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449539

Sigma-Aldrich

Chlorocyclopentadienyl[(4S,5S)-2,2-dimethyl-α,α,α′,α′-tetraphenyl-1,3-dioxolane-4,5-dimethanolato]titanium

97%

Synonym(s):

(4S,5S)-Chloro-cyclopentadienyl-[2,2-dimethyl-1,3-dioxolan-4,5-bis(diphenylmethoxy)]titanium, (S,S)-Duthaler-Hafner reagent, [(4S,5S)-2,2-Dimethyl-1,3-dioxolan-4,5-bis(diphenylmethoxy)]cyclopentadienyl-chlorotitanium

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About This Item

Empirical Formula (Hill Notation):
C36H33ClO4Ti
CAS Number:
140462-73-3
Molecular Weight:
612.96
UNSPSC Code:
12352000
PubChem Substance ID:
24868490

Assay

97%

optical activity

[α]20/D +246°, c = 1 in chloroform

mp

209-213 °C (lit.)

SMILES string

Cl[Ti].[CH]1[CH][CH][CH][CH]1.CC2(C)O[C@@H]([C@H](O2)C(O)(c3ccccc3)c4ccccc4)C(O)(c5ccccc5)c6ccccc6

Application

A novel highly enantioselective allyl-transfer reagent. Excellent regio-, diastereo-, and enantioselectivities (usually >95% ee, >95% de) are obtained for the addition of allyl nucleophiles to aldehydes. Although this reagent is used in stoichiometric amounts, the chiral ligand and monocyclopentadienyltitanium trichloride can be easily recovered.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Duthaler, R.O. Hafner, A.
Chemical Reviews, 92, 807-807 (1992)
Duthaler, R.O. et al.
Pure and Applied Chemistry. Chimie Pure Et Appliquee, 64, 1897-1897 (1990)
Duthaler, R.O. et al.
Pure and Applied Chemistry. Chimie Pure Et Appliquee, 62, 631-631 (1990)
Duthaler, R.O. et al.
Inorgorganica Chimica Acta, 222, 95-95 (1994)
A. Hafner et al.
Journal of the American Chemical Society, 114, 2321-2321 (1992)

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