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405965

Sigma-Aldrich

2,2′-Methylenebis[(4S)-4-tert-butyl-2-oxazoline]

99%

Synonym(s):

(S,S)-2,2′-Methylenebis(4-tert-butyl-2-oxazoline)

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About This Item

Empirical Formula (Hill Notation):
C15H26N2O2
CAS Number:
132098-54-5
Molecular Weight:
266.38
Beilstein:
4190673
MDL number:
MFCD00192290
UNSPSC Code:
12352005
PubChem Substance ID:
24865343
NACRES:
NA.22

Assay

99%

optical activity

[α]20/D −118°, c = 0.5 in chloroform

mp

51-53 °C (lit.)

SMILES string

CC(C)(C)[C@H]1COC(CC2=N[C@H](CO2)C(C)(C)C)=N1

InChI

1S/C15H26N2O2/c1-14(2,3)10-8-18-12(16-10)7-13-17-11(9-19-13)15(4,5)6/h10-11H,7-9H2,1-6H3/t10-,11-/m1/s1

InChI key

WCCCBUXURHZPQL-GHMZBOCLSA-N

Application

2,2′-Methylenebis[(4S)-4-tert-butyl-2-oxazoline] (BOX ligand) can be used as a C2 symmetric ligand for enantioselective asymmetric catalysis. It easily forms bidentate coordination complexes due to the strong affinity of the oxazoline nitrogen for various metals.
C2 symmetric ligand for enantioselective catalysis. Easily forms bidentate coordination complexes due to the strong affinity of the oxazoline nitrogen for various metals.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

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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C 2-Symmetric bis (oxazolinato) lanthanide catalysts for enantioselective intramolecular hydroamination/cyclization
Hong S, et al.
Journal of the American Chemical Society, 125(48), 14768-14783 (2003)
Heterogeneous bisoxazoline/copper complex: A green catalyst for the enantioselective reaction of nitromethane with substituted benzaldehydes
Maggi R, et al.
European Journal of Organic Chemistry, 2011(28), 5551-5554 (2011)
Selective oxidation of alkenes and alkynes catalyzed by copper complexes
Alvarez LX, et al.
Applied Catalysis A: General, 325(2), 303-308 (2007)
Gant, T.G. Meyers, A.I.
Tetrahedron, 50, 2297-2297 (1994)
Pfaltz, A.
Accounts of Chemical Research, 26, 339-339 (1993)
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Articles

C2-symmetric chiral bisoxazolines (BOX) ligands

BOX ligand complex enhances catalytic enantioselective aziridination of styrene, with phenyl substituents proving superior over t-Bu groups.

C2-symmetric chiral bisoxazolines (BOX) ligands

BOX ligand complex enhances catalytic enantioselective aziridination of styrene, with phenyl substituents proving superior over t-Bu groups.

C2-symmetric chiral bisoxazolines (BOX) ligands

BOX ligand complex enhances catalytic enantioselective aziridination of styrene, with phenyl substituents proving superior over t-Bu groups.

C2-symmetric chiral bisoxazolines (BOX) ligands

BOX ligand complex enhances catalytic enantioselective aziridination of styrene, with phenyl substituents proving superior over t-Bu groups.

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