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223670

Sigma-Aldrich

Bis(cyclopentadienyl)zirconium(IV) chloride hydride

95%

Synonym(s):

Di(cyclopentadienyl)zirconium(IV) chloride hydride, Schwartz’ reagent, Zirconocene chloride hydride

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About This Item

Empirical Formula (Hill Notation):
C10H11ClZr
CAS Number:
37342-97-5
Molecular Weight:
257.87
EC Number:
253-479-5
MDL number:
MFCD02089401
UNSPSC Code:
12352101
PubChem Substance ID:
24853395
NACRES:
NA.22

Assay

95%

form

powder

reaction suitability

core: zirconium
reagent type: catalyst
reagent type: reductant

SMILES string

[H][Zr]Cl.[CH]1[CH][CH][CH][CH]1.[CH]2[CH][CH][CH][CH]2

InChI

1S/2C5H5.ClH.Zr.H/c2*1-2-4-5-3-1;;;/h2*1-5H;1H;;/q;;;+1;/p-1

InChI key

PSYHEBZUPSHSKK-UHFFFAOYSA-M

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General description

Bis(cyclopentadienyl)zirconium(IV) chloride hydride, also known as Schwartz′s reagent, is utilized as a catalyst in in olefin polymerization.

Application

Bis(cyclopentadienyl)zirconium(IV) chloride hydride can be used:
  • To convert amides to aldehydes.
  • As a reagent for the functionalization of olefins and alkynes.
  • As a reducing agent in the preparation of (E)-vinyl organochalcogenides.
  • To prepare a dioxaborolane derivative, which is a key intermediate for the synthesis of bridged-nicotine analogs.

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H261,H314

Hazard Classifications

Skin Corr. 1B - Water-react 2

Storage Class Code

4.3 - Hazardous materials which set free flammable gases upon contact with water

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Organic Syntheses, 71, 83-83 (1992)
Bruce Ganem et al.
The Journal of organic chemistry, 72(11), 3981-3987 (2007-03-27)
In this Perspective, which describes the achievements recognized by the 2007 ACS Award for Creative Invention, we discuss the discovery of a new synthetic reaction and its translation into a substantially improved method for manufacturing a major pharmaceutical product--the blockbuster
Jared T Spletstoser et al.
Journal of the American Chemical Society, 129(11), 3408-3419 (2007-02-24)
An investigation of the use of Cp2Zr(H)Cl (Schwartz's reagent) to reduce a variety of amides to the corresponding aldehydes under very mild reaction conditions and in high yields is reported. A range of tertiary amides, including Weinreb's amides, can be

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