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
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)
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
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.
N-Bromosuccinimide Price
- Product number
- 223670
- Product name
- Bis(cyclopentadienyl)zirconium(IV) chloride hydride
- Purity
- 95%
- Packaging
- 1g
- Price
- $42.6
- Updated
- 2024/03/01
- Product number
- 223670
- Product name
- Bis(cyclopentadienyl)zirconium(IV) chloride hydride
- Purity
- 95%
- Packaging
- 5g
- Price
- $143
- Updated
- 2024/03/01
- Product number
- Z0010
- Product name
- Zirconocene Chloride Hydride
- Purity
- >96.0%(T)
- Packaging
- 1g
- Price
- $39
- Updated
- 2024/03/01
- Product number
- Z0010
- Product name
- Zirconocene Chloride Hydride
- Purity
- >96.0%(T)
- Packaging
- 5g
- Price
- $118
- Updated
- 2024/03/01
- Product number
- L15164
- Product name
- Bis(cyclopentadienyl)zirconium hydridochloride, 95%
- Packaging
- 1g
- Price
- $38.5
- Updated
- 2023/06/20
Bis(cyclopentadienyl)zirconium chloride hydride Chemical Properties,Usage,Production
Reaction
- Reagent for the hydrozirconation of olefins.
- Reagent for the hydrozirconation of alkynes.
- Catalyst for the hydroboration of olefins.
- Mediates the reduction of tertiary amides to aldehydes, without reduction of cyano, nitro, ester, or α,β-unsaturated groups.
- Catalyst for the asymmetric vinylation and dienylation of ketones.
- Useful reagent for dimethylzinc mediated additions alkenylzirconocenes to aldimines.
- Useful reagent for the synthesis of oxidized amides from nitriles.
- 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
Preparation Products
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View Lastest Price from Bis(cyclopentadienyl)zirconium chloride hydride manufacturers
- 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
- 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
- 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