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515701

Sigma-Aldrich

N-(9-Anthracenylmethyl)cinchonindinium chloride

85%

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About This Item

Empirical Formula (Hill Notation):
C34H33ClN2O
CAS Number:
199588-80-2
Molecular Weight:
521.09
MDL number:
MFCD02093681
UNSPSC Code:
12352005
PubChem Substance ID:
329757711
NACRES:
NA.22

Assay

85%

mp

158-161 °C (lit.)

SMILES string

[Cl-].OC(C1CC2CC[N+]1(CC2C=C)Cc3c4ccccc4cc5ccccc35)c6ccnc7ccccc67

InChI

1S/C34H33N2O.ClH/c1-2-23-21-36(22-31-27-11-5-3-9-25(27)19-26-10-4-6-12-28(26)31)18-16-24(23)20-33(36)34(37)30-15-17-35-32-14-8-7-13-29(30)32;/h2-15,17,19,23-24,33-34,37H,1,16,18,20-22H2;1H/q+1;/p-1

InChI key

PICKZKQBJJCSSV-UHFFFAOYSA-M

General description

N-(9-Anthracenylmethyl)cinchonindinium chloride can be prepared by reacting cinchonidine with 9-chloromethylanthracene.

Application

N-(9-Anthracenylmethyl)cinchonindinium chloride may be used in the preparation of O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide, a cinchona-based chiral phase-transfer catalyst (PTC).

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

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBD5898V
MKBD5898
MKBD5897
MKBC4044
MKBB2826

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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)
Cinchona-based phase-transfer catalysts for asymmetric synthesis.
Jew SS and Park HG.
Chemical Communications (Cambridge, England), 46, 7090-7103 (2009)

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