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Bis(cyclopentadienyl)zirconium chloride hydride

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Bis(cyclopentadienyl)zirconium chloride hydride Basic information

Product Name:
Bis(cyclopentadienyl)zirconium chloride hydride
Synonyms:
  • ZIRCONOCENE CHLORIDE HYDRIDE
  • Di(cyclopentadienyl)zirconium(IV) chloride hydride
  • bis(3-cyclopentadienyl)chlorohydrurozirconium
  • Bis(cyclopentadienyl)zirconium chloride hydride (Schwartz's Reagent),
  • Bis(cyclopentadienyl)zirconiumchloridehydride~Schwartz'sReagent~Zirconocenehydrochloride
  • Zirconocenechloridehydride,95%
  • Bis(cyclopentadienyl)zirconiumchloridehydride(Schwartz'sReagent),95%
  • Di(cyclopentadienyl)zirconium(IV) chloride hydride, Schwartz reagent, Zirconocene chloride hydride
CAS:
37342-97-5
MF:
C10H11ClZr
MW:
257.87
EINECS:
253-479-5
Product Categories:
  • Zr
  • Classes of Metal Compounds
  • Metallocenes
  • Reduction
  • Synthetic Organic Chemistry
  • Titanocene, etc.
  • Transition Metal Compounds
  • Zr (Zirconium) Compounds
  • Auxiliaries,Catalysts
Mol File:
37342-97-5.mol
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Bis(cyclopentadienyl)zirconium chloride hydride Chemical Properties

Melting point:
300 °C
storage temp. 
Keep in dark place,Inert atmosphere,2-8°C
form 
Powder
color 
off-white
Water Solubility 
reacts
Sensitive 
Light, Air & Moisture Sensitive
Hydrolytic Sensitivity
8: reacts rapidly with moisture, water, protic solvents
Merck 
14,8396
Exposure limits
ACGIH: TWA 5 mg/m3; STEL 10 mg/m3
NIOSH: IDLH 25 mg/m3; TWA 5 mg/m3; STEL 10 mg/m3
CAS DataBase Reference
37342-97-5(CAS DataBase Reference)
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Safety Information

Hazard Codes 
F,C
Risk Statements 
11-15-34
Safety Statements 
16-26-27-36/37/39-8-45
RIDADR 
UN 3131 4.3/PG 2
WGK Germany 
3
8-10-23
HazardClass 
4.3
PackingGroup 
II
HS Code 
29319090

MSDS

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Bis(cyclopentadienyl)zirconium chloride hydride Usage And Synthesis

Reaction

  1. Reagent for the hydrozirconation of olefins.
  2. Reagent for the hydrozirconation of alkynes.
  3. Catalyst for the hydroboration of olefins.
  4. Mediates the reduction of tertiary amides to aldehydes, without reduction of cyano, nitro, ester, or α,β-unsaturated groups.
  5. Catalyst for the asymmetric vinylation and dienylation of ketones.
  6. Useful reagent for dimethylzinc mediated additions alkenylzirconocenes to aldimines.
  7. Useful reagent for the synthesis of oxidized amides from nitriles.
  8. Reagent for the hydrozirconation of propargylic alcohols.


Chemical Properties

Dicyclopentadienylzirconium hydride chloride, zirconocene hydride chloride, Schwartz’s reagent, Cp2ZrHCl (Cp = C5H5), is a white microcrystalline powder, mp >300℃(dec.). Under the influence of light or heat the color changes to pink, then gradually to dark red. The compound is sensitive to moisture; it is virtually insoluble in the usual organic solvents such as ethers, consistent with its polymeric character. It dissolves in halogenated solvents with evolution of heat, forming Cp2ZrClX, where X = Cl, Br, or I.

Uses

Functionalization of unsaturated systems via an organozirconium intermediate. Schwartz’s reagent is used in limited amounts in organic synthesis for the selective hydrozirconation of alkenes and alkynes. The reaction takes place rapidly and quantitatively at room temperature, forming zirconium alkyls or alkenyls that may be converted into useful functionalized derivatives. For example, reaction with carbon monoxide followed by removal of the zirconium-containing part of the molecule yields a variety of carbonyl compounds.

Uses

Bis(cyclopentadienyl)zirconium hydridochloride is used in the conversion of amides to aldehydes. It is also used as a pharmaceutical intermediate.

Preparation

Schwartz’s reagent is produced by reaction of zirconocene dichloride (Cp2ZrCl2) with LiAlH4 or LiAlH[OC(CH3)3]3 in THF solution. The commercial product (Alfa Ventron, Aldrich) is slightly pink.

Purification Methods

It is moisture and light sensitive. Determine its purity by reaction with a slight excess of Me2CO whereby the active H reacts to produce Cp2ZrClOPri and the integrals of the residual Me2CO in the 1H NMR will show its purity. The presence of Cp2ZrH2 can be determined because it forms Cp2Zr(OPri)2. For a very active compound, it is best to prepare it freshly from the dichloride (see below) by reduction with Vitride [LiAl(OCH2CH2OH)2H2], the white precipitate is filtered off, washed with tetrahydrofuran, then Et2O and dried in a vacuum. Store it dry in the dark. [Carr & Schwartz J Am Chem Soc 101 3521 1979, Negishi & Takahashi Synthesis 1 1988, Beilstein 16 IV 1770.]

Bis(cyclopentadienyl)zirconium chloride hydride Preparation Products And Raw materials

Raw materials

Bis(cyclopentadienyl)zirconium chloride hydrideSupplier

Sinocompound Catalysts Co., Ltd. Gold
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0512-67216630 18962121273;
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Zhengzhou HQ Material Co., Ltd. Gold
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0371-67759225 13526468238
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Wuhan Pengo Technology.,Ltd. Gold
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027-60707801 13628634921
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J & K SCIENTIFIC LTD.
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Meryer (Shanghai) Chemical Technology Co., Ltd.
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4006608290; 18621169109
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