Diisopropylzinc

Last updated
Diisopropylzinc.png
Diisopropylzinc 3D ball.png
Identifiers
  • 625-81-0 Yes check.svgY
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.221.415 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
  • InChI=1S/2C3H7.Zn/c2*1-3-2;/h2*3H,1-2H3; Yes check.svgY
    Key: KDUNMLRPPVCIGP-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/2C3H7.Zn/c2*1-3-2;/h2*3H,1-2H3;/rC6H14Zn/c1-5(2)7-6(3)4/h5-6H,1-4H3
    Key: KDUNMLRPPVCIGP-LSPCJBSIAV
  • CC(C)[Zn]C(C)C
Properties
C6H14Zn
Molar mass 151.56 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Diisopropylzinc is an organozinc compound with the chemical formula ZnC6H14. [1]

It is the key reagent in the Soai reaction, which is both autocatalytic and enantiospecific. [2] This chemical is pyrophoric, bursting into flame in air or in contact with water. It is generally packaged in toluene. [3]

Related Research Articles

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Cryptochirality

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Soai reaction

In organic chemistry, the Soai reaction is the alkylation of pyrimidine-5-carbaldehyde with diisopropylzinc. The reaction is autocatalytic and leads to rapidly increasing amounts of the same enantiomer of the product. The product pyrimidyl alcohol is chiral and induces that same chirality in further catalytic cycles. Starting with a low enantiomeric excess produces a product with very high enantiomeric excess. The reaction has been studied for clues about the origin of homochirality among certain classes of biomolecules.

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BTX (chemistry)

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Donna Blackmond, Ph.D., is an American chemical engineer and the John C. Martin Endowed Chair in Chemistry at Scripps Research in La Jolla, CA. Her research focuses on prebiotic chemistry, the origin of biological homochirality, and kinetics and mechanisms of asymmetric catalytic reactions. Notable works include the development of Reaction Progress Kinetic Analysis (RPKA), analysis of non-linear effects of catalyst enantiopurity, biological homochirality and amino acid behavior.

Kensō Soai is a Japanese organic chemist. He is a university lecturer in the Applied Chemistry Department of Tokyo University of Science.

References

  1. Benjamin Bederson; Herbert Walther (2002). Advances in Atomic, Molecular, and Optical Physics. Gulf Professional Publishing. pp. 250–. ISBN   978-0-12-003848-0 . Retrieved 2013-08-06.
  2. Shibata, Takanori; Morioka, Hiroshi; Hayase, Tadakatsu; Choji, Kaori; Soai, Kenso (1996). "Highly Enantioselective Catalytic Asymmetric Automultiplication of Chiral Pyrimidyl Alcohol". Journal of the American Chemical Society. 118 (2): 471–472. doi:10.1021/ja953066g.
  3. "Diisopropylzinc 1.0M toluene 625-81-0". MilliporeSigma. Retrieved 8 January 2022.