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Merck
CN

405965

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

99%

Synonym(s):

(S,S)-2,2′-Methylenebis(4-tert-butyl-2-oxazoline)

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About This Item

Empirical Formula (Hill Notation):
C15H26N2O2
CAS Number:
132098-54-5
Molecular Weight:
266.38
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24865343
MDL number:
MFCD00192290
Beilstein/REAXYS Number:
4190673

Key Documents

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Product Name

2,2′-Methylenebis[(4S)-4-tert-butyl-2-oxazoline], 99%

InChI

1S/C15H26N2O2/c1-14(2,3)10-8-18-12(16-10)7-13-17-11(9-19-13)15(4,5)6/h10-11H,7-9H2,1-6H3/t10-,11-/m1/s1

SMILES string

CC(C)(C)[C@H]1COC(CC2=N[C@H](CO2)C(C)(C)C)=N1

InChI key

WCCCBUXURHZPQL-GHMZBOCLSA-N

assay

99%

optical activity

[α]20/D −118°, c = 0.5 in chloroform

mp

51-53 °C (lit.)

functional group

ether

Quality Level

200

Related Categories

Application

2,2′-Methylenebis[(4S)-4-tert-butyl-2-oxazoline] (BOX ligand) can be used as a C2 symmetric ligand for enantioselective asymmetric catalysis. It easily forms bidentate coordination complexes due to the strong affinity of the oxazoline nitrogen for various metals.
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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000145434
0000120428
0000076289
0000071362

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Heterogeneous bisoxazoline/copper complex: A green catalyst for the enantioselective reaction of nitromethane with substituted benzaldehydes
Maggi R, et al.
European Journal of Organic Chemistry, 2011(28), 5551-5554 (2011)
Selective oxidation of alkenes and alkynes catalyzed by copper complexes
Alvarez LX, et al.
Applied Catalysis A: General, 325(2), 303-308 (2007)
C 2-Symmetric bis (oxazolinato) lanthanide catalysts for enantioselective intramolecular hydroamination/cyclization
Hong S, et al.
Journal of the American Chemical Society, 125(48), 14768-14783 (2003)
Pfaltz, A.
Accounts of Chemical Research, 26, 339-339 (1993)
Gant, T.G. Meyers, A.I.
Tetrahedron, 50, 2297-2297 (1994)
View All Related Papers

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.

C2型轴对称手性双噁唑啉（BOX）配体

使用络合Cu(I)OTf的BOX配体进行不对称催化苯乙烯合成氮杂环丙烷的反应，BOX配体带苯基取代基的优于具有位阻需求的叔丁(t-Bu)基团。

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