Key Documents

(+)-2,2′-Isopropylidenebis[(4R)-4-phenyl-2-oxazoline]

Name: (+)-2,2′-Isopropylidenebis[(4<I>R</I>)-4-phenyl-2-oxazoline]
Brand: ALDRICH
Price: 82.5 USD
Availability: InStock

97%

Synonym(s):

(R,R)-2,2′-Bis(4-phenyl-2-oxazolin-2-yl)propane, (R,R)-2,2′-Isopropylidenebis(4-phenyl-2-oxazoline)

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Pack Size	SKU	Availability	Price
250 mg		Available to ship TODAYfromMILWAUKEE	$110.00 $82.50
1 g		Available to ship TODAYfromMILWAUKEE	$297.00 $222.75

About This Item

Empirical Formula (Hill Notation):

C₂₁H₂₂N₂O₂

CAS Number:

150529-93-4

Molecular Weight:

334.41

UNSPSC Code:

12352005

NACRES:

NA.22

PubChem Substance ID:

24865413

MDL number:

MFCD00192244

Beilstein/REAXYS Number:

4266906

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Properties

Quality Level

100

assay

97%

form

solid

optical activity

[α]20/D +160°, c = 1 in ethanol

mp

56-58 °C (lit.)

functional group

ether, phenyl

storage temp.

−20°C

SMILES string

CC(C)(C1=N[C@@H](CO1)c2ccccc2)C3=N[C@@H](CO3)c4ccccc4

InChI

1S/C21H22N2O2/c1-21(2,19-22-17(13-24-19)15-9-5-3-6-10-15)20-23-18(14-25-20)16-11-7-4-8-12-16/h3-12,17-18H,13-14H2,1-2H3/t17-,18-/m0/s1

InChI key

JTNVCJCSECAMLD-ROUUACIJSA-N

Description

Application

(+)-2,2′-Isopropylidenebis[(4R)-4-phenyl-2-oxazoline] in the presence of copper iodide, can catalyze the asymmetric cyclopropanation reaction of phenyliodonium ylides with alkenes to form cyclopropane α-amino acid esters.[1]

C₂ symmetric ligand for enantioselective catalysis. Easily forms bidentate coordination complexes due to the strong affinity of the oxazoline nitrogen for various metals.

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This Item	405000	405973	674737
Sigma-Aldrich 406961 (+)-2,2′-Isopropylidenebis[(4R)-4-phenyl-2-oxazoline]	Sigma-Aldrich 405000 (−)-2,2′-Isopropylidenebis[(4S)-4-phenyl-2-oxazoline]	Sigma-Aldrich 405973 2,2′-Bis[(4S)-4-benzyl-2-oxazoline]	Sigma-Aldrich 674737 (R)-3,3′-Bis(triphenylsilyl)-1,1′-bi-2-naphthol
assay 97%	assay 97%	assay 98%	assay 96%
form solid	form -	form solid	form solid
functional group ether, phenyl	functional group ether, phenyl	functional group ether, phenyl	functional group -
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. −20°C	storage temp. −20°C	storage temp. -	storage temp. -
optical activity [α]20/D +160°, c = 1 in ethanol	optical activity [α]20/D −160°, c = 1 in ethanol	optical activity [α]20/D −40.6°, c = 1 in ethanol	optical activity [α]20/D +114°, c = 1 in chloroform

pictograms

GHS06

signalword

Danger

hcodes

H301 + H311 + H331

pcodes

P261 - P264 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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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.

Expedient synthesis of cyclopropane alpha-amino acids by the catalytic asymmetric cyclopropanation of alkenes using iodonium ylides derived from methyl nitroacetate.

Benoît Moreau et al.

Journal of the American Chemical Society, 127(51), 18014-18015 (2005-12-22)

A highly enantioselective (up to 97.5% ee) and diastereoselective (95:5 dr trans/cis) Cu(I)-catalyzed cyclopropanation of alkenes using phenyliodonium ylide generated in situ from iodosobenzene and methyl nitroacetate is reported. The cyclopropanation took place with high enantioselectivity for a wide range

Bolm, C.

Angewandte Chemie (International Edition in English), 30, 542-542 (1991)

Gant, T.G. Meyers, A.I.

Tetrahedron, 50, 2297-2297 (1994)

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Global Trade Item Number

SKU	GTIN
406961-250MG	04061833055199
406961-1G	04061826732618

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