1-[2-(4,5,6,7-tetrahydro-2H-inden-2-id-1-yl)ethyl]-4,5,6,7-tetrahydro-2H-inden-2-ide; dichlorozirconiumbis(ylium)

• ChemBase ID: 149472
• Molecular Formular: C20H24Cl2Zr
• Molecular Mass: 426.53456
• Monoisotopic Mass: 424.03021013
• SMILES: C1CCC2=C([CH-]C=C2C1)CCC1=C2C(=C[CH-]1)CCCC2.Cl[Zr+2]Cl
• Canonical SMILES: C1CCC2=C[CH-]C(=C2C1)CCC1=C2CCCCC2=C[CH-]1.Cl[Zr+2]Cl
• InChI: InChI=1S/C20H24.2ClH.Zr/c1-3-7-19-15(5-1)9-11-17(19)13-14-18-12-10-16-6-2-4-8-20(16)18;;;/h9-12H,1-8,13-14H2;2*1H;/q-2;;;+4/p-2
• InChIKey: SHESCSHSEDIGEY-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[2-(4,5,6,7-tetrahydro-2H-inden-2-id-1-yl)ethyl]-4,5,6,7-tetrahydro-2H-inden-2-ide; dichlorozirconiumbis(ylium)
• IUPAC Traditional name: 1-[2-(4,5,6,7-tetrahydro-2H-inden-2-id-1-yl)ethyl]-4,5,6,7-tetrahydro-2H-inden-2-ide; dichlorozirconiumbis(ylium)
• Synonyms: Dichloro[rel-(7aR,7′aR)-1,2-ethanediylbis[(1,2,3,3a,7a-η)-4,5,6,7-tetrahydro-1H-inden-1-ylidene]]zirconium; Dichloro[rac-ethylenebis(4,5,6,7-tetrahydro-1-indenyl)]zirconium(IV); Dichloro[(R,R)-ethylenebis(4,5,6,7-tetrahydro-1-indenyl)]zirconium(IV); Dichloro[(S,S)-ethylenebis(4,5,6,7-tetrahydro-1-indenyl)]zirconium(IV); [rac-乙烯双(4,5,6,7-四氢-1-茚基)]二氯化锆(IV); [(R,R)-乙烯双(4,5,6,7-四氢-1-茚基)]二氯化锆(IV); [(S,S)-乙烯双(4,5,6,7-四氢-1-茚基)]二氯化锆(IV)

Database IDs

• CAS Number: 109429-79-0; 150131-28-5; 100163-29-9
• MDL Number: MFCD00672123
• PubChem SID: 24877859; 24877844; 162243637; 24877845
• PubChem CID: 71311414

CALCULATED PROPERTIES

• Acid pKa: 15.696604
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 4.8452644
• LogD (pH = 7.4): 4.8452644
• Log P: 7.3724
• Molar Refractivity: 86.6746 cm^3
• Polarizability: 33.253742 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 160-165 °C(lit.); 163-167 °C(lit.); 267-271 °C(lit.)
• Optical Rotation: [α]20/D +93°, c = 0.07 in methylene chloride; [α]20/D -89°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Corrosive (C); Irritant (Xi)
• UN Number: 3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2
• Risk Statements: 22-34; 36/37/38
• Safety Statements: 26-36; 26-36/37/39-45
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H302-H314; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C20H24Cl2Zr

DETAILS

Sigma Aldrich - 531839

Packaging
100 mg in glass bottle

Sigma Aldrich - 531847

Packaging
100 mg in glass bottle
Application

• Chiral Ziegler-Natta catalyst1

Sigma Aldrich - 532126

Packaging
500 mg in glass bottle
Application
Catalyst for:
• Regiochemistry in Negishi carboaluminations1
• Polymerization of olefins2
• Diastereoselective intramolecular olefin alkylations3
• Asymmetric carbomagnesiation4
• Reduction of esters to alcohols5
• Enantioselective synthesis of allylic amines6