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416428

Sigma-Aldrich

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

97%

Synonym(s):

(S,S)-2,2′-Methylenebis(4-phenyl-2-oxazoline)

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About This Item

Empirical Formula (Hill Notation):
C19H18N2O2
CAS Number:
132098-59-0
Molecular Weight:
306.36
Beilstein/REAXYS Number:
4202633
MDL number:
MFCD00192295
UNSPSC Code:
12352005
PubChem Substance ID:
24866074
NACRES:
NA.22

assay

97%

form

viscous liquid

optical activity

[α]20/D ~−90°, c = 1 in ethanol

refractive index

n20/D 1.586 (lit.)

bp

131-134 °C/0.01 mmHg (lit.)

density

1.28 g/mL at 25 °C (lit.)

functional group

ether
phenyl

SMILES string

C1OC(CC2=N[C@H](CO2)c3ccccc3)=N[C@H]1c4ccccc4

InChI

1S/C19H18N2O2/c1-3-7-14(8-4-1)16-12-22-18(20-16)11-19-21-17(13-23-19)15-9-5-2-6-10-15/h1-10,16-17H,11-13H2/t16-,17-/m1/s1

InChI key

IUFHJPXOLHSJTC-IAGOWNOFSA-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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
1413156V
1404173
1413156
1418606
MKAA2500

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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.

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