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405000

Sigma-Aldrich

(−)-2,2′-Isopropylidenebis[(4S)-4-phenyl-2-oxazoline]

97%

Synonym(s):

(S,S)-2,2′-Isopropylidenebis(4-phenyl-2-oxazoline), (S,S)-2,2-Bis(4-phenyl-2-oxazolin-2-yl)propane

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About This Item

Empirical Formula (Hill Notation):
C21H22N2O2
CAS Number:
131457-46-0
Molecular Weight:
334.41
Beilstein:
4266906
MDL number:
MFCD00192245
UNSPSC Code:
12352005
PubChem Substance ID:
24865286
NACRES:
NA.22

Assay

97%

optical activity

[α]20/D −160°, c = 1 in ethanol

bp

193 °C/0.03 mmHg (lit.)

mp

37-41 °C (lit.)

density

1 g/mL at 25 °C (lit.)

storage temp.

−20°C

SMILES string

CC(C)(C1=N[C@H](CO1)c2ccccc2)C3=N[C@H](CO3)c4ccccc4

InChI

1S/C21H22N2O2/c1-21(2,19-22-17(13-24-19)15-9-5-3-6-10-15)20-23-18(14-25-20)16-11-7-4-8-12-16/h3-12,17-18H,13-14H2,1-2H3/t17-,18-/m1/s1

InChI key

JTNVCJCSECAMLD-QZTJIDSGSA-N

Application

C2 symmetric ligand for enantioselective catalysis. Easily forms bidentate coordination complexes due to the strong affinity of the oxazoline nitrogen for various metals.

related product

Product No.
Description
Pricing

912255

sBOX(tBu), ≥95%

912778

sBOX(iPr), ≥95%

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Bolm, C.
Angewandte Chemie (International Edition in English), 30, 542-542 (1991)
Gant, T.G. Meyers, A.I.
Tetrahedron, 50, 2297-2297 (1994)
Pfaltz, A.
Accounts of Chemical Research, 26, 339-339 (1993)

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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