Skip to Content
MilliporeSigma
All Photos(1)

Documents

499617

Sigma-Aldrich

O-Allyl-N-(9-anthracenylmethyl)cinchonidinium bromide

90%

Synonym(s):

O(9)-Allyl-N-9-anthracenylcinchonidinium bromide, O(9)-Allyl-N-9-anthracenylmethylcinchonidium bromide, O-Allyl-1-(anthracen-9-ylmethyl)cinchonidinium bromide, O-Allyl-N-(9-anthracenylmethyl)cinchoninium bromide, O-Allyl-N-[(9-anthracenyl)methyl]cinchonidium bromide

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C37H37BrN2O
CAS Number:
200132-54-3
Molecular Weight:
605.61
MDL number:
MFCD01632446
UNSPSC Code:
12352005
PubChem Substance ID:
24873293
NACRES:
NA.22

assay

90%

optical activity

[α]20/D −345±30°, c = 0.45 in chloroform

mp

170 °C (dec.) (lit.)

SMILES string

[Br-].[H][C@@]12CC[N+](C[C@@H]1C=C)(Cc3c4ccccc4cc5ccccc35)[C@@]([H])(C2)[C@H](OCC=C)c6ccnc7ccccc67

InChI

1S/C37H37N2O.BrH/c1-3-21-40-37(33-17-19-38-35-16-10-9-15-32(33)35)36-23-27-18-20-39(36,24-26(27)4-2)25-34-30-13-7-5-11-28(30)22-29-12-6-8-14-31(29)34;/h3-17,19,22,26-27,36-37H,1-2,18,20-21,23-25H2;1H/q+1;/p-1/t26-,27-,36-,37+,39?;/m0./s1

InChI key

QOWNPAUSLGATNL-JNKXQCINSA-M

General description

O-Allyl-N-(9-anthracenylmethyl)cinchonidinium bromide is a cinchona-based chiral phase-transfer catalyst (PTC) that can be used in asymmetric synthesis. It can be prepared from N-(9-anthracenylmethyl)cinchonindinium chloride.

Application

O-Allyl-N-(9-anthracenylmethyl)cinchonidinium bromide can catalyze the asymmetric alkylation of tert-butyl glycinate-benzophenone Schiff base with different arylmethyl bromides in a micellar medium.

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Asymmetric Alkylation of tert-Butyl Glycinate Schiff Base with Chiral Quaternary Ammonium Salt under Micellar Conditions.
Okino T and Takemoto Y.
Organic Letters, 3(10), 1515-1517 (2001)
Cinchona-based phase-transfer catalysts for asymmetric synthesis.
Jew SS and Park HG.
Chemical Communications (Cambridge, England), 46, 7090-7103 (2009)
Preparation of O-Allyl-N-(9-Anthracenylmethyl) cinchonidinium Bromide as a Phase Transfer Catalyst for the Enantioselective Alkylation of Glycine Benzophenone Imine tert-Butyl Ester:(4S)-2-(Benzhydrylidenamino) pentanedioic Acid, 1-tert-Butyl Ester-5-Methyl Ester.
Corey EJ and Noe MC.
Organic Syntheses, 38-45 (2003)

Articles

Maruoka Catalysts

Asymmetric phase transfer catalysis using the Maruoka catalysts has proven to be an ideal method for the enantioselective preparation of natural and unnatural α-alkyl and α,α-dialkyl-α-amino acids from glycine derivati

Cinchona Alkaloids

Asymmetric phase-transfer catalysis (PTC) has been recognized as a “green” alternative to many homogeneous synthetic organic transformations, and has found widespread application. Synthetically modified cinchona alkaloids are typical chiral organocatalysts used in asymmetric PTC.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service