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405973

Sigma-Aldrich

2,2′-Bis[(4S)-4-benzyl-2-oxazoline]

98%

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Synonym(s):
(S,S)-4,4′-Dibenzyl-2,2′-bi(2-oxazoline), (S,S)-2,2′-Bis(4-benzyl-2-oxazoline)
Empirical Formula (Hill Notation):
C20H20N2O2
CAS Number:
Molecular Weight:
320.39
Beilstein/REAXYS Number:
4756827
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

form

solid

optical activity

[α]20/D −40.6°, c = 1 in ethanol

mp

129-132 °C (lit.)

SMILES string

C1OC(=N[C@H]1Cc2ccccc2)C3=N[C@H](CO3)Cc4ccccc4

InChI

1S/C20H20N2O2/c1-3-7-15(8-4-1)11-17-13-23-19(21-17)20-22-18(14-24-20)12-16-9-5-2-6-10-16/h1-10,17-18H,11-14H2/t17-,18-/m0/s1

InChI key

OIEQQWQZUYZCRJ-ROUUACIJSA-N

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This Item
405000406147405965
form

solid

form

-

form

-

form

-

Quality Level

100

Quality Level

100

Quality Level

-

Quality Level

-

mp

129-132 °C (lit.)

mp

37-41 °C (lit.)

mp

89-91 °C (lit.)

mp

51-53 °C (lit.)

optical activity

[α]20/D −40.6°, c = 1 in ethanol

optical activity

[α]20/D −160°, c = 1 in ethanol

optical activity

[α]20/D −120°, c = 5 in chloroform

optical activity

[α]20/D −118°, c = 0.5 in chloroform

Application

2,2′-Bis[(4S)-4-benzyl-2-oxazoline] can be used as:
  • A catalyst for the enantioselective hydrosilylation of ketones.
  • A Schiff base ligand in the preparation of rhodium(I) and palladium(II) coordination complexes.
  • A ligand in the formation of copper(I) halide complexes; applicable in the synthesis of coordination polymers.

pictograms

Exclamation mark

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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Rhodium (I) and palladium (II) complexes with the Schiff base 2, 2′-bis ((4S)-4-benzyl-2-oxazoline)
Jones MD, et al.
Inorganica chimica acta, 357(11), 3351-3359 (2004)
Copper (I) halides: A versatile family in coordination chemistry and crystal engineering
Peng R, et al.
Coordination Chemistry Reviews, 254(1-2), 1-18 (2010)
Helmchen, G. et al.
Synlett, 257-257 (1991)

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