MilliporeSigma
All Photos(2)

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
Empirical Formula (Hill Notation):
C21H22N2O2
CAS Number:
Molecular Weight:
334.41
Beilstein:
4266906
MDL number:
PubChem Substance ID:
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.

Packaging

1 g in glass bottle
250 mg in amber glass bottle

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

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

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

C2-symmetric chiral bisoxazolines (BOX) are privileged structures because they promote a great number of transformations with unprecedented selectivity.1

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