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477494

2,6-Bis[(4R)-(+)-isopropyl-2-oxazolin-2-yl]pyridine

99%

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About This Item

Empirical Formula (Hill Notation):
C17H23N3O2
CAS Number:
131864-67-0
Molecular Weight:
301.38
NACRES:
NA.22
PubChem Substance ID:
24871378
UNSPSC Code:
12352005
MDL number:
MFCD01321334

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InChI

1S/C17H23N3O2/c1-10(2)14-8-21-16(19-14)12-6-5-7-13(18-12)17-20-15(9-22-17)11(3)4/h5-7,10-11,14-15H,8-9H2,1-4H3/t14-,15-/m0/s1

SMILES string

CC(C)[C@@H]1COC(=N1)c2cccc(n2)C3=N[C@@H](CO3)C(C)C

InChI key

CSGQGLBCAHGJDR-GJZGRUSLSA-N

assay

99%

optical activity

[α]20/D +118°, c = 0.7 in methylene chloride

mp

154-156 °C (lit.)

functional group

ether

Quality Level

100

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This Item
369756496065496073
2,6-Bis[(4R)-(+)-isopropyl-2-oxazolin-2-yl]pyridine 99%

Sigma-Aldrich

477494

2,6-Bis[(4R)-(+)-isopropyl-2-oxazolin-2-yl]pyridine

2-Phenyl-2-oxazoline 99%

Sigma-Aldrich

369756

2-Phenyl-2-oxazoline

2,6-Bis[(4R)-4-phenyl-2-oxazolinyl]pyridine 98%

Sigma-Aldrich

496065

2,6-Bis[(4R)-4-phenyl-2-oxazolinyl]pyridine

2,6-Bis[(4S)-4-phenyl-2-oxazolinyl]pyridine 98%

Sigma-Aldrich

496073

2,6-Bis[(4S)-4-phenyl-2-oxazolinyl]pyridine

assay

99%

assay

99%

assay

98%

assay

98%

functional group

ether

functional group

ether, phenyl

functional group

ether, phenyl

functional group

ether, phenyl

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

mp

154-156 °C (lit.)

mp

12 °C (lit.)

mp

171-175 °C (lit.)

mp

171-175 °C (lit.)

optical activity

[α]20/D +118°, c = 0.7 in methylene chloride

optical activity

-

optical activity

[α]22/D 187°, c = 1 in methylene chloride

optical activity

[α]20/D −224°, c = 1 in chloroform

Application

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]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCG8309
MKBW5463V
MKBV7646V
MKBD7647V
MKBD7647

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Iryna D Alshakova et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 25(50), 11734-11744 (2019-07-19)
This work unveils the reactivity patterns, as well as ligand and additive effect on alkali-metal-base-catalyzed transfer hydrogenation of ketones. Crucially to this reactivity is the presence of a Lewis acid (alkali cation), as opposed to a simple base effect. With
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)

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