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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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500 MG
$234.00

About This Item

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

$234.00

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assay

99%

optical activity

[α]20/D −118°, c = 0.5 in chloroform

mp

51-53 °C (lit.)

functional group

ether

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.[1][2]
C2 symmetric ligand for enantioselective catalysis. Easily forms bidentate coordination complexes due to the strong affinity of the oxazoline nitrogen for various metals.[3][4][5]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000145434
0000120428
0000076289
0000071362

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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)
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)
Pfaltz, A.
Accounts of Chemical Research, 26, 339-339 (1993)
Gant, T.G. Meyers, A.I.
Tetrahedron, 50, 2297-2297 (1994)
View All Related Papers

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.

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