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406147

Sigma-Aldrich

2,2′-Isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]

99%

Synonym(s):

(S,S)-2,2′-Isopropylidene-bis(4-tert-butyl-2-oxazoline)

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250 MG
CLP 167,500

CLP 167,500

Estimated to ship onApril 30, 2025

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250 MG
CLP 167,500

About This Item

Empirical Formula (Hill Notation):
C17H30N2O2
CAS Number:
131833-93-7
Molecular Weight:
294.43
MDL number:
MFCD00192243
UNSPSC Code:
12352005
PubChem Substance ID:
24865358
NACRES:
NA.22

CLP 167,500

Estimated to ship onApril 30, 2025

Request a Bulk Order

Assay

99%

optical activity

[α]20/D −120°, c = 5 in chloroform

mp

89-91 °C (lit.)

functional group

ether

SMILES string

CC(C)(C)[C@H]1COC(=N1)C(C)(C)C2=N[C@H](CO2)C(C)(C)C

InChI

1S/C17H30N2O2/c1-15(2,3)11-9-20-13(18-11)17(7,8)14-19-12(10-21-14)16(4,5)6/h11-12H,9-10H2,1-8H3/t11-,12-/m1/s1

InChI key

DPMGLJUMNRDNMX-VXGBXAGGSA-N

Application

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

related product

Product No.
Description
Pricing

912255

sBOX(tBu), ≥95%

912778

sBOX(iPr), ≥95%

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000069485
0000063053
0000043775
0000038763
0000026162

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Mauro Marigo et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 10(9), 2133-2137 (2004-04-28)
The first general catalytic asymmetric bromination and chlorination of beta-ketoesters has been developed. The reactions proceed for both acyclic and cyclic beta-ketoesters catalyzed by chiral bisoxazolinecopper(II) complexes giving the corresponding optically active alpha-bromo- and alpha-chloro-beta-ketoesters in high yields and moderate
Tetrahedron Letters, 44, 7849-7850 (2003)
L C Madoff et al.
Infection and immunity, 60(12), 4989-4994 (1992-12-01)
Group B streptococci (GBS) cause the majority of cases of neonatal sepsis and meningitis in the United States. Immunization of women of childbearing age is one strategy under consideration for the prevention of neonatal disease. The beta C protein, a
Nicholas Gathergood et al.
Organic & biomolecular chemistry, 2(7), 1077-1085 (2004-03-23)
The direct aldol reaction of 2-ketoesters catalyzed by chiral bisoxazoline copper(II) complexes has been investigated. First the direct homo-aldol reaction of ethyl pyruvate is reported which proceeds to give diethyl 2-hydroxy-2-methyl-4-oxoglutarate. This was isolated as the more stable optically active
Tetrahedron Letters, 45, 4213-4216 (2004)
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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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