Reaction
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Bis(cyclopentadienyl)zirconium chloride hydride

Reaction
Product Name
Bis(cyclopentadienyl)zirconium chloride hydride
CAS No.
37342-97-5
Chemical Name
Bis(cyclopentadienyl)zirconium chloride hydride
Synonyms
SCHWARTZ REAGENT;SCHWARTZ'S REAGENT;ZIRCONOCENE CHLORIDE HYDRIDE;BIS(CYCLOPENTADIENYL)ZIRCONIUM(IV) CHLORIDE HYDRIDE;BIS(CYCLOPENTADIENYL)ZIRCONIUM HYDRIDOCHLORIDE;Schwartz's;oride hydride;)zirconium chL;SCHWART'S REAGENT;SCHWARTZ' REAGENT
CBNumber
CB7105513
Molecular Formula
C10H11ClZr
Formula Weight
257.87
MOL File
37342-97-5.mol
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Bis(cyclopentadienyl)zirconium chloride hydride Property

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
InChI
InChI=1S/2C5H5.ClH.Zr.H/c2*1-2-4-5-3-1;;;/h2*1-3H,4H2;1H;;/q;;;+2;-1/p-1
InChIKey
DWFXOSDSYIGRKR-UHFFFAOYSA-M
SMILES
[Zr+2](C1CC=CC=1)C1CC=CC=1.[Cl-].[H-]
CAS DataBase Reference
37342-97-5(CAS DataBase Reference)
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Safety

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
F 
8-10-23
HazardClass 
4.3
PackingGroup 
II
HS Code 
29319090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H261In contact with water releases flammable gas

H314Causes severe skin burns and eye damage

Precautionary statements

P223Keep away from any possible contact with water, because of violent reaction and possible flash fire.

P231+P232Handle under inert gas. Protect from moisture.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
223670
Product name
Bis(cyclopentadienyl)zirconium(IV) chloride hydride
Purity
95%
Packaging
1g
Price
$42.6
Updated
2024/03/01
Sigma-Aldrich
Product number
223670
Product name
Bis(cyclopentadienyl)zirconium(IV) chloride hydride
Purity
95%
Packaging
5g
Price
$143
Updated
2024/03/01
TCI Chemical
Product number
Z0010
Product name
Zirconocene Chloride Hydride
Purity
>96.0%(T)
Packaging
1g
Price
$39
Updated
2024/03/01
TCI Chemical
Product number
Z0010
Product name
Zirconocene Chloride Hydride
Purity
>96.0%(T)
Packaging
5g
Price
$118
Updated
2024/03/01
Alfa Aesar
Product number
L15164
Product name
Bis(cyclopentadienyl)zirconium hydridochloride, 95%
Packaging
1g
Price
$38.5
Updated
2023/06/20
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Bis(cyclopentadienyl)zirconium chloride hydride Chemical Properties,Usage,Production

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.

reaction suitability

core: zirconium
reagent type: catalyst
reagent type: reductant

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

Toluene Sodium Carbon tetrachloride Tetrahydrofuran Lithium Aluminum Hydride Zirconium tetrachloride 1,3-Cyclopentadiene

Preparation Products

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Bis(cyclopentadienyl)zirconium chloride hydride Suppliers

Belgium 1 China 156 Germany 3 India 3 Japan 3 Russia 1 Switzerland 1 United Kingdom 5 United States 19 Global 192
Protheragen-ING
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View Lastest Price from Bis(cyclopentadienyl)zirconium chloride hydride manufacturers

XINXIANG RUNYU MATERIAL CO., LTD.
Product
Bis(cyclopentadienyl)zirconium chloride hydride 37342-97-5
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
0.96
Supply Ability
500kg
Release date
2021-11-30
Zhengzhou HQ Material CO.,LTD.
Product
Bis(cyclopentadienyl)zirconium chloride hydride 37342-97-5
Price
US $0.00-0.00/Kg/Drum
Min. Order
100g
Purity
99%+
Supply Ability
25kg
Release date
2021-12-10
Zhuozhou Wenxi import and Export Co., Ltd
Product
Bis(cyclopentadienyl)zirconium chloride hydride 37342-97-5
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10

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