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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:
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.)

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

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

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
1413156V
1418606
MKAA2500
1413156
1404173

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Pfaltz, A.
Accounts of Chemical Research, 26, 339-339 (1993)
Bolm, C.
Angewandte Chemie (International Edition in English), 30, 542-542 (1991)
Gant, T.G. Meyers, A.I.
Tetrahedron, 50, 2297-2297 (1994)

Articles

C2-symmetric chiral bisoxazolines (BOX) ligands

C2-symmetric chiral bisoxazolines (BOX) are privileged structures because they promote a great number of transformations with unprecedented selectivity.1

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