. 76, p.86 (1999) Article.
6. ^ Organic Syntheses, Coll. Vol. 6, p.327 (1988); Vol. 59, p.113 (1979) Article.