Chloro(hydrido)zirconium;bis(cyclopenta-1,3-diene)
Basic information
- CAS
37342-97-5- Standard SMILES
[Cl][ZrH].[c-]1[c-][c-][cH-][c-]1.[c-]1[c-][c-][cH-][c-]1- InChIKey
ZTGAKANMZMGNRO-UHFFFAOYSA-M- Molecular formula
- C10H3ClZr-10
- Average molar mass
- 249.8 g/mol
- Monoisotopic mass
- 247.897027
Names & identifiers
- Preferred name
- Chloro(hydrido)zirconium;bis(cyclopenta-1,3-diene)
- IUPAC
- chloro(hydrido)zirconium;bis(cyclopenta-1,3-diene)
- English name
- Bis(cyclopentadienyl)zirconium chloride hydride
- Molecular formula
- C10H11ClZr
- Molecular weight
- 257.87
Names & synonyms
NSC379439SCHWARTZ'S REAGENTSCHWARTZ REAGENTZIRCONOCENE CHLORIDE HYDRIDEschwartzBIS(CYCLOPENTADIENYL)ZIRCONIUM(IV) CHLORIDE HYDRIDEZIRCONOCENE HYDROCHLORIDESCHWART'S REAGENTBIS(CYCLOPENTADIENYL)ZIRCONIUM HYDRIDOCHLORIDEZirconocene chloride hydride, 94%, reagent gradeSchwartz's
Database identifiers
- CAS
37342-97-5- PubChem CID
- 435938
Properties
Computed structural properties
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 0
- Heavy atoms
- 12
- Formal charge
- -10
- Complexity
- 148
Physicochemical properties
- Melting point
- 300 °C · 300 °C
- storage temp.
- 2 · 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 · 8: reacts rapidly with moisture, water, protic solvents
- Merck
- 14 · 14,8396
- Exposure limits
- 5 mg/m3; · ACGIH: TWA 5 mg/m3; STEL 10 mg/m3NIOSH: 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 · 37342-97-5(CAS DataBase Reference)
- FDA UNII
- 84 D01XQGL · S84D01XQGL
- UNSPSC Code
- 12352101 · 12352101
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 8-10-23
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- ridadr
- UN 3131 4.3/PG 2
- hs_code
- 29319090
- risk_code
- 11-15-34
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS05
- hazard_code
- F,C
- safety_code
- 16-26-27-36/37/39-8-45
- hazard_class
- 4.3
- Storage Class
- 4.3 - Hazardous materials which set free flammable gases upon contact with water
- packing_group
- II
- Hazard statements
- H261-H314
- Limited Quantities
- 0.5 Kg (1.1 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- Hazard Classifications
- Skin Corr. 1BWater-react 2
- Precautionary statements
- P223-P231+P232-P260-P280-P303+P361+P353-P305+P351+P338
Chemistry & industry
Applications
UsesFunctionalization 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.
UsesBis(cyclopentadienyl)zirconium hydridochloride is used in the conversion of amides to aldehydes. It is also used as a pharmaceutical intermediate.
Preparation methods
PreparationSchwartz’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.
Upstream & downstream products
Upstream raw materials
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